Account Executive

Location: San Francisco, CA or Toronto, ON preferred - Hybrid (1-2 days/week in our downtown office)

About Billables AI

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

This is a career-defining role at a company that's reimagining how lawyers work through the power of AI. We've hit real traction - and we're growing the sales team to match. You'll join a tight team of operators responsible for growing ARR, shaping the go-to-market strategy, and closing meaningful deals. It’s a rare opportunity to join a grounded but ambitious team building a category-defining company.

What you’ll work on

Manage multi-stakeholder deals from initial engagement to close, with a focus on maximizing deal size and long-term value
Convert inbound demand - we've built significant top-of-funnel volume, and you'll help convert and qualify that interest efficiently
Proactively generate pipeline - identify and outbound into ICP accounts, with the opportunity to drive additional pipeline through legal conferences and industry events
Collaborate with cross-functional teams to ensure that customer feedback informs our product roadmap and that customer expectations are met
Use Hubspot to manage sales activities and accurately forecast monthly pipeline
Optimize the sales process - you’ll have a meaningful voice in how we sell and iterating the playbook as we scale

What we’re looking for / Who you are

Minimum 3 years selling SaaS solutions to mid-market or enterprise accounts; full-cycle sales experience preferred
Track record of closing complex deals with multiple stakeholders
Experience selling to professional services firms - legal, financial or similar.

We aren’t looking for a traditional sales rep. We’re looking for someone who thrives in a high-growth environment and is:

A team player in the truest sense - you collaborate generously, share wins, and make everyone around you better
Founder-minded - hungry, resourceful, and resilient
A creative problem-solver - quick on your feet, proactive, and solution driven
Empathetic and energizing - you bring warmth and genuine curiosity to every customer conversation
AI-forward - you're genuinely excited about AI tools, actively seek them out, and use them to sharpen your own workflow
Data-driven and coachable - you use numbers to iterate, and you welcome feedback