Revenue Mavericks

Justin Shriber
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The podcast for revenue leaders who need full visibility, disciplined execution, and signal-driven decisions to win. Hosted by Justin Shriber, CEO of Terret, each episode features operators who've mastered the art of identifying risk early, capitalizing on emerging opportunities, and driving predictable growth at the edge of complexity. Discover the strategies and mindset shifts that separate high-performing revenue engines from the rest. If you're ready to operate with precision under pressure, this is your show.

  1. 4d ago

    S3E5: Why the Best Sales Leaders Never Waited for Permission to Start -- Lessons from CRO @ Blackbird AI, Anna Osborn

    Anna Osborn started working at 9 years old. Growing up in a household where finances were a constant source of tension, she decided early that she would never depend on someone else for financial security. That drive took her from babysitting jobs on Cape Cod to the Sydney Olympics at 14, and eventually into executive sales leadership at Thomson Reuters, Kroll, Exeger, and now Blackbird AI. Before becoming CRO at Blackbird AI, a narrative intelligence platform that helps organizations detect and respond to disinformation campaigns, Anna learned something that reshaped her entire career: getting fired can be the best thing that ever happens to you. In this episode, Anna and Justin get into: Why growing up around financial instability became the foundation for a career in revenue leadershipThe moment she was escorted out by security after maternity leave, and how it broke open a version of imposter syndrome she'd never experienced beforeWhat it means to recognize that your most authentic professional self isn't for every company at every stage, and why that realization is freeing rather than limitingHer philosophy of "diabolical focus" in startups, and why finishing one thing before starting the next is the discipline most early-stage teams lackHow leading a team at Blackbird AI, a category-creating company in narrative intelligence, requires teaching customers skills they've never needed before Anna is currently the Chief Revenue Officer at Blackbird AI. She previously served as CRO at Exeger and held leadership roles at Kroll and Thomson Reuters. She's a single mom of three, a self-described four-seasons person who recently traded Manhattan for the suburbs, and someone who has been building teams and chasing outcomes since she was old enough to ride a ten-speed up and down hills for $25 a week.

  2. Sep 23

    S3E4: Why the Best Revenue Leaders Build From Scratch -- Lessons from VP Revenue Operations @ Replit, Quoc Tran

    Quoc Tran has built revenue operations teams from the ground up at Autodesk, Zendesk, Okta, and now Replit. But the playbook he keeps coming back to didn't start in enterprise software. It started at a dry cleaner in the Bay Area, where his mom remembered every customer by name and never took a day off for 20 years. In this episode of Revenue Mavericks, Quoc sits down with Justin Shriber to talk about what it actually takes to build a go-to-market motion from zero, why process has to come before the AI layer, and how the best RevOps leaders will stay relevant as automation reshapes the function. Key moments from this conversation: Why Quoc's mom running a dry cleaner for 35 years taught him more about customer experience than any enterprise roleWhat happened when he landed in Singapore as a first-time manager and his boss told him "you'll figure it out"The case for two weekly 1:1s with every direct report, and why separating work talk from development talk changes the dynamicWhy layering AI onto a team without established processes creates chaos instead of efficiencyHow he built comp plans, territories, and quotas at Replit in his first month, then migrated from HubSpot to Salesforce in three monthsWhere he sees the RevOps function heading in five years, and why the value shifts from execution to asking the right questions Quoc Tran is VP of Revenue Operations at Replit. He previously held revenue operations leadership roles at Okta, Zendesk, and Autodesk, where he spent 11 years including a stint building out the Asia Pacific team from Singapore.

  3. Sep 16

    S3E3: Why the Best Sales Leaders Run Their Quarter Like a Semester -- Lessons from Fractional CRO & GTM Advisor, Lesley Young

    What if the best operating model for a sales team isn't a sales playbook at all, but a college syllabus? Lesley Young has led go-to-market teams at Oracle, Informatica, Box, and Fox. Now, as a Fractional CRO and GTM Advisor, she's bringing a framework to the companies she works with that reframes how leaders think about the quarter: treat it like a semester. Give your people a syllabus. Tell them what week one looks like, what's expected by mid-month two, and what the final stretch demands. Because the teams that struggle most aren't missing talent. They're missing clarity. In this episode, Lesley and Justin get into: Why Lesley's "Semester Mindset" gives sales teams the structure they need to do their best work, and why most leaders skip this step entirelyHer Three Ps framework (Pipeline, Process, People) and how it forces leaders to confront whether they're actually running a business or just reacting to oneThe deal she was sure she'd won, the executive override that killed it, and the painful lesson about what a real champion actually looks likeWhy a board member at Informatica told her to stop thinking like a sales leader and start learning the P&L, and how that advice changed the trajectory of her careerHow she used data to coach a rep at Box who hit her number every quarter but had no idea how she got there, and why MEDPIC is a deal testing tool, not a forecasting toolThe personal hardships that taught her the most important word in leadership: choice Lesley doesn't deal in theory. Every framework she teaches was built from a moment where something went wrong and she had to figure out what to do next.

