The LeanScale Podcast · Episode 133

The Change Management Playbook You Can't Outsource

Susan Rothwell on rebuilding the revenue engine at a fifteen-year-old company: a finance-built forecast that was blind rather than wrong, RevOps as the interpreter, a CRM used as an order system, reversing an inherited reorg in the open, the AI test she applies to every process, and the one job consultants can't do for you

Susan Rothwell · Chief Revenue Officer, Simpli.fi · Simpli.fi Hosted by Anthony Enrico
Published Updated 00:47:03 43 min read 8600 words
Executive Summary

The one-paragraph brief, extended

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

Susan Rothwell is Chief Revenue Officer at Simpli.fi, the Blackstone- and GTCR-backed advertising platform that serves more than 2,000 agencies and brands. She came from large companies with strong forecasting and modeling foundations: at Epsilon she led more than $1 billion in revenue and a go-to-market transformation, and at Vericast she ran a business of roughly $2.5 billion. Simpli.fi was different. Anthony Enrico describes it as a 15-year-old business doing about a quarter of a billion dollars with no RevOps, no forecasting of its own and a barely used CRM.

What she found was not a bad forecast but a blind one. Finance built it, with no bottoms-up roll-up from the field, so it could not show what was happening with customers, churn and downsell, or where the company was winning. "I found that I had a lot of questions and not a lot of answers and no place to go find them." Two months in, her first move was to hire a revenue operations lead and an analyst to sit alongside finance as the interpreter between the sales data and the financial plan that goes to the board. Salesforce was up for renewal and barely used: the team only entered deals once they knew they had them, so it worked as an order system rather than a forecasting system. She built a forecasting cadence, taught the team to use it, and changed the forecast weighting.

Most of the conversation is about change management. Her playbook comes from Epsilon, where three sales organizations called on the same clients with no overall client lead. She looked at customers through a data lens, chose to verticalize into seven verticals, and announced the decision at an all-hands before every detail was settled, then kept communicating as decisions were made. She accepts the risk rather than have people assume leaders are deciding things in a back room. She collects input down to the individual contributor, because every seller and CS rep is asking how the strategy affects them. The Epsilon transformation took about a year and a half with roughly monthly updates.

At Simpli.fi she inherited a consultant-led reorg that moved CS from regions to segments and split sellers into hunters and farmers without much input, which created angst and trust problems. She is now reversing the CS change in the open: the move to segments "was not the right decision," and the team is going back to regional alignment, which she calls "what is old is new again with a twist." A curated focus group of top sellers and CS staff, run by a neutral leader with neither her nor the CS leader in the room, was asked to report what is working as well as what isn't. She ends listen-and-learn sessions by asking people what advice they would give themselves if they ran sales and CS.

On AI, she argues for an overarching strategy, training and governance rather than unguided experiments, and applies one test: ask how AI would do the process, not how AI would fix it, so you don't put AI on top of a process that doesn't work. Engineering and finance brought previously siloed data into a data lake, and the company ran an organization-wide definitions exercise covering terms such as what counts as a new logo. Her closing point is about consultants. They bring useful outside thinking and playbooks, but most have never sat in the operator's seat and won't live with the decisions. The change management plan is the leader's job and can't be handed to them.

Key Takeaways

14 things worth stealing

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

01

A finance-built forecast isn't necessarily wrong. It can be blind

At Simpli.fi, finance did most of the forecasting, and none of it came from a bottoms-up roll-up of what was happening with clients. Susan says it wasn't a bad forecast, but it couldn't explain what was going on with customers, churn and downsell, or where the company was winning, which a CRO needs to know in a competitive media and ad tech market.

Why it matters: Checking whether the top-line forecast was accurate is not enough. A forecast that hits the number but can't answer why still leaves the revenue leader with questions and nowhere to find the answers.

Revenue ExecutivesRevOps LeadersFounders
02

Make RevOps the first hire, as the interpreter between sales and finance

Two months after joining, Susan hired a revenue operations lead and an analyst, adding a layer above the existing sales operations and enablement teams. Their job was to sit alongside finance so that as finance talks about the financial plan that rolls up to the board, someone translates sales data into it. Their remit also covers revenue per rep and the metrics leaders need to coach their teams.

Why it matters: If you are inheriting a company without forecasting infrastructure, she would start with the people who can connect field data to the financial plan before buying tools.

Revenue ExecutivesRevOps Leaders
03

A CRM where deals appear only once they're won is an order system

Simpli.fi had Salesforce, was up for renewal and wasn't really using it. Reps entered deals when they knew they had them. Susan's team built a forecasting cadence, taught everyone how to use it and changed the forecast weighting, which didn't make much sense as it was.

Why it matters: The test is when opportunities enter the system. If they arrive at the close, the CRM records orders and can't support a forecast.

RevOps LeadersSales Leaders
04

Announce the direction before every answer is known

At Epsilon, Susan told the company at an all-hands that it was moving to a vertical strategy and promised to communicate each decision as it was made. Some people see that as risky because employees struggle without knowing the end point. She thinks that risk is better than people believing leaders are making decisions in a back room without communicating or asking for input.

Why it matters: Openness costs some short-term uncertainty and buys trust. People who aren't worried about a surprise decision can return to their day jobs while the change happens.

Revenue ExecutivesSales LeadersFounders
05

Every seller is asking how the change affects them

While leaders talk about the big strategy, Susan says, the seller or CS person is only thinking about how it affects them. She gets input down to the individual contributor, explains the why repeatedly (people need to hear it several times), and knows the message has landed when people in roundtables explain the strategy and verticalization back to her.

Why it matters: Plan communication from the individual contributor's point of view, and measure understanding by whether the team can repeat the strategy, not by whether it was announced.

Sales LeadersCustomer SuccessRevenue Executives
06

A reorg imposed without input creates angst, even if the design is defensible

Before Susan arrived, a consulting firm moved Simpli.fi's CS team from regions to segments and split sellers who had both hunted and farmed into hunters and farmers, with little input. It caused trust problems and unhappiness with new roles. People whose roles change need support: a pure farmer has to learn to multi-thread and grow existing accounts, which is very different from hunting.

Why it matters: Any role change needs a training plan alongside it. Simpli.fi had to lay the groundwork for that training after the fact.

Sales LeadersCustomer SuccessRevenue Executives
07

Reverse a decision publicly when it isn't working

Simpli.fi is moving CS back from segments to regional alignment. Susan says the segment decision was not the right one and disrupted clients and the team. The reversal is being made in the open, with a focus group of top sellers and CS staff, an all-hands led by the CS leader and a survey. She describes it as "what is old is new again with a twist," the twist being what the team learned.

Why it matters: She treats admitting a wrong call as a leadership skill, not a loss of authority, as long as the reversal follows the same input and communication process as the original change should have.

Revenue ExecutivesCustomer SuccessSales Leaders
08

Ask what's working, not only what's broken

When forecasts are missed or products slip, everyone focuses on what went wrong. Susan pushes for equal attention on what is going right. In a top-70 account review about 2027 planning, clients said they love the service, the new products and the AI being built into them, yet internal calls still asked why deals were lost rather than why they were won.

Why it matters: Wins carry information too. She ties this back to RevOps: the analytics should explain what drives wins as well as churn so the team knows what to double down on.

Revenue ExecutivesSales LeadersRevOps Leaders
09

Curate the feedback group, and stay out of the room

For the CS change, Susan picked a cross-functional group with different levels of experience and backgrounds, not only veterans, and had a more neutral leader run it. Neither she nor the CS leader attended. She defined the conversations she wanted, then held an open discussion to address concerns, and asked group members to collect feedback from their own teams.

Why it matters: Who is in the group and who leads it decide how honest the feedback is. Asking members to canvass their teams spreads the conversation and, she hopes, builds trust.

Revenue ExecutivesSales LeadersCustomer Success
10

Put strategy, training and governance in place before AI tools

Experimenting is useful, Susan says, but an organization needs guidance on why it is using AI, which tools (Claude, ChatGPT, Gemini or a few of them) and what for. She wants basic training for everyone, for example on effective prompts and on not pulling in too much information, because more data often gives a worse answer.

Why it matters: Not everyone is an AI expert, and leaving people to work it out alone won't get the most out of the tools.

