GTM Engineer

Billables Incorporated; Toronto; On-site; CAD 60,000 - 90,000; Full time

Job summary

Billables AI is hiring a Business Development Representative (BDR) to accelerate our go-to-market in Toronto and beyond. The role blends outbound prospecting with opportunity qualification, building relationships with law firms and generating qualified pipeline for Account Executives.

You’ll work with sales leadership, receive hands-on coaching, and have a clear path to an Account Executive role as we scale.

Qualifications

• 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.

Responsibilities

• Generate qualified pipeline through outbound prospecting across email, phone, LinkedIn, conferences, and other channels.
• Engage and qualify inbound leads, surfacing high-potential opportunities for the sales team.
• Research and prioritize target accounts, identifying key decision-makers at mid-market and enterprise law firms.
• Book meetings and create opportunities for Account Executives through thoughtful 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.

Skills

BDR experience

Pipeline generation

Outbound prospecting

HubSpot

Communication

Tools

HubSpot

Job description

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 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

Why Billables AI

Named Legal Tech Company of the Year at LegalWeek 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

Clear path for career growth into an Account Executive role as the company scales

Apply Now