Miro had 60-70 million users, world-class UX, and reps were overachieving on their numbers. Then the pandemic tailwind died and the product became an easy target to replace with free alternatives. The problem wasn't that people didn't love Miro. The problem was that nobody had ever tied it to anything strategic enough to survive a renewal conversation. Pipeline looked great because the team was monetizing usage. But usage without a business case doesn't survive a CFO asking "what do we actually need this for?"

In this episode, Rachael Bueckert sits down with Sangeeta Chakraborty, former CRO of Miro and current CRO of Amagi, for a conversation on how she rebuilt Miro's entire go-to-market motion from the ground up. The conversation covers how she redesigned ICP, the use-case sales plays, and how the value engineering function helped buyers build business cases they'd never built before.

Resources Mentioned in This Episode:

GTM Ops Frameworks

00:22 - 70M users loved the product but renewals were breaking

01:39 - Walking into the first QBR and seeing the cracks

04:40 - Monetizing usage vs. selling outcomes

06:41 - Finding the preponderance of use case across 70M users

18:03 - Command of the Message and building use-case sales plays

18:26 - Why the ICP became the product manager

19:06 - Pepsi: a potato chip that took 3 years cut to 10 months

26:04 - Value engineering: helping buyers build business cases

34:11 - Entry and exit gates at every stage of the sales process

42:04 - A cheaper competitor came knocking

43:54 - How competitive pressure made the team stronger

46:17 - "Don't get fooled by vanity metrics"

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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Anders Krohn spent years deploying AI into enterprise go-to-market organizations and kept hitting the same wall. The models weren't the problem. The data was. When his team anonymized and aggregated proof-of-concept data across dozens of companies, they found that 86% of CRM records had some kind of entity data error. Not missing fields or stale phone numbers. Structural errors at the entity layer: accounts mapped to the wrong parent companies, subsidiaries treated as headquarters, local offices confused with global entities because they share the same domain. And every enrichment tool, every territory plan, every AI agent built on top of that data inherits the same errors downstream.

In this episode, Rachael Bueckert sits down with Anders Krohn, founder and CEO of Kernel, for a conversation on why the entity and hierarchy layer is the root cause of broken CRM data, how 20% of accounts assigned to reps are flat wrong, why companies spending millions on data providers are still unhappy, how AI exposed a problem that humans used to work around, and what it actually takes to fix the foundation before layering anything else on top of it.

Resources Mentioned in This Episode:

GTM Ops Frameworks

01:15 - Every revenue leader has had this moment

04:06 - Garbage in, garbage out: learning the hard way

05:49 - 86% of CRM records have entity data errors

08:18 - Spending millions on data and still unhappy

08:40 - Territory planning and AI: the two triggers that expose bad data

10:22 - How deep the entity layer problem actually goes

14:57 - 20% of accounts assigned to reps are wrong

20:21 - The domain problem: Starbucks HQ vs. Starbucks around the corner

21:13 - Two parts to solving a data problem

22:51 - Data governance vs. letting reps loose: when each makes sense

23:20 - Data debt and why it compounds as companies scale

39:21 - What this means for AI deployment right now

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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Buyers are doing what Doug Landis calls an "invisible evaluation." They're using ChatGPT, Claude, and Perplexity to research solutions, build shortlists, and form opinions without ever visiting your website, downloading your content, or triggering a single intent signal. By the time they show up on a discovery call, they've already decided what they believe. The old linear, seller-controlled sales process wasn't built for this. And running your reps through a stage-gated pipeline that assumes the buyer is starting from zero is why your deal reviews feel like theater.

In this episode, Eddie Reynolds sits down with Doug Landis, CRO and co-founder of StoryPath, former Chief Storyteller at Box, and former Growth Partner at Emergence Capital, for a conversation on what selling actually looks like when the buyer controls the process. Doug walks through the concept of situational fluency, the Buyer Situation Operating Model he's built to replace the traditional sales process, why "what does the buyer need to believe next?" is the only question that matters in a deal review, and how stories are the mechanism that actually moves buyers from one belief to the next.