Revenue ExecutivesFoundersRevOps Leaders
11

Ask how AI would do it, not how AI would fix it

Susan has learned to step back and ask whether a process is right before applying AI, rather than "band-aiding" AI over a process that doesn't work. She looks at transformation from the AI lens rather than the current-process lens. Otherwise AI just churns through a bad process a little faster.

Why it matters: Anthony adds the data side: agents need the right data and an understanding of it, and building a separate data silo for each agent is a losing approach compared with fixing the process and data model as a whole.

Revenue ExecutivesRevOps LeadersFounders
12

Make AI concrete by having reps show their own use cases

Simpli.fi launched Slackbot, connected to the whole organization. At a sales and CS all-hands, sellers and CS staff showed how they use it in their daily work: pulling pipeline, setting call reminders, and for CS, looking for signals of downturn or upsell.

Why it matters: Peer demonstrations bring AI down to the individual contributor's job, which a top-down mandate does not do.

Sales LeadersCustomer SuccessRevOps Leaders
13

Agree on definitions and put them in writing

Building a sales executive dashboard showed Simpli.fi that its data sat in separate groups. Engineering and finance brought it into a data lake, and the company ran an organization-wide definitions exercise. Even a new logo needed a definition. Each sales segment (new business, growth and strategy, local) has its own monthly KPIs that roll up, and the measures have to be agreed with finance as well as within revenue.

Why it matters: Without agreement, the board gets different stories and leaders lose time to confusion. Anthony's version: write the definition down, assign an owner and get everyone at the table to agree, even if the definition is a compromise.

RevOps LeadersRevenue ExecutivesFounders
14

Consultants bring playbooks, but you live with the decisions

Susan values consultants' cross-company experience and outside thinking, especially for analyzing data without internal bias and for challenging an org design leaders have grown attached to. But they push their playbook, its details may not fit your business, and most have never been operators. They hand over the playbook and leave, and you live with the result.

Why it matters: Her rule is that the change management plan can't be outsourced, and that a leader has to be ready to push back firmly when consultants push hard. Anthony frames his own agency's role the same way: it can advise and implement, but it can't make or be accountable for the decision.

Revenue ExecutivesFounders
Frameworks Discussed

11 named models

Every framework Jimmy names, defined and time-stamped.

Blind, Not Bad: The Finance-Built Forecast

01:50

A forecast built by finance without a bottoms-up roll-up from the field may land on the number, but it can't explain churn, downsell, where deals are being won or what is happening with customers.

Susan's diagnosis of Simpli.fi on arrival. Finance did most of the forecasting, and the CRM wasn't used for it, so the CRO had plenty of questions and no system to answer them. The fix was organizational (RevOps) and procedural (a forecasting cadence in Salesforce) rather than a new forecast model.

RevOps as the Interpreter Between Sales and Finance

03:54

Revenue operations sits alongside finance and translates sales data into the financial plan that rolls up to the board, and also supplies the metrics leaders use to coach.

Susan's first hire at Simpli.fi, two months in, was a RevOps lead plus an analyst, added above existing sales operations and enablement. Beyond the sales number and the plan, the team looks at revenue per rep and performance metrics, which she calls turning on the lights for sales and, eventually, CS.

Order System vs. Forecasting System

06:02

If reps enter opportunities only once they know they have the deal, the CRM is recording orders, not supporting a forecast.

Simpli.fi's Salesforce was up for renewal and largely unused for forecasting. The fix was a forecasting cadence, training for everyone on how to forecast in it, and new forecast weighting.

Susan Rothwell's Change Management Playbook

13:34

Start with strategy and the outcomes you want, explain the why, write a communication plan and an input plan, give frequent transparent updates, and iterate, including admitting when a call was wrong.

Developed during Epsilon's verticalization, where three sales organizations calling on the same clients became one go-to-market across seven verticals over about a year and a half. She looks at customers through a data lens (what they buy, how they buy, their potential), announces direction before every detail is set, gets input down to individual contributors, and checks understanding in roundtables where people explain the strategy back to her. She calls change personal, so the plan has to account for the individual.

What Is Old Is New Again, With a Twist

12:38

There are only so many ways to organize a team. Returning to an earlier model is fine when it carries what you learned from the detour.

Susan's description of moving Simpli.fi's CS team back from segments to regions after an inherited consultant-led change disrupted clients and staff. The twist is keeping what worked, dropping what didn't, and listening to the CS team that said the segment model wasn't working.

The "If You Were in My Role" Question

17:29

End every roundtable or listen-and-learn by asking: if you were running sales and CS, what one piece of advice would you give yourself?

Susan says the question surprises people but often gets good advice, such as asking for more success stories or for her to spend more time in front of clients. It follows from her other rule: "I don't have all the answers."

The Curated Feedback Loop

18:50

For a specific change, pick a cross-functional group with mixed experience and backgrounds, have a neutral leader run it with senior leaders absent, script what you need from it, respond openly, then have members collect feedback from their own teams.

Used for Simpli.fi's CS realignment. Susan asked the group to focus on what was working, though early feedback went straight to what wasn't. It runs alongside agenda-free listen-and-learns, an all-hands led by the CS leader and a survey, with roughly monthly updates for long transformations.

AI Strategy, Training and Governance Before Experiments

26:19

Give the organization an overarching AI strategy (purpose, approved tools, intended uses), basic training such as prompting and limiting context, and governance, instead of leaving everyone to work it out.

Susan supports experimentation but says not everyone is an AI expert. She calls out the beginner's mistake of thinking more data is better, when too much information often gives a worse answer. Peer demos at all-hands, such as sellers and CS staff showing their own Slackbot uses, make it real for individual contributors.

How Would AI Do This, Not How Would AI Fix This

28:08

Before applying AI, ask whether the process is right. Design from the AI lens (how AI would do the work) rather than the current-process lens (how AI could patch it).

Susan's test against band-aiding AI onto a broken process, which only makes the bad process run a little faster. Anthony connects it to the data model: agents need access to the right data and an understanding of it, and building a separate data silo for each agent is a losing strategy.

Codify Definitions, Name an Owner, Get Agreement

33:41

Write down what each term and KPI means, such as new logo, win rate, MQL, bookings and ARR, assign an owner, and get everyone at the table, finance included, to agree, even when the definition is a compromise.

Simpli.fi ran an organization-wide definitions exercise covering products, processes and revenue terms. Segment KPIs (new business, growth and strategy, local) roll up to company KPIs. Susan's reasons: you know how you're really doing, the sales plan can be reconciled to the financial plan, and leadership gives aligned answers to the board. Anthony adds that the definition doesn't have to be perfect, only agreed and codified.

Consultants Advise, Operators Decide and Live With It

40:16

Use outside firms for outside thinking, unbiased data analysis and challenge to your org design, but keep the change management plan and the decisions in-house, because the operator lives with the results.

Susan's view is that consultants bring playbooks that worked elsewhere and push hard, but the details may not fit and most have never been operators. A leader's job is to push back and advocate for the company. Anthony agrees from the agency side: outside help can offer options and implement, but someone inside has to pick and be accountable.

Best Quotes

20 lines worth clipping

Pulled verbatim. Copy or share any of them.

