Chief of Staff Coaches, Events, and Resources

With extensive experience in strategic leadership and operational excellence, I am exceptionally qualified to serve as a Chief of Staff Coach on Leland, guiding professionals seeking to excel in this pivotal role. My background includes over 11 years as a Naval Officer, culminating in my position as Deputy Chief of Staff to the Navy Chief of Legislative Affairs, who reports directly to the Secretary of the Navy and the Chief of Naval Operations. In this capacity, I collaborated closely with US Senators/Congressmen and Senate/House Committee staff, managing high-stakes legislative initiatives and ensuring alignment across executive branches. Complementing this, my five years in product management at leading tech companies such as Amazon, LinkedIn, and Guideline have refined my expertise in cross-functional coordination, strategic planning, and driving organizational priorities to achieve measurable results. As a coach, I am dedicated to empowering people to break into the Chief of Staff role and enhance their strategic leadership capabilities. My approach draws from proven experience as a strategic partner in executive stakeholder management, optimizing operational workflows, and delivering high-impact organizational outcomes in dynamic environments. By providing tailored guidance on frameworks such as OKRs, stakeholder mapping, and strategic communication, I equip people with the tools to articulate their value, build executive trust, and navigate complex challenges effectively. My commitment is to offer people actionable strategies and personalized mentorship to realize their Chief of Staff aspirations with confidence and precision.

I can coach on the Chief of Staff role because I’ve held the position myself for two years and am active in the Chief of Staff Network. Having both firsthand experience and insight from interviewing for multiple Chief of Staff roles previously, I deeply understand the nuances, expectations, and pathways to success in this position. I'd love to help you select a role, prepare for an interview, or uplevel your skillset.

I have served as Chief of Staff for a high-net-worth family office for the past 2.5 years.

Welcome to my profile! With a robust background in management consulting at Bain & Company, where I served as a Senior Associate Consultant, and my role as Chief of Staff and VP of Strategy and Corporate Development at BioLite, I bring a wealth of experience to my coaching practice. My journey has equipped me with the strategic insights and leadership skills necessary to excel in high-impact roles. I specialize in guiding aspiring Chiefs of Staff to navigate their career paths effectively, leveraging my firsthand experience in both consulting and executive support. Whether you're looking to refine your strategic thinking, corporate development / M&A, or enhance your leadership capabilities, I'm here to help you achieve your career goals. Let's connect and chart your path to success!

I'm a two-time chief of staff who has navigated the gamut of the role in both Private Equity and Venture Capital backed companies. From managing executives to leading through difficult company events to bringing special projects to life, I've built up a strong CoS toolkit. In my first CoS role, I successfully transitioned from CoS to our VP of Partnerships of Operations in only 9 months. As a Stanford MBA graduate, I served as a leadership coach and helped students to find their management style. I have successfully coached half a dozen individuals, helping them navigate the complexities of the Chief of Staff role and achieve their career goals. Let's connect to explore how I can support your professional journey!

The Chief of Staff role is one of the most misunderstood and under-scoped positions in high-growth companies — and I've lived at the intersection of strategy and execution where that role sits. I work with professionals trying to break into a CoS role who need to understand how to position their background and tell a compelling story, current Chiefs of Staff navigating what "good" looks like when the job description changes every quarter, and founders hiring a CoS who need help defining the scope, interview process, and first-90-days expectations. If you're building the bridge between a founder's vision and the team's execution, or trying to figure out whether this role is right for you, I bring the operator perspective and the strategic lens to help you move with clarity.

With over a decade of leadership and operational experience, I help people sharpen their professional presence, build effective career strategies, and position themselves to land the Chief of Staff role they’re aiming for. After my MBA, I joined a seed-stage AI startup in the political tech space. Startups are never easy, but ours faced unique challenges: navigating election-cycle swings, operating within a complex procurement system, and building trust with AI skeptics—not to mention the backdrop of political headwinds. While my experience was in a niche market, the lessons I learned apply everywhere, such as exercising judgment to prioritize what matters, finding clarity amid ambiguity, and adapting to solve problems you’ve never faced before. The Chief of Staff role is demanding but deeply rewarding, equipping you with the skills to thrive and lead in any environment. I know what it takes, and I’d love to help you get there.

I'm an experienced startup Chief of Staff; I served as a fractional Chief of Staff for 10+ companies as a self-employed startup consultant, and later joined one of my clients (a YCombinator-backed leading Democratic political tech startup) in-house as founding Chief of Staff. I was later promoted to COO of the same company, which I led for several years until the company's acquisition by ActBlue in 2025. Importantly, I've been an informal leadership coach and Chief of Staff mentor to numerous peers and junior staffers along my journey. I have formal experience developing a coaching and professional development program for second-in-command executives. I'm extremely familiar with the unique dynamics and demands of the Chief of Staff role - as a middleman between executives and staff, as a combined strategist-and-executor, and all of the other many ways that being a Chief of Staff is different than almost any other role in the professional world. I'm here to help you find a Chief of Staff role for the first time, and/or navigate a new role as a Chief of Staff.

I specialize in helping professionals land and thrive in Chief of Staff roles at high-growth technology startups — whether you're coming from consulting or finance and looking to make the leap, or you're already a CoS looking to level up. With hands-on experience as the Chief of Staff for two high-growth SaaS businesses, I've lived the transition from investment-driven work to operating at the center of a fast-moving business. The Chief of Staff role sits at a unique intersection - part strategist, part operator, part trusted advisor - and getting it right requires more than a strong resume. My coaching covers the full arc: figuring out whether the CoS role is the right fit for you, identifying the right company stage and CEO dynamic to target, building a compelling narrative around your background, and preparing you to interview with confidence for one of the most judgment-dependent roles in any organization. I combine practical frameworks with firsthand context - so you're not just ready to land the role, but to make an immediate impact once you're in it. If you're ready to make the leap into one of the most high-leverage seats in a startup, I can help you get there.

When I stepped into the Chief of Staff role at Microsoft after my years at BCG, I quickly learned that it’s one of the most multifaceted jobs in a company. In my role I oversaw financial planning, strategic initiatives, HR partnerships, and internal operations, while also serving as a trusted advisor to senior leaders. I had to constantly balance big-picture strategy with day-to-day execution and influence without formal authority. Because of this experience, I understand the unique challenges Chiefs of Staff face: shaping strategy while staying behind the scenes, navigating complex relationships, prioritizing in the face of endless demands, and growing into broader leadership roles. This is why I coach aspiring and new Chiefs of Staff, helping them build confidence, clarify their role, and develop the skills to succeed in a position that can often feel ambiguous but is also a powerful career accelerator.