Resources Mentioned in This Episode:

GTM Ops Frameworks

01:13 - The sales process is dead

04:15 - The invisible evaluation: buyers research without triggering any signal

06:33 - Situational fluency vs. process compliance

08:33 - "What buying situation are we actually in?"

12:15 - Problem aware but not urgency aware

14:26 - How call prep has to change when the buyer already has beliefs

21:05 - Building the Buyer Situation Operating Model

22:29 - The top ten buyer situations every org faces

25:34 - Stories create belief: the mechanism behind every deal

29:40 - Redesigning deal reviews around buyer reality

33:36 - "What does the buyer need to believe next?"

49:55 - Where to start: one change CROs can make tomorrow

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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Emir Atli started his first product at 18 from his parents' living room in Turkey. Now he's co-founder and CRO at HockeyStack, where he's scaled to over 300 enterprise customers in under two years, multiplied revenue 4.5x in a single year, and just closed a $50 million funding round. When he first built the SDR team, he watched reps spend 80% of their time clicking between ZoomInfo, the CRM, and Outreach. Not selling. So he ripped the whole motion apart and rebuilt it from scratch with AI handling everything that wasn't a human conversation.

In this episode of CRO Stories, Rachael Bueckert sits down with Emir for a conversation on how he built the outbound motion alongside AI from day one, the experiment framework he uses to prove an AI motion works before rolling it out, why delegating AI experiments entirely to leadership is the single biggest mistake, and how making sales engineers full-cycle solved the handoff problem that was killing expansion.

Resources Mentioned in This Episode:

GTM Ops Frameworks

01:06 - Intro to Emir Atli and HockeyStack

02:21 - 4.5x revenue in one year and the GTM engine behind it

03:13 - Building outbound on top of inbound, not instead of it

07:10 - 80% of SDR time was clicking buttons, not selling

09:02 - Building the automation from Clay to custom APIs

14:27 - Cold outbound vs. warm outbound: two different systems

16:15 - Advice for legacy outbound teams layering on AI

17:53 - Quota relief: how to get reps to actually run the experiment

19:31 - The biggest mistake in designing AI experiments

22:12 - Results: what the first 30 days should actually look like

27:22 - Where AI handles outbound vs. where humans stay

39:24 - Full-cycle SEs and fixing the expansion handoff problem

46:04 - The metrics on his office TVs and why he ignores quarterly forecasts

48:38 - Study your top 20 deals and build the blueprint

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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This episode is a guest appearance by Eddie Reynolds, CEO of Union Square Consulting, on the Selling AI podcast with Warren Kucker. You can find the original episode on Apple Podcasts.

Eddie digs into why most CRM implementations fail before they start, what happens when sales behavior and data entry aren't aligned, and how AI fits into a go-to-market engine only after the foundational processes and definitions are in place. The conversation covers the real challenges behind deal qualification and pipeline visibility, how AI tools can automate the parts of selling that reps shouldn't be doing manually, the role of customer journey mapping in building a GTM strategy that actually holds up, and why CROs need to think like systems architects before they think like closers.

Resources Mentioned in This Episode:

GTM Ops Frameworks

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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You invested six figures in Salesforce, hired a rev ops team to build dashboards, and six months later nobody's looking at them. Or worse, people are looking at them but spending every team meeting arguing about whether the numbers are right instead of deciding what to do about them. One rep shows an 85% close rate, another shows 15%, and the blended number looks fine on paper. The CEO says visibility is their number one priority. The CRO says they know their deals. And the data underneath all of it is fiction.

In this episode, Eddie Reynolds and Rachael Bueckert break down why most go-to-market reporting is useless and what it actually takes to get data you can trust. The conversation covers the definition debates that burn entire team meetings, the real story behind massive close rate gaps, why your best rep might be ignoring half her territory and you'd never know it, how to build reporting that an average rep on an average day can feed accurately, and why focusing on one metric at a time beats trying to fix everything at once.

