Building a winning culture that sticks with Jake Haulsic

January 22, 2026

Jake Haulsic has some 15 years of experience in technology sales, with Velosio and Tribridge. He founded Trofeo, a fast-scaling cloud consultancy specializing in Microsoft Azure, in 2024. On this episode Business Observer Managing Editor Mark Gordon and Jake talk about how he built his company, not only around product and service, but culture. He also talked about some early decisions at Troefo that helped shape its trajectory, and his mentors that have helped guide the business along the way.

3 Takeaways

(11:50) Leaders need to trust their employees
(12:40) The best leaders practice patience
(14:50) Every failure needs to be a learning opportunity

Timestamps

(00:00) Introducing Jake Haulsic, Trofeo, founder
(02:55) What is Trofeo?
(05:10) Jake’s mentors
(06:50) What did you learn from Tony DiBenedetto?
(09:00) What does culture mean to you?
(11:40) Leadership characteristics
(12:20) Best leadership advice you have received
(13:15) What role does storytelling play in Trofeo’s growth?
(14:00) Resilience
(15:50) How do you want to be remembered as a leader?
(16:45) Trofeo in 2026

Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders and much more.