“It wasn't a bad forecast, but what it didn't allow us to do was really understand what was going on for our customers, what was happening with churn and downsell, where were the opportunities we were winning.”
Susan Rothwell 02:06
“So I found that I had a lot of questions and not a lot of answers and no place to go find them.”
Susan Rothwell 02:27
“I needed someone to sit alongside finance to make sure that as finance is talking about the financial plan that rolls up to the board, that there is an interpreter that takes the sales information, the sales data, and it ties it together, meaning RevOps.”
Susan Rothwell 03:54
“It was more of an order system than a forecasting system. When we knew we had something, the team would put it in.”
Susan Rothwell 06:08
“As you're talking about this big giant strategy, all that that seller or that CS person is thinking about is, how does that affect me?”
Susan Rothwell 09:58
“That decision to go to segments was not the right decision. It caused a lot of disruption with our clients, it caused a lot of disruption internally.”
Susan Rothwell 12:18
“What is old is new again with a twist, because there's only a certain amount of ways you can do things, and you learn and you iterate on those, and that's the twist.”
Susan Rothwell 12:38
“Being open to the fact that learning and listening and saying, yeah, that wasn't the right call and we need to fix something, I think that leadership needs to be able to do that.”
Susan Rothwell 14:08
“I don't have all the answers. I just don't. I actually don't want the pressure to think you think I do.”
Susan Rothwell 17:10
“If you were sitting in this role, not if you were Susan, but if you were sitting in the role running sales and CS, what would be the one piece of advice you would give yourself?”
Susan Rothwell 17:29
“As a leader you should always be taking just that time to just check in without an agenda, and that's my listen and learns. It's not me talking, it's me listening.”
Susan Rothwell 20:13
“I've done it a few times and it works every time. It's when you skip the involvement and the feedback that sometimes it doesn't work as well.”
Susan Rothwell 23:46
“I joke that I took an AI course like a year ago and everything I learned doesn't matter.”
Susan Rothwell 25:55
“Sometimes you think that AI can fix things, but you need to take a step back and say, is the process right, or am I just band-aiding AI over a process that may not be actually the right process?”
Susan Rothwell 27:48
“When you start to look at transformation with AI, I think you need to look at it from the AI lens versus the current process lens. How would AI do this versus how would AI fix this?”
Susan Rothwell 28:08
“In order for your agents to be effective, they have to have access to the right data and understanding of the data, and a lot of people are starting with the agents first.”
Anthony Enrico 30:35
“The worst thing in any organization is when there's a lack of alignment. That's when things slow down. That's when you get stuck.”
Susan Rothwell 39:15
“You cannot lean on the consultants to do your change management plan.”
Susan Rothwell 40:04
“Realize that the decisions you're making along the way, you're going to live with. They will not live with.”
Susan Rothwell 41:59
“We can come in, we can give you ideas, we can execute and implement things. We can't make decisions for you, though, and we can't be accountable for those decisions.”
Anthony Enrico 44:24
Practical Advice

What should you actually do?

The playbook, split by the seat you sit in.

Revenue Executives

  • On arrival, check whether the forecast is built bottoms-up from the field or top-down by finance. A forecast that hits the number but can't explain churn, downsell or wins is blind.
  • Hire RevOps early to sit alongside finance and translate sales data into the board plan.
  • Announce the direction of a big change before every detail is settled, then communicate each decision as it is made.
  • Ask for feedback on what is working as well as what isn't, and end listen-and-learns by asking people what advice they would give themselves in your role.
  • If an inherited or earlier decision isn't working, say so and reverse it through an open, input-driven process.
  • Keep the change management plan in-house. Use consultants for outside thinking and challenge, and push back when their playbook doesn't fit.

RevOps Leaders

  • Test the CRM: if opportunities appear only when deals are won, it is an order system. Build a forecasting cadence, train the team and revisit the forecast weighting.
  • Give leaders revenue-per-rep and performance metrics they can coach with, not only the plan number.
  • Analyze what drives wins as well as churn, so the business knows what to double down on.
  • Bring siloed data into one data lake with engineering and finance before building executive dashboards or agents.
  • Write down every KPI definition, including new logo, win rate, bookings and ARR, assign an owner and get finance to agree.

Sales Leaders

  • When a role changes, for example from hybrid to pure hunter or farmer, provide training for the new role, such as multi-threading and growing existing accounts.
  • Explain each change from the rep's point of view: how does it affect their daily job?
  • Have reps demo their own AI uses, such as pulling pipeline or setting call reminders, to make adoption concrete.
  • Know each rep's average close rate and what they need to close to reach quota, using agreed definitions.

Customer Success

  • If a segment-based CS model is disrupting client relationships, regional alignment can be the right answer, with lessons from the segment model carried over.
  • Use AI assistants to look for signals of downturn and upsell in accounts.
  • Track whether revenue is retained, not just logos, and use whitespace dashboards to find accounts that could buy more products.

Founders

  • Strong product-market fit can carry a company a long way without forecasting, RevOps or CRM discipline, but expect to build that foundation when you bring in a CRO.
  • Set an AI strategy, approved tools, training and governance instead of leaving AI to individual experiments.
  • Before automating a process with AI, ask whether the process is right, and how AI would do it from scratch.
AI Takeaways

How AI actually changes GTM

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

The thesis

AI transformation fails when it is layered onto broken processes and siloed data or left to individual experiments. Susan Rothwell's approach is to set strategy, tools, training and governance first, redesign processes by asking how AI would do the work rather than how it could fix it, and make adoption concrete through peers showing their own uses.

Agent & automation ideas

  • A CS signal agent that watches account activity for downturn and upsell signals and alerts the account owner.
  • A whitespace agent that flags clients buying one product line but not another, such as programmatic but not platform media.
  • A pipeline-pull assistant in Slack that gives sellers their pipeline and call reminders on request.
  • A win-analysis agent that summarizes why deals were won, not only why they were lost, for weekly reviews.
  • A definitions assistant that answers what a KPI means at the company and who owns that definition.
  • An ICP prospecting agent that finds and engages target accounts to generate leads for sales.
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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Customer Operations

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Metrics Mentioned

The numbers, with context

$1B+
Revenue led at Epsilon

From the show notes: Susan's revenue responsibility as CRO at Epsilon, where she merged three selling organizations into one customer-facing team.

About $2.5B
Business run at Vericast

From the show notes: the business Susan drove to consistent double-digit growth as CRO at Vericast.

About a quarter of a billion dollars
Simpli.fi revenue scale

Anthony's description of Simpli.fi when Susan joined: a 15-year-old business at that scale with no RevOps, no forecasting of its own and a barely used CRM.

2,000+
Agencies and brands served

Simpli.fi's customer base as given in the episode introduction.

Two months
Time to first RevOps hire

Susan hired a revenue operations lead, plus an analyst, two months after joining Simpli.fi.

3
Sales organizations at Epsilon before the transformation

Three separate sales organizations were calling on the same clients with no overall client lead.

7
Verticals at Epsilon

The key verticals Epsilon reorganized around to create a unified go-to-market strategy.

About a year and a half
Epsilon transformation timeline

How long the Epsilon go-to-market transformation took, with roughly monthly updates throughout.

Top 70 accounts
Top-account review

Simpli.fi's current review of its 70 largest accounts covering 2027 planning.

27+
Years in sales and marketing leadership

From the show notes: the length of Susan's career in sales and marketing leadership.

Entities

Companies, people & tools mentioned

Auto-extracted and linked into the knowledge graph.

Companies

Simpli.fiAdTech / Programmatic Advertising

Susan's company, where she is Chief Revenue Officer. A Blackstone- and GTCR-backed advertising platform serving more than 2,000 agencies and brands. Anthony describes it as a 15-year-old business doing about a quarter of a billion dollars with no RevOps, no forecasting of its own and a barely used CRM when she arrived. Covers her RevOps hire, the Salesforce forecasting rebuild, the inherited consultant-led reorg and its reversal in CS, the Slackbot rollout, the data lake and definitions exercise, and a top-70 account review for 2027 planning.

00:00 · 01:38 · 03:11 · 11:11 · 15:23 · 28:38 · 31:28Company →
EpsilonMarketing Services / AdTech

Where Susan was previously CRO and was brought in to drive a go-to-market transformation. Three sales organizations were calling on the same clients with no overall client lead or strategy. She verticalized into seven key verticals and communicated the change step by step, and the transformation took about a year and a half.

03:17 · 07:40 · 07:46 · 24:28Company →
VericastMarketing Services

Named in the show notes as Susan's earlier CRO role, running a roughly $2.5 billion business. One of the large companies with strong forecasting and modeling foundations she contrasts with Simpli.fi.

Company →
BlackstonePrivate Equity

One of Simpli.fi's private equity backers. Susan mentions a Blackstone commercial leader event the week before recording that was entirely about AI, with roundtables on how portfolio leaders are using it.

00:05 · 26:00Company →
GTCRPrivate Equity

Private equity firm that backs Simpli.fi alongside Blackstone, named in the introduction.

00:05Company →
LeanScaleGTM Operations

Anthony's company. He calls himself an agency owner when asking where outside help fits, and describes LeanScale's role as offering ideas and implementation but not making or owning the client's decisions.

39:50 · 44:24Company →

People

Tools & software

SalesforceCRM

Simpli.fi's CRM. It was up for renewal and barely used, with deals entered only when won. Susan's team built a forecasting cadence in it, retrained the team and changed the forecast weighting. She also notes Salesforce's increased investment in AI and says account data such as parent-company hierarchies still needs realigning.

LookerBI / Data Modeling

Used by Simpli.fi's finance team, among other products, to build the dashboards that existed before RevOps arrived.

