Sydney Crescenzo
6+ years managing product designers, 13+ as an active product designer.
Roles + Case Studies · Leadership · Speaking · Contact
Hello and welcome 👋 I'm Sydney.
I currently manage a team of Product Designers at ed-tech nonprofit Khan Academy, and represent Design at the leadership level for strategizing how AI is used in the classroom via our multi-sided district product.
I've managed designers of varying disciplines across product, systems, and brand, and I spend as much time iterating on how AI is changing the design process as I do about the products we design and ship with it.
I'm driven by curiosity & community, both at work and in my home state of Rhode Island.
Roles & Case Studies
My experience spans multiple industries, company stages, and roles, but for the past several years, specifically as a design team leader and people manager. I've primarily worked within startup-to-mid-size teams who have big goals and limited resources, and personally enjoy the growth and challenges that come from wearing multiple hats.
Khan Academy
CurrentSenior Design Manager · 2023–Present
Khan Academy is a non-profit ed-tech platform with the ambitious mission of providing a free education to anyone, anywhere.
I joined the day the team publicly announced Khanmigo, our AI-based tutor, and spent my first year leading the team building our the student experience.
In year two, I was tapped to help lead a cross-functional, ground-up rebuild of our multi-sided District platform, partnering directly with C-suite and a team of cross-department leads. There was a Year 1 Pilot, and a Year 2 phased rollout that started August 2026 (see the announcement →).
Crosstie (formerly Gain Life)
Product Design Lead · 2020–2023
Crosstie is building AI-driven workflow software for the insurance industry. I joined as the company's sole designer, designing for a two-sided platform for both insurance companies and claimants.
As the company grew, I grew with it, stepping into a player-coach role, hiring and mentoring a team of product designers, and building a research and data practice. While there, I also led foundational research that helped the company expand into new lines of business.
American Express
Additional experience designing for U.S. Small Business Credit Card customers during the onset of COVID-19, including rapid-response messaging and a large-scale redesign of the credit card application flow.
Additional in-house and agency experience is available on my LinkedIn.
Leadership
I moved into design management for the same reason I moved into design in the first place: I enjoy the challenge of problem solving, and I like building relationships and shipping good work with talented people.
The people I lead and manage have shared appreciation for my transparent communication, directness, and "us vs the problem" mentality. Social proof available on request :)
Speaking
I speak at both virtual and in-person design and technology events.
While I love the energy of a conference or large event, I'm especially drawn to smaller settings where real two-way conversation can happen. I particularly enjoy working with students and helping upskill the next generation of creatives.
Recent engagements include presenting at the SCOUT Conference, guest-speaking at a course on AI and Education at Northeastern University, and a Q&A with a nonprofit community coding group.
My recent talks explore the intersection of design, AI, and the nonprofit sector.
Your time is valuable, thank you for spending it here. I welcome outreach about opportunities to speak, collaborate, or have industry-chats.