The LeanScale Podcast · Episode 151

$50K to $8M ARR in 3 Years: The Warmly Playbook

Keegan Otter on taking the SDR seat first, cutting qualification to three questions, the closed-lost process that resurfaced deals every quarter, pitching founders on the first hires with two paths on a whiteboard, the routing and ACV math past $5M, and why he told Warmly's executive team to build the brand or die

Keegan Otter · AI Strategy, HubSpot Sales Hub · HubSpot Hosted by Anthony Enrico
Published Updated 00:57:56 58 min read 11698 words
GTM Strategy Sales Leadership Outbound & Sales Development Revenue Operations Brand & Positioning AI in GTM
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Executive Summary

The one-paragraph brief, extended

Why this conversation matters — and who should spend the hour.

Keegan Otter oversees AI strategy for HubSpot's Sales Hub products, where he is helping build the next set of agents inside the CRM. Before that he was co-founder and CRO of Warmly, the person-level website intent and AI inbound agent company. He joined when it was four people and about $50,000 in revenue. A little over three years later it was doing roughly $8 million in ARR, or $12 million in total sales including non-SaaS products, and HubSpot acquired it in 2026. He has worked as an SDR, RevOps director, VP of sales and CRO.

The first thing he built was not a hiring plan. He found the founders automating everything and seeing what stuck, so he reviewed call recordings, built the CRM in HubSpot and cut qualification to three questions: why buy anything, why now, why Warmly. Though he had been a sales leader at a Series B company, he took the SDR seat, watched the CEO close for about two months, then started closing himself. He moved the list from what he jokes were everyone's mothers and grandmothers to directors and above in revenue, sales development and marketing, and stopped asking for design partners. Warmly reached half a million in revenue three to four months after he arrived.

His outbound ran on two clocks: a long-term play to get buyers into Warmly's network and educate them with content, and short-term manual touches by LinkedIn DM, email and calls to engaged leads. Cold calling, which had made him money as a rep, ranked low among the 12 channels Warmly used. The first thing to break was closed-lost data, since nobody had recorded why deals were lost. Once the team fixed that, he says, Warmly resurfaced two to three closed-lost deals every quarter and won one to two.

For founders, the most useful section is how he got the CEO to let go. He drew two paths on a whiteboard, one where he stayed the main seller and one where two people he had worked with came in, and Warmly hit a million in about nine months. He then pushed the CEO into product to make the boulder smaller. Person-level identification and agentic chat followed, and Keegan puts the win rate against 6sense at about 70%. He also explains how taking ownership outside his number made him a co-founder, and why disagreeing with the CEO was part of the job.

Past $5 million the work changes to routing, segments, ACV floors and payback math, with an executive layer on the biggest deals. Keegan's closing argument is brand. He told Warmly's executives at a retreat in Portugal that they had to build the brand or die, and that people follow people rather than logos. In a market where building gets cheaper, he says he would shrink the sales development budget to fund it. The episode suits founders, first sales leaders and CROs working from zero to about $15 million.

Key Takeaways

15 things worth stealing

The load-bearing ideas, each with the business implication and who should care.

01

Take the SDR seat before you hire one

Keegan had been a sales leader at a Series B company, but at Warmly he became the SDR, finding the right meetings for the co-founder and CEO. He watched the CEO close for about two months, then started closing himself, and an SDR hired overseas then fed them both. He calls it crawl, walk, run.

Why it matters: An experienced leader who starts at the bottom of the funnel learns which talk tracks and targets work before anyone is hired to repeat them. Keegan's phrase is taking a couple of steps back to go 10 steps forward, and he credits it with half a million in revenue in three to four months.

FoundersSales LeadersRevenue Executives
02

Instrument the CRM and cut qualification to three questions

Keegan found no tracking and no strategic targeting. He reviewed calls that went well and badly, then built HubSpot to capture channels, timestamps for meeting set and meeting held, the associated SDR and AE, deal owner and stages. He replaced a full MEDDPICC or MEDDIC with the three whys: why buy anything, why now, why Warmly.

Why it matters: He says the three questions were open-ended enough to collect much of what a longer framework asks for, which gave Warmly a sales process it could scale from the start.

RevOps LeadersSales LeadersFounders
03

Fix the list before you fix anything else

When Keegan arrived, Warmly's meetings were with titles that would never buy and were not in the right department. He stopped pursuing SDRs and SDR managers and went after directors and above in revenue, sales development and marketing.

Why it matters: His view is that it always comes down to who you target. Meetings with the wrong titles feel like traction and produce no customers.

Sales LeadersFoundersMarketing Leaders
04

Stop asking for design partners and say what you sell

Warmly had been reaching out for early design partners. Keegan changed the message to what the company does, who it solves for and what it solves, and put prospects on a demo so the expectation was clear. He says he has told cold callers himself not to make it sound fancy.

Why it matters: Directness qualifies faster, and early adopters of a good tool still get the benefit. The company needed customers, not more free design partners.

FoundersSales Leaders
05

Cold call engaged leads, not as the lead motion

Keegan made a lot of money cold calling as a rep, but says its effectiveness was starting to fall. Of the 12 channels or styles Warmly used, he recalls cold calling ranking below seventh or eighth, partly because Warmly mostly sold to marketers, who do not want to pick up their phones.

Why it matters: He still believes every team should cold call. He told reps to call engaged leads, and he did not make it the forefront KPI. Channel mix should follow the audience you sell to.

Sales LeadersRevenue Executives
06

Run omni-channel on a long clock and a short clock

The long-term play was getting prospects into Warmly's network on LinkedIn so they saw company content repeatedly, plus case studies and third-party data on falling inbound rates, so Warmly looked like an expert to follow. The short-term play was manual LinkedIn DMs, emails and calls. Some prospects loved a LinkedIn message and hated email, and others were the reverse.

Why it matters: You cannot know how a given buyer prefers to be reached. Anthony's summary is to build the list, flood them, add value first and then come in over the top.

Sales LeadersMarketing Leaders
07

Closed-lost data is your second at-bat

The first thing Keegan saw broken was that nobody could say why deals were lost. He frames revenue as a failing statistic: win three of ten and you are a Hall of Famer, so the data has to tell you how to go after the other seven. He held off making more deals until the team agreed what to collect, and put lost deals in a rehash bucket with their requested features.

Why it matters: Keegan says that every quarter Warmly resurfaced two to three closed-lost deals and won one to two. Without the data you have a leaky bucket, and the deals you lost are gone in the ether once the product catches up.

RevOps LeadersSales LeadersRevenue Executives
08

Hand out owners before the org chart exists

Below $1 million everyone at Warmly had equal titles and marketing and sales were not aligned. Keegan pulled the team together and assigned each person an area: competitive analysis to one co-founder, marketing to another colleague, budget for gaps from the CEO. He also moved positioning from marketers only to go-to-market leaders generally.

Why it matters: He was nervous about overstepping, but says people thanked him for getting on them like a football coach. Clear roles are what got the team rowing in the same direction.

FoundersRevenue Executives
09

Give the founder two paths, not an opinion

Keegan believes the CEO wanted him as the main AE for the first full year. On a whiteboard he laid out two paths. In one he alone scales revenue and reaches a million in a year to a year and a half, with churn unmanaged. In the other, two people he had worked with come in, Warmly passes a million in under a year, and churn and upsell get attention while the CEO goes back to being CEO.

Why it matters: Founders treat the company like their baby, and Warmly had already pivoted three times. Laying out the outcomes of each option, while saying he would support either, made the decision the CEO's. The hires took Warmly to a million in about nine months.

FoundersSales LeadersRevenue Executives
10

The CEO's job can be making the boulder smaller

When Keegan joined, Warmly's chatbot was very manual, its visitor identification worked only at the company level, and it was effectively a down-market reseller of 6sense. He told the CEO, who had a project management background at Google, that without product improvements customers would start leaving. Keegan would push the rock uphill for revenue while the CEO made it smaller.

Why it matters: Keegan calls the CEO's move into product one of the most vital points at Warmly. Once person-level identification and agentic chat shipped, he says sales exploded, the win rate against 6sense reached about 70%, and 6sense pulled the partnership.

FoundersRevenue Executives
11

Co-founder is earned through ownership and disagreement

The title began as a way into co-founder events, which the CEO suggested when he was too busy to attend. Keegan was already presenting in board meetings, negotiating tools across the business and getting to know the engineers. The founders then voted to make him a co-founder, and the board said it thought he already was one.

Why it matters: A co-founder told him he cared about more than his own number. Keegan adds that the role is not being a yes man: he and the CEO argued often, and he says each of them saved the other from wrong decisions. Anthony describes the same dynamic with LeanScale's COO, and says that without pushback the seat is lonely and hard to trust.

FoundersRevenue Executives
12

Zero to five finds the process, five to fifteen rebuilds it

Keegan describes zero to five as building processes to see what works and testing how far they bend. Perhaps 25 to 50% carry you, and then it is like remodeling an old building: reinforce it, add to it, or sometimes start from scratch. Warmly went from three or four sellers to 10 AEs, which needed new routing, real segments, and Keegan moving out of deals into an executive layer.

Why it matters: Executives coming in on the big deals helped win rate and scaled better than selling them directly. Anthony adds that segment is usually the first axis of specialization once you pass five.

Revenue ExecutivesRevOps LeadersSales Leaders
13

Set ACV floors by segment from payback

Past five, Keegan calculates the ACV each segment needs and how long it takes to close. An AE earning $140K to $150K in the SMB segment cannot touch deals below $15,000 to $20,000, and anything below the floor should go self-serve or skip a human. Warmly's strategic segment, upper mid-market to enterprise and six-figure deals, was a different equation.

Why it matters: He pays strategic AEs hundreds of thousands of dollars knowing they may not close until month five, six, seven or a year in. He says it was worth it, but the other departments have to be trained on why that segment runs differently.

RevOps LeadersRevenue ExecutivesSales Leaders
14

Build the brand or die, and build it on people

At an executive retreat in Portugal, Keegan told the team that competitors would catch up on product and that brand was the differentiator. He says people did not follow Warmly, they followed its executives on revenue, product, marketing and AI. A large company evaluating Qualified told Warmly it kept popping up on LinkedIn, in LLMs and in G2 reviews, and that its founders were everywhere. Warmly was brought in late and won.

Why it matters: Brand decides the deals you were not invited to. Asked about AI lowering the barrier to building, Keegan says it is brand and positioning, and that he would shrink the sales development budget to fund brand building, while still needing someone to convert that engagement.

FoundersMarketing LeadersRevenue Executives
15

Position the founder for the buyer you want

Keegan advises a founder selling a SOC 2 agent to enterprises to talk about her services background and about being a mother, and she told him it works well. He argues enterprise buyers have families and are put off by founders bragging about 996. His own Window Screen Guys business leans on the story of white-collar homeowners tired of unreliable contractors.

Why it matters: Content has to explain why you are in the space, what you have seen and what motivates you. Keegan says customers of the window screen business pick it despite fewer reviews than competitors because the story hits home.

FoundersMarketing Leaders
Frameworks Discussed

10 named models

Every framework Jimmy names, defined and time-stamped.

The Three Whys

02:31

A simplified qualification framework of three open-ended questions: why buy anything, why now, and why this vendor.

Keegan built it as a modern, stripped-down take on MEDDPICC or MEDDIC when he set up Warmly's CRM. Why buy anything asks why the buyer is looking at software at all. Why now asks why this moment rather than six months to a year from now. Why Warmly asks why this vendor. He says the questions are open-ended enough to collect much of the data a longer framework asks for.

A Couple of Steps Back, 10 Steps Forward

03:04

An experienced sales leader joining an early company starts in the SDR seat, feeds the founder meetings, watches how the founder closes, then closes, then hires behind themselves.

Keegan describes it as crawl, walk, run. He set meetings for the CEO, watched him close for about two months until a repeatable process emerged, started closing himself, and then an SDR hired overseas fed them both. He attributes it to humility: taking a couple of steps back to perfect the process in order to go 10 steps forward.

