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Founding GTM at Settle
Founding Account Executive / Head of Sales — title flexes to the candidate · New York, NY (in person) · Full-time
Settle is an AI-native enterprise data migration platform: the agent proposes every mapping and transform, deterministic engines validate, humans approve. Pre-seed, backed by Antler, with a paying enterprise customer in production.
The role
First dedicated GTM hire. Full-cycle ownership of the sales motion — sourcing, qualifying, running POCs, navigating security review, closing — and building the repeatable playbook alongside the founder. No SDRs, no sales engineer, no inbound. You carry the bag.
What we're looking for
- Technical credibility with technical buyers. You can hold a real conversation about schemas, field mapping, and validation logic with PS Ops and technical services leaders — with no sales engineer in the room. This is the hardest filter for this role.
- You've closed complex, multi-stakeholder enterprise deals: operator champion, technical evaluator, economic sponsor, a security/TPRM gate, and a POC inside the cycle.
- You've personally scoped, run, and converted technical pilots end to end.
- Ruthless qualification discipline — you qualify out fast.
- Full-cycle ownership: you source, run, and close without leads handed to you.
- Founder-stage temperament: you create structure from zero.
- You open doors through relationships and cold-start outbound.
Especially compelling
- You've sold data integration, ETL, iPaaS, MDM, data quality, or migration tooling.
- Early or founding rep at a seed–Series B infrastructure or data startup.
- Former implementation / solutions consulting / professional-services person who moved into sales — you were the buyer once, and it shows. The founder ran Fortune 500 migrations at Deloitte before building Settle; this profile mirrors that arc.
- Comfortable in procurement and security reviews; you understand SOC 2 gating.
- MEDDPICC or comparable enterprise qualification methodology.
Not a fit
- Big-company AE who runs a mature, lead-fed machine.
- Wants to build a team before carrying quota.
- PLG / SMB / transactional background — wrong muscle.
- Can't go a layer deep technically.
- Wants fully remote or 9-to-5.
The motion
Discovery-first, POC-driven; MEDDPICC qualification. Buyers are PS Ops and technical services / implementation leaders with VP/SVP economic sponsors. Stack: HubSpot, LinkedIn Sales Navigator, Clay, DocSend, Calendly, Granola.
What we offer
- Title: Founding AE / Head of Sales / Founding GTM — flexes to the candidate
- Equity: 0.5–1.5% common stock · 4-year vest, 1-year cliff
- Cash: $120K–$150K base · OTE ~$240K–$300K (roughly 50/50, tied to closed ARR)
- Location: NYC. In person. Travel to customer sites as needed.
- Stage: Pre-seed, backed by Antler.
Apply
Email kaan@settledata.ai with subject "Founding GTM" and five lines on the most complex deal you personally sourced and closed — the buyer, the cycle, and what almost killed it.
Apply nowHow we work
- Investigation-first engineering — we read code before we change it
- Two-stop pattern: investigation report → implementation
- AI-augmented development — Cursor and Claude Code in the workflow
- Direct communication, no filler
- Ship frequently, validate with customers
- Correctness over novelty
- Enterprise-first — every architectural decision considers SOC 2, audit, RBAC