Salary range: $240k base | $300k OTE | Equity: 0.25-0.5% | In-person Brooklyn, NY

Role Overview

We're hiring our first sales rep - someone who can run the full cycle of sales; sourcing leads, managing the sales process, and closing deals, all while building the playbook that future hires will run on.

Datalab makes document AI infrastructure that powers extraction at scale. We're at 8-figure revenue, and have grown revenue >5x YoY, with a team of 7. Anthropic uses Datalab. So do hundreds of other companies across FAANG, frontier AI labs, financial services, insurance, logistics, healthcare, and government. Our open-source projects (Marker, Surya, Chandra) have 60k+ stars and wide community adoption.

Sales today is founder-led. The goal of this role is to build a real sales motion on top of that foundation - outbound, ICP definition, enterprise process, and the playbook itself. You won’t be selling alone - engineers and the founder are heavily involved in the sales process, and the whole company pitches in to unblock deals and support customers.

This is a high-ownership, high-ambiguity role. We have standard pricing in some areas and open questions in others. We have strong signals about who our best customers are, but ICP isn't fully defined. You'll work alongside the founder and our GTM team to figure those things out by closing deals.

If you want to inherit a polished playbook, this isn't the right role. If you want to build that playbook at a company with real product-market fit, a steady inbound pipeline, and serious enterprise customers, this is a great fit. There's a clear path to sales leadership for the person who builds the function well.

Day to day you will:

• Run the inbound deal cycle at volume on enterprise opportunities - discovery, demos, technical evaluation, pricing, security review, procurement, and close.
• Own the customer through successful deployment - you're the primary point of contact through onboarding and go-live. After deployment, accounts move to team support for reactive issues; you retain expansion and renewal on accounts you closed.
• Prioritize ruthlessly for enterprise accounts. Disqualify smaller inbound back to the self-serve flow, so we can learn from it.
• Define our ICP through every closed-won and closed-lost, in close partnership with the founder and chief of staff.
• Navigate technical sales - know when to loop in engineering for a POC, when to bring in the founder, and how to drive procurement, legal, and public-sector vehicles like GSA/SEWP.
• Keep CRM clean - every deal, every stage, every next step, forecasts that reflect reality.
• Build the outbound motion as inbound capacity stabilizes - identify high-fit accounts, run sequences, measure conversion, and double down on what works. By month 3 this should be producing meaningful self-sourced pipeline.
• Build the playbook - discovery scripts, demo flows, objection libraries, competitive battle cards, pricing guidance, qualification criteria.
• Close the product feedback loop - track what customers are blocked on and which features would unblock deals, prioritize by revenue impact, and bring structured signal to product and engineering on a regular cadence.

What success looks like

By month 3

• Running the inbound deal cycle independently for most enterprise accounts.