Long-Term and Short-Term Omni-Channel

09:14

Run two outbound clocks at once: a long-term play that gets buyers into your network to see your content over time, and short-term manual touches to get in front of them now.

Long term, prospects connect on LinkedIn and see repeated company content and case studies, which Keegan compares to targeted advertising. Short term, reps send LinkedIn DMs and emails and call engaged leads. He says he would use this playbook again and again, because some buyers respond only on LinkedIn and others only by email.

The Closed-Lost Rehash Bucket

11:32

Treat revenue as a failing statistic and capture structured reasons and requested features for every lost deal, so the losses can be retargeted once the product or timing changes.

If a team wins three of ten at-bats, the data should show how to go after the other seven. Keegan refused to keep creating deals until the team agreed what to collect, then put lost deals in a rehash bucket. A rep should be able to say quickly who they spoke to a year or six months ago, what that person wanted, and which requested feature now exists. Keegan says it produced two to three resurfaced deals and one to two wins every quarter.

Two Paths on a Whiteboard

17:55

To get a founder past founder-led sales, lay out two concrete options with their outcomes and risks, say which you lean toward and why, and let the founder choose.

Path one kept Keegan as the sole seller, reaching a million in a year to a year and a half with churn unmanaged. Path two brought in two people he had worked with, dedicated to specific functions, for over a million in under a year with churn and upsell covered and the CEO freed up. He told the CEO he would support either. The founders voted for path two the next morning.

Make the Boulder Smaller

22:19

The revenue leader pushes the rock uphill while the CEO works on product, budget and engineering so that the rock itself gets smaller.

Keegan told the CEO that without product improvements Warmly would hit a wall and customers would leave. Moving the CEO into product led to person-level identification and agentic chat, after which Keegan says sales exploded. Anthony tells listeners the boulder gets smaller after five as the product gets better.

Bend It or Remodel It

38:53

A process that took you from zero to one should be tested for how far it bends. Past that point, reinforce and extend it like an old building being remodeled, or start from scratch.

Keegan asks whether each process that worked can stretch to the next stage or will break. He estimates 25 to 50% of processes carry you to five. From five to 15, he says, you reinforce those, add to them, and sometimes rebuild, as Warmly did with routing, segments and an executive layer on deals.

ACV Floors and Payback by Segment

40:28

Past $5M, calculate the ACV each segment needs, how long it takes to close and the payback on seller, ad and SDR spend, and route anything under the floor away from a human.

Keegan's SMB example is that an AE earning $140K to $150K cannot work deals under $15,000 to $20,000, with win rate, ad spend and SDR spend set against a payback period. Below the floor, deals go self-serve or skip a human. The strategic segment has its own equation, with six-figure deals that may not close until month five, six, seven or a year.

Build the Brand or Die

43:27

When competitors catch up on product, differentiation comes from a brand built on named people, each with a recognizable lane, rather than on the company logo.

Keegan told Warmly's executive team that without a brand it would not differentiate or build trust. People followed each executive on their own subject: the CEO, Keegan on revenue tips, others on product, creative marketing and the future of AI. He says that when competitors got in front of buyers first, those buyers remembered Warmly and evaluated it too, and Warmly usually won those deals.

Position the Founder for the Buyer

46:26

Founder content should mix expertise with why the founder is in the space, what they have lived through and what motivates them, chosen to resonate with the buyer being targeted.

Keegan's example is a founder of a SOC 2 agent company targeting enterprise, who he advised to talk about her services agency, her motivation and being a mother. He argues enterprise buyers want founders with balance. He applies the same logic to his window screen business, positioned as white-collar homeowners who got tired of unreliable contractors.

Best Quotes

20 lines worth clipping

Pulled verbatim. Copy or share any of them.

“If I hire an AE that makes 140, 150 in the SMB segment, they can't be touching deals less than 15 to 20K.”
Keegan Otter 00:50
“And a lot of people don't realize like, that's what it takes is taking a couple steps back to perfect the process to go 10 steps forward.”
Keegan Otter 04:31
“I made the joke that when I first came in, their meetings were with everyone's mothers and their grandmothers, 'cause I'm like, this title would never buy.”
Keegan Otter 05:16
“We don't need any more free design partners. We need customers.”
Keegan Otter 06:07
“Marketers don't wanna pick up their phones, right?”
Keegan Otter 07:16
“Don't be afraid to say what you do and what you're selling.”
Keegan Otter 08:36
“'Cause remember, sales is a losing statistic. The revenue game is a losing statistic, even in marketing.”
Keegan Otter 11:32
“And if you look at the history of Warmly's revenue growth, every quarter, we would resurface two to three deals that were previous closed-lost ops and be able to pull one to two as a closed-won.”
Keegan Otter 12:45
“I'm like, no, no, no, no, speed wins. Speed with a plan wins. I'm like, we're not an enterprise. We can't sit and think and think and think.”
Keegan Otter 19:43
“And if you can work on working with the team on product and unlocking budgets and getting people and motivating them and pushing them and maybe more headcount engineering, that's gonna make the boulder that we're pushing smaller and make it easier.”
Keegan Otter 22:27
“But I think a co-founder to me going back to that is that story tells you like, I just took ownership.”
Keegan Otter 28:58
“It was, no, Max, I disagree. No, you're wrong. And here's why. No, you need to step away and let me own it. That's why you brought me here.”
Keegan Otter 31:10
“If nobody's pushing back, am I really making a good decision here?”
Anthony Enrico 34:07
“It's like an old building getting remodeled. You have to reinforce, you have to add more to it for that five to 15.”
Keegan Otter 39:06
“I'm paying an AE to work the strategic segment, hundreds of thousands of dollars knowing that they probably won't close the deal until about month five to six or seven or a year.”
Keegan Otter 41:20
“We have to build our brand or we die.”
Keegan Otter 43:27
“We were not the first ones in their mind. But as they started doing their search, our brand appeared.”
Keegan Otter 44:54
“I would shrink my sales development budget to go dump more into brand building.”
Keegan Otter 45:48
“They wanna know that these founders have balance. They don't wanna know the founder that has the 996. That's very unattractive to the upmarket.”
Keegan Otter 47:26
“You have to build a brand that people can trust and they can relate to and they wanna buy from.”
Anthony Enrico 57:31
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Founders

  • Review real call recordings and check how pipeline is tracked before anyone new starts selling.
  • Stop pitching for design partners once the product can be sold. Say what you sell and put prospects on a demo.
  • When a sales leader brings you a hiring plan, ask for the options and outcomes side by side, then decide quickly.
  • Move out of day-to-day selling and into product when the product is what will limit growth.
  • Give founders and executives a public lane of their own so buyers have people to follow.
  • Tell your own story in content, chosen for the buyer you want. Do not brag about 996 if you are selling upmarket.

Sales Leaders

  • Target titles that can actually buy, and be willing to drop whole levels such as SDRs and SDR managers.
  • Qualify on why buy anything, why now and why you before adding a longer framework.
  • Cold call engaged leads, and reach everyone else across LinkedIn, email and content, since you cannot know which channel a buyer prefers.
  • Do not let reps move on from a lost deal until the agreed reasons and feature requests are recorded.
  • When you add sellers, consider people you have already worked with, and tell them the risk up front.
  • As the team grows, move yourself out of deals and into an executive layer on the largest ones.

RevOps Leaders

  • Build the CRM to capture channel, meeting set and held timestamps, associated SDR and AE, deal owner and stage from the first deals.
  • Make closed-lost reasons and feature requests retrievable so a rep can quickly see what a buyer wanted six months or a year ago.
  • Rebuild routing when the team moves from two or three AEs to around 10.
  • Calculate the ACV each segment needs from seller cost, win rate, ad spend and SDR spend against a payback target.
  • Send deals under the segment floor to self-serve or skip a human.

Revenue Executives

  • Test each process that got you here and decide whether it bends, needs reinforcing or needs rebuilding past $5M.
  • Fund a separate strategic segment knowing deals may take five months to a year, and train other departments on why it runs differently.
  • Consider shifting sales development budget into brand, and keep someone responsible for converting that engagement into opportunities.
  • Once you have reps, train newer ones at in-person events and send them in your place when the event is not a major one.
  • Argue with your CEO openly on hiring, market and product decisions, and know which areas belong to whom.

Marketing Leaders

  • Position for the whole go-to-market buying group when the product also serves sales, rather than for marketers alone.
  • Publish educational content and third-party data that make the company look like an expert worth following.
  • Check where the company shows up when a buyer researches a competitor, including LinkedIn, LLMs and G2 reviews.
  • Invest in content on your website, with the founder's background and motivation mixed in so that it makes sense to the reader.
AI Takeaways

How AI actually changes GTM

LeanScale's signature read on the AI-in-GTM question this episode wrestles with.

The thesis

As AI makes products cheaper to build, Keegan's answer to where companies should compete is brand and positioning. On the product side, his work at HubSpot is to bring agents into the CRM that qualify and route without traditional workflows.

Agent & automation ideas

  • A closed-lost resurfacing agent that matches shipped features against lost deals' recorded requests and flags which to retarget each quarter.
  • A qualification agent that extracts answers to why buy anything, why now and why us from call transcripts and writes them to the CRM.
  • A segment-floor router that checks expected ACV against each segment's payback floor and sends smaller deals to self-serve.
Operations Takeaways

By function

The same conversation, filtered for RevOps, pipeline/marketing ops, and customer ops.

Revenue Operations

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Pipeline & Marketing Ops

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Metrics Mentioned

The numbers, with context

4 people, about $50K in revenue
Warmly when Keegan joined

Anthony's framing, repeated in the show notes. He adds that Keegan has said that might as well be zero.

About $8M ARR; $12M total sales
Warmly at acquisition

Keegan's figures, in about three years. The difference comes from non-SaaS products.

3–4 months
Time to $500K in revenue

Measured from when Keegan joined.

About 9 months
Time to $1M

After Keegan persuaded the founders to hire two sellers he had worked with.

3
Warmly's pivots before Keegan

Keegan says he came on at the final pivot.

Below 7th or 8th of 12
Cold calling among Warmly's channels

Keegan's recollection of where cold calling ranked among the 12 channels or styles Warmly used.

25% to maybe 40%
Typical conversion in revenue roles

Keegan's general estimate, from his point that revenue is a failing statistic.

2–3 deals per quarter, 1–2 won
Closed-lost resurfacing

What Keegan says Warmly's closed-lost process produced every quarter.

About 70%
Win rate against 6sense

Keegan's figure for head-to-head deals after person-level identification shipped.

25–50%
Processes that carry to $5M

Keegan's estimate of the share of early processes worth reinforcing for five to 15.

3–4 to $5M; 10 AEs past it
Sellers by stage

Keegan says Warmly maxed out at three or four sellers, including him, from zero to five. He cites 10 AEs in the next stage.

$15K–$20K
SMB AE minimum deal size

Keegan's floor for an AE earning $140K to $150K in the SMB segment.

Month 5–7, or up to a year
Strategic segment time to close

How long Keegan expected AEs on six-figure upper mid-market and enterprise deals to take to close.

Under 6 months to private beta
HubSpot lead qualification agent timeline

Keegan says the team was less than six months in with the agent live in private beta, and a public beta planned for December.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

WarmlyWebsite Visitor Identification

The person-level website intent and AI inbound agent company Keegan joined at four people and about $50K in revenue. It reached roughly $8M in ARR, or $12M in total sales including non-SaaS products, in about three years. HubSpot acquired it in 2026.

01:07 · 04:03 · 12:45 · 21:14 · 43:01Company →
HubSpotCRM / Marketing

Keegan's current employer, where he oversees AI strategy for Sales Hub products. It acquired Warmly in 2026, when Keegan says Warmly thought it was heading for a Series B. Its product organization, he says, is like a mini series of startups.

