GTM Engineer

About Thoughtly

Thoughtly is the AI-native voice platform that's turning every lead into a real conversation. Thoughtly's agents call, qualify, and convert pipeline at scale — no SDRs, no static funnels, no code required. For the first time in our customers' history, they can reach 100% of all leads. Enterprise teams at 2U, Siemens, and Nomad are augmenting their outbound teams with Thoughtly, with customers seeing close rates jump from 16% to 38% on their lowest-rated leads.

This is a once-in-a-generation opportunity to build for a $1T annual market. Voice was just the beginning — Thoughtly is building the first fully autonomous CRM. It doesn't just track work — it does the work. The system of record becomes the system of action. This seed-stage rocket ship is backed by top investors like Armory Square Ventures, Afore, and Greycroft.

About the role

As Thoughtly's first GTM Engineer, you'll build the systems that make every GTM team member, campaign, and workflow unreasonably effective. Your impact will be direct and measurable: faster enrichment, cleaner data, fewer manual hours, more pipeline. No duct-tape integrations, no "we'll fix it later" scripts gathering dust.

We don't need someone to maintain the stack we have — we need someone to walk in, audit it, rip out what's broken, and ship what's missing. You know when to reach for Clay and when to build something custom. You think two steps ahead on how today's workflow fits into tomorrow's architecture. When you do this job right, our GTM team will operate at a level that companies twice our size can't match.

What You'll Do

• Own and maintain the data layer: enrichment (Clay, Apollo), HubSpot hygiene, and ICP segmentation — so every rep works clean data and every workflow targets the right accounts

• Audit the stack on day one: we have tools, overlap, and gaps. Walk in with a point of view, generate your own backlog, and start fixing things — nobody's handing you a roadmap (lots of greenspace to leave your mark on!)

• Ship rep productivity workflows at startup speed: AE asks for something Monday, it's live by Wednesday. Triage from the field, find the low-hanging fruit, build it, move on

• Build custom when low-code hits its ceiling: Clay and Zapier get you far. When they don't, spin up something purpose-built with AI coding tools. Make that call with judgment, not default

• Wire the stack together end-to-end: HubSpot, Clay, Apollo, Zapier — data flows between all of them or it's useless. You own the integrations, the syncs, and the reliability

• Consolidate ruthlessly: we have duplication across enrichment, routing, and engagement. Shrink the stack, kill the redundancy, build toward fewer tools that actually work together

• Think in systems, not band-aids: every workflow you build has upstream and downstream implications. No technical debt that someone else unwinds in six months

• Document what you build: if people can't find it, understand it, or trust it, it doesn't matter how well it works.

Required Experience:

• 2+ years in GTM Engineering, workflow automation, or a technical RevOps role — ideally at a high-growth B2B SaaS company.

• Hands-on experience with Clay/Apollo as a primary enrichment and workflow tool — you have opinions about how to use it well and you've pushed it to its limits.

• Experience with HubSpot — you know the data model, you've built on it, and you're comfortable owning CRM-level changes.

• Practical experience with APIs and webhooks — you've pushed and pulled data across systems and understand how integrations actually work in production.

• Fluency with AI coding assistants (Claude Code, Cursor, or similar) — you're actively building with these tools, not just experimenting with them.

• A track record of owning end-to-end automation workflows — from experimentation and prototyping through rollout and adoption, not just contributing to or consuming them.

• Proficiency with integration platforms (Zapier, Make, n8n, or similar) and judgment on when they get you 80% of the way versus when they become the bottleneck.

• Strong cross-functional communication — you partner effectively with both technical and non-technical stakeholders, from individual contributors to the founding team.

Nice to Have

• Proficiency in Python, JavaScript, or SQL

• Experience with engagement platforms (Outreach, Nooks, or similar) and how they connect to CRM and enrichment workflows

• Admin-level HubSpot experience — custom objects, workflows, reporting, and integrations

• A BDR or AE background that gives you intuition for what the sales team actually needs

• Familiarity with data warehouse or BI tooling — not as a data engineer, but as a consumer and builder on top of the data layer

What Good Looks Like

You don't need to have done this exact job before. You need to care about the craft. The best GTM Engineers are the ones who spot a broken workflow in Slack at 11pm, open a fix the next morning, and ship it before standup. They're the ones who, when the sales team complains about bad data, don't just route it to someone else — they dig in and find the upstream issue. If that sounds like how you work, we want to talk.

Compensation

Thoughtly's compensation package includes a competitive base salary benchmarked against real-time market data, as well as equity for all full-time roles. We also offer exceptional benefits. Our compensation range for this role is: $120,000 – $160,000. Final offers may vary from the amount listed based on geography, candidate experience and expertise, and other factors.