Revenue Problem Solvers

Operationalize
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Revenue Problem Solvers is the sales and revenue leadership podcast for founders, executives, and operators who are done with generic advice. One question drives every conversation: what's the most significant revenue initiative you've ever led, or the most challenging problem you've solved or are currently solving? The conversations span the entire GTM function from sales, marketing, ops, CS, product, leadership, and AI. Real stories. Specific lessons. No filler. New episodes weekly.

  1. 3d ago

    Your Best Growth Quarter Could Be Hiding Your Next Churn Wave

    Your best quarter for new logos could be setting up your worst quarter for churn. Christina Singh has spent almost 20 years on the post-sale side of growth-stage SaaS. She helped scale UserTesting from $60M to $110M, and grew Split.io from $8M to $35M ARR while keeping retention above 90% for 7 straight quarters. Her take: most churn starts as conflict inside your own company, long before a customer cancels. Karl and Christina get into what happens to your ideal customer profile when growth takes off. Deals close outside the ICP while everyone celebrates. A feature gets built for one big logo and lands on the roadmap. Early reps and new hires sell to different customers. And when the ICP shifts, nobody plans for the customers it left behind. You'll hear why Christina's angriest customers are her favorite ones, how a customer maturity model at Split.io gave sales and customer success one shared playbook, and how to take a pattern you've spotted to your exec team so they act on it. Then take her Monday-morning ICP audit: bucket every current customer and see where the revenue really sits. Find Christina on LinkedIn https://www.linkedin.com/in/christinawongsingh/ and at https://www.linkedin.com/company/norastudiosf/ This episode is sponsored by Docket. Wrong-fit customers often start with an unqualified conversation. Docket talks to your website visitors in real time, qualifies them on the spot, and books meetings with full context. Visit docket.io and mention the show for a special rate.

    Your Best Growth Quarter Could Be Hiding Your Next Churn Wave

  2. Sep 25

    Is Your Value Prop Losing You Deals? | Matt Darrow

    Your team is proud of how the product works. Your buyers might be tuning it out. Matt Darrow, co-founder and CEO of Vivun, learned that the hard way. His team built a sales reasoning model they say beats the frontier labs at a tenth of the cost. Buyers shrugged. Then they stopped explaining the tech and started talking about what it made possible: expertise, live, on the calls where deals are won or lost. Before Vivun, Matt helped build Zuora's global pre-sales org through IPO, then rebuilt a product line's value proposition and doubled its ARR. When AI reshaped his market, he took his board a plan to start over and relaunched with Hiro, an AI sales teammate. Karl and Matt get into the label that pushed away users and buyers at the same time, why a new value prop needs its own name instead of a rebrand, why selling your old and new product together splits your company in two, and how pricing can teach buyers what to value. If you're pitching something new to a market that remembers the old you, this one is worth your time. Connect with Matt on LinkedIn https://www.linkedin.com/in/matthewdarrow/) and learn more at vivun.com. This episode is sponsored by Docket. Like Matt's point about value getting decided in the moment, Docket talks to your website visitors in real time, qualifies them in the conversation, and books meetings with full context. Visit docket.io and mention the show for a special rate.

    Is Your Value Prop Losing You Deals? | Matt Darrow

  3. Sep 18

    He Wouldn't Pay for the Product He Was Hired to Run | Doug Camplejohn

    Doug Camplejohn was hired to run a quarter-billion-dollar product. His honest opinion of it? He wouldn't have paid for it himself. Doug has founded four companies, three of them acquired, including Fliptop, acquired by LinkedIn in 2015. LinkedIn brought him in to run product for Sales Navigator. He used it, wasn't impressed, and told the CEO exactly that, even though the business was already worth $250 million. He rebuilt it anyway. Sales Navigator is now a billion-dollar product. He did it again at Salesforce running Sales Cloud. Now he's doing it a third time, on purpose, with Coffee.ai, an AI-native CRM built for companies stuck on Salesforce or HubSpot who can't rip the system out overnight. In this episode, Doug breaks down how he diagnosed what was actually broken instead of guessing: a customer roadshow, a rotating sales advisory council, and a metric he built that predicted churn with 5x accuracy based on what a user did in their first two weeks. He also covers why LinkedIn moved to a quarterly release cadence and how to get sales and product teams working like co-CEOs. This episode is brought to you by @DocketIO, the inbound demand agent that qualifies your website visitors in real time and delivers booked meetings with full context. Visit docket.io and mention the show for a special rate. Find Doug on LinkedIn or at coffee.ai This is the Revenue Problem Solvers Podcast, for revenue leaders who aren't afraid to say they're stuck and need a real answer.