Resources Mentioned in This Episode:

GTM Ops Frameworks

01:11 - The problem with GTM reporting right now

02:13 - Visibility is the CEO's #1 priority but nobody trusts the data

05:54 - The 18-month CRO cycle and why reporting never matures

09:02 - The MQL definition debate that burns every team meeting

11:54 - One rep at 15%, another at 85%: both numbers are fiction

16:32 - Your best rep is ignoring half her territory

21:13 - Stop looking for rainmakers, build for the average rep

23:09 - What it takes to build reporting you can actually trust

45:28 - What actually belongs on an executive dashboard

46:53 - The Moneyball approach to go-to-market data

50:06 - Pick one metric and fix it before touching anything else

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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Betsy Matthies took over a 150-person team at AWS whose entire job was to help customers save money on their cloud spend. A cost center by every definition. Sales hated them because every optimization call meant less revenue on the books. But Betsy saw something nobody else did: those same customer conversations were surfacing stalled opportunities that could be unblocked with the dollars being saved. She flipped the team's motion from pure optimization to reinvestment, and it became a demand generation engine with 60% average growth and a full return in five and a half months. And that's just one of the three stories on hidden revenue that Betsy shares with us in this episode.

In this episode, Rachael Bueckert sits down with Betsy Matthies, VP of Global Revenue Operations and Enablement at GitHub, for three stories about finding revenue hiding inside go-to-market operations. The conversation covers the reinvestment model that turned customer savings into new pipeline at AWS, how AI on RFP scoring drove a 145% productivity increase with fewer people, the $500M P&L she took from bottom performer to number two in 12 weeks, and what any ops leader at a $50M-$500M company can apply from these playbooks right now.

Resources Mentioned in This Episode:

GTM Ops Frameworks

01:40 - Intro to Betsy Matthies and three stories of finding hidden revenue

03:44 - AWS: turning a cost center into a demand gen engine

06:31 - How the reinvestment model actually worked

12:36 - The customer that grew 3x from optimized dollars alone

18:09 - 145% more productive with fewer people after a RIF

27:05 - $500M P&L: bottom performer to #2 in the region

31:43 - Flying blind: what happens when the data isn't there

35:57 - Win rooms and the "Prioritizing Our Prospects" meeting

38:03 - The 12-week churn contraction model

40:34 - What translates to a $50M-$500M company right now

44:23 - The most common operational mistake at scale

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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CROs are buying AI tools expecting transformation and getting nothing back. Jonathan Kvarfordt teaches an AI strategy course to revenue leaders at $20M-$200M+ companies, and the first question is always the same: what tools should I get? It's not a bad question. It's just the wrong place to start. When all you do is give a rep a copilot license with no training, no context, and no redesigned process, all you get is the same broken motion running faster. And faster doesn't fix a buyer experience that was already terrible.

In this episode, Eddie Reynolds sits down with Jonathan Kvarfordt, CEO of GTM AI Academy, former VP of GTM Strategy and Marketing at Momentum (acquired by Salesforce), and host of the GTM AI Podcast, for a conversation on why optimizing for the seller instead of the buyer is the number one mistake, how one company replaced 15 SDRs with 2 and generated the same pipeline by month two, why 70% of your sales cycle length is caused by internal friction not the customer, and the friction-mapping exercise every CRO should do before buying another AI tool.