SlackTeam Messaging

Simpli.fi rolled out Slackbot, connected across the organization and for the whole company, not just sales. At a sales and CS all-hands, sellers and CS staff showed how they use it for pulling pipeline, call reminders and spotting downturn or upsell signals.

ClaudeAI Assistant

Named as one of the AI assistants an organization's AI strategy should decide between.

ChatGPTAI Assistant

Named alongside Claude and Gemini as an AI assistant an organization's AI strategy should choose among.

GeminiAI Assistant

Named alongside Claude and ChatGPT as an AI assistant an organization's AI strategy should choose among.

Methodologies referenced Bottoms-up forecasting cadenceData-lens account review before restructuringListen-and-learns and roundtablesNeutral-led focus groupsTop-70 account reviewPeer AI demos at all-handsOrganization-wide definitions exerciseOutsourced AI lead-generation setup
Frequently Asked Questions

Straight answers

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

What is wrong with a forecast built by finance?

It may not be wrong, but it can be blind. When Susan Rothwell joined Simpli.fi as CRO, finance did most of the forecasting, with no bottoms-up roll-up from what sellers saw with clients. She says it wasn't a bad forecast, but it couldn't explain what was happening with customers, churn and downsell, or where the company was winning, so she had many questions and nowhere to find answers. Her fix was to hire a RevOps lead and analyst to sit alongside finance and to build a sales forecasting cadence in Salesforce.

Why should a new CRO hire RevOps first?

Susan Rothwell hired a revenue operations lead and an analyst two months after joining Simpli.fi because she needed someone to interpret between sales and finance. Finance owns the financial plan that goes to the board, and RevOps takes the sales data and ties it to that plan. The team also supplies the metrics, such as revenue per rep and performance data, that sales leaders use to coach, and it helps make sense of CRM data once the team starts using it.

How can you tell if your CRM is being used as an order system instead of a forecasting system?

Look at when deals enter it. At Simpli.fi, reps put opportunities into Salesforce only when they knew they had them, so the CRM recorded orders and couldn't support a forecast. CRO Susan Rothwell's team responded by building a regular forecasting cadence, teaching everyone how to forecast in the system and changing the forecast weighting.

How do you lead a sales organization through a major change?

Susan Rothwell, CRO at Simpli.fi and formerly at Epsilon, starts with strategy and the outcomes she wants, then explains the why repeatedly, because people need to hear it several times. She writes a communication plan and an input plan, announces the direction before every detail is set, gets input down to individual contributors, and gives regular, transparent updates, roughly monthly over a long transformation. She checks understanding in roundtables by listening for people to explain the strategy back to her, and iterates, including admitting when a decision was wrong. At Epsilon this process turned three sales organizations into seven verticals over about a year and a half.

How should a leader reverse a reorganization that isn't working?

Openly, and with the same input process a good change should have had. At Simpli.fi, a consultant-led reorg had moved customer success from regions to segments, which disrupted clients and staff. CRO Susan Rothwell said plainly that the decision was not the right one and is moving CS back to regional alignment, which she calls "what is old is new again with a twist." She used a curated focus group of top sellers and CS staff run by a neutral leader, an all-hands led by the CS leader, and a survey, and asked the group what was working as well as what wasn't.

What does "how would AI do this, not how would AI fix this" mean?

It is Susan Rothwell's test for AI transformation. Before applying AI to a process, step back and ask whether the process is right, rather than band-aiding AI over a broken one, which only makes the bad process run a little faster. Design from the AI lens, meaning how AI would do the work from scratch, rather than the current-process lens. Anthony Enrico adds that agents also need the right data and an understanding of it, so the data model has to be fixed as a whole rather than one silo per agent.

What should a company put in place before rolling out AI to its revenue team?

According to Simpli.fi CRO Susan Rothwell: an overarching AI strategy covering why the company uses AI, which tools (such as Claude, ChatGPT or Gemini) and for what; basic training for everyone on effective prompts and not overloading the model with information; governance; and data in order. To make it real, Simpli.fi had sellers and CS staff demonstrate their own Slackbot uses, such as pulling pipeline, call reminders and spotting upsell or downturn signals, at an all-hands.

What should you never outsource to consultants?

Your change management plan, according to Susan Rothwell, CRO at Simpli.fi. Consultants bring useful cross-company experience, outside thinking, unbiased analysis of your data and challenge to your org design. But they bring playbooks that may not fit your business, they push hard, most have never been operators, and they leave after implementation while you live with the decisions. Her advice is to take their input, push back when the playbook doesn't fit, and keep the decisions and accountability in-house.

Why do revenue and finance need agreed KPI definitions?

Without them, leaders tell different stories and lose time to confusion. Simpli.fi ran an organization-wide definitions exercise, including what counts as a new logo, with segment KPIs rolling up to company KPIs and the measures agreed with finance. Susan Rothwell gives three reasons: you know how you are really doing, the sales plan can be reconciled to the financial plan, and leadership gives consistent answers to the board. Anthony Enrico adds that a definition can be a compromise, but it has to be written down, owned and agreed by everyone at the table.

Full Transcript

The whole conversation

Broken into chapters, searchable, verbatim from the audio. Speakers inferred (not diarized).

00:00Cold open + intro

0:00 My guest today is Susan Rothwell, Chief Revenue Officer at Simplify,

0:05 the Blackstone and GTCR-backed advertising platform that serves more than 2,000 agencies and brands.

0:12 I found that I had a lot of questions and not a lot of answers and no place to go find them.

0:18 It sounds like this is a ton of change all at once. Sometimes maybe things could break.

0:24 Because the business is always moving. We'll get it now with AI. It's moving quicker than ever,

0:28 right? Stats say that companies that don't adopt it, they're not going to be here in three years.

0:32 Well, maybe we can get into something that is the most disruptive force on the face of the planet

0:38 right now, AI. I took an AI course like a year ago and everything I learned doesn't matter,

0:44 you know, like it's just kind of crazy. To a lot of people listening, they might

0:47 think it sounds easy to understand what a new logo is or can you close something.

0:52 And the worst thing in any organization is when there's a lack of alignment. That's when

0:57 that's when things slow down. That's when you get stuck. You know, it's hard to grow.

01:11Week one: a fifteen-year-old company with no forecast of its own

1:11 Susan, you joined a 15 year old business doing a quarter of a billion dollars that had no RevOps,

1:18 no forecasting, barely used at CRM. What was the first week like? And when did you realize

1:25 how deep that actually went? Yeah, so it was very different than what I had come from, right? Some

1:31 large companies with really great foundations of forecasting and modeling and things like that.

1:38 And when I got to Simplify, it was a company that had grown and had a ton of success without having

1:44 a lot of that foundational support needed to really understand what was going on in the business. So

1:50 what I found out was that our finance team was the ones that were doing most of the forecasting.

1:57 None of it was really informed by like a bottoms up roll up of what was going on with clients.

2:06 It wasn't a bad forecast, but what it didn't allow us to do was really understand,

2:12 you know, what was going on for our customers, what was happening with churn and downsell,

2:17 where were the opportunities we were winning and all those things you need to understand

2:21 in a very dynamic environment in order to win in this extremely competitive, you know,

2:27 media and ad tech world marketplace. So I found that I had a lot of questions and not a lot of

2:34 answers and no place to go find them. That's what I found. Well, and I think first of all,

2:41 it's incredible that they're able to kind of get to the point without a lot of the key infrastructure

2:46 that tends to come much earlier. So I think it really speaks volumes to the product and the

2:52 market fit that simplifies in. I'm curious though, some of these things, they're not just

2:58 technical changes. It's not just go into a system, make a couple of tweaks and everything's fixed.

3:04 Where did you have to start? Because I'm sure there were a lot of

3:07 cultural changes that needed to take place as well.

03:11The first hire: RevOps as the interpreter between sales and finance

3:11 Yeah. Well, I knew when I came into Simplify that, you know, the role was going to be a little

3:17 different than some of my other roles, right? Where I was brought in specifically at Epsilon

3:22 to drive a go to market transformation at Simplify. It was brought in to use some of my

3:28 background and my ability to build different types of teams to operate sales, to lay that

3:35 foundation for Simplify because it really needed to have some of the rigor that it didn't really

3:40 have as it, you know, became a pretty successful organization. So, you know, what I ended up doing

3:47 was, you know, going in with a plan and my initial plan was that I needed a revenue operations

3:54 organization. Like I needed someone to sit alongside finance to make sure that as finance

4:02 is talking about the financial plan that rolls up to the board, that there is an interpreter

4:08 that takes the sales information, the sales data, and it ties it together, meaning RevOps.

