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

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 Whispered's 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 Braze's 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 GoTo's 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

S2E4: Why the Best Sales Leaders Learn How to Forget -- Lessons from Braintrust's Bryan Cox

In his own words, Bryan Cox was just an average college tennis player. His record was roughly .500. But in his own mind, he was winning all the time. That disconnect wasn't delusion. It was a skill. Somewhere between the thousands of points lost and the matches that didn't go his way, Bryan had taught himself something most people never figure out: how to forget. Not how to ignore failure. How to metabolize it, extract the lesson, and then let it go so it doesn't weigh you down the next time you step on the court. Or the next time a deal worth a third of your quarterly forecast evaporates overnight. That discipline has carried Bryan from his early career through Flexera and Grafana Labs to his current role as Vice President of Worldwide Sales at Braintrust, one of the fastest-rising AI companies in enterprise tech. This past quarter, he watched a massive deal disappear at the start of Q2 through no fault of his team. His take: if you've put in maximum effort and exhausted every angle, you can live with the outcome. What you can't live with is knowing you left something on the table. The team finished well above their number anyway, and Bryan says he's prouder of that than any single deal closing. That resilience traces back to a culture Bryan has been building deliberately since making the leap from individual contributor to sales leader. A colleague at Grafana told him bluntly that he was talented but "living in a small pond." Bryan took the hit, moved to Grafana, and discovered what elite execution actually looked like. But the bigger shift came when he stopped optimizing for his own performance and started asking why he was doing the work in the first place. The answer was coaching. Seeing other people flourish. His framework for running the sales org is borrowed from Steve Kerr's Golden State Warriors. Bryan calls it the motion offense. When the team reaches a certain stage of an opportunity, everyone circles it and starts passing the ball. He sends a note. An SE pulls someone aside to talk through technical requirements. Someone meets the prospect for coffee. The board gets engaged. Field marketing steps in. No one plays hero ball. Everyone touches the rock. It only works if every function operates at a high level and if you hire people who genuinely want to play within a system. Bryan's less interested in the LeBron types and more interested in players who move without the ball. What we cover: * Why learning to forget is the most underrated skill in sales leadership * How losing a deal worth a third of the quarter's forecast became a point of pride * The moment Bryan realized he was "living in a small pond" and what changed when he left * Why Braintrust runs under capacity on purpose and lets product-market fit drive growth * The motion offense: how Bryan's team circles opportunities like the Warriors pass the ball * Why having a technical founder in a technical space is non-negotiable when choosing where to work This conversation is for sales leaders who believe the best teams are built on resilience, selflessness, and knowing when to pass the ball.