Resources Mentioned in This Episode:

GTM Ops Frameworks

02:45 - Why you're not seeing ROI with AI

04:04 - "What tools should I get?" is the wrong first question

08:15 - Optimizing for the seller vs. optimizing for the buyer

10:39 - Psychological safety: the exit criteria nobody measures

14:50 - Friction is your friend: map it before you fix it

18:22 - 15 SDRs replaced by 2, same pipeline by month two

21:28 - What they specifically uncovered rebuilding the motion

24:44 - Stack-ranking the 100 best accounts with AI and signal data

29:21 - Where humans still outperform AI in outbound

41:00 - The slingshot effect: why slowing down speeds you up

48:54 - Where to start if you want to move the needle right now

49:04 - 70% of your sales cycle is internal friction

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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Steven Birdsall walked into the SAP boardroom and asked for €20 million to build an entirely new business unit. The pitch: take everything SAP was known for — complex, expensive, long implementations — and package it into fixed-scope, fixed-fee solutions that customers could be live on in ten weeks or less. The board said yes. Then every sales rep, every consultant, and every partner told him it would never work. He was zero for three on internal buy-in before he ever sat down with a customer.

In this episode of CRO Stories, Rachael Bueckert sits down with Steven Birdsall, CRO of Alteryx, for a conversation on how the first customer conversation changed everything, the operational playbook behind scaling from zero to 1,000 packages in 18 months, the comp plan accelerators that got SAP's field team to sell it without being forced, how McLaren became the proof point that transformed the business from push to pull, and why the same lessons apply to every CRO trying to figure out AI right now.

Resources Mentioned in This Episode:

GTM Ops Frameworks

00:22 - Intro to Steven Birdsall and the SAP story

01:11 - The €20M board pitch and the thesis behind it

04:21 - 60 days to build a business from scratch

05:44 - Zero for three: sellers, consultants, and partners all said no

09:12 - "You had me at hello" — what happened when he talked to customers

09:57 - 100 packages built internally, partners built 900 more

11:20 - McLaren: 11 packages that transformed an entire business

12:14 - €1B in 2.5 years

13:00 - The operational plumbing behind scaling the business

18:51 - Turning sellers into ambassadors through joint customer meetings

21:59 - How partners went from skeptics to building their own packages

24:58 - Fast time to value: the lesson that applies to AI today

34:04 - From doubling every quarter to annual-to-quarterly quota shifts

45:17 - The playbook for any CRO launching a new motion today

50:09 - The revenue leadership story he doesn't get to tell enough

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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Jackie Rousseau-Anderson walked into a company approaching $100M and realized that the revenue everyone was celebrating looked very different once you layered in gross margins by segment. Some enterprise clients had been compressing margins for years because the sales team did whatever it took to keep them happy. The top-line number looked great. The profitability underneath it told a completely different story. So she did something most CROs won't: she intentionally shed millions in bad revenue, let unprofitable customers churn, and rebuilt the go-to-market around the revenue that actually had margins, lifetime value, and room to grow.

In this episode of CRO Stories, Rachael Bueckert sits down with Jackie Rousseau-Anderson, CRO of InformData, for a conversation on how to run a gross margin analysis that reveals which customers are actually profitable, the behavioral segmentation model that changed how her team sold and serviced every account, how restructuring comp plans around good revenue shifted rep behavior overnight, why intentional churn drove net retention above 110%, and what she's learned working with PE firms like Vista and STG on scaling through these inflection points.

Resources Mentioned in This Episode:

GTM Ops Frameworks

01:27 - What happens when not all revenue is good revenue

05:00 - When to hit the pause button on celebrating every dollar

07:30 - Gross margin analysis by segment: what the data actually showed

10:20 - Behavioral segmentation: archetypes inside your customer base

13:06 - Training reps that it's okay to say no to a deal

17:35 - Restructuring comp plans to reward good revenue

20:47 - Sales process gates that reps actually appreciate

26:24 - Tying marketing to the good revenue segments

27:56 - Sales cycles down 10-20%, good churn reduced 15%, NRR above 110%

29:25 - Shedding millions in bad revenue on purpose

34:59 - Scaling with PE: Vista, STG, and international firms

40:40 - Biggest advice for CROs working with PE companies

44:15 - The soundboard metaphor: every knob affects another

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GTM STRATEGY & AI ENGINEERING FOR B2B TECH

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