00:08 · 21:30 · 30:41 · 37:46 · 53:46Company →
Window Screen GuysHome Services

Keegan's window screen business in Arizona, which he describes as run by a co-founder as CEO with him as investor and visionary on marketing and positioning. Its brand is white-collar homeowners who got tired of unreliable contractors.

48:14Company →
LeanScaleGTM Operations

Anthony's company. He compares Keegan's relationship with his CEO to his own with LeanScale's COO, a friend since high school who joined about a year and a half after it started.

33:08 · 56:29Company →

People

Keegan Otterguest

AI strategy for HubSpot's Sales Hub. Former co-founder and CRO of Warmly, which grew from about $50K to roughly $8M in ARR before HubSpot acquired it.

AI Strategy, HubSpot Sales HubProfile →
Anthony Enricohost

Co-founder of LeanScale and host of The LeanScale Podcast.

Co-FounderProfile →

Tools & software

HubSpotCRM

The CRM Keegan chose and built out at Warmly, because reps pick it up easily and he doesn't need a certified expert to build it. At HubSpot he is now working on agents for Sales Hub, including the lead qualification agent (LQA), which was in private beta at recording with a public beta planned for December.

Website ↗
6senseABM & Intent

Keegan says early Warmly was effectively a down-market reseller of 6sense. After person-level identification shipped, he puts Warmly's head-to-head win rate against it at about 70%, and says 6sense pulled the partnership.

Website ↗
QualifiedInbound

The competitor Keegan names as the alternative buyers weighed against Warmly. A large customer was evaluating Qualified when Warmly kept appearing in its research.

Website ↗
RB2BWebsite Visitor Identification

Named by Keegan as a competitor with a good brand that came to life in Warmly's market, in his case for why Warmly's own brand paid dividends.

Website ↗
OutreachSales Engagement

Where Keegan started his cold-calling career as a rep.

Website ↗
LinkedInSocial Platform

Central to Warmly's outbound: connections meant prospects saw company content repeatedly, alongside manual DMs. Also where a large buyer kept seeing Warmly while evaluating a competitor, and where Keegan posts videos of new HubSpot agent updates.

Website ↗
G2Software Reviews

Part of why a large buyer evaluating Qualified added Warmly: its G2 reviews presented it as a strong alternative.

Website ↗
Methodologies referenced Three-question qualificationCrawl, walk, run sales buildContent over the top of outboundClosed-lost data gateExecutive layer on large dealsDelegating the event circuit
Related LeanScale Services

Where this shows up in the work

Fractional RevOps

Embedded, field-facing RevOps leadership and execution — the operator model Jimmy describes, delivered as a service.

Keegan's playbook runs on RevOps foundations: CRM instrumentation from the first deal, closed-lost data capture, routing rebuilt as the team grows, and ACV floors by segment from payback math.

AI for GTM

Agents and workflows that multiply operator throughput — the 'make humans superhuman' thesis, operationalized.

The episode covers agentic chat as Warmly's growth unlock and HubSpot's lead qualification agent, which qualifies and routes leads without traditional workflows.

Frequently Asked Questions

Straight answers

Generated from the conversation, marked up for search and AI extraction.

How did Warmly grow from $50K to about $8M in ARR?

Keegan Otter joined Warmly as its sales leader when it was four people and about $50,000 in revenue. He reviewed sales calls, built the CRM in HubSpot, cut qualification to three questions and took the SDR seat himself. He changed the target list to directors and above, made the messaging direct, and ran omni-channel outbound. Warmly hit $500,000 in three to four months and $1 million in about nine. Product improvements led by the CEO, including person-level identification and agentic chat, then accelerated growth to roughly $8 million in ARR and $12 million in total sales in about three years, before HubSpot acquired it in 2026.

What are the three whys in sales qualification?

The three whys are a simplified qualification framework Keegan Otter built at Warmly in place of a full MEDDPICC or MEDDIC. The questions are why buy anything (why are you looking at software at all), why now (why this moment rather than six months to a year from now) and why this vendor. He says they are open-ended enough to collect much of the data a longer framework is designed to capture, which gave an early-stage company a sales process it could scale.

How should a startup run a closed-lost process?

Keegan Otter's approach at Warmly was to agree on what data to collect before creating more deals. He treats revenue as a failing statistic: if a team wins three of ten, the data on the other seven is what makes the next attempt more likely to succeed. Reps should be able to see quickly who they spoke to six months or a year ago, what the buyer wanted, and which requested features now exist. Lost deals go in a rehash bucket for later. Keegan says this resurfaced two to three deals every quarter at Warmly and won one to two of them.

How do you convince a founder to make the first sales hires?

Keegan Otter drew two paths on a whiteboard for Warmly's co-founder and CEO. In the first, he stayed the main seller and Warmly reached a million in a year to a year and a half, with nobody managing churn. In the second, two people he had worked with came in, Warmly passed a million in under a year, churn and upsell got attention, and the CEO could go back to being CEO. He said which he favored and why, and that he would support either. The founders chose the second path, and Warmly reached a million in about nine months.

What changes in go-to-market between $5M and $15M in revenue?

Keegan Otter says zero to five is about building processes to see what works, and perhaps 25 to 50% of them carry you there. From five to 15 you reinforce those like an old building being remodeled, or start from scratch. At Warmly that meant new routing for 10 AEs rather than two or three, real segments, an ACV floor and payback calculation for each segment, and executives joining the largest deals instead of selling them directly. Anthony Enrico adds that segment is usually the first axis of specialization at that point.

How do you decide the minimum deal size an AE should work?

Keegan Otter works back from payback period. His SMB example is that an AE earning $140K to $150K should not be touching deals below $15,000 to $20,000, with win rate, ad spend and SDR spend all set against that payback. Deals under the floor should go self-serve or skip a human. A strategic segment of six-figure upper mid-market and enterprise deals needs a different equation, because those AEs may not close until month five, six, seven or a year.

Does brand matter more now that AI makes products easier to build?

Keegan Otter's answer is that it comes down to brand and positioning, and that he would shrink a sales development budget to invest more in brand building, while still keeping people to convert the engagement into opportunities. At Warmly he told executives they had to build the brand or die, because competitors would catch up on product. He says people followed Warmly's executives rather than the company. One large buyer evaluating Qualified added Warmly after seeing it on LinkedIn, in LLMs and in G2 reviews, and Warmly won the deal.

What is HubSpot's lead qualification agent?

HubSpot's lead qualification agent, or LQA, is an AI inbound agent that Keegan Otter, who oversees AI strategy for Sales Hub products, described as being in private beta at recording, with a public beta planned for December. It qualifies and routes leads based on different products, verticals and industries. Users train it rather than building workflows, and tell it which links to feed prospects, such as a quote form or a calendar link, including external calendar links.

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00:00Intro: Keegan Otter, from Warmly to HubSpot 01:07What he built first: call reviews, the CRM and the three whys 04:18From VP to SDR: two steps back to go ten forward 04:43Fixing the list: no more meetings with everyone's grandmothers 11:05What broke first: no closed-lost data 17:10The first hires: two paths on a whiteboard 20:58Moving the CEO into product: make the boulder smaller 38:21Zero to five vs. five to fifteen: what changes 43:01Build the brand or die 53:35What he's building at HubSpot now
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00:00Intro: Keegan Otter, from Warmly to HubSpot

0:00 - It's brand and positioning.

0:02 I would actually double down on brand more than,

0:04 I would shrink my sales development budget

0:06 to go dump more into brand building.

0:08 - My guest today is Keegan Otter,

0:10 who oversees AI strategy for HubSpot Sales Hub products,

0:14 which makes him the operator in the room

0:16 telling the product team whether what they're building

0:18 will actually hold up for a sales team.

0:21 - And I tell people that humility was me again,

0:24 being a sales leader at a series B company prior,

0:27 coming in and saying, hey, I'll be your SDR.

0:29 - That's a huge, huge moment for so many companies.

0:33 - I mean, I was just so ready to go.

0:34 I called and he's like, whoa, whoa, slow down.

0:36 I'm like, no, no, no, no.

0:37 - Speed wins. Speed with a plan wins.

0:40 I'm like, we're not an enterprise, we can't sit and think.

0:42 - I've heard you say, you know, zero to five.

0:46 That's the ruthless, brutal part.

0:48 - The 5.15 starts to get easier.

0:50 - If I hire an AE that makes 140, 150 in the S&P segment,

0:54 they can't be touching deals less than 15 to 20K.

1:00 (upbeat music)

01:07What he built first: call reviews, the CRM and the three whys

1:07 - Keegan, you walked into Wormly when it was four people,

1:10 about 50 grand in revenue, which you've said might as well

1:13 be zero because nobody's getting paid on that.

1:16 What did you build first before anyone was really selling?

1:20 - Yeah, so I walked in, I actually flew in to meet,

1:23 we were a remote company, but I flew in to meet

1:25 with the founders to have that first work week together.

1:28 Walk in and I'm like, let me see the recordings

1:30 of what we're doing, let me understand how we're tracking

1:33 our customers and how we're tracking, you know,

1:36 how are we tracking like building pipeline?

1:38 And Max, the co-founder and CEO was like, well,

1:43 like we're just automating everything

1:45 and seeing what sticks.

1:46 I'm like, ah, okay, so the just firing off

1:49 on all cylinders, no strategic targeting approach.

1:52 So the first thing I did was review kind of the calls

1:55 that went well and some that didn't.

1:57 So I could see like the talk tracks that were working

1:59 versus weren't.

2:00 And then I actually went in and built out the CRM.

2:03 I chose HubSpot, I've been a huge avid user of HubSpot

2:06 before even getting acquired by HubSpot.

2:08 I've used it a lot of startups.

2:09 I think it's easy for reps to pick up.

2:11 It's easy to build out.

2:12 I don't need a certified expert to help me build it out.

2:15 So I went in there, built out how we track

2:18 from every motion of what channels we're gonna use

2:20 to go get new customers, the timeline, the dates,

2:23 everything, all these timestamps of like meeting set,

2:25 meeting held, who is what, the associated SDR

2:28 and the AE, the deal owner, the stages.

2:31 And then I made almost like a modern med pick

2:34 or medic criteria and we simplified it to the three whys.

2:39 Why buy anything?

2:41 So why are you looking at software?

2:43 Why now?

2:44 Why are you looking to buy now at this time

2:47 versus like just in six months to a year from now?

2:50 And then why are you looking at warmly, right?

2:53 And so that usually actually those three questions

2:57 were so open-ended that it would allow you

2:58 to collect a lot of that data.

3:00 So we created a scalable sales motion and process there.

3:04 And then I actually was the SDR.

3:06 I took a step back from being the, you know,

3:09 always the director of sales or the VP of sales

3:11 to be a SDR to go find the right type of meetings,

3:14 to feed to our co-founder and CEO Max.

3:17 And then when I watched him close a couple that I would set,

3:20 we found a repeatable process

3:21 and then I would be the one closing

3:23 and then we would hire, we then hired an SDR

3:25 overseas to then feed both of us

3:27 while we were also trying to find our own meetings.

3:29 And so it was like a crawl walk run.

3:31 So much fun, a lot of chaos.

3:35 We weren't like a legit company.

3:36 It was, but we actually had to sit down and be like,

3:39 I think we were half a million in revenue

3:41 about three months in, of me and three to four months in.

3:44 And we were like, okay, we're a legit company now.

3:46 We gotta have process.

3:48 And that's kinda that mindset of going in,

3:51 getting nitty gritty, taking step back,

3:53 to make sure everything from beginning to end

3:55 was solid and scalable.

3:57 And then telling everyone the mindset shift of like,

4:00 this is real, like we have to start

4:01 following procedures and process.

4:03 That's what allowed us to scale to total 12 million

4:06 'cause we had some non SaaS products too.

4:08 So 12 million in sales, 8 million in ARR in three years,

4:11 which for most startups, that's pretty amazing growth.

4:15 That's pretty quick growth.

4:16 - No, it's fantastic.

4:17 It's fantastic growth.