4:13 So, the first thing I did two months after I came into the organization was I hired a revenue

4:21 operations lead. We did have a sales operations team, an enablement team, but what I did was we

4:29 added a layer where we had a leader and then we also brought an analyst in, right, to really help

4:35 us, you know, drive as we started to uncover some of the information as we started to use the CRM

4:42 and we started to get Salesforce moving in the right direction to interpret what does that mean

4:48 and what are those results have because it's not only delivering the sales numbers or delivering

4:54 the plan, it's also looking at, you know, revenue per rep and how are revenue performing and, you

5:00 know, the different types of metrics that allows our leaders to coach our members of our teams as

5:06 well. So, it's a multifaceted in, you know, the way that, you know, I was bringing revenue

5:12 operations into the organization and kind of turning on the lights of what that could do for

05:17The CRM she inherited: "more of an order system than a forecasting system"

5:17 the sales organization and ultimately CS as well. Did you have technical resources too? I know the

5:24 GTM tech stack has continually been growing, getting more complex, layering in AI in there as

5:30 well. Did you already have a lot of those in-house? Did you have to bring those from the outside as

5:34 well? Yeah, we brought some things in from outside. So, the finance team had done a really

5:42 good job of building some dashboards, you know, with Looker and different types of products

5:49 and then we did have Salesforce, but we were up for renewal and we were not really using it,

5:55 right? So, first thing that we had to do is kind of build in a cadence for sales forecasting as

6:02 well as teach everyone how to use sales forecast. We had to actually change, you know, the weighting

6:08 of the forecast because it didn't really make a lot of sense. People, like I said, it was more of

6:12 an order system than a forecasting system, like when we knew we had something, the team would put

6:17 it in. So, you know, we used some of that now we're using, you know, a lot of the technology that

6:24 Salesforce has, you know, done and you and I had spoken about, like they've really increased their

6:28 investment in AI and have quickly, you know, become a leader in that. And then from an

6:35 enablement perspective, we used, our enablement team was pretty savvy and used some of our own

6:42 made AI tools and agents as well. And then from a lead generation perspective, we brought in an

6:49 outsourced, an outsourced company to help us, you know, set up AI agents that could go after ICPs

6:57 and really help us drive, you know, go-to-market link to our marketing to get leads, you know,

07:04Pacing change: the Epsilon verticalization playbook

7:04 for our sales organization. It sounds like this is a ton of change all at once.

7:12 I know sometimes if you bring that level of change to an organization, sometimes maybe

7:17 things could break. How do you think about approaching a big problem like this in terms

7:24 of how you prioritize what you're going to do first and also how do you pace things out?

7:29 Yeah, you know, when I think about change and how you drive change into an organization,

7:36 you know, I could go back, I'll go back to, I'll go back to Epsilon and then I'll kind of

7:40 bring it back to where I'm instituting some of this within Simplify. When I got to Epsilon,

7:46 as you talked about in the introduction, there was three different sales organizations and all of

7:52 them were calling on the same clients, right? So you had no overall client lead, no overall client

7:57 strategy. So one of the playbooks that I use is I take a step back, I take a look at, you know,

8:04 who are our customers? What are they buying from us? How are they buying from us? I look at that

8:09 through a data lens. What is their potential to buy more? You know, all of those things. And at

8:15 Epsilon, it became very clear to me that one of the best ways for us to drive a unified go-to-market

8:21 strategy was to verticalize. You know, verticals just popped up. There were seven key verticals.

8:27 And so, you know, we started to, I had a group of leaders that were working with me, sales leaders

8:33 and some cross-functional leaders. And we start to message out, you know, what that strategy was,

8:38 you know. So I think it's really important to understand the why at the very broadest level,

8:45 right? Like why are we even doing this? Because I do sometimes think like people think, oh,

8:49 they're just sitting around to do change for the sake of change and always say, no, it's very hard,

8:53 we're not. But I also truly believe if you don't change, you know, you can't stay competitive and

8:59 you ultimately risk the business, right? Because the business is always moving. We'll get it now

9:03 with AI. It's moving quicker than ever, right? Stats say that companies that don't adopt it,

9:07 they're not going to be here in three years. So, you know, you need to be flexible in the way you

9:13 design things. So we started by letting people, letting, you know, on a hall hands, letting

9:18 people know we made the decision to go, you know, into a vertical strategy. As we continue to make

9:23 decisions, we will make sure that we are communicating the decisions. Some people think

9:29 that is a very risky strategy, that people can't handle not knowing what the end point is. And they

9:35 do struggle with that a little bit, but I think that risk is worth not having them think that

9:40 leaders are in a, in a back room making decisions, not communicating, not getting input. Because the

9:47 other big thing is I always make sure that I get input, not only at the CRO, you have layers in

9:52 there, but at the individual contributor level, like making sure stuff you're thinking about their

9:58 daily job and what they're doing. Because as you're talking about this big giant strategy,

10:04 all that, that seller or that CS person is thinking about is how does that affect me? Right?

10:12 So the ability to communicate the strategy, to get a lot of input, to give updates with

10:18 transparency along the way, right? To make sure you are constantly talking about the why,

10:25 right? And why verticalization works, why having a client lead driving the overall strategy works,

10:30 what it means for the business, what it would mean for you, you can start to get people to really

10:36 rally around that and they need to hear it multiple times. The other part of it is, you know,

10:43 when I do those touch spaces, I do listened and learns or roundtables. I know that the message is

10:50 being clear and people are starting to understand where we're going when I'm in those roundtables

10:54 and I start to hear them talk about the strategy back to me and then talk about verticalization

10:59 and why a client lead matters and why all these things, you know, will align us to better growth

11:06 and really ultimately serving our customers better, which is the most important thing to

11:11The consultant-led reorg that created the angst

11:11 be that customer-centric company. When it came to Simplify, there had been a whole motion of changes

11:18 that had happened prior to me coming. There was a consulting company that came in, they switched the

11:23 CS team from being aligned to regions to be in segment, it's aligned to segments, they switched

11:31 sellers from doing both hunting and farming to hunters and farmers and it created a lot of

11:36 angst within the organization and they also did it without a lot of input. So there was a lot

11:43 of trust factors, there was a lot of people not being happy with what roles they were given,

11:48 people need to have support if their roles change in their new roles. So if somebody becomes purely

11:54 a hunter, you have to teach them how to multi-thread, how do you sell across different portions of an

12:00 account, right? How do you grow the existing business and it's very different than just

12:05 hunting for new business. So we had to lay the groundwork for all that training, which we have

12:10 done and we're in the middle right now of looking at our CS organization and believe it or not,

12:18Going back: "that decision was not the right decision"

12:18 saying you know that decision to go to segments was not the right decision caused a lot of disruption

12:24 with our clients, it caused a lot of disruption internally and now getting that team back on board

12:30 right to say hey we're going to go back to a regional type of you know alignment and I always

12:38 say to people what is old is new again with a twist because there's only a certain amount of

12:42 ways you can do things and you learn and you iterate on those and that's the twist. The twist

12:48 is iterating knowing that some things we did didn't work, some things we did did work, but we're

12:53 listening to our our client success team and they're saying some of this stuff isn't working

12:59 and that's why we need to make some of the changes that we're making. So we're going to do it,

13:03 we're doing it in a much more open environment, we have a focus group of people that from our

13:08 bestsellers and our best CS team giving us feedback on what is working because sometimes we don't look

13:14 enough at what is working, we always look at what's not working and making sure as we talk and decide

13:21 on things that we're getting input at every level of the organization and people clearly understand

13:27 where we're at at any given time. So to sum it up I think that you know leading companies through

13:34 change and leading teams through change is a very personal thing, people take it very personally so

13:39 you have to think about that individual but you need to start with the strategy, you need to

13:44 understand why are you strategically doing this, what outcomes are we looking when we do it,

13:49 what is the communication plan, what is the input plan, who am I getting inputs, making sure that

13:56 you constantly give updates, you communicate along the way as I said and then really again iterating

14:03 as you go along because you're not going to always get it right, I don't know anybody that does but

14:08 being open to the fact that learning and listening and saying yeah that wasn't the right call

14:13 and we need to fix something I think that leadership needs to be able to do that.

