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

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 it * The 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 leader * The 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 team * Team sale: Grafana's ego-less selling motion where anyone in the company, from SDR to board member, can jump into a deal * The weekly company email Dave has written for 15 years across three companies, and why his Donner Party email is still referenced years later * Why 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.

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 system * The John Wooden conversation that turned a losing season into seven years of historic wins * Why first-line sales managers are the hardest role in the org and how to set them up to succeed * How servant leadership actually works in practice, not just as a buzzword * What Mark Cuban's prediction about the return of the enterprise AE means for the future CRO * Why Al logs road miles Monday through Friday and what that signals to his team Al 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.

S2E7: Why the Best RevOps Leaders Ask One Question Before Taking Any Job -- Lessons from Founder of Whispered, Andy Mowat

Andy Mowat was sitting in a room with a PE investor in 2008, trying to figure out whether to buy a background screening company. He wasn't sure if the market was any good. The investor got up, walked out, and came back with a whiteboard sketch of a classic S-curve. Then he told Andy to ask one question: of the last hundred customers you've added, how many are brand new to what you do versus switching from a competitor? Andy asked the CEO. The answer was immediate. "We switch everybody." He walked away. And that single question became the filter Andy has used to evaluate every company he's joined since, including Carta, Box, Upwork, and Culture Amp, four unicorns where he built and led RevOps through periods of breakout growth. But the episode isn't just about picking winners. Andy graduated from Stanford Business School in 2001, straight into the dot-com collapse. No job for six to nine months. Princeton degree, investment banking, private equity background, and none of it mattered. That stretch of unemployment forced him to learn how to network with intention, how to help people without an agenda, and how to build the kind of social capital that compounds quietly for decades. That identity, the connector who keeps a weekly tally of how many introductions he makes (somewhere between 50 and 100), is what eventually led him to found Whispered, a platform that helps senior GTM executives find unposted roles and get plugged into relevant events. The conversation also goes deep on a question Justin has been watching closely: whether RevOps leaders are ready for the CRO seat. Andy's answer is nuanced. They understand the full go-to-market motion better than almost anyone. But the dividing line is willingness to own a number. If you're not ready to carry that weight, the C-suite path closes. And in the final segment, Andy makes the case for customer advocacy as the most underutilized growth channel in B2B. Not in theory, but in practice: Typeforms that capture sentiment in seconds, specific asks instead of generic G2 review requests, and a company-wide metric around advocacy that goes well beyond the marketing team. In this episode: * The one S-curve question that tells you whether a company is breaking out or flattening * Why the dot-com bust taught Andy that networking with generosity is the most durable career skill * How he evaluates any role: who you work for, company trajectory, and whether the CEO is a good person * The case for RevOps leaders moving into the CRO seat, and the one prerequisite most of them resist * Why customer advocacy should be a company-wide metric, not a marketing-team initiative * The Whispered model: how senior execs are co-searching for roles in ways that didn't exist five years ago

S2E6: Why the Best Sales Leaders Shake the Nest -- Lessons from CRO @ Braze, Ed McDonnell

Ed McDonnell was three weeks into ninth grade at an all-boys Catholic high school in New York when his mother told him they were moving to Denver. She'd taken a new role as director of nursing education. Ed left behind every friend he'd ever known, enrolled in another all-boys Catholic school in Colorado, and started over. He made new friends. He figured out a new culture. He found his footing. Then, midway through junior year, his mother took a VP of nursing job back in New York — and they moved again. Three high schools. Four years. Two cross-country relocations. And a 14-to-17-year-old learning in real time how to walk into a room full of strangers and build relationships from scratch. That ability to lead through change didn't just become a skill for Ed. It became his operating system. Today, Ed is the Chief Revenue Officer at Braze, where the company recently posted an $821 million quarterly revenue run rate with nearly 30% year-over-year growth and rising net dollar retention. Before Braze, he held the CRO seat at Asana, spent more than a decade helping build the marketing practice at Salesforce, and cut his teeth in enterprise software at Eloqua before its acquisition by Oracle. But this conversation isn't about a résumé. It's about a leadership philosophy forged in disruption. Ed talks about the advice his father — a New York police officer — gave him before college that still guides how he builds relationships today. He shares the career moment where getting let go became the catalyst for reinventing himself. And he walks through the 6P's, the framework he uses to run every quarter: People, Pipeline, Programs, Process, Performance, and Possibilities. In this episode: * The "Be the USA Today" advice from his father that changed how Ed connects with people * How getting let go became the most important inflection point of his career * The 6P's framework Ed uses to run the revenue engine at Braze * Why the best performance cultures start with leadership being in the work, not above it * How Braze maintains a performance mindset while celebrating wins at every level * The operating rhythm that keeps Ed's organization accountable quarter after quarter This episode is for sales leaders who believe that resilience isn't something you learn in a workshop, it's something that gets forged every time the nest gets shaken.

S2E5: Why the Best Sales Leaders Know Hard Things Take Time -- Lessons from CRO @ GoTo, Peter Mahoney

One of the most important lessons Peter Mahoney carries throughout his career was inspired by his daughter Marianne. She was born with significant special needs, and in that moment, everything Peter expected about his life shifted. But Marianne set a goal for herself when she was young: she wanted to live independently. It took ten years of work. And about two years ago, she got there. Watching that journey taught Peter something he's never let go of - the most important things take time and persistence. There are no shortcuts to the things that actually matter. You set a direction, you keep showing up, and you trust the process even when the progress is slow. It also put everything else in perspective. Today Peter is the Chief Commercial Officer at GoTo, a billion-dollar company going through significant transformation. People around him ask all the time why he isn't more stressed. His answer is honest: he's seen what real hard looks like. A tough quarter or a deal that falls apart matters, but it's not the kind of hard that should rattle you. That calm isn't detachment, it's clarity. And it changes how he leads, how he makes decisions, and how the people around him show up under pressure. That same patience shaped his career. Peter has never been afraid to take a step backward to move forward. From leaving a 30-person team to start over as an individual contributor, to spending a full year in IBM's training program before he ever sold anything. The moves looked unconventional. They were deliberate. In this episode: * The lesson Marianne taught Peter about persistence, patience, and keeping perspective * Why he never panics under pressure, and how that steadiness shapes the teams around him * The Sunday reflection system where he maps his week against his goals and writes down the honest truth * Why he gave up a leadership role to become an IC product manager, and how that detour built his path to CEO * His philosophy on AI: give me the framework, but let me do the thinking