04:18From VP to SDR: two steps back to go ten forward

4:18 - And I tell people the humility was me again,

4:21 being a sales leader at a series B company prior,

4:24 coming in and saying, hey, I'll be your SDR.

4:27 I'll see how you close first for the first two months,

4:30 and then I'll start closing.

4:31 And a lot of people don't realize like,

4:32 that's what it takes is taking a couple steps back

4:35 to perfect the process to go 10 steps forward.

4:37 And we had fun doing it 'cause we were in Europe.

4:40 (laughing)

4:41 - No, that's awesome.

4:42 That's awesome.

04:43Fixing the list: no more meetings with everyone's grandmothers

4:43 Can I hang in the gritty part for a little bit?

4:46 Because I think a lot of people

4:50 really underestimate what it takes

4:51 to go from that zero to one stage.

4:54 I'm curious, tactically,

4:56 like what was in your mind of who we needed to target?

5:00 How did you reach out to them?

5:01 What was the messaging?

5:03 Were you hitting them up on LinkedIn, email?

5:05 What was the strategy and tactics

5:08 to get that first group of customers in the door?

5:10 - So it came to building the list.

5:13 It always comes down to who you target.

5:16 I made the joke that when I first came in,

5:18 their meetings were with everyone's mothers

5:20 and their grandmothers,

5:23 'cause I'm like, this title would never buy.

5:26 This title isn't even in the right department

5:27 we wanna sell to.

5:29 We're just getting meetings to show 'em.

5:31 And we had to go from this,

5:32 oh, we're looking for product designers

5:35 or like early customer, early design partners.

5:38 That's the word.

5:39 We're looking for early design partners

5:41 to being like, no, we're a startup.

5:43 This is what we sell.

5:44 This is what we sell.

5:45 Like, this is what we sell for.

5:46 This is what we sell.

5:47 Would you guys be of interest in trying it?

5:49 Like early adopters, usually if it's a good tool,

5:51 get the benefit.

5:53 So we went with that hardcore tactic of like,

5:56 don't beat around the bush, tell 'em what we do.

5:58 Tell 'em what we do, who we solve for,

6:00 what we solve for, and what it's gonna be.

6:05 Get 'em on a demo so that the expectation's clear.

6:07 We don't need any more free design partners.

6:09 We need customers.

6:10 So that was the first thing

6:12 of getting the messaging right

6:14 and then the lists of who we're gonna target.

6:17 And so I didn't want us to go after SDRs.

6:20 I didn't want us to go after SDR managers.

6:22 I want us to go after directors

6:24 and above revenue, sales, development, marketing.

6:27 That's what we needed.

6:28 And then what we did is figure out the channels

6:30 that would work best.

6:32 Funny enough, I was not,

6:36 I made a lot of money personally

6:37 as a sales rep cold calling,

6:39 but I've led enough teams to realize

6:41 the shift of cold calling and its effectiveness

6:44 was starting to go down.

6:46 And don't get me wrong.

6:47 Every team should always still cold call,

6:49 my team's cold call,

6:50 but it wasn't gonna be the forefront of my KPI.

6:52 It was not gonna be the number one thing

6:54 to lead our growth.

6:55 In fact, actually to date of our growth,

6:59 cold call only attributed to,

7:02 I think it was of the 12 channels we used

7:05 or the 12 styles that we used,

7:08 it was like the bottom, it was under seven or eight.

7:12 It wasn't the most effective for us,

7:15 for the audience we sold to.

7:16 Marketers don't wanna pick up their phones, right?

7:18 Sales people, sure,

7:19 but most of the time we started selling to marketers.

7:21 And so I knew that knowing I've sold to marketers before

7:25 and I've sold to sales people.

7:27 I used to work at outreach.ao as a rep.

7:28 That's where I started my cold calling career.

7:30 And so I told the reps,

7:32 I want you to cold call on engaged leads,

7:34 but I actually really want you to work on getting

7:36 in front of them on LinkedIn and email,

7:38 but then flooding them with educational content.

7:41 Make it seem like we're a consultant.

7:43 Make it seem like we're like these experts

7:45 that everyone should follow

7:46 on how to optimize their inbound if you're a startup.

7:50 And it worked.

7:51 We would connect with people on LinkedIn.

7:53 We would then start posting content as our company.

7:56 People that followed us would see,

7:57 okay, the more people they followed at warmly,

7:59 the more of the content they would see.

8:01 It's almost like advertising, targeted advertising.

8:03 It was like repeat, repeat.

8:05 And then on top of that, we would send case studies.

8:06 We would send industry third-party case studies

8:09 of like how inbound rates have dropped,

8:12 how you have to have other channels

8:14 other than cold calling.

8:15 So a chat bot's another channel, right?

8:17 So we really started educating

8:19 and then we would come over the top with the call.

8:21 So it was basically a long-term marketing play,

8:26 but short-term like get in front of them

8:28 via like human touch points of a call if they're engaged.

8:31 And it worked great.

8:32 It worked great.

8:33 First started with being scrappy of change the messaging.

8:36 Don't be afraid to say what you do and what you're selling.

8:41 Don't beat around the bush.

8:42 No one likes that.

8:43 I don't.

8:43 I've literally taken cold calls and be like,

8:45 you can tell me what you, like, don't make it sound fancy.

8:49 What the heck do you do?

8:49 I'm a busy guy.

8:51 And then when someone goes, oh, okay, we do this.

8:53 I'm like, actually, that's relevant.

8:54 Sweet.

8:55 You're gonna talk to my VP of RevOps

8:56 and he's gonna vet it out first and then you'll get it to me.

8:59 But thank you for being direct.

9:00 Now I know who to point you to, right?

9:02 So you gotta be direct.

9:03 Then what we did is we had to be really good

9:06 with who we were targeting, right?

9:08 We're not going after our moms and our grandparents anymore.

9:12 We're going after real titles, real buyers.

9:14 And then what we did is we had an omni-channel approach

9:18 that had a long-term effect and a short-term effect, right?

9:21 Long-term was get them in our network

9:23 so they could see our content over time

9:25 if we didn't get them right away.

9:26 The short-term was we're gonna also manually touch them

9:29 on LinkedIn with DMs and cold calls.

9:32 And like emails all the time to try to get in front of them.

9:35 On top of the, hey, now that they've followed us

9:38 and they're in our kind of our umbrella,

9:40 we could start posting content on the regular

9:42 and educating them.

9:43 And I would use that playbook again and again.

9:46 - Well, I love the full breadth of the approach

9:48 and taking that omni-channel approach

9:50 'cause I think a lot of teams will index on one,

9:52 live and die by one of those channels.

9:54 And then, first, build the list.

9:59 And then once you know the people,

10:02 you don't know if they're someone who picks up the phone,

10:04 someone who reads LinkedIn,

10:05 someone who goes through their emails,

10:06 like what type of person are they, it's tough to know.

10:08 So I think just flooding them and then adding value first

10:11 and then coming in over top, incredible.

10:12 - I'm 30, so I'm a millennial.

10:15 I used to be really big at email management

10:18 and now I've switched to LinkedIn.

10:20 So I love managing my LinkedIn inbox, right?

10:23 And so you're not gonna hear from me right away on email

10:26 as if you hit me up on LinkedIn.

10:28 And that was so true for some folks.

10:29 It was like, they're like,

10:30 "I can't believe you'd messaged me on LinkedIn."

10:32 We'd send, right?

10:34 And then we'd send the next person a LinkedIn message.

10:36 They'd be like, "Oh, we love this, yes, let's meet."

10:37 And then vice versa, the email.

10:38 Some would be like, "It's a terrible email.

10:40 "I don't check my email.

10:41 "I get inundated by emails."

10:43 But then the next person would be like,

10:44 "Oh, this is such a thoughtful email, thank you."

10:46 And cold calling, some people pick up, some people don't.

10:48 It's why you gotta do the omni-channel.

10:50 You just never know.

10:52 - No, and I appreciate the effort in that.

10:53 Okay, so you start to get some traction.

10:56 Like, "Hey, we gotta go full force."

10:58 And that's what zero to one is.

10:59 You're not sleeping a lot.

11:00 You're moving fast.

11:02 You're trying new things.

11:02 You gotta do everything.

11:03 You gotta lean team.

11:05What broke first: no closed-lost data

11:05 What started to break and make you take a step back

11:09 and say, "Okay, we gotta start putting in some process

11:12 "into this."

11:13 What were those early signals of that?

11:18 - The breaking was when I asked him,

11:19 "Hey, where are closed-loss deals?

11:22 "Why did we lose deals?"

11:24 That's when I saw that there was no process

11:28 of collecting the right data to know how to retarget folks.

11:32 'Cause remember, sales is a losing statistic.

11:35 The revenue game is a losing statistic, even in marketing.

11:39 You're not converting 80 to 100% of your people.

11:42 You're 25 to maybe 40%, right?

11:46 But in baseball, if you have a 300 batting average,

11:49 which is three out of 10, you're gonna be a millionaire.

11:51 You're gonna be a Hall of Famer.

11:52 So you gotta learn that it's a failing statistic.

11:56 So I know that my team will win three of their 10 at bats.

11:59 So if I can collect all this great data along the way,

12:02 I then know how to go target those seven.

12:04 And it's like, "I'm batter up again."

12:06 I have a higher likelihood of getting a hit,

12:09 hitting a home run, getting a customer.

12:11 And so I told him that where it's broken is,

12:14 if we don't start collecting this data now,

12:15 we'll never know how to retarget people

12:17 once we do build out the product more.

12:19 We won't be able to go back

12:21 and get those opportunities the second time around,

12:23 which we have a statistical chance of winning more.

12:26 And so, what I did is I said,

12:29 we're not going to move deals forward

12:31 and start going to make more deals

12:34 until we start lining what data we wanna collect.

12:37 And we made that process super early

12:39 to where I could go back and show in the early days

12:42 on the way to a million what we were tracking

12:44 and why we retargeted folks.

12:45 And if you look at the history of warmly's revenue growth,

12:48 every quarter, we would resurface two to three deals

12:52 that were previous closed loss ops

12:53 and be able to pull one to two as a closed one.

12:56 - That's so impressive.

12:57 And that's gotta be a huge amplification of the growth

13:02 and a testament to how you grew so quickly too.

13:06 And if you're not collecting that data early on,

13:08 you're missing out on so many opportunities as you go.

13:12 - So, basically where I was like,

13:14 it's broken if you can't quickly say,

13:16 we talked to this person a year ago or six months ago

13:19 and here's what they were interested to do.

13:21 Here's the future request they had,

13:24 they asked for that we didn't have that we now do.

13:25 If you couldn't quickly diagnose that,

13:27 like you had a broken, you basically had a leaky bucket.

13:31 If you didn't close them,

13:33 you would just lose them in the ether.

13:34 And so I wanted to stop that and say,

13:36 I wanna put them in a rehash bucket for later.

13:40 - What else?

13:40 Started to feel like maybe the wheels were falling off,

13:44 things that you needed to know

13:45 that you couldn't get visibility into,

13:46 decisions you needed to make

13:48 that you felt you didn't have the right data for

13:50 or people not running as optimally as it was

13:54 when it was a smaller team.

13:55 Were there any other big things that you can recall

13:58 that felt like, okay, this is a turning point

14:01 for where we're gonna need to start shifting?

14:03 - Yeah, I had to be basically the one

14:07 that kind of got everyone together.

14:09 There was like a different team for marketing.

14:12 There was, and this,

14:13 I wasn't overseeing marketing quite then.

14:15 Like this is like sub a million, right?

14:17 So we were still just, hey, everyone's equal titles,

14:20 everyone's this.

14:21 I come from like a structured company previous to this,

14:24 where I'm like, I never operated that way.

14:26 So I kind of had to wrangle everyone together,

14:28 good choice of words, wrangle everyone together

14:30 and say, hey, you're gonna be in charge of this.

14:33 And I just took the leadership reins.

14:34 I said, you're gonna, I was hired to grow this company

14:37 and brought on.