    He Wouldn't Pay for the Product He Was Hired to Run | Doug Camplejohn

  4. Sep 11

    Why Your Sales Team Might Be Costing You the Deal | John Ravaris

    A cleaning company got named as a competitive threat in the industry's largest player's own SEC filing. Three years earlier, they were just another vendor competing on price. John Ravaris explains what changed. He stopped letting salespeople make promises and started putting operations people in the room with clients instead, the ones actually doing the work. Revenue doubled. Then the market's biggest competitor had to respond. In this conversation, John breaks down the discovery process that uncovered why clients were really unhappy (it wasn't about the service quality), what "transparent metric-based service" actually means, and why most value propositions are just corporate speak with no backup behind it. If your sales team is the only group in your company who can articulate what makes you different, this episode will change how you think about who should be selling. John is Chief Growth Officer at Flow Control Management, serving as CRO across three portfolio companies at once, and the author of the new book Define Value, Drive Growth. This episode is brought to you by Docket, the inbound demand agent that talks to your website visitors in real time and delivers booked meetings with full context. Visit Docket and mention the Revenue Problem Solvers Podcast for a special rate.

    Why Your Sales Team Might Be Costing You the Deal | John Ravaris

  5. Sep 4

    From NFL Locker Room to Tech Founder | Mark Clayton

    One in three headphones in his first Kickstarter batch came back with a virus on them. That was the moment Mark Clayton, a former first-round NFL draft pick, almost walked away from the company he built out of a broken pair of headphones. Mark spent 7 seasons in the NFL with the Baltimore Ravens and St. Louis Rams before starting LIVV Audio with zero background in consumer electronics. In this conversation with Karl Ortmanns, he breaks down how a personal training problem turned into a headband redesign, why a factory defect forced a full product recall, and what it costs to learn an entirely new industry from scratch. If you are building something outside your area of expertise, or navigating a major identity shift after a high-performance career, this episode is for you. Mark gets specific about manufacturer selection, waterproofing tradeoffs, and the mentorship that helped him avoid an even more expensive education. This episode is brought to you by Docket, the inbound demand agent that talks to every visitor to your website in real time, answers real product questions, and qualifies them inside the conversation. What lands in your CRM is not another MQL, it is a booked meeting with full context attached. Visit docket.io and mention the show for a special rate. Revenue Problem Solvers is built for revenue leaders who are not afraid to say they are stuck and need a real answer. Subscribe for more conversations on solving the revenue problems that actually matter.

    From NFL Locker Room to Tech Founder | Mark Clayton

  6. Aug 28

    The Brand Metric Your CEO Doesn't Know Exists | Sandra Rand

    Your CEO just told you brand can't be measured. Sandra Rand has heard that line more times than she can count, and she's done letting it slide. Sandra is the VP of Marketing at Spreetail, one of the largest e-commerce operators in the country. Before that, she led a rebrand at Thrasio that drove a 168% increase in lead flow, and grew user acquisition by 24% at GETIDA with marketing responsible for over 70% of pipeline. She's not guessing about brand and revenue being connected. She's got the receipts. In this conversation, Sandra breaks down why brand isn't the warm and fuzzy afterthought most executives treat it as, and why it's actually what your revenue is downstream of. She and Karl get into the Stanley Cup viral moment that everyone remembers but nobody's actually unpacked, the Heineken Olympics story that almost became a PR disaster, and the specific metrics you can use when a CMO demands proof that brand spend is working. If you've ever sat in a room and struggled to defend a brand budget against a wall of performance marketing dashboards, this episode gives you the language and the framework to make that case, and to actually prove it's working six months later. This episode is brought to you by Virtual Causeway. If Sandra's point about winning your buyer before they're even in-market resonated, that's exactly what Virtual Causeway helps B2B companies do. They get you found earlier in the buying process by the right people through the right channels. Visit virtualcauseway.com and mention the show for a special rate. This is the Revenue Problem Solvers Podcast, built for revenue leaders who aren't afraid to say they're stuck.

