He Made Millions in Tech Sales — Then Retired to Sail the World with His Family

Mark O’Leary was my former Solutions Engineer and one of the most brilliant partners I ever had when I was the #1 Enterprise AE at Salesforce. He wasn’t just along for the ride — he helped quarterback many of our biggest wins.

00:00 – Intro
01:03 – Mark's Journey from Tech Sales to Sailing
05:36 – Why Mark Left Corporate Life for a Sabbatical
07:00 – Secrets of a High-Performing AE-SE Team
10:01 – Curiosity and Strategic Account Planning
15:11 – Why Mark Transitioned from SE to AE
21:30 – Tripling Quota: Time Management & Focus
30:32 – Spotting Real Change Agents and Executive Sponsors
38:30 – Discovery Framework: Illuminate & Architecting the Solution
45:00 – Executive Communication, Passion & Resilience
52:08 – Mark’s Long-Term Vision and Growth Mindset

He was #1 SE at Salesforce for three straight years, and then he did what most SEs only dream of — he jumped into sales. Within two years, Mark became a top-performing AE, finishing 350% of quota in FY22 and 302% in FY23, earning 7-figures, and making President’s Club.

Then he did something wild…

He bought a boat and set sail around the world with his wife and daughter.

Mark joined me for a Fireside Chat (live from his boat) to share the exact playbook he used to go from SE to top 1% seller — and ultimately create financial freedom to live life on his terms.

🔥 Here are some of the biggest takeaways:

✅ Sales is the path to freedom — IF you treat it like a craft
Mark didn’t chase quota. He chased mastery. He went deep on every account, qualified ruthlessly, and thought like a CFO. He sold fewer deals — but made a lot more money.

✅ Serve, don’t sell
Mark credits his success to being obsessed with customer outcomes. He’d say no to internal noise and yes to doing deep discovery, aligning on a North Star vision, and earning the right to be a trusted advisor.

✅ Quarterback like a boss
As an SE, Mark led technical teams like a GM. As an AE, he continued that discipline. He coordinated exec sponsors, architects, and partners with military precision — even closing deals in the middle of the Atlantic with Starlink Wi-Fi.

✅ Missed quota year 1. Crushed it years 2 and 3
Most people would’ve quit. Mark doubled down. He qualified harder, planned better, and focused only on the highest-potential accounts. From there, it snowballed into back-to-back 7-figure years.

✅ Focus on quality, not quantity
His biggest accounts had massive deals, multiple exec sponsors, and deep workshops. You don’t need more meetings. You need better ones, with the right people, aligned to the right problems.

Mark is living proof of what’s possible when you stop selling and start serving — and when you commit to becoming elite.

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