14:38 And like, I was like, you know,

14:40 maybe I'm gonna just take the mindset of a co-founder.

14:42 And funny enough, I became one.

14:44 And so I said, hey, I wanna grow this company

14:47 as if it's my own.

14:48 You're gonna run this 'cause you're really good at this.

14:50 So you're gonna run this part of marketing.

14:52 You're gonna be in charge of this.

14:54 You're gonna look up competitor analysis, Allen,

14:56 our co-founder.

14:57 You're gonna see where our biggest threats are externally.

15:01 Derek, you're gonna help run the marketing.

15:03 And we need to market it this way

15:05 because it needs to also compliment

15:06 what sales is trying to do.

15:08 They need, there needs to be cohesion.

15:10 Okay.

15:11 And then Max, you're gonna give me this X amount of budget.

15:14 So if we do have gaps, we can, you know,

15:16 hire someone to help scale it

15:18 or bring on a tool to help automate more.

15:23 Like upgrading our host pod instance

15:25 or a sequencer or something like that, right?

15:27 And once I kind of started giving everyone like,

15:30 hey, we're a team, here's your different roles

15:32 so we can go win the game.

15:34 Then we started rowing in the same direction.

15:36 It was awesome.

15:37 It was insane.

15:38 Like I had people coming up to me like,

15:39 I'm glad you sat us all down

15:40 and kind of got on us like a football coach.

15:43 Like we needed this.

15:44 So that was nerve wracking, but very needed.

15:47 'Cause you get nervous, right?

15:48 You're like, oh, am I overstepping here?

15:50 But it needed to be done.

15:51 We needed to come together.

15:52 What I would say where things were broken is,

15:56 you know, marketing originally had it

15:58 where we were only selling to marketers.

16:01 And I said, I think we're selling to go to market leader.

16:03 So once we align that like,

16:05 yes, marketers love the idea of an inbound agent,

16:07 but because we had all these retargeting automations

16:10 like an SDR, an SDR and sales leader might want this.

16:13 So we need to position it for a go to market leader.

16:15 We need to position it for a marketing, a growth

16:18 and a sales leader, all the above.

16:21 And once we changed that message,

16:23 you'd be a little bit more broad

16:24 to how we can grow in different ways.

16:26 Your company, we definitely started scaling further.

16:29 And then the other part was Max being afraid

16:32 to make our first hire outside of me.

16:35 I think he wanted me to be like the main AE

16:39 for the first full year.

16:40 I got him to hire someone three months in

16:42 because we grew to half a million in three to four months.

16:46 I was like, listen, I could take us all the way to a million,

16:50 but then you're losing traction against your competitors.

16:52 We already have the early signs.

16:54 We already have the process.

16:55 Let's hire two people that have worked with me before

16:59 as AEs and SDR like self sourcing AEs and let's scale it.

17:04 And that's what took us to a million in under a year.

17:07 We just really quit in like nine months.

17:10The first hires: two paths on a whiteboard

17:10 - Can I double click on that moment for a little bit?

17:13 So that's a huge, huge moment for so many companies.

17:16 And I'd say it's probably one of the number one moments

17:22 where people just completely fumble the ball.

17:24 You have either the founder who's closing,

17:26 co-founder in your case.

17:27 I want to get into that story a little bit later too.

17:29 And then once you start bringing in people

17:31 from the outside to try to do what you have been doing

17:36 and you have the benefit of all this context,

17:38 you've been in the field, you've been to the trenches,

17:41 you know, it's resonating, it's not resonating.

17:42 How did you start to pass that down

17:44 in a way that would be effective?

17:47 - I've had a resume already

17:49 like building out teams from scratch.

17:50 Like I've done the whole zero to one,

17:53 one to five at three other companies, right?

17:55 I just told them like, there's two paths.

17:57 And I actually, I remember we were in a room

17:59 and I wrote on the whiteboard.

18:00 There's two paths, Keegan and Max,

18:04 just scale revenue and we'll get there,

18:06 but we will get there in over a year.

18:09 Might take a year, a year and a half

18:11 'cause we're going to have some churn

18:12 and we don't have someone to manage churn

18:13 because we're not looking at it right now.

18:14 We're just looking at growth.

18:17 So I called out like, you know,

18:18 I know what happens if you only look this way

18:20 and you don't think about the defense of things slip.

18:25 Or what we could do is we're showing good signs.

18:28 We can hire two people letting them know

18:31 that this is a risk upfront for them,

18:32 but it could, if it works out, it's going to be huge growth.

18:36 And it's people I've worked with.

18:38 So we have a bias of how each other's working relationship

18:41 is, how we gel together and how we operate.

18:43 So that's kind of an advantage.

18:45 And we could scale to over a million in less than a year

18:48 and also start attacking churn and work on upsell.

18:51 And he was like, oh my gosh, that was like,

18:53 when I gave him the two paths of like,

18:55 we could grow and focus on this and we will get there,

18:58 but we'll also have some leaky buckets.

19:00 Or we could accelerate the growth

19:01 by dedicating these two people to be really dedicated

19:05 to these two workflows or these functions.

19:08 And then I can oversee this while you as CEO go be CEO.

19:13 And we could slowly move away from founder led,

19:16 which allows for more growth, but it's your choice.

19:20 What do you want to do?

19:21 I'm here regardless.

19:24 I'm in, I'm all in.

19:25 I told him like, I will support,

19:27 but I'm leaning towards this way and here's why,

19:28 'cause I've done it.

19:31 And he was like, you know what?

19:33 Let me talk to the co-founders.

19:34 And I just grabbed my phone.

19:35 I said, great, let's call him.

19:38 So, I mean, I was just so ready to go.

19:41 I called, we called.

19:42 He's like, whoa, whoa, slow down.

19:43 I'm like, no, no, no, no, speed wins.

19:45 Speed with a plan wins.

19:47 I'm like, we're not an enterprise.

19:48 We can't sit and think and think and think.

19:51 We hopped on a call.

19:52 Obviously he was like, let's not call him now.

19:54 So I didn't call him now.

19:54 And then we hopped on a Zoom, I think the next morning.

19:57 They're all like, you know what?

19:59 He's already surpassed the half a million

20:01 in the faster timeline than we thought.

20:03 Let's do it.

20:05 And so they all voted.

20:07 We did it and we hired them on it.

20:09 And it was just acceleration after that, right?

20:11 But it was the, it's just having to be like real

20:14 and having to, I think CEOs and founders,

20:17 like it's their baby.

20:18 Like I could see it.

20:19 Like Max was like, I can't mess this up.

20:21 Like they've had to pivot three times.

20:23 I came on on the final pivot.

20:25 And I just had to give him the assurance of like,

20:27 here's the two plans, like the paths.

20:29 Here's how they would work

20:30 and the outcomes we would achieve.

20:32 Which one do you want?

20:35 And once I made it clear that we can scale at a faster rate

20:38 and then allow him to go work on other units of the business,

20:41 it made him have that aha moment of like,

20:43 okay, like you do know what you're doing.

20:45 You do have a plan laid out.

20:47 It's a plan that I didn't even,

20:48 the steps that I didn't even think of.

20:51 I should remove myself and go focus on the other things.

20:54 I'm like, there you go.

20:56 - That's, that is awesome.

20:57 That's absolutely awesome.

20:58Moving the CEO into product: make the boulder smaller

20:58 But I'm curious from your vantage point,

21:03 what did you actually want to push him to go work on?

21:05 What did you feel like were the other fires that,

21:07 hey, give me go to market, give me growth.

21:11 I actually need you to be doing these other things.

21:14 - I needed him to work on maturing the product.

21:19 So people don't realize this.

21:20 Like when I joined,

21:21 'cause one of these are really

21:22 badass robust inbound agent now in the DNR.

21:25 Like we were, I mean, we have such big logos.

21:27 We can't even share them that used warm and,

21:30 that's why HubSpot was like, yeah, we've heard of you.

21:32 Like we want you guys when they acquired us.

21:35 And so, but there was a time,

21:38 there was a time where the chat bot was,

21:42 all it was was coming on the site and going,

21:44 hi, like it was super manual, like very, very not great.

21:50 And then that the DNR was only company level.

21:53 Like people don't realize like we didn't start

21:55 with person level, we started with company level.

21:57 We were the first to break into person level.

22:01 But we were just like a reseller of six cents down market.

22:04 And so I told him like, listen, I know these space.

22:08 I know MarTech, right?

22:09 I've been in this my whole career.

22:11 If we don't make some product improvements,

22:14 we will hit a wall and then people will start leaving

22:17 in terms of like customers.

22:19 So if you can let me focus on pushing the rock uphill

22:22 to get revenue,

22:24 'cause that's where we were kind of at

22:25 as a product and maturity of a company.

22:27 And if you can work on working with the team on product

22:30 and unlocking budgets and getting people and motivating them

22:34 and pushing them and maybe more headcount engineering,

22:37 that's gonna make the boulder that we're pushing smaller

22:40 and make it easier.

22:42 And that's was probably one of the most vital points

22:46 of warmly is when he started going into product as CEO

22:49 and really helped because his background was Google.

22:51 He was a project manager.

22:52 So he knows how to manage that in product.

22:55 And so, and to his credit, he's one hell of a seller too.

22:58 He learned to be a really good seller.

22:59 We still would use him later on for the enterprise deals.

23:04 But when he went to product

23:06 and we unlocked person level Dean on

23:08 and then actual agentic chat, we exploded.

23:11 We exploded with growth.

23:12 I mean, at that point people were like,

23:14 it's either you or qualified.

23:16 It's either you or I, I mean we were crushing six cents

23:22 on head to head deals so much

23:23 that they pulled their partnership.

23:24 That's fine, we had other debt vendors.

23:26 And that our win rate against six cents was like 70%.

23:30 'Cause we could give them exactly what six cents gave them

23:34 plus person level contacts.

23:37 And people were like, this is a no brainer.

23:39 'Cause if JP Morgan goes on your site, great.

23:41 Who do you do you do you do you Morgan?

23:42 Well, with warmly you'd be like Keegan,

23:45 director of finance JP Morgan out of Seattle office

23:48 is on your site.

23:49 Here's his LinkedIn and email, go get him.

23:50 And that was just mind blowing

23:52 for these at market companies.

23:54 So when we had that product maturity stage

23:58 sales just exploded.

24:00 But thank God for the nitty gritty

24:02 because we had to learn what processes

24:04 would take us to that point that we can then scale further.

24:07 - Before we get into that part

24:08 and I'm very excited to get into that one too.

24:11 You mentioned something and I'm curious

24:13 how you think about it.

24:14 'Cause I've seen this a couple of times at a few companies.

24:19 What does co-founder mean to you?

24:22 And how does, what was the moment where it made sense

24:27 to have that part of your title?

24:31 - What happened is I got invited to,

24:33 so I've sat in on board meetings

24:37 before I used to make the decks for when I was 25 years old,

24:40 I got the honor to go start making like the rev ops decks

24:42 and the sales decks for the VP of sales and the CEO

24:46 and then the CFO.

24:47 And I was working under CFO at previous companies,

24:50 one of my previous companies that already exited.

24:53 I mean, he walked away with 20 plus million.

24:55 I mean, he would host us at his like,

24:57 he had a mansion in California.

24:59 He would bluntly say like his base salary was like 100 grand.

25:02 He would literally say I came back out of retirement

25:05 'cause I got bored.

25:05 He was only like 45, no he was 50, he was like 50.

25:08 So he was young, awesome guy.

25:11 Still like connect with him.

25:13 You know, he goes to all the fun like tennis shows

25:15 across the country, he was very involved in his family.

25:18 Like he's someone you look up to like, wow,

25:19 you joined a startup as a CFO employee number four.

25:23 And then that company sold for a billion dollars.

25:26 His executive assistant became a millionaire, right?

25:28 Like, and so he's the example of take a risk, big reward.

25:31 But he had fun with it.

25:32 And he taught me a lot on how to negotiate budgeting

25:35 and pricing, how to fight for things with a CFO.

