GTM Engineer

Toronto or San Francisco preferred - Hybrid (1-2 days/week in our downtown offices). Fully remote considered for exceptional candidates.

About Billables

Billables AI is building the AI-powered operating layer for professional service firms, and we're starting where the pain is deepest: the legal industry. Our platform automates the manual overhead that slows lawyers down, bringing together intelligent timekeeping, work activity capture, and operational visibility so firms can understand how work happens and build a more efficient, profitable practice. The best work happens when people aren't buried in administrative burden, and that's exactly the problem we're solving.

Named Legal Tech Company of the Year by Law.com in 2026, Billables AI is one of the fastest-growing companies at the intersection of AI and legal technology. Our team brings together expert AI researchers and veteran startup builders who know how to move fast, build with conviction, and deliver software that sits at the core of how our customers work and generate revenue. Based in San Francisco, we empower everyone on the team to drive meaningful work end-to-end.

About the Role

Inbound demand is strong. Now we're building outbound to match – and that's where you come in.

As Billables AI enters its next phase of growth, we're looking for a GTM Engineer to build the systems that generate pipeline and qualified meetings for our sales team.

You'll build our outbound infrastructure from the ground up, embedding AI into every stage of how we find and reach firms, from prioritizing the right accounts and finding buying signals to using creative channels to sequence outreach that actually lands, plus the systems to engage and nurture inbound leads. Working closely with our founders and go-to-market team, you'll own the engine that turns our ICP into booked meetings and closed business. You'll be in the pipeline yourself, crafting the messaging and running the plays, and what you learn there flows straight back into the systems you build.

This is a hands-on role for someone who loves building. There isn't a predefined playbook – you'll experiment, move quickly, and shape how we generate pipeline as we scale.

What You'll Work On

Build and optimize the outbound engine that turns target firms into sales-ready conversations for our AEs.
Own and refine our ICP framework: the tiering, segmentation, account scoring, and buying-signal detection that decide which firms we go after, and in what order.
Build automated prospecting, personalization, and enrichment workflows that reach the right decision-makers inside each firm with the right message, using tools like HubSpot, Clay, Instantly, LinkedIn Sales Navigator, n8n, AI agents, and APIs.
Find creative, non-traditional channels to reach prospects, going beyond email and calling to social, messaging, and wherever decision-makers actually pay attention, and turn them into signal-based plays.
Own the plays end to end: create the messaging, run the sequences, and feed what actually lands back into sharper systems.
Design automated workflows that engage and nurture inbound leads, ensuring every opportunity receives timely and relevant follow-up.
Prototype and deploy AI-powered internal tools that help our commercial team work faster, make better decisions, and spend more time selling.
Own the data and workflows behind our GTM stack, from the HubSpot object model to enrichment, routing, and data quality, so information flows cleanly between systems.
Measure performance, run experiments, and iterate quickly to improve conversion across the top of the funnel.

Who You Are

You've built outbound or demand-generation systems that produced measurable pipeline – not just configured them.
You're outcome-obsessed: you care about real meetings and real pipeline, and you'll build the systems that scale them and roll up your sleeves to do whatever it takes to book them.
You're technical enough to build the systems yourself, calling APIs, wiring integrations, and automating manual work, and you're fluent in modern GTM platforms like HubSpot, Clay, Instantly, LinkedIn Sales Navigator, and n8n.
You think in systems. You spot the bottleneck, fix the root cause, and scale what works.
You're curious and constantly experimenting with new AI tools, and it's a bonus if you've built with Claude or OpenAI APIs in production.
You move fast and take ownership. You'd rather ship a great first version than perfect a plan, and you'd rather help define the playbook than follow one.