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Thinkful

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Thinkful · Online mentorship to advance your career

New York City, United StatesFounded 2012Edtech
Valuation $50–100M Last recorded · 2019
Headcount 100–500 Current team size
Total funding $10–50M Disclosed equity funding
Unlock exact values This page shows ranges. Dealroom has the exact numbers for Thinkful and the history behind them.

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 data

At 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

Funding history

5 recorded events

Company financing events and reported valuations.

Deal typeDateAmountValuationInvestorsSource
ACQUISITION✓Exit Sep 2019 $80M $80M Chegg —
SERIES A✓Equity / VC Jan 2018 $9.6M $38M Floodgate · Peter Thiel · RRE Ventures · Tribeca Venture Partners —
Showing the latest 2 of 5 recorded eventsBook a demo for the full funding history →

Growth signals

Thinkful website traffic

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.

Latest monthly visits2.6K 3-month web change-18.8% 1-year team growth-46%
Summary metrics are public; monthly history is available with a demoCompare with peers →

Investors

15 investors on the cap table

From Dealroom's funding and investor records, grouped by the round each investor first entered.

Seed7 investors entered at this stage

Series A3 investors entered at this stage

Other known investors5 additional known investors

Team profiled 100 named & role-tagged
Founders Hidden — book a demo/100 quality score
Key operators 1 quality Hidden — book a demo/100
Potential founders Hidden — book a demo likely future founders
Startup mafia Hidden — book a demo alumni-founded startups
Talent movements Hidden — book a demo in · Hidden — book a demo out past 12 months

Source: Dealroom Talent Intelligence.

Global footprint

Workforce and web traffic by country
Workforce by country
5 countries with
team presence
🇺🇸 United States98.8%
🇦🇺 Australia0.3%
🇩🇪 Germany0.3%
🇨🇦 Canada0.3%
🇮🇳 India0.3%
5 countries shown

Market sentiment

Posts on X, past 7 days

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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