25:39 Like he's like, I'm gonna teach you how to beat me

25:41 in a conversation so you can get those approvals.

25:43 Like he was really about mentoring the youth.

25:46 And so he would like advocate

25:48 that I should be in some of these board meetings

25:50 since I was a director at the point

25:52 and had a lot of the SDRs and some of the AEs.

25:55 So I got to be in some of these board meetings.

25:57 And when I told Max that like I had experienced

26:00 like with a series B raise under my belt

26:02 and making the decks and being in these meetings,

26:04 he's like, well, you know,

26:05 I think we should let you attend.

26:06 Like maybe we can learn something from you.

26:09 And I would start to go to the board meetings

26:12 and I was not really getting shellacked.

26:14 I was like bringing them,

26:15 like when they had hard questions,

26:17 I already had the data pulled up.

26:19 I had the deck ready and like it was mind blowing.

26:22 And I think what I earned there was like the trust of like,

26:24 oh, he doesn't just care about his role.

26:26 Like he cares about how the company is perceived,

26:29 how it looks, how it's on brand.

26:31 Like I would fly out and live on a plane

26:33 the first year working at Warmly.

26:35 And I lived in Europe partially.

26:37 I would go to New York overnight

26:40 and then fly back to San Francisco.

26:41 And I lived in Arizona still.

26:42 So I wasn't, so New York, San Francisco, home, Seattle,

26:47 go see family, do a pop-up event in Seattle

26:49 'cause that's a big tech community

26:51 and then come back home.

26:52 Like I was just all over the board.

26:54 I would drive.

26:56 If I knew that I was gonna be somewhere for like

26:58 almost a week, I would just drive.

26:59 So that way I could take my truck to the local gym

27:02 and I would just get an Airbnb.

27:03 So I lived out of Airbnbs and hotels

27:06 for the first nine months.

27:08 I was single.

27:09 I was, you know, I didn't have a dog.

27:10 I didn't have a house, so it made sense.

27:12 And I think when Max saw that conviction

27:14 that I would tell people, you know,

27:17 I am a co-founder so I can get into

27:19 the co-founder invite events.

27:20 And that's what he told me.

27:21 He said, just put yourself as co-founder

27:23 to get in these events.

27:23 I mean, I'm busy.

27:25 Like I'm in Europe, I can't.

27:27 'Cause he was living in Europe when we started the company.

27:29 And the other co-founders, they were more technical.

27:30 So they didn't wanna, they were busy building

27:34 and they didn't wanna do like the selling part

27:36 of the in-person.

27:38 And so we kinda joked and made me a co-founder.

27:40 Like when I went to Saster, my title said co-founder.

27:43 And it worked.

27:44 I got invited to a lot more events

27:46 and started speaking on behalf of a co-founder.

27:49 And then people would be like,

27:49 yeah, we met your other co-founder Keaton.

27:51 We didn't even know he was a co-founder.

27:52 That's awesome.

27:53 Oh, we wanna try warmly now.

27:55 It's just so nice hearing a co-founder

27:57 of like how they have such conviction in the product.

27:59 Like, you know, we're willing to start.

28:01 And Max was like, okay, he's sitting on our board meetings.

28:04 He's literally telling people he's a co-founder.

28:07 Going to these events and winning them over

28:09 and building trust.

28:11 And he's telling us that we need to build our brand

28:13 as a company.

28:14 And so I was stepping into marketing.

28:15 I was stepping into, you know, conversations

28:18 of how we can negotiate tools across the whole business.

28:20 So I would step in on the HR tools.

28:22 I was trying to do everything to help us win

28:25 and save money and grow our brand.

28:27 And so Karina and Max and Alan sat down and said,

28:31 hey, we have some news for you.

28:32 We voted and we're making you a co-founder.

28:35 And when I went to the board meeting,

28:36 the board said, congrats.

28:37 They're like, we ain't gonna lie.

28:38 We already thought you were a co-founder.

28:39 Like, we thought when you got introduced

28:41 to the board meetings a year ago,

28:42 like that, you were like one of the co-founders.

28:46 So they're like, so we voted all,

28:49 like no one pushed back when they voted at the board level.

28:52 They all thought I was already.

28:54 So it was funny.

28:56 I think it's 'cause we just, you know,

28:57 pretended enough and it happened.

28:58 But I think a co-founder to me going back to that

29:01 is that story tells you like, I just took ownership.

29:04 And that's what Alan, one of,

29:06 he's just such a real co-founder, such a real guy.

29:10 He's very bold with what he says.

29:11 And he thinks a lot before he says something.

29:13 And he goes, you're just such a good owner.

29:15 He's like, you didn't just care only about your number.

29:18 He's like, you cared of like, what was going on in HR.

29:22 You cared about what was going on in product

29:25 and how the engineers were being motivated.

29:27 He goes, the engineering team, when I went to Brazil,

29:30 would literally be like, is Keaton coming?

29:32 You know, like, and I had nothing,

29:34 like when the other co-founder that was technical would go.

29:37 Because I was just wanting to get to know the whole company

29:39 and win as a full fledged team.

29:43 And then, you know, I would work the,

29:44 some of the weekends or whatever to get ahead

29:46 because I had the passion.

29:48 And so I think what happened is we just started this idea

29:51 that, oh yeah, he's an owner, he's a co-founder.

29:54 And then it just became a reality.

29:55 It was such a blessing.

29:57 And I was so proud of when they announced it

30:00 that I actually did cry.

30:01 Like I cried with Max and I was like, thank you, man.

30:02 Like, this is awesome.

30:04 - That is such a cool story.

30:05 And I do think it's unbelievably rare

30:08 to find people that take that level of ownership.

30:11 And there is, there's like a founder gene, founder mode

30:14 that people can operate in and very few people can do it.

30:18 And I know exactly what you mean,

30:19 the level of ownership fully outside of your role.

30:23 And I'm happy, really, really happy that they recognized it.

30:26 And that's hilarious that the board thought

30:29 that that was already the case.

30:31 Like, wait, did I miss some minutes?

30:32 I thought he was the co-founder this whole time.

30:34 Did something happen?

30:35 - And this was before the acquisition.

30:37 Like, this was before we even knew

30:38 all this stuff was gonna happen.

30:39 Like, we thought we were going for our Series B.

30:41 And then HubSpot came in and had other plans,

30:43 which we're stoked about.

30:44 But like, I was telling people like this happened

30:47 'cause we were like, we're making you a co-founder

30:49 'cause we're gonna go to this growth.

30:50 And part of being a co-founder I wanna talk about

30:52 is not being a yes man.

30:54 People do not realize this.

30:55 Max and I are friends.

30:56 Like, we know our partners, each other's partners.

31:00 We know each other's families.

31:01 We've traveled together.

31:02 'Cause we had to live in Europe together while building this.

31:04 So when you're building an idea to a business, you bond.

31:06 And it wasn't just, yes, sir.

31:09 Okay, yes, CEO.

31:10 It was, no, Max, I disagree.

31:12 No, you're wrong.

31:13 And here's why.

31:14 No, you need to step away and let me own it.

31:16 That's why you brought me here.

31:18 And, or it was Max being like, Keegan,

31:20 I appreciate your thoughtfulness on this department.

31:24 Like, I'm CEO.

31:25 Like, let me handle this part.

31:26 Okay, sure.

31:27 You handle this, I'll handle this.

31:29 And you have to, it's a balance.

31:32 And you have to earn that spot.

31:34 But Max and I actually would debate and argue a lot

31:38 about how the business should be ran.

31:41 That's what led me to be president.

31:44 Is he wanted someone in the corner that would challenge.

31:50 And that's what solidified the co-founder movement

31:52 is because the other co-founders liked it.

31:54 We all challenged each other.

31:56 There was obviously times we all voted yes on stuff.

31:59 But I would raise a lot of question of like,

32:01 do we favor this product or do we favor this product?

32:04 Do we hire for this or do we invest into this?

32:08 And like, when he wanted to invest, I would say hire.

32:11 When he wanted to move to this market

32:14 in this product vision, I would counter.

32:17 And sometimes it would be two co-founders

32:19 and two co-founders, but you need that.

32:23 Like you can't, if I would have just been a yes, man,

32:26 we would have made a lot of bad decisions.

32:28 If I would have been approved and he didn't come in

32:32 and say, no, no, I see you, I'm gonna handle this.

32:34 I would have made wrong decisions.

32:35 So it was good to have that.

32:38 - I have a very similar relationship with our COO.

32:42 So him and I actually best friends in high school,

32:46 roommates in college, moved apart after college

32:51 and ended up having our own individual careers in tech.

32:53 He came up through sales.

32:55 He ended up being a CRO of company called Assembly AI.

32:58 He found his own company.

33:00 I navigated RevOps, had a few companies, had an exit at one.

33:05 And then I started LeanScale.

33:08 And then he joined about a year and a half

33:11 after we kicked things off.

33:13 And the relationship you're describing

33:16 is very much how him and I operate.

33:19 So his name's Joe Zegul.

33:21 And I have never had more conflict with anyone,

33:26 I think in my entire life.

33:28 And I'm gonna throw my wife and other people in that too.

33:32 So him and I are butting heads all day long,

33:35 but it is the best thing for the business

33:38 because I've told them time and time again.

33:40 It's like, Joe, you have saved me

33:42 from driving this company off of a cliff so many times.

33:46 And he says the same thing in the other way.

33:48 So if, and before I had that,

33:53 it's a very lonely position to be in because you know,

33:58 you're like, hey guys, I think we should do this.

34:00 And everybody nods their head and says, that sounds great.

34:04 You know, like, okay, is this really good?

34:07 If nobody's pushing back,

34:09 am I really making a good decision here?

34:11 And then you start like questioning,

34:13 but like when you have that iron sharpening iron

34:16 and when you both kind of finally get to that point,

34:18 then you know and have conviction like, yeah,

34:21 we've hashed the hell out of this thing

34:23 let's move forward and go.

34:24 - Oh yeah.

34:25 I mean, there was times where we would have to say like,

34:27 you know what, I don't want to talk to you right now.

34:28 I gotta take a walk and think about this.

34:31 - Yeah.

34:32 - The passion was there, but the respect was also there

34:35 of like, ah, we got to figure out a way to do it.

34:37 But like there was times I would say like he saved my ass

34:41 and there was times where I stepped in to save a pivot.

34:44 And so it's needed, but we look back and we laugh.

34:48 Like we used to, we would have,

34:51 Max isn't drinking anymore, he just, he's very healthy guy,

34:55 trains for marathons, but in the early days,

34:57 we'd go have a beer and just like talk about it at night

35:00 at like 11 to 12 PM, you know, 11 to midnight,

35:03 end of the day on a Tuesday, we'd just go grab a beer

35:06 and we turned it more to, I would still grab the beer

35:08 and he would have a soda or alcohol free.

35:11 But we would just be like, ah man, remember three months ago

35:13 when we were like thinking we should have done this,

35:15 but then we kind of debated and we went this and way

35:17 and he goes, I'm glad that worked out.

35:19 I'm like, hey, remember when I had this crazy idea

35:21 and you were like, I don't think we should do that

35:23 from the CEO's perspective,

35:24 'cause you knew a little bit more of why not.

35:27 And then we didn't, what if we did, oh my man,

35:29 we wouldn't be here anymore.

35:30 Like, you know, it's key to the moment,

35:35 but when you look back and it all works out,

35:36 you're thankful that you have that.

35:39 - I have a list of moments just like that too.

35:43 - And it makes it fun.

35:45 - It does make it fun.

35:46 And especially, I think it's the respect.

35:48 When you're working with somebody where you have

35:49 that type of respect, it's really productive,

35:53 but you have a good time doing it.

35:54 And I think you find people that have love of the game.

35:58 You're like, yes, we want a good outcome.

36:01 We want to grow, we want to get paid.

36:03 We want to get the accolades for it.

36:05 But at the end of the day,

36:07 like I know we actually just love this game.

36:11 I love thinking about what we should do,

36:12 why we should do it.

