Powering Human Progress.
About Rethink Education
We are a venture capital firm investing in companies that expand human potential and economic mobility at scale.
We back founders building enduring businesses at the intersection of technology, capability, and access — where innovation creates measurable advantage for people who have historically been overlooked by traditional systems.
Our conviction is simple: expanding access to opportunity is one of the largest untapped growth markets in the world.
OUR STRATEGY
We invest at the pre-seed, seed, and Series A stages, partnering early with founders building category-defining companies that expand access to opportunity and generate meaningful gains in earnings and access.
We focus on white spaces where incentives are aligned and where better tools help people build valuable skills, access higher-quality work, navigate complex systems, and increase their earning power.
Many of our portfolio companies partner with school systems, employers, government agencies, and insurers to deliver scalable solutions through embedded distribution channels. We also selectively back consumer models — particularly accessible or freemium products — when they demonstrate strong engagement, clear willingness to pay, and a compelling return on investment for the end user.
Founder–market fit is foundational to how we invest. We seek visionary leaders with differentiated insight into the problems they are solving and a deep, sustained commitment to building in the space.
Our approach is grounded in venture fundamentals: scalable business models, strong margins, capital efficiency, defensible moats through network effects or data advantages, and the potential to shape new categories.
Our Investment Verticals

EdTech

Workforce

Health Equity

Financial Inclusion
Our Impact
Meet the Team
Matt Greenfield
Founder & Managing Partner
Matt Greenfield is a pioneer investor in EdTech with 25+ years of experience in venture capital and angel investing and deep industry connections. He is eager to transform education to be more joyful, collaborative, and purposeful, which he strives to achieve through his role as founder and managing partner of Rethink Education.
Matt has a robust background in entrepreneurship and education as the co-founder of Rethink First, a $100m ARR company serving 3 million neurodivergent learners a year, and former English professor at Bowdoin College and the City University of New York (CUNY). During his time as a professor, Matt served on a committee overseeing admissions, helped launch an interdisciplinary learning community program for first-year students, taught in a teacher preparation program, and led graduate courses in literature to teachers from the New York City Public Schools.
Matt is a board member of Southern New Hampshire University (SNHU) and several Rethink Education portfolio companies including Stellic, CareAcademy, GetSetUp, Major League Hacking, Ignite Reading, and NoRedInk.
Matt received his B.A., M.A., and Ph.D. in English from Yale University, where he won five academic prizes and fellowships from the Mellon and Whiting Foundations and served on the editorial board of the Yale Journal of Law and the Humanities.
Andre Bennin
Managing Partner
Andre (“Dre”) Bennin is a Managing Partner of Rethink Education where he is a key player in both firm strategy and leading investments, actively shaping the portfolio, positioning, and thesis. Dre brings 10+ years of venture and private equity investing experience to the team, formerly serving as Managing Partner of Juvo Ventures and as Managing Director of Corporate Development at Strada Education Network. While at Strada, Dre led $580mm of investments and acquisitions, served on the boards of Authess, Cell-Ed, BridgeEdu, and Roadtrip Nation, and was an advisory board member of Kenzie Academy and GSV Ventures.
Dre originally joined Strada in 2013 as Senior Advisor and Deputy Chief of Staff to the CEO, playing an integral role in the organization’s transition and mission development. Before rejoining Strada as Managing Director in 2018, Dre pursued a role in the public sector as Senior Operations Director for the Office of the Governor of Indiana, Eric J. Holcomb, where he supervised all workforce training and economic development agencies for the state and spearheaded the creation of its $250mm investment vehicle, the Next Level Fund.
Dre was recognized in Savoy Magazine’s 2020 Most Influential Black Executives in Corporate America. He earned his bachelor’s degree in molecular biology and his Juris Doctorate from Brigham Young University. Dre is a West African immigrant, born in Côte d’Ivoire to two Ghanaian parents and grew up in Alexandria, VA. He currently resides in Indianapolis, IN with his three children. Dre is a native French and Twi speaker.
