Greg Caplan

Co-founder and CEO of Upcraft (Chicago, AI sales agents) which Labelbox acquired on Feb 10, 2026 to automate recruiting, qualification and engagement of Alignerr experts; now listed as Labelbox VP of Growth. Effectively owns the machinery that grows Labelbox's expert supply.

Background

Consumer/marketplace operator background: prior companies listed on The Org include Cameo, Spot Meetings, Groupon and Lightbank. Founded Upcraft in 2021.

What they run now

Applying agentic outreach to Alignerr supply growth (sourcing and engaging domain experts at scale).

Career

2026 – presentVP of Growth, Labelbox
2021 – 2026Co-founder & CEO, Upcraft — acquired by Labelbox
—Cameo
—Groupon / Lightbank

On the record

Acquisition · 2026-02

Says joining Labelbox gives Upcraft far more reach to make AI more accessible, and cites Labelbox's superintelligence vision. source

Connections

Manu Sharma — reports to (per The Org)

Why it matters here

If Alignerr ever opens a design/visual-arts supply category, his team decides how experts are sourced; also a model of how incumbents automate expert recruiting, which a small specialist has to compete with on quality rather than volume.

How to reach

Speculative: growth leaders respond to supply-side ideas (niche communities, conversion data). A creative-community sourcing partnership is the plausible hook.

What we could not establish

Roles at Cameo/Groupon/Lightbank not specified
The Org profile is unverified
LinkedIn/X not verified

Background

What they run now

Career

On the record

Connections

Sources

Manu Sharma

Brian Rieger