    The Brand Metric Your CEO Doesn't Know Exists | Sandra Rand

  7. Aug 21

    How to Build a Demand Generation Engine From Scratch | Brydon McMillen

    Most companies build a demand gen engine, hit their number, and walk away. Brydon McMillen says that's exactly the moment it starts to break. Brydon's path here wasn't typical. He came up drafting electrical diagrams for billion-dollar energy projects with a chemical engineering degree, until a co-op placement handed him a broken chatbot nobody else wanted. He rebuilt it, drove a 352% increase in qualified leads, and pivoted into paid search for good. From building an agency's PPC department from scratch to founding his own shop, Plateau PPC, and hitting $26,000 a month in recurring revenue in just three months, Brydon has built demand generation from zero more times than most people do in a career. In this conversation, Brydon and Karl dig into what it actually means to build a demand gen engine, why "strangers buying from you" is the real finish line, and how AI Overviews and disappearing cookie data have quietly changed the rules of paid search. Brydon breaks down Broad Match, AI Max, and Performance Max in plain language, and shares the two things any advertiser should check this week to stop wasting ad spend. Want to connect with Brydon or see what he's building? Find him on LinkedIn or check out Plateau PPC. This episode is brought to you by Virtual Causeway. Visit virtualcauseway.com and mention the show for a special rate. Revenue Problem Solvers Podcast is for revenue leaders who aren't afraid to say they're stuck, and want a real answer.

    How to Build a Demand Generation Engine From Scratch | Brydon McMillen

  8. Aug 14

    How Bad Hiring Creates Customer Churn | Mark Grimwood

    There's a job title at Salesforce that doesn't exist anywhere else, and once you hear what it does, you'll wonder why every company doesn't have one. Mark Grimwood spent almost two decades at Salesforce, rising from corporate recruiter to SVP of Recruiting for the company's entire global sales organization. Along the way he held a role most people have never seen: VP of Recruiting for Global Customer Success. Recruiting and customer success, one job. Mark and Karl dig into a question most revenue leaders never ask: is hiring actually the first stage of customer success, not just a department that feeds it? They cover where AI genuinely helps in recruiting and where it still falls short, what quality of hire really means beyond a vanity metric, and a live diagnostic for one of the most common blind spots in sales leadership: figuring out whether a struggling rep is a bad hire or just sitting on a bad book of business. Mark also breaks down a redeployment number most companies never track, and why high turnover might actually signal a healthy organization, not a broken one. If you lead a sales team, sit in RevOps, or run talent acquisition, this one will change how you think about your next hire. Connect with Mark on LinkedIn, he's active there and always up for a conversation on this stuff. This episode is brought to you by Virtual Causeway. Visit virtualcauseway.com and mention the show for a special rate.

    How Bad Hiring Creates Customer Churn | Mark Grimwood
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About

Revenue Problem Solvers is the sales and revenue leadership podcast for founders, executives, and operators who are done with generic advice. One question drives every conversation: what's the most significant revenue initiative you've ever led, or the most challenging problem you've solved or are currently solving? The conversations span the entire GTM function from sales, marketing, ops, CS, product, leadership, and AI. Real stories. Specific lessons. No filler. New episodes weekly.

Information

  • Creator
    Operationalize
  • Years Active
    2025 - 2026
  • Episodes
    67
  • Rating
    Explicit
  • Copyright
    © Operationalize
  • Show Website
    Revenue Problem Solvers