# David Boskovic

> David Boskovic is the founder and CEO of Obvious, the company formerly known as Flatfile. A self-taught programmer who began coding in his teens, he spent years building B2B software before turning repeated frustration with CSV imports into Flatfile. After raising a $50 million Series B in 2022, the company expanded in late 2025 into Obvious, an AI workspace, while continuing to support Flatfile. His current focus is agent-directed software production, including Obvious's Frontier build sprints.

- **Role:** Founder and CEO at Obvious
- **Organizations:** Obvious, Flatfile, Envoy, Rainmaker
- **Known for:** Co-founded Flatfile and developed it from a side project into an enterprise data-onboarding company., Led Flatfile through a $35 million Series A in 2021 and a $50 million Series B in 2022., Helped establish data onboarding as a distinct enterprise software category.

## Career timeline

- **Early teens** — Taught himself web development while building an e-commerce platform for his father's small business; by age 15, he said he could code nearly anything.
- **2010-2016** — Co-founded Rainmaker and served as CTO.
- **2016-2018** — Worked as platform architect at Envoy, where a recurring enterprise data-import problem helped inspire Flatfile.
- **2018** — Built the first version of Flatfile as a side project with Eric Crane after what he described as two weekends of 'rage designing.'
- **2019** — Flatfile raised its first $2 million seed round after early customer validation.
- **2021** — Flatfile raised a $35 million Series A; public reporting said it had more than 300 customers.
- **2022** — Flatfile announced a $50 million Series B led by Tiger Global Management and reported serving 500 customers.
- **2025** — Flatfile, the company, rebranded as Obvious while Flatfile remained an actively supported data-migration product.
- **2026** — As CEO of Obvious, focused on an AI workspace and Frontier build sprints for agent-directed software delivery.

## Achievements

- Co-founded Flatfile and developed it from a side project into an enterprise data-onboarding company.
- Led Flatfile through a $35 million Series A in 2021 and a $50 million Series B in 2022.
- Helped establish data onboarding as a distinct enterprise software category.
- Expanded the company from Flatfile into Obvious while retaining Flatfile as a supported product.
- Built and publicly taught an agent-directed software delivery method through Obvious Frontier sprints.

## Latest updates

- **2026-08** — Promoted upcoming Obvious Frontier build sprints and spoke publicly about software factories and agent-driven engineering velocity.
- **2026-07** — Appeared on the Exception Handlers podcast to discuss what happens when software engineers stop writing code directly and instead underwrite agent-produced work.
- **2026-06** — Reported results from multiple Frontier cohorts, including teams shipping roadmap work during two-day, in-person build sessions.
- **2025-12** — Flatfile announced that the company had become Obvious, with Flatfile continuing as the data-migration product and Obvious expanding into a broader AI workspace.

## Links

- Website: https://obvious.ai
- LinkedIn: https://www.linkedin.com/in/dboskovic
- Twitter/X: https://x.com/dboskovic

---

Profile page: https://yespress.io/david-boskovic
Published by YesPress — https://yespress.io
Last updated: 2026-08-18