RevOps Corner

Jeff Perry joined Carta in late 2018 when it was a 275-person startup selling cap tables to founders. Eight years later, it's a $650 million private markets platform with 50,000 companies on the platform, a fund administration business for venture and PE firms, a total compensation product, tax advisory, and a recently acquired law firm. The cap table business is still healthy, but it has a ceilin...

On paper, everything looks healthy. Reps are hitting activity. Leads are coming in. Pipeline looks full. And yet deals are slipping, cycles are running long, and customers keep churning out the back. So much of that comes back to an ICP definition that's too broad, too shallow, and stuck in a doc that nobody uses. In this episode, Eddie Reynolds and Rachael Bueckert break down how to turn your ICP...

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 mo...

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...

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...

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, th...

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...

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 visibi...

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 sa...

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 proce...

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 w...

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 d...

Ryan Milligan's team at QuotaPath hit 100% blended quota attainment eight of the past ten quarters. The way they got there wasn't by adding headcount. It was by looking at every step in the funnel where a rep was spending time on something that wasn't uniquely human, and putting AI on it. The result: reps went from spending 25% of their time selling to closer to 50%, and ARR per rep tripled. In th...

Duane Dufault was staring at a trial registration flow that took ten days to get a lead in front of a rep, attribution data that was 80% wrong, and a founder who was ready to shut off marketing based on numbers that weren't real. He could have started layering AI on top of all of it and joined the chorus. Instead, he spent six months fixing the plumbing. The result: ACV up 30%, sales cycles cut by...

Sangram Vajre has been asking rooms full of CEOs and revenue leaders the same question for the past year: how many of you are using AI? Every hand goes up. How many of you are seeing an impact? Every hand goes down. The disconnect isn't that AI doesn't work. It's that companies are layering it on top of a foundation that was never built in the first place. And no amount of copilots, agents, or aut...

More than half of net new revenue last year came from existing customers. Yet most companies still treat expansion as a side effect of good relationships instead of a deliberate, measurable motion with its own process, capacity plan, and target list. The reason is simple: expansion is harder to measure than new business. There's no clean CAC payback formula for convincing your CFO to fund more CSM...

Michael Maimone walked into Lucid Link expecting to build on top of what was already there. The company had product-market fit, real market pull, and was growing. But when he looked under the hood, there was no segmentation model, no defined ICP tied to actual data, and reps were fishing in each other's ponds. Junior reps were working enterprise accounts while strategic reps chased mid-market deal...

Amy Konary coined the term "SaaS" when she was an industry analyst at IDC. She sized the first market at $40 million, watched it grow into a multi-hundred-billion-dollar industry, and spent nearly two decades advising the companies that built it. Now she's watching the same dynamics that killed the perpetual license model start to eat SaaS from the inside: 6x renewal increases that customers won't...

Every CRO knows that retaining customers is cheaper than acquiring new ones. But when it comes time to ask the CFO for budget to hire more CSMs or invest in retention programs, the conversation stalls. New business ROI is simple math. Customer success ROI is not. The numbers are always moving, attribution is murky, and the CFO is looking at you wondering whether that $500K spend is actually going...

Mark Kosoglow has built revenue organizations at every stage; from a 100% commission territory seller to first employee at Outreach to CRO at Catalyst to founding Operator. Now eight months into running revenue at Docebo, a publicly traded LMS company doing $230M ARR, he's applying everything he's learned across both sides of the bow tie. In this episode of CRO Stories, Rachael Bueckert si...

Jessica Robertson is 11 months into her first CRO role and she's building a go-to-market engine around something most revenue leaders talk about but never operationalize: relationships. After scaling Accessibly from under $10M to $50M as VP of Sales, she watched the outbound playbook she'd relied on for years stop working. The 1:1 capacity math that used to be predictable fell apart, and n...

Every CRO has been here: you ask your ops team for a read on the pipeline and the numbers come back looking reasonable on the surface. But then you dig in and one rep is sitting at an 85% close rate while another is at 10%. Half the pipeline is zombie deals past twice the average sales cycle that nobody wants to mark as lost. The blended metrics look passable, but they're masking what's ac...

This episode is a guest appearance by Eddie Reynolds , CEO of Union Square Consulting, on the FP&A Today podcast. Follow the FP&A Today Podcast on Spotify here and Apple Podcasts here . Eddie opens up about the often-fraught relationship between CFOs and CROs, drawing on his journey from banking and private equity to account executive at Salesforce, where the company forecast within 5% acc...

Before you fire your SDR leader, swap out your data provider, or change your cadence software, have you actually looked at what's underneath? Most of the time when an SDR team isn't hitting targets, the problem isn't the people. It's that the operational foundation was never built in the first place. No defined ICP, no capacity-based territories, no step-by-step process that reps can actually exec...

Before Stevie Case was a CRO, she was the first female professional gamer—dropping out of college to compete in Quake and eventually building games in the early days of the shooter universe. That competitive drive never left. It's the same thing that made her the number one enterprise seller globally at Twilio, and it's what's driven her nearly four-year run as CRO at Vanta, where she&...