36:13 We're running with limited resources.

36:15 Where do we allocate them?

36:16 What's going to be the best bet?

36:18 I think there's very few things

36:20 that are more fun than that.

36:21 - I think the only downside of warmly being acquired,

36:24 and I ran into a lot of people that went their separate ways

36:27 and went to join other startups,

36:30 is I'll get texts out of the blue

36:33 from some of the hardest working ICs I've had,

36:36 or even some of the class clown that crushed it.

36:39 But they were always like the jokester

36:40 and I'll run into them at conferences

36:43 or old leaders that I hired and respected a lot out of them.

36:47 So I would look for them for direction under me.

36:50 And they'd be like, you know what I miss?

36:51 And I'm like, what?

36:52 And we all kind of had it in our head,

36:53 like I miss the culture we had.

36:55 I miss the back and forth.

36:58 I miss the debates.

36:59 I miss the, you know, the riveting moments

37:03 of like end of quarter and we hit.

37:06 Or we had this big goal and we can't hit a growth milestone

37:09 or the hiring is at a freeze until we hit this

37:12 and we would hit.

37:13 I remember, you know, we were thinking

37:15 we were just going to plummet

37:16 and we were going to lose our jobs.

37:18 And we ended up actually having

37:19 one of the best quarters ever.

37:20 They're like, I miss that culture and grit.

37:22 And I go, me too.

37:24 Like I would run into these folks at conferences

37:26 and I'd be like, me too.

37:27 That's the part we did miss was that culture we built.

37:31 Happy to say though, everyone that I've checked in with

37:33 and to go to market side from CS to sales leadership

37:36 to AE to SDRs is killing it at their roles.

37:40 They just miss having that cohesive group together.

37:44 And it's been awesome at HubSpot, I will say that.

37:46 HubSpot on the product side is like a mini series

37:49 of startups 'cause each product's different.

37:52 And so that's been a lot of fun.

37:54 But if I can go back and reflect of how we grew warmly,

37:57 the one thing I was super proud of is the culture.

38:00 Even on the days that were hard, you know, you look back

38:03 and you're like, I would do it all over again.

38:04 It was such a fun place to work.

38:06 - Oh, for sure, for sure.

38:08 And I think you need to have that culture

38:11 to be successful when you're at that stage.

38:15 And especially in that zero to one

38:17 that we kind of talked about, I'm curious though,

38:21Zero to five vs. five to fifteen: what changes

38:21 you mentioned, I've heard you say, you know, zero to five,

38:26 that's the ruthless, brutal part.

38:29 The 5.15 starts to get easier.

38:31 What do you see start to shift and change

38:35 once you cross that proverbial $5 million mark?

38:39 - I think the zero to like five is a lot

38:41 about building processes that you know

38:44 all are gonna stick, like it's building processes

38:46 to see what works following the data

38:48 and then seeing, okay, now how malleable is this?

38:51 Can I, like, okay, it took us from zero to one.

38:53 Can I bend it and have it take us to zero to five

38:55 or sorry, one to five or will it break, right?

38:58 So once you find out the 25 to 50% of the processes

39:03 that'll take you there, you then have to like reinforce.

39:06 It's like an old building getting remodeled.

39:08 You have to reinforce, you have to add more to it

39:11 for that five to 15.

39:12 And sometimes you just have to really start from scratch.

39:15 Zero to five, I think we maxed out at like three

39:18 or four sellers, including me, I was selling.

39:21 Five to the 15, 'cause we were, you know,

39:23 like I said, the 12, we were on our way to 15.

39:26 That's when we ran into, okay, it doesn't make,

39:30 I had to remove myself from deals.

39:31 I could come in as an executive layer

39:33 'cause that was more scalable, right?

39:35 And that did help our win rate if I was to be able

39:37 to touch more deals as a CRO and co-founder.

39:40 And then when Max could also come in

39:42 on our enterprise deals we were breaking into,

39:43 like that was a new play, didn't make sense.

39:45 Zero to five, it would just be me

39:47 or the AEs can handle the SMBs.

39:48 But when we got to the really big stakes,

39:51 it made sense to have an executive come on

39:52 to sell that executive vision to them.

39:55 And so that was a new play.

39:57 Another one was routing, right?

39:59 I had 10 AEs.

40:02 The routing for 10 AEs is different between two or three.

40:05 So definitely had to build out a lot new playbooks

40:09 around that and then segments came to life.

40:12 Zero to one or even one to five,

40:14 you don't really need that nuance segments.

40:16 It's this is a self-serve, this is getting in front of an AE.

40:21 And we're still figuring out our ACB.

40:24 By the time you get to five, you're sure you know your ACB.

40:26 But like once you're at five to 15,

40:28 you have to then calculate,

40:29 I need XACB for this segment to hit this revenue growth.

40:34 This ACB usually takes X amount of time, right?

40:37 This other segment, ACB, this other segment,

40:39 the S&B segment, ACB should be this.

40:42 If it's less than this, it should go self-serve

40:44 or we don't even loop into human anymore.

40:47 Those kinds of processes and nuance need to be figured out.

40:50 And especially of like, what's my payback period?

40:52 If I hire an AE that makes 141.50 in the S&B segment,

40:56 they can't be touching deals less than 15 to 20K.

41:00 Doesn't make sense, right?

41:03 And the win rate needs to be X.

41:04 The ad dollars, the ad spend, the SDR spend

41:07 needs to be this with the payback period being this.

41:09 Different equation for what we call our strategic,

41:12 which was our mix of upper mid market to enterprise, right?

41:16 Our six figure deals.

41:17 And that was a whole different beast.

41:18 Like you can't say, oh yeah, it's gonna close in a quarter.

41:20 Nope, I'm paying an AE to work the strategic segment,

41:24 hundreds of thousands of dollars knowing

41:26 that they probably won't close the deal

41:27 until about month five to six or seven or a year.

41:31 But it'll be worth it.

41:32 And it was, it was.

41:34 But you have to train, you have to build the processes

41:37 and then train the other departments of like,

41:39 this is how this operates and here's why.

41:42 So I think there's a lot.

41:44 And I think people that are watching this will understand

41:47 of like, yep, starting to realize that now

41:49 that I'm over 3 million or I'm at 4 million

41:51 or I'm just hitting 5 million, like the game has changed

41:54 of like how I would scale beyond that.

41:56 And you've seen that for your business with scaling

41:59 and you probably have people now,

42:01 you probably have different account managers

42:03 or CSMs that manage, there's one that's really good

42:06 at managing an up market and one that's dedicated

42:08 to the mid market or down market.

42:09 And that's how it should be.

42:11 When you're zero to one on the way to five,

42:13 it doesn't matter as much as when you're at five

42:16 and beyond, you do need that structure.

42:19 - Yeah, I think beyond the five,

42:22 the specialization starts to become important.

42:24 I do think that is the first axis of specialization too.

42:27 It's enterprise, mid-market, SMBs, self-serve,

42:30 if it's a, if you have a product led growth motion.

42:35 But I think you also get a lot of tailwind after that point.

42:40 I actually really love the metaphor.

42:42 I've never heard it described that way.

42:43 Like you're pushing the ball up the hill

42:45 and it feels like after five, that ball gets smaller,

42:49 whether you've made a lot of investments in the product

42:51 or you start to have some tailwind on brand recognition,

42:56 partners know who you are.

42:58 Did you experience the same thing at Wormly as well?

43:01Build the brand or die

43:01 - I sat us down in an executive retreat in Portugal.

43:06 And I said, hey, if we don't build our brand-

43:07 - Amazing place to have a retreat, by the way.

43:09 I keep having them out here in Phoenix.

43:11 And I think we need to up our venues a little bit.

43:15 - Portugal was an amazing place.

43:16 I can't say that the mountainous region is just,

43:18 it's so beautiful and the little villages, it was cool.

43:21 Like we were almost like off grid for like a week.

43:23 I would say the best conversation I sat down with the team

43:27 was it's like, we have to build our brand or we die.

43:29 I'm like, other people are gonna start creeping up

43:31 in terms of product competitiveness.

43:33 If you don't build a brand,

43:34 we're not gonna differentiate ourselves.

43:36 We're not gonna have that trust in that rapport.

43:38 And people don't follow Wormly.

43:40 They follow Max at Wormly.

43:41 They follow Keegan on revenue tips at Wormly.

43:44 They follow Carina on product,

43:46 how to build product at Wormly.

43:47 They follow Alan for creative marketing

43:50 and what the future of AI is gonna be at Wormly.

43:53 And that paid dividends because a lot of like RB2B

43:57 came to life and he had a good brand.

44:00 And then other companies would try to come up like Vector

44:03 and all these other ones and they had kind of brands.

44:05 But a lot of people were like, oh, I heard of them.

44:07 Or they got in front of me,

44:08 made me realize I should evaluate this.

44:09 And then I remembered, oh, I've heard of Wormly.

44:11 So I need to go evaluate you guys.

44:13 And we would usually win those deals.

44:15 We weren't the first sometimes I got in front of people,

44:17 but because our brand was so well known,

44:19 they had to check out Wormly.

44:21 Some large company that we closed, I can't say who,

44:25 super huge, everyone uses them in tech.

44:29 They said, we're evaluating qualified.

44:32 When we are evaluating qualified

44:33 and we are doing our research,

44:34 Wormly just keeps popping up everywhere.

44:36 Whether it's LinkedIn, whether it's on the LLMs,

44:39 you guys kept popping up as a really great alternative.

44:42 Your G2 reviews say that.

44:44 So, and then Mike, when we look to you guys up,

44:46 we see your founders everywhere.

44:48 So we wanted to do an email.

44:49 We won that deal.

44:51 We were not the first ones to put in there.

44:54 We were not the first ones in their mind.

44:55 But as they started doing their search, our brand appeared.

44:58 So we then became, looped into the process and won.

45:02 Late stage, that was a fun win.

45:05 - That's incredible.

45:06 And moving forward, I mean, new age of AI,

45:10 especially this year, I think it's getting to that,

45:13 at least in the tech industry, that mass adoption range.

45:17 We're seeing barriers of entry to build

45:20 start to drop a little bit.

45:22 So I know technology can still be a differentiator,

45:26 but it's not the only one.

45:28 Do you still think brand is the way to compete?

45:32 Would you invest even more in that

45:34 and index even further on brand than maybe in the past?

45:38 And are there other areas that you need to be cognizant of

45:40 in the age of AI?

45:42 - It's brand and positioning.

45:46 I would actually double down on brand more than,

45:48 I would shrink my sales development budget

45:50 to go dump more into brand building.

45:53 Because you could build the brand and the engagement

45:57 and the community, and then you need someone to go

45:59 after those folks and convert them

46:01 into conversations and opportunities.

46:05 But I advise a couple startups, and it's so hard,

46:08 and I have to remind myself,

46:10 yeah, we were the same way at Warmly,

46:11 but what we found success is when we built a brand.

46:14 So I'm advising these folks, hey,

46:16 invest into content agents,

46:18 invest into content on your website,

46:20 and you need to prioritize content, content, content,

46:24 but it has to make sense, right?

46:26 You need to mix in, here's why I'm in this space,

46:29 here's what I'm changing, here's my background,

46:31 here's who I am.

46:32 So I actually advise the CEO and founder,

46:34 she's breaking into the security space

46:39 after running her own services agency of security.

46:42 So she built an agent that does SOC 2 and all those,

46:45 and it's really robust, it's really proactive,

46:47 it's pretty amazing, 'cause I've used some of the other ones

46:50 as a CRO, or I'm like, okay, this is very reactive,

46:52 and I'm getting bogged down until I get this task done,

46:55 and stuff like that.

46:56 And I told her, lean in on that you're a mother,

47:00 and that you're doing this 'cause you're very passionate

47:03 about the industry, and talk about your experience

47:05 before starting a company, a product company,

47:07 tell them about your agency you ran,

47:09 and how you've definitely done the service side,

47:11 and you know the nuances that go into it,

47:12 which is why you built an agent that could do it.

