EP 83: From Sales Leader to CEO: Mark Kosoglow’s Leap into Entrepreneurship

Most outbound sales strategies rely on volume and noise. Mark Kosoglow is betting on something different: relevance, proof, and actually caring about the people on the other end.

 

Mark helped scale Outreach to over $230 million in revenue as its first sales hire. Now he’s a first-time founder and CEO at Operator, a startup built inside the GTM Fund, where he’s rethinking what outbound should look like and calling out what’s broken. What happens when you stop chasing reply rates and start focusing on provable business problems? How do you build a company without tying your self-worth to the outcome?

 

In this episode, Mark sits down with Alex Raymond to talk through the emotional ups and downs of entrepreneurship, the decision to say yes to starting something new after being fired, and how “work hard and have fun” became the filter he uses to make decisions. He shares lessons from working alongside leaders like Manny Medina and the Chu Brothers, his take on building authentic company culture, and why he treats the CEO role like a sales role: listening first, solving second.

 

If you’re tired of the spray-and-pray approach to sales or wondering how to stay grounded while building something ambitious, this conversation will land.

 

Episode Breakdown:

00:00 Mark Kosoglow: From Outreach to Operator

03:16 Lessons from Catalyst and Customer Success

06:56 Why Outbound Is Broken

13:46 The “Great Ignore” and Rethinking Sales Math

17:43 Starting Inside a Venture Fund

21:24 Hiring, Delegating, and Lessons from Past Leaders

27:36 Leading Through the Emotional Highs and Lows

35:20 Daily Habits, Book Recommendations 

 

Links

Connect with Mark Kosoglow:

LinkedIn: https://www.linkedin.com/in/mkosoglow/

Website: https://www.operator.ai/

 

Connect with Alex Raymond:

LinkedIn: https://www.linkedin.com/in/afraymond/

Website: https://amplifyam.com/

 

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