top of page




The winner of the 2023 Yale Angels virtual Pitch Off is StaffOnTap (Kayla Wooley MPH '21), and the runner-up is REALIEF (Claudia See '17, MBA/MD '24). 

StaffOnTap received $10k as the grand prize, and REALIEF received $5k. 

All finalists will be fast-tracked into Techstars NYC, powered by J.P.Morgan. They will also receive high-value pro bono services from Yale alumni.

THANK YOU TO OUR SPONSORS: The Yale University Office of Development and Yale Ventures. 

We would also like to acknowledge Alden Richards '77 for providing his valuable expertise as a startup advisor to our 13 semifinalists and our 5 semifinalists. 

Our partners were: 1stGen Yale, YaleFin, YaleWomen, Yale GALA, Yale Latino Alumni Network, Yale Blue Green, Yale Club of Silicon Valley, the Tsai Center for Innovative Thinking at Yale (Tsai CITY), and the Y-Startup Index. 


EcoPackables - Shervin Dehmoubed, YC '25
StaffOnTap - Kayla Wooley, MPH '21
Mission-Driven Tech - Onyinye Balogun, MD MS '10
Zama - Brendan Sullivan YC '16
- REALIEFClaudia See YC '17, MD/MBA '24


All five finalists will be fast-tracked into consideration for the next cohort of Techstars NYC, powered by J.P. Morgan

Additionally, the following Yale alumni are offering high-value pro bono services to all five finalists:

  • Lisa Brand '91 of Brand Consulting: Lisa will partner with you to more fully leverage your existing product and marketing resources to spur your businesses' growth. She'll help you identify, refine, or detail your specific growth metrics, prioritize initiatives against them, and recommend appropriate new channels and loops for to undergird scalable growth.

  • Adam Brenner '05, Partner, Emerging Growth and Venture Capital, DLA Piper: One hour of pro bono to finalists around planning for a venture financing round. 

  • Nicky Chang M.Arch '12, Founder of Meanwhile Partners: Two 1-hour brand strategy and design consultations. The finalists can choose to use the sessions on clarifying their brand positioning, building a visual identity, packaging designs, UI/UX design, or investor deck improvement. 

  • Jo Ilfeld '96, PhD, CEO of Incite To Leadership: Incite to Leadership is a boutique executive coaching firm in the San Francisco Bay Area. Jo will provide her leadership coaching services to all five finalists. Company CEOs and founders can use this session to tackle an ongoing leadership question, to strategically think about their leadership team, or to discuss leadership development within their company.

  • Michael Lewittes '89, Founder of GossipCop (successfully acquired): Expert advice on SEO

  • Andrew Winig '91, Elevator Pitch Coach: If you’re ready to get your message out to an even larger audience, I can help! We start with your current messaging and roster of products and services. Then we identify your priority offering and design an approach using your favorite channels to clarify and spread your message. Have an email list but don’t do any business networking? Great! Exactly the opposite? Equally great! Want to identify more speaking opportunities – or never, ever want to speak in front of a crowd? We’ll design a strategy that works for you.


We are honored to host the following judges for our 2023 Pitch Off:

Allison Pickens ‘07

Founder & General Partner, The New Normal Fund 

Allison Pickens is a solo GP investor and independent board director who spends her time supporting SaaS CEOs, including at dbt Labs (on the board), Jasper (the fastest growing SaaS company ever), Mutiny, Oyster HR, Hex, Tackle, and others. She also serves on the board of Commvault (NASDAQ: CVLT). As the former COO at Gainsight, having scaled the company from $1M to $85M ARR, Allison is a thought partner to CEOs on many topics related to scaling the business. She has published hundreds of blog posts and podcasts, as well as a book through Wiley. More about her at and on her Substack.

Lindsay Siegel MBA ‘11

Head of Impact, Company Ventures

As Head of Impact for Company Ventures 

Lindsay Siegel is committed to shift the culture of tech for a more equitable and sustainable future. She leads the Boost Founder Fellowship and City Fellowship, collaborating with the NYC Economic Development Corporation to catalyze the businesses of underserved entrepreneurs in NYC. She also advises Grand Central Tech founders to codify their startups' values and purpose, with a DEI lens. She has long worked at the intersection of social good, business and technology, and spent nearly 5 years at The City College of New York, CUNY, as the Executive Director of the Zahn Innovation Center leading the campus entrepreneurship program. She sits on the advisory board of CUNY Tech Prep and has participated in the selection process for various grants and fellowships including Zebras Unite, CIV:Lab and Echoing Green. Lindsay earned her MBA from Yale School of Management and her BS from Northwestern University.

Gary Stewart ‘96, JD ‘99

Managing Director, TechStars NYC powered by J.P. Morgan, Visiting Lecturer of Entrepreneurship at Yale Law School, and Founder of FounderTribes

Gary Stewart is the Managing Director of the Techstars New York City Accelerator powered by J.P. Morgan. Born in Jamaica, he grew up in the Bronx, where he attended the Bronx High School of Science before attending Yale College, where he graduated magna cum laude, Phi Beta and Yale Law School, where he was co-executive editor of the Yale Law Journal and published a well-cited article. He is a VC-backed, exited serial entrepreneur; an early-stage investor that managed a $1.6 billion start-up portfolio; a professor who has taught entrepreneurship at Yale Law School and IE Business School in Madrid, and been invited to speak at Cambridge, Oxford, Stanford and INSEAD; and a former contributor to Forbes Magazine.

Tessie Decker YC '97

Angel Investor and Fund Manager, Seattle Angel Conference

Tessie Decker is an angel investor and the fund manager for the 23rd Seattle Angel Conference, which recently awarded $200K+ to its spring winner.  She founded and currently runs an Angel Braintrust group welcoming women into angel investing.  She is an LP for First Row Partners and Portfolia, a Coralus Activator, has completed ACA Angel University and is a recent Laconia Venture Fellow.  Her professional background includes product management roles with Amazon's worldwide display ads team as well as leading the Los Angeles Times / Tribune's national entertainment vertical.  Past consulting experience includes work with LEK's Los Angeles media and entertainment practice.  As a consultant at Prophet, a brand strategy consulting firm, she advised corporations on customer experience, portfolio architecture, and brand positioning.  She began her career working in film and television production.  A power generalist, Tessie loves to read books and listen to podcasts about startups, VC, business strategy, psychology, and decision-making. Tessie received her MBA from Wharton and her BA from Yale University.


To learn more about our pitch off sponsorship rates and benefits, to volunteer your services on a pro bono basis to the finalists, or for any other questions, please contact Wendy Maldonado D’Amico ‘93 ( or Ellen Su '13 ( 

bottom of page