Title: Outbound Sales Development Representative (SDR) Location: Canada (Remote) Job Type: Full-time Compensation: $80,000–$100,000 CAD OTE/Year (uncapped commission) + benefits package At Puzzle, we're not just building accounting software - we're fundamentally reimagining it. To help us achieve our goals, we're looking for an Outbound Sales Development Representative to find the founders and companies who need Puzzle before they find us. The best time to reach a founder about their books is right after something changes: they've just raised, hired their first employee, or hit their first tax deadline.

You'll find those moments, reach out with something relevant, and turn cold prospects into qualified meetings with our Account Executives. This role is for a creative, persistent prospector who would rather send ten well-researched messages than a thousand generic ones. You'll also help us build relationships with accounting firms who could bring Puzzle to their clients.

This is an opportunity to join a quick-growing startup, help build our outbound motion, and grow your sales career at the intersection of accounting and fintech. Build target account lists of funded US C-Corps, pre-seed through Series A, using funding announcements, hiring signals, and other triggers Research each account and contact so every message is relevant to what's happening at that company Identify and prospect accounting firms that serve startups, as potential partners Outreach Run multi-channel sequences across email, phone, and LinkedIn Write personalized messaging built on trigger events, such as a new raise, first payroll, or a move from cash to accrual Test subject lines, angles, and sequences, and double down on what works Test and iterate on new outbound tools presented by the team,



giving clear feedback on what's working Book qualified meetings with Account Executives and hand off clear context on each prospect Share what's resonating, and what isn't, with Marketing and Sales leadership Work with AEs on account strategy for high-priority targets 1–3 years in an outbound SDR or BDR role, ideally in B2B SaaS, with a track record of hitting meeting targets ~ You’ve chosen the tools, wired them together, and set up the domains, sequences, and reporting yourself. ~ Strong writer: your outreach is short, specific, and sounds like a person ~ Comfortable on the phone and resilient with rejection ~ Curious about new sales tools and quick to adopt, test, and give feedback on them ~ Organized and disciplined about activity, follow-up, and CRM hygiene ~ Proactive self-starter who wants to help build the playbook, not just run one Familiarity with HubSpot, Apollo, Clay, LinkedIn Sales Navigator, and/or Gong/Fireflies Weeks 5–8: Run outbound on your own, hit your meetings-booked target, and start testing the outbound tools the team brings to you. This role has a clear path to Account Executive.

Join Puzzle

Financial at a pivotal growth stage where you'll help redefine and reimagine how companies handle their financials while building your career in a flexible, remote-first environment. 100% paid employee health, dental, and vision plans ~10 observed holidays and a flexible PTO policy so you can recharge ~ Regular company off-sites for face time with your colleagues ~This employer is a participant of the E-Verify program. We welcome and encourage diversity in the workplace regardless of gender, race or color, ethnicity or national origin, age, disability, religion, sexual orientation, gender identity or expression, veteran status, or any other characteristics protected by law. #

📌 SDR - Sales Development (Remote) (Toronto)
🏢 Puzzle
📍 Toronto