Amy Nelson
Managing Partner
Amy Nelson serves as Managing Partner of Rethink Education where she oversees the firm’s operations, strategy, pipeline and portfolio management, and serves on the investment committee. Amy transitioned into a full-time role with the Rethink Education team after three years as Chief Strategy Officer for Rethink Capital Partners, where she led growth and operations across the platform. Amy also sits on the IC for Rethink Food and has been a strategic partner on Rethink Community.
Prior to Rethink, Amy spent seven years at Venture For America (VFA), an organization that selects, trains, and supports the next generation of entrepreneurs, including four years serving as CEO. In her seven years with VFA, Amy helped more than 1,200 recent college graduates launch entrepreneurial careers, directly supported the launch of 120+ businesses, and made direct investments into 40+ pre-seed startups.
Amy has also held business development positions at B Lab, Relief International, and Cambodian Children’s Fund. Amy sits on the boards of the Vivvi, Impact Capital Managers Institute, West Harlem Innovation Network, Partners for Justice, Generation Citizen, and Safe Haven Medical Outreach in Cambodia.
Amy is a graduate of Claremont McKenna College and NYU’s Stern School of Business.
Bridget Duru
Vice President
Bridget Duru is a VP at Rethink Education, focused on pipeline, deal sourcing, and thesis development, currently targeting our life skills investment vertical. She boasts a strong background in leading due diligence for private equity transactions in the education and consumer sectors during her tenure at EY-Parthenon.
Bridget brings an extensive network in venture capital and early-stage education, healthcare, and financial technologies to the team. She serves as the New York Co-Lead of the Emerging Venture Capital Association (EVCA), is the founder of pre-partner EdTech investors group, and is a board observer of Rethink Education portfolio companies: Anthill, GetSetUp, Care Academy, and Vivvi. Bridget has been raising funds dedicated to advancing education since middle school.
She graduated magna cum lade from Brown University with a B.A. in Political Science and Gender Studies.
Monique Malcolm-Hay
Vice President
Monique Malcolm-Hay is a VP at Rethink Education, focused on deal sourcing, portfolio management, and fundraising support. An emerging AI connoisseur in the EdTech sector, Monique is spearheading Rethink Education’s partnership with the Robin Hood Foundation on responsible AI in education and is a frequent speaker on the topic at industry events like SOCAP.
Monique began her career in PwC’s Deals practice on the restructuring team before transitioning to join PwC’s workforce strategy consulting team, where she drove the firm’s AI x upskilling offering. She then joined the early team of Future Fit AI, where she loved supporting the 0 to 1 stage of company building. Prior to Rethink, Monique led Stanford GSB’s Impact Fund, directing early-stage investments with a focus on measurable social impact.
Trained as an accountant (CPA-equivalent), Monique holds an M.B.A. and M.A. in Education from Stanford University, and a B.S. in Business and Management from Aston University.
Board observer of Rethink Education portfolio companies: Brighthive, Voxy, and Major League Hacking.
Michael Walden
Investment Committee Member
Michael Walden serves as Chief Operating Officer and Chief Compliance Officer of Rethink Capital Partners, where he oversees the launch, development and operations of the Rethink Capital Partners venture strategies. Michael also serves as the President & Managing Partner of Rethink Community. Since joining the firm in 2011, he has led the development and launch of four Rethink Capital Partners strategies and developed the firm’s operating division. He is a member of the Investment Committee for Rethink Education, Rethink Impact, Rethink Community and Rethink Healthcare Real Estate.
Michael brings over 25 years of experience establishing, operating and growing businesses in a variety of industries. This includes operating positions in venture-funded growth companies in the technology and telecommunications sectors.
Michael began his career in Washington, D.C. serving on the legislative staff of U.S. Senator Arlen Specter. Mr. Walden received a Bachelor of Science degree in Business Administration from the University of Richmond.