47:16 And then talk about what motivates you,

47:17 talk about your kids.

47:19 And she's like, really?

47:20 You think, I'm like, you're not selling the SMBs,

47:22 I mean, you are, but you're targeting enterprise.

47:25 Those folks have kids and family.

47:26 They wanna know that these founders have balance.

47:28 They don't wanna know the founder that has the 996.

47:30 That's very unattractive to the upmarket.

47:32 That's very disgusting.

47:34 Like, 996 is not attractive.

47:35 Don't brag about it if you're watching this podcast.

47:37 I'm unattracted by it.

47:39 I'll still do a weekend work here and there,

47:41 but do not brag about your 996.

47:44 It's more of a passionate thing.

47:45 It should be a have-to thing.

47:46 So tell these enterprise people

47:49 that you're passionate about this,

47:50 and you've seen these problems, and you solved it,

47:52 and also your motivation is like,

47:54 you wanna build a good company for people to use,

47:56 but also for your own personal life

47:58 to be able to be around with your kids.

48:00 She started leaning on that,

48:01 and she said it works so well.

48:02 Like, people love seeing that I'm a leader

48:06 and a founder, but also a mother.

48:08 And I'm like, yeah, you're selling the enterprises,

48:09 so lean on that brand, right?

48:11 There's another brand.

48:14 Okay, so for example, the window screen guys.

48:16 Our brand is, we are white collar guys

48:20 turned to a blue collar service business.

48:23 Both co-founders come from working in corporate.

48:26 We were both homeowners.

48:27 We tried to get some specialized contract,

48:30 niche contract work done on our house,

48:31 and we were tired of the unreliable.

48:34 Like, yeah, yeah, yeah, we'll show up,

48:35 and then they never showed up, or they'd show up,

48:36 tell us we'd get a bid, and we never did.

48:39 And so we built a business that's, we use AI,

48:41 and I'm pretty removed now

48:43 because he actually runs it as the CEO.

48:45 I was more of the investor in the visionary

48:47 of how we would market and position our brand.

48:49 And now we explode.

48:51 We have people calling that he's gonna go hire

48:53 another person now because business is picking up.

48:56 Anytime there's a storm, anything,

48:57 people say you guys seem super reliable,

49:00 love the story of how you're homeowners,

49:02 white collar, and you just got tired

49:04 of unreliable contractors, we wanna give you a shot.

49:07 You have less reviews than the other guys,

49:10 but it hits me, or it hits home with me

49:13 on how you're reliable, and you've been in our shoes.

49:18 Love it, brand positioning, and I think,

49:22 going back to what you said at the beginning,

49:24 starting with the list, who you're trying to target

49:26 in the first place, and then reverse engineering

49:28 from there, I have a personal question for you.

49:31 I hope you don't mind me asking, but I'm curious

49:34 because I put myself through this thought experiment

49:37 quite often, too, and he said, hey, 996, not impressive.

49:40 I have the same sentiment towards it,

49:42 and I don't know why you're bragging

49:44 that you have to work so hard to make it,

49:47 and then you don't invest anything else in your life

49:49 and nothing else is important,

49:50 but when I looked back earlier in my career,

49:53 I operated that way, for sure.

49:56 Had the luxury of it, though.

49:57 I didn't have kids, I wasn't married,

49:59 so it was easy to do.

50:01 I'm curious, one, if warmly were to start today,

50:06 and you have your family situation now,

50:08 would you take the role?

50:10 Two, if you were to take the role,

50:14 what would you do differently?

50:16 And do you think you'd still be successful?

50:18 - Would I take the role?

50:19 Absolutely.

50:20 My fiance, she knows, and her kiddo,

50:24 her awesome kiddo knows that I love to work.

50:27 I love to build.

50:28 They know I'm a builder, and I'm an entrepreneur,

50:31 so I would take the role again.

50:33 Would I commit to the flying and all that?

50:37 No, I think I've like, you know,

50:39 I would lean on more in-person events.

50:43 I would've probably not done as many Europe trips,

50:46 and had to have like, really spaced it out.

50:49 But would I still have worked on some weekends?

50:51 Yeah, I mean, it's just called, I mean,

50:53 I get up at like 5.30, 6 a.m. or 7 a.m.

50:57 while they're still asleep until 8 or 9 on a weekend,

50:59 and I'll get two, three hours done,

51:01 and then, you know, after dinner,

51:02 when it's time that she's putting her to bed,

51:04 I'll go do another hour or so of work.

51:07 So it's fine, it's more structured.

51:11 It'd be more structured.

51:13 And if I were to do it differently,

51:15 it was something I actually told Max,

51:17 as we matured, of like, you know,

51:18 I am getting towards 30, I'm trying to settle down.

51:21 Let's hire some young bucks, and send them out.

51:24 Give them the opportunity.

51:26 I'll take them the first couple times

51:27 to these in-person events, teach them the way,

51:30 give them the, here's the goals and outcomes,

51:32 and if they keep hitting those goals,

51:33 they get to keep going.

51:34 'Cause it's fun when you're young,

51:36 and you don't have other responsibilities.

51:37 It is fun going to these conferences,

51:38 these happy hours, these hotel, hotel living.

51:41 It's fun seeing these other places,

51:43 New York and Austin and Chicago, Florida,

51:48 going to like a, I went to a yacht event, right?

51:51 For a business thing, that's fun.

51:53 So I would actually delegate that to, you know,

51:56 a newer rookie hire after training them,

51:59 and showing that they can do it.

52:00 I would have delegated more of that.

52:01 And actually, when we hit that maturity point

52:04 of having reps, I started sending reps

52:06 on my behalf to stuff.

52:07 If it was big, like a HubSpot or a Dreamforce, I'd go.

52:12 If it was a fun event or a cool place,

52:14 I would bring my fiance and family.

52:16 I would say, let's do this.

52:18 I'm gonna be gone these days,

52:19 but we'll come in a day or two early,

52:21 and we'll stay a day later to really enjoy it.

52:23 So there's ways to make it, there's ways to make it work.

52:25 But now with a family, if I were to go,

52:27 and I do aim to start up a company again someday,

52:30 I would definitely prepare the family,

52:34 like, hey, this is what we're gonna do and why,

52:35 or what I'm gonna do and why.

52:38 But with that being said, my commitment is,

52:40 I'm still gonna be a coach.

52:42 I'm gonna have to close my meetings at five

52:45 and get back to it at nine or 10 p.m. before going to bed.

52:48 Or I could just do it at 6 a.m., 5.30 a.m., right?

52:51 So it's just about organizing your priorities and structure.

52:55 Instead of me, single me 27 or 26 when I joined,

52:59 saying, yeah, like, I can do this anytime on a Sunday.

53:01 It's like, nope, I gotta get up early in morning Sunday,

53:04 which means I'm not going out on a Saturday.

53:06 Fun fact, when you become a parent and you get married,

53:08 you don't really go out on Saturdays anyways.

53:10 So, you know, I go to bed earlier, wake up earlier,

53:14 start earlier, and still have a full day

53:16 with what matters most, family.

53:19 - I love it, I love it.

53:20 Well, and I think, especially when you go through,

53:23 you can just work on higher leverage stuff,

53:25 you have more experience too.

53:26 But yeah, you gotta give the next generation

53:28 of young bucks a chance too.

53:29 So they can experience it as well.

53:32 Someone gave me that chance, so why can't I give someone else?

53:35What he's building at HubSpot now

53:35 - So you've had incredible story with warmly,

53:39 the founding, the scaling, the exit.

53:42 What's next for you, and what are you building at HubSpot?

53:46 - So what's exciting is we're building

53:49 actually a couple agents at HubSpot.

53:51 They liked our inbound agent.

53:53 We were wanting to build that out,

53:53 and now we're building out

53:54 a couple more robust agents in the sales hub.

54:00 It's really exciting because I've been a user of HubSpot

54:03 for many startups, and I know what they're really strong at,

54:07 and then I know where there's areas that we wanna improve,

54:10 and it's fun to actually come in with that experience.

54:14 And sit on boards now, right?

54:16 Because I've kind of been the guy that's like,

54:18 now I've been there, done that,

54:19 and so other people want someone like that

54:21 on the advisory board, and so I get to still stay close

54:24 to startups or growing companies and see their pains,

54:26 and it's cool now to say, okay,

54:28 I'm taking my own personal experience with HubSpot

54:31 of what worked really well

54:32 and what I would like the product to be improved to.

54:36 I'm hearing that echo chamber with the people I'm advising

54:38 where they're seeing gaps.

54:40 And now I can work with the geniuses and product to say,

54:43 hey, this is what we need to build toward,

54:45 this is what the landscape is looking for.

54:47 And we're actually building it.

54:49 So we've actually built the inbound agent

54:51 in HubSpot, I can share that.

54:52 It's a private beta.

54:54 It's called the, we call it the lead qualification agent,

54:58 LQA, so lead qualification agent in HubSpot.

55:01 It's a private beta, people can sign up for it.

55:03 And you can now have AI basically qualify

55:07 and route your leads based off different products,

55:11 verticals, industries.

55:13 You can build it out, train it, and no more workflows.

55:15 You just train it, build it out, and it goes from there.

55:18 You tell it what links you want it to feed,

55:20 whether it's a quote form, whether it's a calendar link,

55:23 you could use external calendar links.

55:25 We've made it where multiple use cases,

55:28 it can work for that.

55:30 So that's been exciting 'cause we're less than six months in

55:32 and that's live, and that's gonna be a public beta

55:34 come December, where more people can have access to it.

55:37 Right now it's a private beta with a lot of good feedback.

55:40 And then we're building out some other really,

55:43 really exciting agents that I was like,

55:45 I had to always buy another tool for this

55:48 to plug into HubSpot, and now we're building it out,

55:51 I think, to be better than those said tools

55:53 that people will like the idea of just being able

55:57 to be in one place to be able to run more

55:59 of their go to market.

56:00 So very excited about that.

56:03 More to come, if they add me on LinkedIn,

56:04 they'll see I actually post videos of new agentic updates

56:08 or workflows that we've come out with at HubSpot.

56:10 Even if I wasn't on that team, I usually get exposed

56:13 to those tools, play with it, and then record a hey,

56:15 if you're not using this in HubSpot, you could,

56:17 and here's how it can affect your business.

56:18 So that's been fun.

56:20 So I would say more AI advanced products

56:25 coming to a HubSpot near you.

56:27 - I love to hear it.

56:28 Well, I'm a huge fan of HubSpot.

56:29 Everyone here at Lean Scale is a fan of HubSpot.

56:32 Always done a fantastic job of making it easy for teams

56:37 to implement, operate, scale,

56:39 get to their next stage of growth.

56:41 And I know you're not gonna be slowing down.

56:43 So with you working on the products there,

56:46 I'm really excited to see what comes next.

56:48 Keegan, thank you so much for sharing your story,

56:51 for sharing the details of how you built, scaled, exited.

56:57 I think it's an excellent example for anybody listening.

57:00 If you're wanting to join a startup,

57:02 what the real world of it actually looks like,

57:05 if you're in one right now and you're leading one,

57:08 hey, get through that zero to five, it gets easier.

57:11 That ball, that boulder that you're rolling up the hill

57:14 is gonna get smaller as your product gets better.

57:17 And then I think the number one piece of advice

57:19 I'm leaving with is you have to invest in brand

57:22 or else you'll die.

57:23 So anyone right now, especially in the age of AI,

57:27 people can build things quickly, easily.

57:31 You have to build a brand that people can trust

57:33 and they can relate to and they wanna buy from.

57:35 So Keegan, thank you so much.

57:36 Can't wait to see what you do at HubSpot next.

57:41 And thank you for being on the show.

57:43 - Thank you, Anthony.

57:44 And I'll see you at some local business events in Arizona.

57:48 I got my pickleball gear ready to rock and roll.

57:50 - Let's do it.

57:51 All right.

57:52 Thanks, y'all.