Business Development Representative (BDR)

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

This is a career-defining opportunity to accelerate your sales career at a company that's reimagining how lawyers work through the power of AI.

We've hit real traction – and we're growing the go-to-market team to match. As the founding Business Development Representative, you'll be the first point of contact for prospective customers, helping build relationships with law firms and generating qualified opportunities for our Account Executives.

You'll work alongside experienced sales leaders, receive hands-on coaching, and develop the skills needed to grow into an Account Executive role as we scale. If you're ambitious, curious, and excited by AI, you'll have the opportunity to make a meaningful impact while while growing your career.

What You'll Work On

Generate qualified pipeline through outbound prospecting across email, phone, LinkedIn, industry conferences, and other creative channels
Engage and qualify inbound leads, surfacing the highest-potential opportunities for the sales team
Research and prioritize target accounts that fit our ICP, identifying key decision-makers at mid-market and enterprise law firms
Book meetings and create opportunities for Account Executives through thoughtful, personalized outreach
Partner with Marketing and Sales to sharpen messaging, campaigns, and lead conversion
Keep activity and pipeline data accurate in HubSpot
Continuously test, learn, and iterate to improve conversion rates

What We're Looking For / Who You Are

1+ years as a BDR, SDR, or in a similar outbound role – ideally in SaaS, with a track record of high performance
Proven ability to generate pipeline across email, phone, and LinkedIn
Excellent written and verbal communication
Naturally curious and energized by starting conversations and building relationships
Highly organized, resilient, and motivated by achieving goals
Comfortable learning new technologies and navigating ambiguity in a fast-growing startup
Experience using HubSpot is an asset

We aren't looking for a traditional BDR. 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