  4. Sep 9

    S3E2: Why the Best Sales Leaders Are Measured When They Leave the Room -- Lessons from CRO @ EDB, Hervé Timsit

    Hervé Timsit believes the quality of a leader is measured when the leader is no longer in the room. If your team can't operate the way you'd want them to without you standing over them, something is broken upstream. For Hervé, fixing that starts long before anyone runs a deal. It starts with who you hire. When someone asks what he does for a living, he doesn't say he's a CRO. He says his job is to find people. And his process for finding them looks nothing like a traditional interview. He doesn't ask about quota attainment or what you did at your last company. He asks where you were born, what your goals are in life, what you value. He's reading the person, not the resume. That instinct comes from growing up in Casablanca, Morocco, where Hervé attended a French public school filled with every culture, religion, and economic background imaginable. He learned early how to see through cultural formality and understand who someone really is underneath it. That skill became the foundation of a career spent selling across three continents. In this episode, Hervé sits down with Justin Shriber to talk about: Why he still personally interviews sales reps three and four levels below him, and the paranoia that drives itThe four criteria he uses to evaluate every hire, borrowed from John McMahon, and why integrity is the one he refuses to bend onWhat working alongside McMahon's crew at BMC after the BladeLogic acquisition taught him about actionable frameworks versus theoryWhy you cannot motivate people, you can only create the conditions where their own motivation thrives, and why that's the whole job once you've found the right person Hervé Timsit is CRO at EDB, where he leads the global sales organization. His career spans three decades in enterprise software, from building and selling three companies in France to leading international sales at BMC and EMC, before returning to high-growth PE-backed environments. He ran a factory of 50 people at age 23, and he's been finding the right people ever since.

  5. Sep 2

    S3E1: Why the Best Sales Leaders See Potential Others Miss -- Lessons from CRO @ MarkMonitor, Greg Davis

    Greg Davis didn't plan on a career in sales. He planned on a career in finance, maybe bond trading. But before any of that, he was a junior college soccer player who wanted a Division I scholarship and had no connections to get one. So he did what most 17-year-olds wouldn't: he pulled out a college handbook, wrote 200 handwritten letters to coaches, cold-called 50 more, and tracked every conversation on a spreadsheet he built himself. One coach happened to need a player at his exact position. Timing met preparation, and Greg landed at the University of Denver. He didn't realize it at the time, but he was running a full sales process before he'd ever heard the term. In this episode, Greg sits down with Justin Shriber to talk about: How a self-taught outbound system at age 17 became the foundation for a career leading commercial organizations at Thomson Reuters, LinkedIn, Dow Jones, and now MarkMonitorWhy leaders must see potential in people that those people don't yet see in themselves, and the Thomson Reuters promotion that almost didn't happenThe "in the ring" coaching philosophy Greg carries from training UFC fighters to managing sales teams: guide from the corner, but let your people fight their own battlesWhy removing friction for individual contributors matters more than any framework you put on a wallThe quote that's stayed with him for 20 years: "When you're interested, you become interesting" Greg Davis is CRO at MarkMonitor, where he leads the full commercial organization across sales, marketing, strategy, RevOps, and partnerships. Before MarkMonitor, he spent nearly a decade at Thomson Reuters rising from IC to Head of Americas, followed by leadership roles at LinkedIn and Dow Jones. Outside the office, he coaches fighters in mixed martial arts, a discipline that shapes how he thinks about leadership every day.

  6. Jul 23

    S2E10: Why the Best Sales Leaders Think Like C-Level Execs -- Lessons from MD @ MAC Venture Group, Bruce Chesebrough

    Bruce Chesebrough has spent decades building, scaling, and diagnosing sales organizations. As a CRO, he grew Corbis from $15 million to $250 million in revenue, expanded the company from 3 offices to 15 across the globe, and built a 450-person commercial team along the way. Today, as Managing Director at MAC Venture Group, he works with private equity portfolio companies to assess go-to-market performance and architect turnarounds. In this episode, Bruce sits down with Justin Shriber to unpack the frameworks he keeps coming back to after all these years, and why he believes sales has gotten unnecessarily complex. Takeaways from this conversation: How an MBA gave Bruce the confidence and toolkit to sit across from C-level buyers as a peer, not a vendor, and why that shift changes everything about how you sellThe career trade-off most people get wrong: why Bruce says to always prioritize the opportunity over the paycheck, and how to evaluate the risk of going from a big company to a smaller oneThe "Discipline of Market Leaders" framework Bruce uses to diagnose every portfolio company he walks into, and why most companies fail because they try to occupy all three strategic squares instead of picking oneFive levers of growth that Bruce applies to every commercial transformation: upsell/cross-sell, new customer acquisition, retention, price optimization, and operational efficiencyWhy sales organizations can only absorb two or three initiatives at a time, and what happens when leaders try to pour a Big Gulp into a Dixie Cup Bruce's advice is grounded in pattern recognition across dozens of companies and decades of experience. Whether you're a seller trying to break into the C-suite or a leader trying to simplify your go-to-market, this conversation will challenge you to strip things back to what actually works.

