Entrepreneur-in-Residence

DonorsChoose Internal Applicants and Referrals•New York City, NY

2d•$207,000 - $229,500•Hybrid

About The Position

Entrepreneur-in-Residence DonorsChoose is at a pivotal moment. As one of the nation’s leading education nonprofits, we’ve supported millions of teachers and students by channeling over $1.8B in resources to classrooms across the U.S. Today, we’re pushing ourselves to evolve, from a project-based crowdfunding platform into a system-level engine for educational equity, unlocking new funding models, launching new products, and modernizing how we operate. About the Role DonorsChoose is launching Engine 2 : a focused, independently-led effort to develop and scale a new product or business model that can dramatically expand our impact beyond the constraints of our current classroom-project giving model. Hiring for this role is a deliberate investment in tomorrow’s DonorsChoose. This role will build and lead a new team. As the Entrepreneur-in-Residence you will operate as an internal founder by setting direction, building and managing a small team, making hard tradeoffs, and ultimately building a new giving experience that can successfully attract a new donor segment, at scale. In this role you’ll own the end-to-end discovery, validation, and early scaling of this new product that leans on the strengths of DonorsChoose but creates a net new giving experience. Reporting to the CEO, this role will work closely with senior leaders across the organization while maintaining the speed, focus, and autonomy required for successful innovation. This role is intentionally high-ownership and high-stakes with a defined mandate, timeline, and success criteria. While DonorsChoose will invest meaningfully in this work, continued placement at the organization beyond ~2 years is not guaranteed if Engine 2 does not demonstrate viability. Our aim is to provide the authority, resources, and clarity needed to build something real and to determine decisively what should scale.

Requirements

You have a founder and builder mindset.
You have deep experience launching new products, programs, or business models, whether at a startup or on an innovation team, and are energized by ambiguity, ownership, and learning fast.
You are comfortable with real accountability.
You’re excited by clear goals, defined timelines, and meaningful risk.
You understand that not all bets succeed and you value clarity and decisiveness over comfort.
You combine strategy with execution.
You can zoom out to set direction and zoom in to write emails, run interviews, analyze data, or prototype ideas.
You’re not precious about role boundaries or afraid to get your hands dirty.
You are deeply mission-aligned.
You care about public education, equity, and delivering real value to teachers and students.
You’re motivated by impact as the ultimate goal.
You are externally oriented and evidence-driven.
You seek truth from users, markets, and data.
You test assumptions early and change course when evidence demands it.
You are excited to travel and get out of the building.
You recognize that to learn quickly, you must interface regularly with real stakeholders and are willing to do what it takes to get in front of them.
You are a strong leader.
You know what should come next and how to manage and get the best work out of a team of experienced folks.

Responsibilities

Within 2-years, validate a new giving experience that will meaningfully grow dollars supporting K-12 classrooms through DonorsChoose. Whether you achieve this goal is the ultimate measure of success in this role.
Validate and invalidate ideas rapidly
Design and run MVPs, pilots, and experiments to validate user demand, value proposition, and unit economics.
Engage deeply with teachers, funders, and vendors to ground decisions in real user needs.
Rapidly answer key questions in the market through work that’s directly in touch with the target users and/or funders; answering a key question every 1-2 weeks is the expected pace of work.
Meet with the CEO and a selected governing body to report on learnings every month; report to the board on progress 3-times a year.
Prioritize speed and learning over polish, making evidence-based decisions to iterate, pivot, or stop.
Root approaches in lean start-up models.
Define and refine high-potential product or business concepts capable of reaching $5–10M in annual revenue within 2-years, with a credible path to much larger scale over time.
Understand and effectively serve the needs of a new funder segment
Root this product in the DonorsChoose mission, ensuring it will deepen teacher engagement and equip K–12 public school classrooms.
Leverage DonorsChoose’s existing owned advantages (school access, procurement capabilities, trusted platform), driving efficiency and competitive advantage without sacrificing speed or customer needs.
Evaluate ideas against clear innovation constraints, including scalability, operational simplicity, and revenue potential, building a clear, data-backed investment case for viable ideas, including a believable financial model
Define and track early success metrics, including adoption, retention, operational feasibility, and early revenue signals
Build and lead a small, high-impact team
Hire and lead a lean Engine 2 team (2–4 people) with strong, complementary skillset.
Build and maintain a healthy team culture; establish norms for decision-making, accountability, experimentation, and collaboration that differ from the core org; ensuring a lack of friction without heavy time spent driving buy-in versus doing the work.
Coach team members operating in high ambiguity and ensure momentum through clear milestones.
Define and advocate for a budget and financial investments over time.
Manage relationships with Engine 1 leaders to stay aligned without slowing progress.
Navigate tradeoffs transparently, surfacing tensions early and clearly.