Work with Stephen
Chief of Staff Strategy Session: Lite
$175
Chief of Staff Strategy Session & Game Plan
Starting at
$350
Craft a Winning Chief of Staff Resume
Starting at
$350
About
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.
Stephen also coaches for Business Operations & Strategy and FP&A. View all.
Stephen’s Chief of Staff Qualifications
Experience level: Vice President
60+ Chief of Staff clients
VP Ops & Finance at a Series B, ex-PE/IB, 100+ people coached. I help Wall Street professionals, especially from private equity and investment banking, make the leap into high-impact startup roles. I've made that move myself, from PE to Chief of Staff to running Ops and Finance at a Series B SaaS company. We'll work through the full arc together: - Find your best fit: Chief of Staff, BizOps, Strategy, StratFin, or Corp Dev, and the right company stage - Build a transition story that turns deal experience into operator value - Reposition your resume and LinkedIn for the roles you want - Interview with confidence You won't just land the role. You'll be ready to hit the ground running once you're in it.
Stephen can help with:
AI Automation
Interview Prep
Networking Strategy
Resume Review
Salary Negotiation
Strategic Planning
Why do I coach?
Early in my career in PE, I crossed paths with a mentor who helped me understand how my PE skills are incredibly valuable in operating companies. But nobody hands you the translation, you have to learn how to reframe what you know and how you operate - and that's hard to do alone. That same mentor eventually hired me as his #2 at a high-growth SaaS company, which is how I made the leap into strategy, operations, and strategic finance. My skillset translated - but there was a learning curve I didn't see coming, and it had nothing to do with the actual work. It's something almost every finance-to-startup transplant runs into, and it's one of the first things we unpack together. I coach on Leland because I've been on both sides of that gap - and I know how much a little clarity on role fit, narrative, and confidence can change the outcome. If someone invested that time in me, the least I can do is pay it forward.
Work Experience
VP, Operations & Finance
Tapcart
July 2026 - Present
Chief of Staff and Head of Strategy, Operations & Finance
Tapcart
January 2025 - June 2026
Hiring Manager
- Series B startup; B2B e-commerce SaaS platform - Developed medium-term corporate strategy, and responsible for AI growth strategy and pricing model, driving increased profitability while scaling the business and investing in growth, and optimizing retention rates through product and GTM strategy
Private Equity - Portfolio Operations
Peterson Partners
June 2023 - December 2024
Hiring Manager
- Portfolio operations for generalist PE firm (top quartile fund) across $225m Fund IX and $265m Fund X - Owned and oversaw value creation for 5 portfolio companies, including development of strategic roadmaps, execution of operational improvements, and management of FP&A across a mix of software, professional services, and healthcare companies
Director of Strategy
Airspace
August 2020 - May 2023
Hiring Manager
- Venture-backed logistics-tech startup (Uber for B2B time-critical shipping) - Created and executed strategy to scale business from a ~$30m ARR domestic courier to a ~$120m ARR global freight-forwarder - Led efforts to identify and launch 3 growth opportunities which expanded TAM by 3x and produced an incremental $35m+ ARR - Drove ~700 bps of margin expansion by adding higher-value services, augmenting pricing strategy, and utilizing new driver pool - Partnered with President to lead fundraising of equity (Series B, C, and C+) and debt
Private Equity Investor
Clearlake Capital
July 2018 - July 2020
Interviewer
- Software and industrials private equity firm - Closed 8 buyouts and 4 distressed credit investments across $3.6B Fund V and $7.0B Fund VI - Spent 5 months onsite with portco CEO to identify and resolve growth blockers; achieved gross margin expansion of ~200 bps, doubled resource utilization of sales managers, and increased ROIC by reducing dead stock levels from 4% to 2%
Investment Banking Analyst
Credit Suisse
July 2016 - July 2018
Interviewer
- Financial Sponsors Group - New York City - Group ranked #1 Sponsors Group on Wall Street for revenue generated
Education
Brigham Young University
Bachelor of Science - BS, Finance
- Co-President of Investment Banking Association (300+ members) - Marriott School's Dean's List (Top 5% academically of business school students)
Chief of Staff Strategy Session: Lite
$175
Chief of Staff Strategy Session & Game Plan
Starting at
$350
Craft a Winning Chief of Staff Resume
Starting at
$350
Nail your Chief of Staff Interviews
Starting at
$350
Land a Chief of Staff Offer: Complete
Starting at
$1,163.75
Nail your Chief of Staff Interviews
Starting at
$831.25
Land a Chief of Staff Offer — Getting Started
Starting at
$831.25
Stephen also coaches for Business Operations & Strategy and FP&A. View all.
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