Account Executive

Account Executive

Location:

Toronto, ON preferred - Hybrid (1-2 days/week in our downtown office). Fully remote considered for exceptional candidates.

About Billables AI

At Billables AI, we’re building an AI-powered timekeeping and operational intelligence platform to transform how professional service providers work, freeing them to focus on the most creative and high-value parts of their business. We build workflows that eliminate manual overhead, starting with automated time tracking for attorneys. We're also giving firms deeper visibility into how work happens and the data to price and operate more efficiently.

Based in San Francisco and built by some of the sharpest minds at the intersection of AI and legal tech, we're scaling fast and building something that matters.

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

Why Billables AI

• Named Legal Tech Company of the Year at Legal Week 2026
• Hybrid work with real flexibility
• Work alongside some of the brightest minds in AI and legal tech
• Be a key player on a talented team where you can truly make an impact