Tammy Mank Wincup
Venture Partner
Tammy Wincup is a Venture Partner of Rethink Education, formerly serving as an Investment Committee Member for nearly four years. Tammy now serves as the Chief Executive Officer of Securly, a tech company developing student safety and wellness solutions that help school leaders and educators keep students safe, secure, and ready to learn.
Prior to that, Tammy served as an interim Chief Operating Officer at Get Well, President & Chief Commercial Officer of Revolution Foods, and the founding President of Protocol, a media company covering the power center of tech. Founded as a part of POLITICO Media Group and sold to Axel Springer Media in 2021, Tammy grew Protocol from a pre-launch idea to a dominant player in the tech media space with a growing editorial team supported by a thriving advertising model.
In 2019, Tammy was a Senior Advisor to The RISE Fund. The RISE Fund is a $2 billion global impact fund led by private equity firm TPG in collaboration with a group of renowned stakeholders including U2 lead singer Bono. During her time, Tammy led the go-to-market revenue strategy for a TPG portfolio company.
From 2010 to 2019, Tammy was the Chief Operating Officer (COO) at EVERFI, the leading education technology company focused on using digital learning to teach learners of all ages critical skills. As COO, Tammy oversaw EVERFI’s 600 team members; led the development of national and global corporate partnerships; oversaw the development of EVERF’s digital learning technology platform; and spearheaded the implementation of that technology in over 21,000 K-12 schools and 1500 college campuses, and supporting the over 4,000 corporate customers that purchased the technology. Founded in 2008, EVERFI is a venture-backed company with investments from TPG, The RISE Fund, Amazon Founder Jeff Bezos, Twitter Founder Evan Williams, and Google Chairman Eric Schmidt.
After September 11th, 2001, Tammy was appointed to the U.S. Department of State, where she helped develop and manage the Middle East Partnership Initiative, a $300 million fund focused on economic and education foreign assistance to the Middle East. In 2006, she refocused in the U.S. working with leading companies on growth business plans.
Early in her career, Tammy worked in South Africa and Egypt leading economic growth and democracy projects for Price Waterhouse’s International Strategy Group. She returned to the United States to run customer success for a technology start-up in San Francisco, and at Diamond Technology Partners, a public company focused on helping Fortune 500 companies innovate with technology.
Tammy is a Pahara Aspen Institute Fellow, a competitive program for leaders. She is also active on a number of education non-profit boards in Washington, D.C.
Michelle Dervan
Venture Partner
Michelle Dervan is a Venture Partner of Rethink Education, formerly serving as a partner on the team and now the CEO of SkillsTrust, a Rethink Education portfolio company working to simplify pay transparency compliance and culture.
Michelle was a Director of Strategic Partnerships at Pearson Education where she focused on sourcing and structuring partnership deals with large and small tech companies. She previously held a number of education, EdTech and economic development roles at Enterprise Ireland, an Irish government agency.
Michelle holds an MBA from Columbia Business School and a Bachelor’s degree in European Studies, French and Russian from Trinity College Dublin, Ireland.
Our Portfolio
For over a decade, we’ve partnered with founders driven by conviction — building companies that expand opportunity and reshape critical systems.
Want to be part of that work? Discover roles across our portfolio companies.
*As of February 2026. The holdings listed may not represent the full portfolio and are provided for informational purposes only. Investment positions may change without notice due to market conditions or portfolio management decisions.
Our Value Add
“There are investors that are there for you on your good days, there are investors who antagonize you on your good days, and then there are the investors, like those at rethink education, who are there for you on your worst day and their faith is not shaken, or if it is, they don’t show it, and they cheer for you, they support you, they tell you you’re where you need to be, and they tell you to keep going. And we did keep going, and now things are working out.” – Jess Gartner, CEO of Allovue
This statement was provided by a representative of a portfolio company that is an investment of a private fund advised by Rethink Education. This relationship creates a material conflict of interest, as the representative may benefit from the success of the portfolio company and the Fund’s investment. No compensation was paid for this statement.