14:18Focus on what's working, not only what's broken

14:18 I want to go back to something you said, I have a lot of questions to dig a little bit deeper

14:26 into some specifics but I do want to go back to something that you said that I think was

14:29 interesting, you said people tend to not focus enough on what's working and they're only talking

14:35 about the things that are not working, can you go a little deeper on that maybe give some context

14:40 or examples or why you feel like that can be significant when you're moving an organization

14:46 through change? Well because I think when people think about change they think about

14:53 the negativity of change right versus the positivity right and so the way I think about

15:00 it sometimes is in my role when numbers when we don't hit forecast or when you know or when

15:06 I'm working with product and a product doesn't come out exactly in time when we should right

15:11 everybody's focused always on all the things that went wrong and there's times I say but

15:17 what are some of the things that are going right? So for example right now we're doing a top 70

15:23 account review and you know with all of our top 70 accounts we're getting in front of them we're

15:29 talking about 2027 planning and you know you're hearing a lot from our clients about what is

15:37 working right they love our service they love our new products we're introducing right they love

15:44 the fact that you know we are infusing AI and into our solutions and yet a lot of times when

15:51 we're on calls we're talking about why did we lose that deal not why did we always win the deals so

15:57 that goes back to my initial conversation on RevOps right and understanding you know really the

16:02 analytics behind the numbers and what's what's causing churn and what's causing wins because

16:08 we tend to just slide to what's not working and focus on that instead of double downing you know

16:14 on what is working and saying this is what we need to fuel and I think it just comes from the fact

16:19 that we're always worried about you know what's not working and and I just kind of remind everyone

16:24 like yes but we need just as much attention on what is working just best practices success

16:30 stories you know why are clients saying great things and that's part of the strategy when you

16:36 move forward yeah and I think it brings me back to what you said early on too we're not doing

16:43 change just for the sake of change so if something is working we're not here to try to fix something

16:47 that's not broken but keeping our focus on okay here's the few things that we can do where we

16:53 think we're going to have an effect having a strong lie behind that and then hey if it's working well

16:58 then leave alone or double down even yeah I can't emphasize enough you know how important it is to

17:05"I don't have all the answers" — and the question she always asks

17:05 get feedback especially from a leadership perspective you know one of my other sayings

17:10 is I don't have all the answers I just don't I actually don't want the pressure to think you

17:15 think I do you know that that you know I need I need guidance I need feedback people aren't always

17:22 comfortable giving that a lot of times when I do roundtables or listen and learns all my last

17:29 question to the the people on the call will be if you were sitting in this role not if you were

17:34 susan but if you were sitting in the role running sales and cs what would be the one thing one piece

17:43 of advice you would give yourself in that role if you were me and or you were in that role and it's

17:50 it's pretty people are a little blown away by that that question but you often get really

17:56 good advice sometimes it's like um you know we need we need more we need more success stories

18:01 we need you know we need you focused more on getting out in front of some of our clients

18:06 or whatever it would be but um I always find that like one of my favorite questions to ask

18:12 I love that I love that and and I want to get into some of the specifics two things in particular

18:20What a real feedback loop looks like — and why she stayed out of it

18:20 if we can give some barometer I know every business is a little different every

18:24 initiative will be a little different but when it comes to getting feedback from the field

18:30 and a constant communication what does that actually look like somebody may hear that and say

18:35 I'm constantly updating them every annual all hands we let them know what our strategy is so

18:40 I don't know why people don't know it and then they may say well I did talk to one person

18:45 on the in the field so I got my feedback in terms of like volume and magnitude what does it look

18:50 like when you're doing it really well you need to be thoughtful in how you pick the team that's

18:56 going to give you the feedback right so making sure that it is a good cross-functional team of

19:03 if it would be sellers and cs that they're that they have various experience right they're not

19:08 they're not all veterans they're not they have different backgrounds right because you do want

19:13 a mix of of feedback coming in so I think that you've got to curate that team to make sure it's

19:21 got a lot of diversity of thinking in it right so that that would be my one piece of advice when

19:28 when I did this this just currently at simplify with the cs and sales organization is I picked

19:34 a leader that was a more neutral leader to actually lead the focus groups and then I was not in them

19:41 the cs leader was not in them but we but we curated kind of what kind of conversations and feedback

19:48 that we wanted them to have to get so that we would get you know that's the meat of what we

19:53 wanted to and it was funny because I asked them to lean on what was working and initially we were

19:58 getting everything that wasn't working and I'm like no no no but we want to know it's working

20:02 so as I that tendency tends to go back so I think you have to be very thoughtful about that feedback

20:07 loop when you're on a specific initiative or strategy change I think is I think as a leader

20:13 you should always be taking just that time to just check in without an agenda and that's my listen

20:19 and learns right where I just invite people to get on a call it's not me talking it's me listening

20:25 so give them an update on what's on my mind so I get some feedback but specifically for an initiative

20:30 or specifically for a strategy I think you have to have that curated team the other thing is that

20:37 then you know after you kind of get the feedback then you know we did come in we did have an open

20:41 discussion with that team on their feedback I had an opportunity to address some of their concerns

20:47 and as we continue to go down this road that group is really an important part of the change

20:54 initiative because as we go to them for feedback I don't I ask them to go to their teams for feedback

21:01 right so then you start to have a spreading of what the conversation is what are the questions

21:06 they're asking you get more broad input and there's a transparency about it that I'm hoping

21:13 right I'm not guaranteed built will build trust and then belief in the fact that what we're trying

21:20 to do is actually a direction we should be going and that my my my opinion matters my experience

21:28 matters and that I can have an impact on the way that we are driving things forward so I do think

21:35 you have to be very very principled about the way you address it and you have to curate it in the

21:42 sense of you know who's the team why are they the team diversity of thought as well as you know what

21:49 specifically am I trying to get out of this and then once you get out of that how are you going

21:55 to continue to dispense you know the information and get the feedback loop going from there so

22:02 where we're at right now is we as we talked about these things we had in all hands with CS the CS

22:09 leader leaded and talked about you know some of the thoughts that we have initially where we're

22:14 going and now we're doing a survey and getting some additional feedback and information as well

22:19 so I know sometimes you have to go faster so this is this is when we're not forced to go fast we're

22:26 taking this upon ourselves because we feel like this is the right thing to do from what we've

22:30 heard from the team but there is as I said I really do feel like you have to be thoughtful even in how

22:36 you're communicating it out you need to have a timeline of specifically you know how you're

22:41 communicating out what are we going to say what is the purpose of that call am I answering the

22:47 questions of an individual contributor sitting in their seat as I'm talking about things because

22:54 they're the ones doing the work the sellers and the CS teams they're doing the work every single

22:58 every day every day I'm not I'm not doing that role and making sure that you're thinking about

23:05 that the effect and then most importantly how's it going to affect our business and our customers

23:10 and are we going to do a better job and have them love us even more I think there's nothing better

23:18 than when you have that buy-in and I think you could even get to the point where they have

23:24 a strong passion for the change yes right at the bottom floor because it's one thing to say it but

23:31 if it doesn't really trickle down and they're not really bought in it's very very difficult to make

23:35 effective so I know you mentioned sometimes you need to go quicker sometimes you know you don't

23:40 have a choice but I think if you can spend that time really getting the buy-in I think it's brilliant

23:46 yeah I mean and and I would say that I've done it a few times and it it works every time it's when

23:52 you skip the the involvement and the and the feedback that sometimes it doesn't work as well

23:58 but you know again I don't have all the answers so I need help absolutely and then on the

24:06 communication I know it's kind of woven in to okay let's get that cross-functional group in

24:12 how often is often enough is this a weekly thing are there daily updates you need to send is it at

24:16 the monthly all hands what does that look like I would say right now I would say most of the time

24:23 I did it on a monthly basis depending on how long you know how big of a transformation was you know

24:28 definitely at epsilon it took us a year and a half to get to where we got to you know it took a while

24:34 so there was constant updates and it was a mixture of you know keep doing your day job keep doing it

24:40 but you know we're this is where we're going to get to so it is a very fine line to to to follow but

24:46 I think what happens is particularly if it's a longer overhaul or strategy people start to get

24:53 used to the fact that that this this is we're talking about this but they can kind of switch

