Chief of Staff Strategy Session & Game Plan
The CoS role looks different at every company. Let's take the time to understand it, talk it through, and build a plan that fits you.
What's included
- How the CoS role really works at a startup
- Map your path from where you are today
- Target companies, stages, and timeline
- A clear game plan you leave with
- Bonus: AI workflows to speed up your search
Meet your expert
Stephen A.
Land the Chief of Staff Role, Then Hit the Ground Running
I started my career on Wall Street as an investment banking analyst at Credit Suisse, advising private equity firms on M&A transactions. That foundation led me to Clearlake Capital, a large-cap PE firm in Los Angeles, where I invested across software and industrials helped drive value creation across the portfolio. After over four years on the investing side, I made the leap into operations. I joined Airspace, a high-growth logistics-tech startup, where I served as Chief of Staff and later Director of Strategy - getting my first real taste of what it means to operate inside a fast-moving company rather than observe it from the outside. From there I returned briefly to PE but as an operating advisor, before landing in my current role at Tapcart, a leading mobile commerce SaaS platform. At Tapcart, I began as the Chief of Staff and Head of Operations, Finance, and Strategy, and now am the VP, Operations & Finance. Across that journey I've sat in a lot of different seats - analyst, investor, operator, strategist, and now a functional leader running multiple departments simultaneously. I know what it takes to make the transition from finance into startups, and I know what separates the people who thrive in those roles from those who struggle to find their footing. I coach on Leland because I've lived the path and because the right guidance at the right moment genuinely changes outcomes.
