LevelUp Podcast Episodes

In this episode of Prospecting Pros, John and Chris chat with Jason Bay, founder of Outbound Squad. Jason breaks down how he helps sales teams turn everyday call data into insights that actually drive revenue. He explains how the best messaging doesn’t come from guesswork, but from real customer conversations, and why teams should treat call recordings like a goldmine for training and enablement. Jason also talks about the growing role of AI in sales and where it can genuinely make an impact. He shares how tools that enrich data, summarize calls, and make coaching easier are game changers, while full “AI SDR” replacements still have a long way to go. The group also digs into what’s working in outbound today, from tighter ICPs and stronger offers to smaller, more personal in-person events that drive trust and connection.

In this episode of Prospecting Pros, John and Chris talk with Scott Lease, a sales leader, consultant, and founder of the Surf and Sales Summit. Scott has spent more than two decades building sales teams and helping create multiple unicorns and successful exits. He’s known for stepping into the toughest stage of a company’s journey, taking startups from zero to one hundred, and thriving under the pressure that comes with it. Scott shares why he’s drawn to early-stage work, what he looks for in hiring, and how grit and life experience matter more than polished resumes. He explains why the best sellers combine strategy with hard work and why they never stop looking for the next challenge. The conversation also covers pipeline strategies for 2025, including referral networks, content that builds trust, and small in-person events, along with why saying no is sometimes the smartest move.

In this episode of Prospecting Pros, John sits down with Mark Osborne, founder of Modern Revenue Strategies and a veteran marketer who’s worked with everyone from scrappy startups to Fortune 500 brands. Mark shares how his early experiments in the 90s with band promotion and email lists led to a career at record labels, radio, and eventually running major marketing programs for companies like Nike and Hulu. Named a “marketing technology trailblazer” by Ad Age, Mark explains why chasing growth hacks and shiny tools rarely works. Instead, he shows why strategy and process must come first, with tools serving to accelerate what’s already working. He discusses why many companies stall without a clear ICP, how to avoid wasted spend, and why systems actually give leaders more freedom. Mark also talks about his work as a fractional CRO and why B2B systems “set you free.”

In this episode of Prospecting Pros, John and Chris sit down with R.J. Jalichandra, a semi-retired CEO who has led six venture and private equity-backed companies ranging from early-stage startups to organizations with over 2,000 employees. R.J. shares what it takes to succeed in the CEO role, explaining why an entrepreneurial mindset, resilience, and a love for solving problems are important. He explains some of the most common mistakes he sees leaders make, like underhiring when trying to scale, growing too fast in venture-backed companies, or private equity pulling out cash too early R.J. also talks about why companies often stall at 2 to 5 million in revenue or around 40 employees, and why building a strong executive team is critical for breaking through. He shares his “do no work” CEO philosophy, the value of coaching, and why you should ignore the highlight reels you see on LinkedIn.

In this episode of Prospecting Pros, John sits down with Josh Roth who talks us through his early experience in inside sales with the New York Mets where he was grinding out 120 manual dials a day and learning to love the reps. He shares how aiming 20 extra calls daily sped up his learning and why he targeted businesses early. After two early-stage startups folded, he helped Mnet Health scale from roughly 5 to 12 million and then found his break as a top BDR manager at WalkMe before leading sales at Lob and Pipefy. Josh values learning over titles and surrounding himself with smarter people. For SDR teams today, he stresses real unit economics, the right tech stack, and measuring conversion rates over vanity activity. When hiring, he looks for hustle, determination, creativity, and coachability. He also shares his thoughts on AI SDR tools and where they stand today.

In this episode of Prospecting Pros, John and Chris sit down with Mike Simmons, founder of Catalyst. Mike never planned on a career in sales, but his journey through operations and customer success eventually gave him the stability and drive to launch his own business. Mike talks about how Catalyst helps family-run manufacturing companies that have stalled in growth by stripping things back to basics. His approach relies on asking the right questions, focusing on what’s working, and testing new ideas in small groups before scaling. He also opens up about working with his son, who recently joined as an SDR, and how they use testing and curiosity to build outbound strategies. The conversation touches on the power of keeping messaging simple, the value of community groups like Pavilion, and how leaders can create space for learning and growth.