Throughout my nearly 30 year career, I’ve successfully built a $1B business segment for a large public company, guided the turnaround of a distressed $100M+ revenue business, launched and sold a venture-backed startup, and led another startup to global scale.
Those very different endeavors led me to obsess over a single question, “how does a founder become a great CEO?” I interviewed hundreds of founders and investors seeking clarity to that question. And when no good answer presented itself, I teamed up with a group of exceptional former founders, operators and investors to create our own solution.
Since 2015, I have led Enjoy The Work, a firm with the singular mission of helping founders become great CEOs. Founders invent miraculous things. Our role is to teach founders how to build high-performing companies to bring those inventions to the world.
I love the early stage journey, particularly uncovering the magical intersection between what the market wants and how to sell it. There are so many open questions, different stakeholders, shifting variables – it’s like a game of chess where the right moves lead to rising revenues and happy customers.
I’ve had the good fortune of wearing many hats in my startup life from business development, to product management to sales. For the last 10+ years, I’ve built and led go-to-market teams for 3 organizations, Jive which went public in 2011, Origami Logic was acquired by Intuit, and TripActions, still a public company valued at over $5B at last check.
Building startups has fed my ambitions for years, and I joined Enjoy The Work so that I could impact not just one startup, but rather a portfolio of them across the globe.
Over the last 20 years, I’ve founded and successfully exited three startups. First was Qloud, a B2C on-demand music streaming service that grew to over 10M monthly unique visitors. Next was Kapost, a B2B SaaS company that we grew to over $13M in revenue and 100+ employees. My most recent was Onward, a ride-sharing service for seniors that partnered with hospitals and medical facilities.
Alongside those experiences, I also experienced hyper-growth at Airbnb. From 2015 to 2019, I served as Head of Product for Airbnb for Work and Airbnb Luxe. While there, we grew our department’s bookings from zero to over $1B in 2.5 years.
Although each company created value in different ways, I grew to appreciate the things that stay consistent. Building a high functioning team, shipping good product, honing a sales motion, raising capital, etc. Now I’m paying it forward as a General Partner at Enjoy The Work, grateful to work with founders bringing the next generation of technology to market.
I’ve worn various hats during my career – attorney, founder, CEO, advisor, investor, and executive. Above all else, I love building companies and being surrounded by founders and creative risk-takers. And never, ever taking myself too seriously.
I began my career as an attorney and left Google’s legal department to become an entrepreneur. I ultimately founded three venture-backed startups, the third of which was Headnote, a legal payments company. Under my leadership, Headnote was acquired twice by two separate private equity firms over a 5 year period, Alpine Investors and Francisco Partners respectively, for a combined exit value of over $400M. Over the past ten years, I’ve also advised and invested in dozens of start-ups across a variety of stages and sectors.
Notably, I have a special advantage when it comes to Enjoy The Work – while serving as CEO of Headnote, I was an ETW client. The ETW partners were my most trusted advisors, from seed stage through exit. I am the first former client to join the firm as a General Partner, and it is my ultimate pleasure to serve our startup founders on their journeys just as the firm did for me not long ago.
When I’m not helping founders, you can find me in San Francisco trying new restaurants, adventuring with my husband and kids on the Marin County coastline, and planning family trips to faraway places.
My career as a startup founder and product leader began after earning my PhD in Game Theory and Behavioral Economics from Caltech. In 2008, I founded my first startup, Crowdcast, and successfully exited the company in 2012. Following Crowdcast, I helped lead three more startups: Spigit (SVP Product), tenXer (Head of Product), and Swerve (Founder, CEO).
After my four startup experiences, I ventured into the enterprise world and joined Salesforce (VP Product), where I helped ship the company’s first AI product. But it was through my involvement in Salesforce’s M&A process that I ultimately realized I wanted to return to startup life.
Each chapter of my career was chosen based off of where I’d find my next challenge. I’m a problem solver at heart, and I take pride in repackaging all that I’ve learned throughout my career in order to effectively mentor the next wave of passionate founders.
With 16+ years experience spanning management, sales and marketing, operations, and analytics, I’ve spent time working for nonprofits and for-profits, agency and in-house, Fortune 100s, and startups.
Tapping my expertise in data-informed operations, I founded Quantified Ardor in 2016 and developed a proprietary methodology to advise growing startups around the world on data-driven decision making.
