Caitlin S.
5.0
(9)
VC Partner | Ex-Startup Operator | Board Member & Advisor
Studied at Harvard Business School
Worked at Lerer Hippeau
Hiring Manager
Available Wednesday at 1:00 PM UTC
Questions? Start chatting with this coach before you get started.
Caitlin's Coaching Offerings
Build a Successful Startup — In-Depth Founder Support
Expert coaching to help you achieve your entrepreneurial goals
$2,55020h of coaching
Build an Investor-Ready Fundraising Deck
Craft a narrative and build a polished deck that drives fundraising success
Starting at $1,27510h+ of coaching
Early-Stage Startup Coaching — Fundraising, Building, Growth
Best for early-stage founders trying to fundraise, build, hire, or grow
Starting at $7505h+ of coaching
Custom hourly · $150/hr
Get help with Interview Prep, Venture Capital Strategy, and .
Caitlin’s Startups Qualifications
Experience level: Executive
100+ people coached for Startups
With over a decade of experience in the venture capital and startup ecosystem, I love helping and supporting entrepreneurs. As a former Partner at Lerer Hippeau, I led investments in over 30+ companies, served on multiple boards and reviewed thousands of startups. Currently, I advise and invest in early-stage startups, helping them navigate the complexities of growth and funding. Whether you're looking to refine your pitch, strategize your business model, or secure venture funding, I'm can provide real and actionable feedback and support.
Caitlin can help with:
Interview Prep
Venture Capital Strategy
Compensation Strategy
Hiring
Business Strategy Development
Branding
Resume
Fundraising
Ideation
About Caitlin
I’m a VC partner, former startup operator, and Harvard MBA, recognized by Forbes 30 Under 30 and Business Insider for my work supporting early-stage companies. I began my career building and scaling startups across product, strategy, and operations before transitioning into venture investing. Over time, I grew from analyst to partner, gaining firsthand experience on both sides of the table. I’ve advised countless founders, operators, and aspiring investors on navigating career transitions, scaling companies, and fundraising. My coaching style is practical, strategic, and tailored to what’s happening in today’s real-world industry landscape. Whether you’re looking to break into startups, land a venture role, or level up into leadership, I can help you execute a clear, actionable plan.
Why do I coach?
I broke into startups and venture capital without a traditional background — no connections, no playbook, no plan. Along the way, the right mentors helped me navigate key transitions, take big leaps, and build a career I couldn’t have imagined at the start. Now, I coach and mentor to pay that forward. Whether you’re breaking into startups, landing a VC role, leveling up in your career, or starting a company, I’m can help you move faster, avoid common pitfalls, and build a clear, confident path forward.
Work Experience
Early-Stage Investor
Self
May 2024 - Present
Hiring Manager
Currently advising, consulting and investing across the startup ecosystem, including early-stage startups and VC firms. I'm currently on the board of Advocate, Hello Cake, Topicals and Aerflo. These companies have raised $200M+ in venture funding. I'm also a Venture Partner at an early stage venture firm that has invested in companies like Coinbase, Harry's, Oscar, Scopely and Task Rabbit.
Partner
Lerer Hippeau
May 2018 - May 2024
Hiring Manager
Lerer Hippeau is the most active early-stage venture fund in NYC with $1.5B+ AUM. Their portfolio includes over 350 leading enterprise and consumer businesses, such as Guideline, MIRROR, Warby Parker, Glossier, K Health, Allbirds, and ZenBusiness among others. As a Partner at Lerer Hippeau, I led Pre-seed, Seed and Series A investments across both enterprise and consumer companies. My involvement includes sourcing, diligence, deal closing, syndicate creation, portfolio support and M&A. I also held board seats and supported companies across early to late stages for over 30+ companies. Companies I’ve had the privilege of partnering and serving as a board member: 10Beauty: Fully automated manicure device for salons Advocate: Turbo Tax for government benefits Aerflo: Carbonation device that reduces single-use plastics Bookkeep: Financial automation for modern businesses Cake: Next-gen sexual health & wellness brand CAMP: Next-gen Toys "R" US for modern families Cure: Better-for-you hydration powder Flare: Personal safety software and device (Acquired by Smart Alert) Learnexus: Learning & Development platform and talent marketplace Medly Pharmacy: Full stack pharmacy for same-day prescriptions (Acquired by Walgreens) Onward: Fintech solution for modern families Pando: Employee progression software for the modern workforce Parade: Next-gen intimates apparel brand for Gen Z (Acquired by Ariela & Associates) Plantible Foods: Developer and distributor of Rubi, a novel plant-based protein Recast: Cross platform analytics for modern brands via Bayesian Marketing Mix Modeling (MMM) Sequencing: Whole genome sequencing and analysis platform Studs: Next-gen brand for ear piercings & adornment Sweet Reason: Cannabis beverage brand (Acquired by Cann) The Inside: On-demand custom upholstered furniture (Acquired by Havenly) Topicals: Skincare brand for chronic skin conditions
Vice President
FirstMark Capital
September 2016 - May 2018
FirstMark is an early stage venture capital firm based in New York City. Our mission is to partner with entrepreneurs who are focused on solving meaningful problems. Firstmark's portfolio includes businesses like Pinterest, Shopify, Airbnb, Riot Games, InVision, and Tapad.
Associate
Flybridge Capital Partners
August 2012 - August 2014
Flybridge is an early-stage venture capital with offices in Boston and New York City. With $1B+ assets under management, the firm is focused on investing in seed and early stage technology companies and is led by a team with domain expertise.
Director of Business Development
LearnVest
February 2012 - August 2012
LearnVest (www.learnvest.com) is a personal finance product for subscription-based access to financial advisors. LearnVest promotes financial literacy and empowerment through content, tools and financial advisory services. LearnVest was acquired by Northwestern Mutual in 2015.
Associate Director of Business Development
behance
July 2010 - March 2012
Behance (www.behance.net) is the leading online platform to showcase and discover creative work. Creative professionals broadcast their work widely and efficiently, and companies access talent on a global scale. Millions use Behance to display and find talent every month. Behance was acquired by Adobe in 2012.
Education
Cornell College
Bachelor of Arts (B.A.), History; Science & Technology Studies
Activities and societies: Sphinx Head Senior Honor Society, Slope Media Group, Slope Radio, Slope TV, Slope Magazine, Kappa Alpha Theta, Mortar Board Honor Society, Lightweight Crew
Harvard Business School
Master of Business Administration (M.B.A.)
2014 - 2016
Activities and societies: Rock Venture Partner, VC/PE Club, Entrepreneurship Club, Startup Lockdown. Led 1st year final exam review session for required course - The Entrepreneurial Manager
9 Reviews
Overall Rating
5.0
Caitlin has helped Leland clients get into RTP Global