24:59 and focus to their day jobs because they're not panicked that a decision is going to be made in

25:03 the back room without them or that their job is going to change tomorrow so I think people can

25:08 kind of settle in a little bit and focus on their day jobs while you know we know that this

25:13AI: strategy, training and governance before tools

25:13 transformation has to take place well maybe we can get into something that is the most disruptive

25:20 force on the face of the planet right now ai yes and understanding okay when you need to

25:31 shift a large organization into adopting implementing doing these things in a meaningful

25:36 way too not just running experiments how are you even approaching this with your team and how are

25:42 you even thinking about what the end state of mission accomplished might even look like

25:48 how are you thinking about this yeah you know um my thinking continues to evolve as I learn right

25:55 I I joke that I took a AI course like a year ago and everything I learned doesn't matter you know

26:00 like it's just kind of crazy I was at a Blackstone commercial event last leader event last week and

26:06 it was all about AI and so we had some roundtables with leaders like myself and talking about you

26:13 know everybody's at various stages you know in their organizations of how they're using AI

26:19 um and I think that I do think one of the things that organizations really need to have is they

26:26 need to have kind of an overarching strategy because a lot of people will experiment with it

26:32 and that can actually is good right because you learn but I do think there needs to be guidance

26:39 from the organization you know on you know how are we how are we using AI um what is the purpose of

26:46 it you know what one are we using you know is it Claude is a chat gbt is it Gemini there might be a

26:51 couple of them you know what people need some I think there needs there also needs to be some

26:58 general understanding of um what you know what you should use it for and what we're using it

27:04 for as an organization um so you know I do think you need to have that overall strategy and then I

27:10 do think you need to do some training you know what what are what are effective prompts how do

27:15 you make sure you're not pulling in too much information like so you can be really specific

27:20 about what you're asking because sometimes I think when people are new to AI they think more

27:24 is better and it often isn't right when there's too much too much data you're pulling from or

27:29 too much information you don't always get the right the best answer I should say so I do think

27:35 there should be training and governance for everyone in the organization just some basic

27:39 things on on the best ways to use to use AI um we're you know engaging in it uh in a big way um

27:48"How would AI do this?" vs "How would AI fix this?"

27:48 the other thing that um I'm learning as I go along is sometimes you think that

27:54 AI can fix things but you need to take a step back and say is the process right

28:01 or or am I just band dating an AI over a process that may not be actually the right process

28:08 and when you start to look at transformation with AI I think you need to look at it from the AI lens

28:15 versus the current process lens how can how can how would AI do this versus how would AI fix this

28:22 right and I think that's really it's a it's an important thing to think about because otherwise

28:27 you're just putting AI on maybe a process it doesn't really work well it's just you know

28:33 churning numbers or churning something a little bit quicker so that's one thing um the other the

28:38 other thing is we we um you know just we we just launched slackbot we connected to everything in

28:43 our organization we're trying to it's not just for sales through seats through it's for the

28:49 whole company but had an all hands a couple weeks ago with sales and cs and one of the things that

28:54 we did was we had sellers and cs teams get on and talk about how are they using it to help their

29:01 everyday job you know and so we had sellers talking about how they're pulling pipelines in

29:06 how they're using it for call reminders you know of different ways because you know it can seem so

29:12 oh my gosh AI up here and I use it for very different things and a seller might use it for

29:17 how do we make it real at that individual contributor level how do we make it real with cs

29:22 how can they use it to see if there's signals for downturn or there's signals for upsell

29:28 opportunities right um so really having sellers on there and cs people and they're talking about

29:34 their own usage and their ways of doing it I think can be really powerful um you know from a data

29:41 perspective you have to have your data in order right that's an important piece of it as well as

29:45 you use it to pull things in um but I but I do think like organizations just making sure that

29:52 they have just some key learnings for everyone because everyone's not an AI expert and just

29:57 hacking your way through sometimes isn't really the best way to to really optimize the powerful

30:02 uses it can be for the company I really like the test that you have of saying can AI do this or

30:10 should AI fix this and I think aiming hey how do we get AI to automate things or take things to the

30:17 next level rather than just a something's broken I'm not going to use my brain power to try to

30:21 fix it let's just hope AI knows exactly what to do I think you're right I think that's a losing

30:26 strategy almost every time like going back to the basics fixing the process also fixing your data

30:35 model I I think that's a big thing people don't realize that in order for your agents to be

30:42 effective they have to have access to the right data and understanding of the data and a lot of

30:49 people are starting with the agents first they're like oh I'm going to go build this forecasting

30:54 agent yeah it's gonna say okay well I need this I need this I need this and then they build all

30:57 these little data model silos for each agent they're doing rather than kind of taking a holistic

31:03 approach have you been running into these roadblocks as well yeah well well well I definitely in all

31:11 my companies we've always had a data problem right like just getting data together right it's just

31:17 it's always a challenge and I think that AI has just made it more prudent to make sure you have

31:22 some type of a data strategy they tend to sit in siloed areas of the organization right you don't

31:28 always have the same data so it's simplified you know with the RevOps team as we're trying to build

31:34 we're building this sales executive dashboard right using some of our tools we realized that

31:43 we had different groups of data and that we needed to bring not only the data together but but and

31:49 this is a little past my pay grade is in technological understanding but we also needed to

31:54 have it like set up the right way right within within the data lake and so there had there had

32:01 we had to bring teams together to get agreement on you know bringing the data together and how

32:05 would that data be set up and accessed you know in into a data lake as well so we we just really

32:14 accomplished that and it was really driven by engineering working with finance to to bring

32:19 that all together and that's just hugely important because you know if your data is not aligned right

32:26 and we still have work to do right the way our data is set up in and our sales force is you know

32:32 needs to be realigned better we need to have you know parent companies and things like that like

32:37 some of that wasn't set up correctly so we're fixing some of that but the actual financial data

32:42 and customer data of like what they buy and sales data and ios and all that stuff you know we're

32:48 starting is is starting to really you know galvanize together and we're able to set up

32:54 you know dashboards very easily where i said you know when i came in it was kind of like what is

33:00 going on here because i couldn't pull a story together to really understand where are the

33:05 opportunities in the marketplace you know where are we seeing maybe different verticals start to

33:10 pop up as areas we should be focused on you know where are some of our new products really you know

33:14 gaining strength where do we have some risk with competitors you know all that stuff is now

33:21 be able to glean a lot of that you know using um ai and and sales force and slackbot and some of

33:28 the other tools that were standing up from a dashboard perspective i think there's absolutely

33:35Getting alignment on what a new logo actually is

33:35 a lot of technical work to be done one of the parts i found most challenging in this and i'm

33:41 curious if you ran into this too is just getting alignment on terms and data definitions and what

33:47 kpis mean like how are we calculating win rate here what is an mql at this company

33:54 what are bookings and how do we articulate what our arr is how how have you codified what terms

34:02 and kpis mean do you have any any tips on getting that done well yeah i think across the board right

34:10 one thing is on like the revenue perspective but actually the organization has undergone like a

34:16 whole definition exercise you know to make sure that we're defining and call like we what we

34:22 call things is the same thing across the organization right that's across the board that's product wise

34:29 that's you know process wise and so much bigger than just uh running revenue but from a kpi

34:35 perspective we have um each of each of the sales teams and the leaders have their own kpis so our

34:42 new business versus um our growth and strategy versus our local team right what are the things

34:47 that matter you know on a monthly basis that they're measuring because it it can be unique

34:54 to the segment of the business right that they're measuring and then that rolls up into the overall

35:00 kpi so you know some of it is um you know our our our win rate for new logos how long you know

35:07 is it take us to get a new logo on board right making sure we have a definition of what an

35:12 actual new logo is because some companies have different definitions of that it's not surprising

35:16 it's like the easiest thing you think that would be the easiest thing to figure out and it's like

35:20 no no no but there's yeah exactly so the definition of a new logo and then um you know it's it goes

35:29 to you know you know retention like retention is huge you know are we are we not only retaining

35:35 our logos but are we retaining the revenue are we we have a measurement we look at how much you know

35:42 solutions are we able to cross sell right we have a dashboard saying we think this client could be by

35:47 you know our platform media and they're not buying platform media they're only buying programmatic

35:52 from us and so there's let's make sure we're focusing on you know growing that account so

35:57 i think the kpis um you know are you know across the board for many different things but you know

