Gigster

Gigster was founded in November 2014 by Roger Dickey (a serial entrepreneur who had previously built Facebook games including Mafia Wars at Zynga after Zynga acquired his company Curiosoft) and Debo Olaosebikan (a Cornell-trained physicist with a PhD in laser physics). The company launched publicly on July 22, 2015, marketed as an 'Uber for software developers': clients could get an instant quote and a fully-managed development team (assembled from a highly selective global freelancer network, with roughly a 7.7% acceptance rate) to build an app or MVP, complete with a dedicated project manager and post-launch maintenance. The launch was backed by a roughly $2.5M seed round from Y Combinator, Greylock Partners, Bloomberg Beta, and Felicis Ventures, plus angel investors including Naval Ravikant, Justin Waldron, Emmett Shear, and Stan Chudnovsky. Early traction was strong — the company reported $1M in bookings within two weeks of launch and 300+ customers by the end of 2015 — and in December 2015 Gigster raised a $10M Series A led by Andreessen Horowitz (with Y Combinator's Continuity Fund, Ron Conway's SV Angel, Ashton Kutcher's Sound Ventures, and Jason Calacanis's Launch Fund also participating), bringing total funding to $12.5M; a16z partner and former SuccessFactors CEO Lars Dalgaard joined the board.

In November 2016, Gigster launched an unusual 'Gigster Fund' designed to give its freelance network economic upside without violating contractor-status rules: a $700K fund (from Bloomberg Beta, Felicis, and a Chinese investor) plus 1% of Gigster's own equity that invested in top clients, with future profits shared monthly across active freelancers. By 2017 the company had pivoted decisively from its original consumer/startup-MVP focus toward enterprise clients (e.g., MasterCard, IBM, and PepsiCo were cited as customers), building teams for machine learning, blockchain, and other specialized enterprise projects with fixed-price guarantees. This 'enterprise pivot' was capitalized by a $20M Series B in August 2017, led by Redpoint Ventures with participation from Andreessen Horowitz, Marc Benioff, Adam D'Angelo, and UC Berkeley AI/statistics professor Michael I. Jordan, bringing total funding to $32.5M. At the time, Gigster reported enterprise clients growing from 3 to 40+, project sizes up 10x, and revenue up 3.5x since the Series A.

The company's momentum did not fully hold. In January 2019, co-founder and CEO Roger Dickey stepped down (having already handed the CEO role to former WaveMaker CEO and VMware executive Christopher Keene in October 2018), saying his passions lay in consumer rather than enterprise technology; at departure, Gigster reported roughly 1,200 clients including nearly 10% of the Fortune 500 and continued profitability, but no further disclosed venture funding after the 2017 Series B suggests the company's growth trajectory slowed and it likely relied on revenue rather than new capital going forward — a common pattern among the 'on-demand talent marketplace' cohort (alongside struggles at peers like Handy and HourlyNerd/Fixate) that had been over-hyped in the 2014-2016 'Uber for X' era. Co-founder/CTO Debo Olaosebikan departed in January 2020. In May 2021, Gigster was acquired by Ionic Partners, an Austin, Texas-based enterprise software investment firm, marking the end of its run as an independent venture-backed company and a relocation of its operational base from San Francisco to Austin.

Business model

Fully-managed, B2B software development-as-a-service / talent marketplace: Gigster sources and manages a global network of vetted freelance engineers, designers and product experts, assembling them into project teams (or providing individual 'talent on demand'/'forward deployed engineers') for fixed-price or staff-augmentation engagements with enterprise clients.

Project-based fees and staff-augmentation/managed-services billing to enterprise clients (fixed-price guaranteed delivery, dedicated-team retainers, and hourly/day-rate talent-on-demand billing); historically also took a cut of what it paid freelance developers on its network.