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Thinkful
Thinkful · Online mentorship to advance your career
About Thinkful
Thinkful emerged in the online education landscape in 2012, established by Darrell Silver and Dan Friedman. The company positioned itself as a provider of skills-based learning, focusing on delivering technical education through a mentorship-driven model. Silver, with a background that includes co-founding the non-profit Perpetuity and serving as an Entrepreneur in Residence at Columbia University, brought a blend of entrepreneurial and educational insight to the venture. Friedman's experience as a software developer and his prior role in creating CourseKit, a learning management system, underscored the company's technological and educational foundations. The core of Thinkful's business model revolves around offering intensive, career-focused programs in high-demand technology fields such as software engineering, data science, and UX/UI design. Its primary clientele consists of individuals aiming to switch careers or advance in their current roles by acquiring specific technical competencies. The company's revenue stream is generated through tuition fees for these online courses, which are structured as bootcamps. A distinctive feature of its model was the 'job guarantee', which promised a tuition refund if a graduate did not secure a qualifying job within a specified timeframe, signaling a strong alignment with student outcomes. Thinkful's educational product is characterized by a one-on-one mentorship structure, pairing each student with an experienced industry professional. This personalized guidance, combined with a curriculum designed for practical application and career-readiness support, formed its key value proposition. Students engaged with a project-based curriculum and had access to a dedicated community and career coaches to assist with job placement. This approach aimed to bridge the gap between education and employment in the tech sector. The company's trajectory culminated in its acquisition by Chegg, a major player in the education technology market, for approximately $100 million in 2019, a move that integrated Thinkful's vocational training into Chegg's broader suite of student services.
Source: Dealroom company dataAt a glance
- Status
- Acquired
- Founded
- 2012
- Headquarters
- New York City, United States
- Employees
- 430
- Open positions
- None listed
- Dealroom signal
- 61.9/100
- Industry
- Education
- Sub-industry
- Education Providers
- Sector
- Edtech, Coach, Lifelong and Consumer Learning, Steam, Education Financing, Upskilling and Reskilling
- Business model
- Marketplace & ecommerce
- Client focus
- b2c
- Investment activity
- 2 companies, latest Apr 2018
- Capital deployed
- —
- Preferred round
- ACQUISITION
Knowledge graph
More headlines
Funding history
Company financing events and reported valuations.
| Deal type | Date | Amount | Valuation | Investors | Source |
|---|---|---|---|---|---|
| ACQUISITION✓Exit | Sep 2019 | $80M | $80M | Chegg | — |
| SERIES A✓Equity / VC | Jan 2018 | $9.6M | $38M | Floodgate · Peter Thiel · RRE Ventures · Tribeca Venture Partners | — |
Growth signals
Latest recorded traffic for Thinkful is 2.6K monthly website visits, down 18.8% over the last three months. Thinkful's team declined 46% over the past year.
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Investments and acquisitions
Recent portfolio relationships for companies that also act as investors or acquirers.
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Viking Code SchoolSan Francisco, United StatesImmersive online software engineering and job placement program
→
Investors
From Dealroom's funding and investor records, grouped by the round each investor first entered.
Seed7 investors entered at this stage
RRE Ventures
Quotidian Ventures
Pathfinder
Darrell Silver
Floodgate
Global Founders Capital
Founders Fund
Series A3 investors entered at this stage
Peter Thiel
Tribeca Venture Partners
Owl Ventures
Other known investors5 additional known investors
Chegg
Baseline Ventures- BHBrian Hirsch.
Learn Capital
Thiel Fellowship
Source: Dealroom Talent Intelligence.
Global footprint
team presence
Market sentiment
An AI-synthesised read of the highest-engagement posts about Thinkful on X, ranked by likes and reposts, corporate channels excluded.
Reading the room on X — pulling top posts and synthesizing themes…
Source: X recent search ranked by engagement (likes + retweets) · Synthesis by Claude · Cached for 1 hour
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