36:05 they're important also because as your sales leader and you're doing one-on-ones understanding

36:10 what the average close rate is for your rep and how much they have to close to get to their their

36:16 quota or their goal you know you need to have all those things really spelled out and that's why

36:21 having dashboards and having clear data and understanding what those measurements are an

36:27 agreement not just with within the revenue stream but also with finance right because

36:32 i said they're looking at the financial plans versus the sales plan um i think really is

36:38 important work to do so that number one we understand how we're really doing number two

36:45 the sales plan should convert into hitting the financial plan right but there there are

36:49 differences in the way they look at it and number three you know when you have the tough questions

36:56 from the board or you know or the chairman or whatever that you have alignment on what the

37:02 answers are because that's when confusion starts that's when doubt starts right you just need to

37:09 make sure that everybody is looking at agreeing on certain measurements and looking at them the same

37:15 way and and it doesn't always happen sometimes you know you don't have alignment and um that can

37:21 cause a lot of swirl and a lot of time trying to understand what's going on the business when you

37:27 really should be out there driving the business yeah i've found that part just unbelievably

37:34 difficult to do and to a lot of people listening they might think it sounds easy to understand

37:41 what a new logo is or when you close something finance should know how much revenue that should

37:47 be but it's not always so easy and sometimes you have to make media you know like because you're

37:53 avoiding things right so yeah i know or if there's usage and you have to like calculate how much is

38:01 variable within the deal um yeah it's very different margins for different products and

38:07 you know like right so that can complicate things as well on what that actual deal level was worth

38:14 and so there's a lot of complexity to it yeah especially if you don't know exactly which

38:19 products they might be using in that particular scenario so like okay we're not going to have a

38:24 perfect definition but as long as we all agree on what the definition is and are okay with some of

38:30 these things kind of being a compromise of absolutes then okay we can move forward and we

38:35 can have productive executive meetings productive board meetings and and do what we need to do but

38:41 until you've sat down and written it codified it written an owner to it looked around the table

38:48 everybody said yes i agree with that it's very difficult to do yeah and even when i said just

38:54 the definitions across the organization right like just in general terms is is going to be

39:00 interesting so but it's important work and i think i think when you lay that groundwork down right

39:05 again some of the fundamentals it's worth the work because in the long term it'll save a lot of work

39:11 because you have agreement you don't have swirl you don't have stories being told that are different

39:15 stories and then um don't have alignment right and then the worst thing in any organization is when

39:22 there's a lack of alignment that's when that's when things slow down that's when you get stuck

39:26 that's when um you know it's hard to grow very hard to grow one one of the things we talked about

39:34Where consultants fit — and where they can't

39:34 during the prep session i think there's a lot of people who want to rush to get outside help for

39:42 some of these things bring in the management consultants um bringing the agencies and being

39:50 an agency owner i kind of know where we fit into the equation of these things but where are some

39:55 areas where hey if you're going outside you're getting help from consultants you're getting help

39:59 from agencies this is where they can fit but this is where they cannot fit what are some of the things

40:04 that you cannot lean on the consultants to do you i you cannot lean on the consultants to do your

40:10 change management plan right like what you can't just outsource it make them do it no you can i

40:16 think i think so consultants are great right they sit across a broad amount a broad amount of

40:22 companies and so they get a lot of experience seeing you know what's out there what's going

40:26 on what's work that doesn't hasn't worked um so it's great to get their input and and their ideas

40:33 and their thoughts because it's outside thinking i the areas that i think that you always have to

40:38 be a little bit um cautious of is the fact that they will push you right and they will push you

40:44 because a lot of times they have a playbook and that playbook is what has worked at these

40:49 other companies they've been at and um sometimes the nuances of the playbook don't fit into your

40:55 business so you have to push them to make sure that you are solving for the the what's going

41:01 on in your current business not just what the playbook fulfills um also i always think about

41:06 the fact that they are brilliant people super smart you look at their linkedins i mean they're

41:11 all you know harvard mba you know graduates or ivy school mba um they they've been consultants

41:20 for a long time but they haven't sat in the operating seat most of them have not sat as

41:26 an operator and i think sitting in that operator seat and knowing that whatever decision is made

41:32 you're going to live with right that the consultants will hand you the the playbook

41:38 work through the playbook help you implement the playbook but then they leave and you have you were

41:44 sitting there you know dealing with whatever decisions you have made you have to be really

41:48 strong about that you have to make sure that you have candid conversations because sometimes they

41:53 will push very very hard and you have to really be strong about what you think is right for the

41:59 organization and not and realize that the decisions you're making along the way you're going to live

42:04 with they will not live with so i think they're i think they're very helpful um but your lot your

42:10 job as a leader is to make sure that you are advocating for what's best for the company

42:16 as you engage with the consultants along the way are there certain areas of the business you've

42:21 really appreciated bringing in that outside help anything specific that you say hey if you're a

42:26 cro and this type of company like bring in some consultants for this type of stuff bring in some

42:31 agencies for these type of things um that you have found been really effective yeah i think that um

42:38 you know really you know helping someone pull together and understand the data from an outward

42:46 out per outside perspective is helpful because um you know taking a look and and mining the

42:53 the data that you're going to be using to make decisions and i say that because when you do all

42:58 the data mining all by yourself in inside your company you can be not have that outside thinking

43:05 right because you could be biased in the way you approach things so i think it's good to have that

43:09 lens and making sure that the way you're pulling the data and using it is is really thoughtful

43:15 from an outside perspective um the other place would be um you know in you know sometimes too

43:23 like pushing you you know in your alignment right you when you have your organizational design done

43:31 a lot of times we just fall in love with our organizational design and how everybody fits into

43:35 it and i think sometimes they can be really helpful in challenging you on decisions and

43:40 why you might have people here or people there i think about um some of the work we did with a

43:47 consultant uh where you know they were pushing me on definitions of like um some account management

43:53 and are they really sales support and you know so some of those conversations can be really helpful

43:59 but i think that um again you know once you get that playbook of how they're in there helping you

44:06 change things you know you have to then put the company lens on it and really understand how

44:11 you're going to you know be rolling that out and what the implications are and what it means you

44:17 know to the people to the company to the bottom line all those things yeah i've always framed it

44:24 in a similar way whenever we're working with companies it's a hey we can come in we can give

44:28 you ideas we can execute and implement things um we can't make decisions for you though right and

44:36 we can't be accountable for those decisions we can give you the options but at the end of the day

44:41 somebody has to pick it and be accountable for it and that's where i think having that real operator

44:47 experience i wish the consultants should he put them on a voyage like hey you gotta go spend five

44:52 years doing something like you gotta go own something yeah they're not all that way i mean

44:55 but the majority of them have not operated it's from what i could what i've experienced anyway

45:00 other people might have different experiences no it's similar i'd say it's really similar in like

45:04 vcpe world too like yes you they see maybe go to market things happening in a lot of their

45:11 portcos and they bring those things to the board meeting or they like value creation teams which

45:16 is helpful but then there's a certain point where it's like yeah but you haven't done this job before

45:22 so maybe you don't have an appreciation for how difficult some of these things might be to do here

45:27 um so but anyway i think everybody kind of has their role in the ecosystem i think really good

45:33 leaders know when to pull someone in and then when they just have to own it and run it internally

45:40 and sometimes you just have to have that conversation when they're pushing really hard

45:44 you know and kind of say hey this is not happening i know you i know you need that to happen but not

45:49 happening so um that that's your role as a leader right 100 that also helps when you have experience

45:57Wrap

45:57 and you've racked up a few wins too um and have that confidence well susan this has been awesome

46:03 thank you so much for everything you shared i think some of the things a lot of companies i

46:08 know we work with them they struggle with that change management aspect and i think some of the

46:13 things you shared of hey you got to be communicating often you have to be getting people from the front

46:18 lines and from different departments and be selective and careful of who you curate to be

46:23 into that group but you have to get that feedback before making the decisions and i think we have a

46:29 lot of things that are coming up that are going to require a lot of businesses to have some immense

46:35 change management initiatives going on so i really appreciate you walking through the playbook you've

46:39 had a fantastic career done it at some amazing companies um so everything you say i listened

46:47 a little extra hard and take it to heart so i really appreciate it um thank you for being on

46:52 the podcast thanks for sharing everything do it to follow appreciate it thanks so much thank you