In this conversation, Alex Kramer, the CRO of Cresta, shares insights from his journey transforming Cresta into a contact center AI leader. He dives into the gritty realities of securing that first enterprise customer and the necessity of team endurance in a competitive landscape. Alex discusses the evolving dynamics of enterprise sales, the role of AI in optimizing success, and the critical importance of resilience, using Shackleton's Antarctic expedition as a metaphor for overcoming business challenges.
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question_answer ANECDOTE
Cresta's Unconventional Start
Cresta's CEO and CTO interned at Intuit to gain access to customer data and understand contact center behaviors.
This hands-on approach allowed them to identify key behaviors for winning sales calls and build a targeted AI solution.
volunteer_activism ADVICE
Targeting Early Customers
Secure a champion within a target company who trusts you and your solution.
Start with mid-sized companies willing to take risks on new innovations, then gradually work your way up to larger enterprises.
insights INSIGHT
The Cold Start Moat
Cold-starting in enterprise is challenging, but creates a competitive moat.
Cresta's initial struggles with Intuit became a strength, deterring competitors.
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building a business when there are no easy answers
Ben Horowitz
In this book, Ben Horowitz shares his personal and often humbling experiences in the tech industry to offer essential advice and practical wisdom. He addresses various hard decisions and challenges that business leaders face, such as firing friends, managing company culture, handling layoffs, and making tough strategic decisions. Horowitz emphasizes the importance of honesty, resilience, and adaptability in leadership, drawing from his experiences with companies like Loudcloud and Andreessen Horowitz.
Endurance
Shackleton's Incredible Voyage
Alfred Lansing
This book details the almost two-year struggle for survival of the 28-man crew of the Endurance, which was beset and eventually crushed by ice floes in the Weddell Sea during the Imperial Trans-Antarctic Expedition of 1914-1917. The crew drifted on ice floes, salvaged lifeboats, and eventually reached Elephant Island. Shackleton then led a perilous journey to South Georgia Island to secure rescue, culminating in one of the most remarkable survival stories in history. Lansing's narrative is based on extensive research, including interviews with surviving crew members and access to their diaries and personal accounts[4][5][3].
What does it take to go from zero to your first enterprise customer? For Cresta, it meant their CEO and CTO becoming interns at Intuit—and their engineering team living in an Airbnb next to the call center they were trying to disrupt.
In this episode, Kyle talks with Alex Cramer, CRO of Cresta, about the unglamorous grind of cold-starting in enterprise, why today’s deals demand more consensus (and skill) than ever, and how to scale a team when every deal feels like a bespoke knife fight.
Plus, Alex’s hardest-won lessons—from equity pitfalls to why endurance separates good CROs from great ones.
New episodes of The Revenue Leadership Podcast with Kyle Norton drop every Wednesday.
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