I’ve also spent the last 6 years as an advisor while holding multiple COO positions for startups at various stages. I’m a mentor with Google Launchpad, Endeavor, 500 Startups, plus several VCs and accelerators in SF, London, and Mexico City and most recently was an Expert in Residence at First Round Capital, advising their portfolio companies on operations and analytics.
I’m thrilled to have the opportunity to bring my first-hand experience to the Enjoy The Work team, where I’m afforded the chance to work closely with dozens of passionate founders.
I joined my first startup more than 25 years ago and was immediately delighted by the blank slate in front of me. I’ve always sought out companies that were early in their growth stories, which led me to join Amazon, Google, and Pinterest many years before they became some of the world’s largest enterprises. The common denominator – novel software, products, and teams that surprised and delighted massive numbers of customers.
My joy comes from bringing new products to the world. I’ve learned that there is a right way, a harmonious way, to ship those solutions. And I’m grateful now to have the experience (and scars) to help others get there faster.
My journey from engineer to CTO to advisor has taught me that there is a cadence of communication, delivery, and metrics core to every successful company. With the right foundation in place, a founder can build a company that delivers on the promise of a better tomorrow.
The best part of advising is having the insight to guide a company towards their own unique answers – the ones that both reflect their values and lead to business success. I am excited to be a General Partner at Enjoy The Work as I continue to teach, learn, and be in awe of the imagination of our founders.
Kristen Hamilton is a technology entrepreneur and CEO with multiple exits. She is a venture partner at leading VCs, a board director of growth stage companies Top Hat, Aduro, Strivr and Fairmatic, and chair of the board of Directors’ Cup Invitational Ski Classic. She co-founded predictive hiring software leader Koru, and was CEO until it was acquired by UK based Capfinity. She previously co-founded e-commerce pioneer Onvia and took it public on NASDAQ. Kristen served as SVP Strategic Partnerships at Guild Education, a unicorn in the education to employment space and as an executive for global enterprises including Microsoft and World Learning.
The primary focus of her career has been driving impact in the technology, talent and education industries. She is a recognized expert in education and HR technology spaces, with a deep focus on the intersection of education and employment.
She grew up near Montreal, and currently splits her time between Seattle and Whistler. Kristen is mom to two teenage daughters and a golden retriever, and has deep passion for skiing, biking, rowing, and spending time outdoors in the mountains.
I’ve had a few careers in various industries, but independent of my functional roles, the most important skill I’ve mastered is the ability to ask good questions.
I’ve developed that skill over a 20 year career that has spanned banking, entrepreneurship, personal coaching and startup advising. I’ve helped start 6 businesses, including co-founding a software company that we built from start-up to a profitable multi-million-dollar global operation to a successful M&A exit.
I have my CPA license, multiple academic degrees and a professional coaching certification but above all else my greatest passions are mentoring my fellow entrepreneurs and volunteering at my kids’ schools.
While I’ve been involved with startups ever since founding my own software company in the mid 1990s, the bulk of my career has been defined by venture capital. In the early 2000s, I co-founded Pittsburgh-based VC firm, Birchmere Ventures.
Over the following 20+ years at Birchmere, we raised and invested six funds and our portfolio companies achieved a cumulative market valuation of $15 billion. Through those funds, I was fortunate to work with dozens of amazing entrepreneurs.
Throughout my career, my highest highs have come when lending a helping hand to well-deserving, high-achieving founders. My passion lies in watching others achieve success. Through Enjoy The Work, I am able to fulfill this passion by taking founder mentorship to a deeper level than I could in the VC world.
I love the underdog. Throughout my career leading both early-stage, venture-backed startups and global private equity-backed corporations, I’ve been motivated to build teams that find creative, often unexpected paths to success.
My journey has taken me from an executive at AOL in the early days of the consumer internet to the management team of two venture-backed startups that successfully exited. I then joined the parent of the New York Stock Exchange as its first Chief Digital Officer. In the past decade, I was a private equity CEO at two different companies, both of which drove 9-figure revenue, and the most recent of which exited successfully in 2019. While a PE CEO, I concurrently founded a software business which we exited to a global travel business.
Over the past 25+ years, I have bought or sold dozens of companies and raised close to $1B in debt and equity. Through my career’s work building executive teams at different companies, I discovered my passion for personal growth. I’m energized by helping others realize the best versions of themselves – particularly the underdogs – and I’m fortunate to do this with ambitious startup founders at Enjoy The Work.