Revenue Blindspots

In this episode of Revenue Blind Spots, host Sam Jacobs speaks with Matt Holtz, President and CRO of Alliance HCM, about navigating the shift from a founder-led business to a role on an executive team. Matt shares his transition to leading "more by influence than you can lead by just being the darn founder". He discusses his biggest blind spot: the "survive to thrive curve", where he focused on grabbing any revenue possible, which resulted in non-sustainable business.

Post-acquisition, most leaders promise: “Nothing changes for 6–12 months.” According to Xero CRO Ashley Grech, that’s exactly how you destroy deal value. In this episode of Revenue Blindspots, Sam Jacobs and Ashley unpack the hidden costs of “leaving the acquired company alone,” how to decide which teams to integrate and when, and why you should start with the customer experience—not org charts. They also dig into the tension between regional vs. functional structures and Ashley’s practical advice for rising revenue leaders in an AI-driven world: deeply understand the underlying workflows before you try to automate them.

Hiring ahead of demand feels like the right move - but it can leave companies overextended and vulnerable. In this episode, Sam Jacobs and Kathleen Booth unpack the blind spots around hiring and firing, the cost of ruinous empathy, and why transparency is the only way to maintain morale. They also explore how AI is reshaping marketing teams and forcing leaders to rethink org design from the ground up.

Too many startups wait until the bank account is empty before building a real GTM engine. In this episode, Sam Jacobs and Dmitri Lisitski unpack the blind spots of relying on referrals, how Influ2 booked 20 meetings a month from a standing start, and why outbound + contact-level ads is still one of the most powerful combos in B2B. They also explore the role of AI in scaling signal-based selling and what SDRs look like in the years ahead.

Too often, growth leaders chase small, incremental wins while overlooking the real driver of scale: upsell. In this episode, Sam Jacobs and Darius Contractor dig into how product design and habit loops unlock expansion, the cultural blind spots that hold teams back, and why AI is quickly becoming a growth leader’s most important tool.

Join Sam Jacobs as he delves into a compelling discussion with Mark Rosenthal, CRO at Castle Systems. In this episode, Mark unveils the significant blind spot of lacking data visibility within a long-standing organization, which operates with a legacy CRM system. Discover how Mark navigated these challenges to drive organizational change and optimize sales processes in a company that's been around for over half a century. This episode is crucial for anyone dealing with legacy systems and looking to modernize their sales operations.

Dive into a conversation with Kyle Norton, CRO of Owner.com, as he reveals the journey of addressing churn in a fast-growing SMB-focused business. Kyle discusses the challenges of identifying the true causes of churn and the strategic decisions required to improve retention. This episode offers valuable insights for leaders managing high-growth companies looking to refine their customer success strategies and enhance product value perception.

Asad Zaman, CEO of Sales Talent Agency, joins Sam Jacobs to challenge conventional wisdom around key person risk. Asad's unique perspective on building a business deeply intertwined with personal brand and long-term vision offers a fresh take on driving growth without the traditional focus on enterprise value. This episode is perfect for leaders questioning the status quo and seeking to build enduring businesses with a personal touch.

Sam Jacobs welcomes AJ Bruno, Founder and CEO of Quotapath, who reveals how a single meeting changed everything he knew about business growth. From nearly tanking his company's retention to creating a legendary "war room" strategy, he'll share the brutal lessons that transformed his approach to customer success. Learn how chasing new logos can be a dangerous game, why AI isn't always the silver bullet, and how one founder turned potential disaster into a $200 million success story. Warning: Contains raw entrepreneurial wisdom, unexpected candy bar history, and plenty of startup battle scars!

Buckle up for a marketing revolution! 🚀 Elaine Zelby, Tofu's co-founder and CRO, drops bombshell hot takes on Revenue Blind Spots, revealing:Why marketing teams should get variable payHow AI can personalize marketing for 1000 accounts instantlyThe counterintuitive truth about data and attributionFrom VC to startup founder, Elaine unpacks the secrets of revenue leadership that will transform how you think about go-to-market strategies. Prepare for insights that challenge everything you know about marketing and sales!