Thinkful has raised $16.0M in total across 3 funding rounds.
Thinkful's investors include Acrew Capital, Angelic Ventures, Bullpen Capital, Catapult Capital, First Round Capital, Floodgate, Great Oaks Venture Capital, MassMutual Ventures, Oak HC/FT, Owl Ventures, Relay Ventures, RRE Ventures.
Thinkful was an edtech company offering self-paced, online coding bootcamps and skills training in web development, data science, cybersecurity, UX/UI design, and mobile app development, delivered through 1-on-1 mentorship with software engineers.[1][2] It targeted career changers—often fully employed professionals—and businesses facing talent shortages, solving the skills gap in tech roles by providing project-driven courses, job guarantees, flexible payments, and employer networks to accelerate career transitions.[1][2][3] Founded in 2012, it raised $14.85M before being acquired by Chegg in 2019 (rebranded as Chegg Skills in 2023), earning recognition as the top U.S. bootcamp by Forbes Advisor in 2023.[1][2]
Thinkful was founded in February 2012 by Roshan Choxi and Dave Paola, who met at the University of Illinois at Urbana-Champaign in 2008 and later moved to San Francisco.[2] The idea emerged from their tutoring students over Skype, leading to a formal platform launch at San Francisco's Launch Festival that year; early traction included $250K seed funding in May 2012, $2M in 2013, and $6M Series A in 2014 from investors like RRE Ventures, Tribeca Venture Partners, Owl Ventures, and Peter Thiel.[1][2] Pivotal moments included headquarters relocation to New York and expansion under Chegg's 2019 acquisition, which boosted offerings for thousands of learners entering tech roles.[1][2]
Thinkful rode the edtech bootcamp boom amid exploding demand for tech skills, as "all jobs became tech jobs" post-2010s digital shift, outpacing traditional education in speed and relevance.[3] Timing aligned with remote learning surges (pre- and post-COVID) and corporate upskilling needs, amplified by its 2019 Chegg acquisition for scaled resources.[1][2] It influenced the ecosystem by bridging supply-demand gaps—training thousands for roles at Big Tech and startups—while validating online mentorship as a scalable alternative to degrees, paving the way for platforms like Chegg Skills.[2][3]
As Chegg Skills post-2023 rebrand, Thinkful's legacy endures in AI-era upskilling, with next steps likely expanding into emerging fields like AI ethics, machine learning, and hybrid cybersecurity amid persistent talent shortages.[2][3] Trends like lifelong learning and corporate reskilling will propel growth, evolving its influence from individual bootcamps to enterprise platforms shaping the "next workforce."[3] This positions it centrally in tech's human capital race, fulfilling its founding promise to arm career changers with indispensable skills.[1]
Thinkful has raised $16.0M across 3 funding rounds. Most recently, it raised $10.0M Series A in January 2018.
| Date | Round | Lead Investors | Other Investors |
|---|---|---|---|
| Jan 1, 2018 | $10.0M Series A | Acrew Capital, Angelic Ventures, Bullpen Capital, Catapult Capital, First Round Capital, Floodgate, Great Oaks Venture Capital, MassMutual Ventures, Oak HC/FT, Owl Ventures, Relay Ventures, RRE Ventures, Sandbox Industries, Tribe Capital, Tribeca Venture Partners, Uncork Capital, Carl Showalter | |
| May 1, 2014 | $5.0M Seed | Acrew Capital, Bullpen Capital, Catapult Capital, First Round Capital, Floodgate, Founders Fund, Great Oaks Venture Capital, MassMutual Ventures, Oak HC/FT, Owl Ventures, Quotidian Ventures, Relay Ventures, RRE Ventures, Sandbox Industries, Tribeca Venture Partners, Carl Showalter, Darrell Silver | |
| Feb 1, 2013 | $1.0M Seed | Bullpen Capital, Floodgate, Founders Fund, MassMutual Ventures, Oak HC/FT, Owl Ventures, Quotidian Ventures, Relay Ventures, RRE Ventures, Sandbox Industries, Seven Seven Six, Tribeca Venture Partners, Carl Showalter, Darrell Silver |
