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Think you might be a fit for a Chief of Staff role? Awesome! Chief of Staff is, in my humble opinion, one of the most exciting and high-leverage roles out there, particularly for generalists who are hungry for rolling up their sleeves and doing the work. I'm an experienced startup Chief of Staff (then promoted to COO); I offer tangible, actionable advice for positioning yourself for a Chief of Staff role, plus a hefty dose of support and honesty to help you reflect on your career and make confident choices about what comes next. I'll be the most helpful for folks who are seeking a Chief of Staff role for the first time, particularly for *startup*/growth company Chief of Staff roles. (But feel free to reach out if your goals are slightly different - seeking a new CoS role even though you already have one, seeking a CoS role at a larger company, etc. - I'm happy to honestly assess whether I can help!): Our work together will be tailored to your particular background and needs, but often will include: - Kickoff and planning to understand what brings you to this inflection point and how you hope to move forward - A comprehensive strategy for your Chief of Staff job search, with specific systems and goals to keep you motivated and focused - Comprehensive resume, cover letter, and LinkedIn review to help you put your best foot forward for the unique dynamics of Chief of Staff roles - Interview prep, negotiation, and offer decision-making once you get to the finish line My focus as a coach/mentor is offering highly specific, actionable advice about your job search - I've helped countless folks organize their job search process and emerge successfully, thanks to my particular point of view on how to organize your materials, optimize your narrative, and maximize your optionality through the interview process.
A specific framework and set of goals to help your job search feel organized and intentional
Polished resume(s), cover letter(s), and LinkedIn profile to help your Chief of Staff applications stand out
Support through all stages of the process, including interviews and offer negotiation
An ally in your corner to organize, strategize, and vent!
Coaching delivered via live sessions and .
Services included:
Interview Prep
LinkedIn Review
Strategic Planning
Cover Letters
Resume Review
Networking Strategy
Executive Support
Schedule a call with a Leland team member who can help you explore your options.
Schedule a call
Get help with Interview Prep, LinkedIn Review, and .
Katy also coaches for MBA, Career Coaching, and Leadership Coaching. View all.
Joined January 2025
Former Chief of Staff (now COO) of YCombinator-Backed Startup
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've led for several years. 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.
10h of coaching