  7. Jul 8

    S2E9: Why the Best Sales Leaders Ride at Dawn: Lessons from CRO @ Grafana Labs, Dave Kranowitz

    Dave Kranowitz was 18 years old, sitting in a lightweight boat, falling behind against Coast Guard in a college rowing race. He could feel the boat start to get lighter. He took the stroke rate up to 35, then 38. The crew was redlining, but something was happening. They started moving through the other boat. When it was over, the coach came over, shook their hands, and the losing team handed over their jerseys. Dave's crew wore them around campus. That was 34 years ago. Dave still talks about the feeling. In rowing, they call it "swing," the rare moment when every blade enters and exits the water in perfect unison and the boat lifts underneath you. It's fleeting, it's earned, and it compounds. Dave has spent his entire career in sales leadership trying to build organizations that find it. Today, Dave is CRO at Grafana Labs, where he's led revenue for nearly seven years through one of the fastest growth runs in enterprise software. Before that, he held sales leadership roles at Turbonomic and Dynatrace, spending two decades in the observability space. In this conversation, he shares what rowing taught him about competitive discipline, two leadership stories that shaped his entire philosophy, and a weekly practice he's maintained for 15 years that most CROs would never think to try. What we cover: Why rowers chase a feeling called "swing," and why the best sales orgs are doing the same thing without knowing itThe last-day-of-quarter phone call where Dave's boss said "How could you be so dumb?" and hung up, and what Dave vowed to do differently when he became a leaderThe voicemail from a VP he barely knew that Dave kept on his phone for years, and how it changed the way he recognizes his own teamTeam sale: Grafana's ego-less selling motion where anyone in the company, from SDR to board member, can jump into a dealThe weekly company email Dave has written for 15 years across three companies, and why his Donner Party email is still referenced years laterWhy vulnerability and humility aren't soft skills but the fastest path to trust with your team, your board, and your customers This conversation is for sales leaders who believe the best orgs aren't built on individual heroics but on teams that train together, compete together, and occasionally feel the boat get light underneath them.

  8. Jul 1

    S2E8: Why the Best Sales Leaders Work for Their Reps, Not the Other Way Around -- Lessons from CRO @ Talkdesk, Al Caravelli

    Al Caravelli was sitting across from John Wooden at a Denny's in Encino. Not as a basketball player nor as a student. As a rugby coach who had just finished a 1-11-1 season leading the US Men's National Sevens team and was ready to quit. Twenty years earlier, Al had been a freshman on UCLA's 1985 NCAA soccer championship squad, the first team to win it and still the only one to go undefeated. At the celebration banquet, Wooden handed him a business card and said to call if he ever needed anything. Al tucked it in a drawer and forgot about it. Two decades later, after a brutal season coaching international rugby, his wife told him to stop feeling sorry for himself and do something about it. He started cleaning out a drawer and found the card. He called. Wooden picked up and remembered him immediately. They sat together for three and a half hours. Wooden told him two things: define success on your own terms, and never waver from the fundamentals. The score will take care of itself. Al took that advice back to the rugby pitch. Over the next seven years, his teams recorded historic first wins over England, New Zealand, Australia, South Africa, Scotland, Wales, and Fiji. Then he carried that same philosophy into enterprise sales. Today, as Chief Revenue Officer at Talkdesk, Al runs his organization like a coaching staff. First-line leaders at a 4:1 ratio. Enablement as a non-negotiable foundation. A culture where leaders hire people better than themselves and treat the role as service to the people they manage, not the other way around. In this episode: Why Al's father made him do push-ups and make his bed at four years old, and how that became a lifelong operating systemThe John Wooden conversation that turned a losing season into seven years of historic winsWhy first-line sales managers are the hardest role in the org and how to set them up to succeedHow servant leadership actually works in practice, not just as a buzzwordWhat Mark Cuban's prediction about the return of the enterprise AE means for the future CROWhy Al logs road miles Monday through Friday and what that signals to his teamAl Caravelli is one of the rare leaders who built his playbook on a rugby pitch, refined it with a coaching legend, and runs it every day at scale.

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About

The podcast for revenue leaders who need full visibility, disciplined execution, and signal-driven decisions to win. Hosted by Justin Shriber, CEO of Terret, each episode features operators who've mastered the art of identifying risk early, capitalizing on emerging opportunities, and driving predictable growth at the edge of complexity. Discover the strategies and mindset shifts that separate high-performing revenue engines from the rest. If you're ready to operate with precision under pressure, this is your show.

Information

  • Creator
    Justin Shriber
  • Years Active
    2026
  • Episodes
    25
  • Rating
    Clean
  • Copyright
    © Justin Shriber
  • Show Website
    Revenue Mavericks