Outbound Sales Development Representative (SDR)

Company: Puzzle Financial Inc.

Location: Canada (Remote)

Job Type: Full-time

Compensation: $80,000–$100,000 CAD OTE/Year (uncapped commission) + benefits package

About Puzzle

At Puzzle, we're not just building accounting software - we're fundamentally reimagining it. Our cutting-edge platform seamlessly integrates with modern fintech tools, offering founders and finance teams a real-time and comprehensive view of their finances like never before.

Our mission is to empower businesses with seamless financial operations, realtime insights and free accountants from bookkeeping tedium. 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.

What We're Looking For

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 mainly target funded startup founders and operators. You'll also help us build relationships with accounting firms who could bring Puzzle to their clients.

You'll be measured on meetings booked and meetings attended. This is an opportunity to join a fast-growing startup, help build our outbound motion, and grow your sales career at the intersection of accounting and fintech.

What You'll Do

• Prospecting & Research
• 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
• Outbound Tools & Experimentation
• Test and iterate on new outbound tools presented by the team, giving clear feedback on what's working
• Measure each tool's impact on reply rates and meetings booked, and recommend which to keep, change, or drop
• Meetings Booked & Attended (Primary Metric)
• Book qualified meetings with Account Executives and hand off clear context on each prospect
• Confirm meetings and keep no-shows low with reminders and pre-call touchpoints
• Track activity, reply rates, meetings booked, and attended rate weekly
• Cross-Functional Collaboration
• Keep HubSpot clean and current
• Share what's resonating, and what isn't, with Marketing and Sales leadership
• Work with AEs on account strategy for high-priority targets

Who You Are

• 1–3 years in an outbound SDR or BDR role, ideally in B2B SaaS, with a track record of hitting meeting targets
• You’ve built outbound from zero before. 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
• Resourceful researcher who knows how to find signals and turn them into reasons to reach out
• Curious about new sales tools and quick to adopt, test, and give feedback on them
• Clear and honest about what Puzzle does and doesn't do
• Organized and disciplined about activity, follow-up, and CRM hygiene
• Proactive self-starter who wants to help build the playbook, not just run one

Nice-to-Haves

• Experience prospecting into startup founders, finance leaders, or accounting firms
• Familiarity with accounting concepts or tools (QuickBooks, Xero, or similar)
• Experience at a fintech, financial SaaS, or accounting technology company
• Familiarity with HubSpot, Apollo, Clay, LinkedIn Sales Navigator, and/or Gong/Fireflies

Your First 90 Days

• Weeks 1–2: Learn Puzzle, our ICP, and our trigger events. Shadow AE demos and review winning sequences.
• Weeks 3–4: Build your first target lists, launch sequences, and book your first meetings.
• Weeks 5–8: Run outbound on your own, hit your meetings-booked target, and start testing the outbound tools the team brings to you.
• Weeks 9–12: Hit your attended-meeting target and share what you've learned about which triggers, messages, and tools work best.

This role has a clear path to Account Executive.

What's in it for you?

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. You'll have the opportunity to make a significant impact, work with innovative founders, and develop valuable expertise at the intersection of modern accounting and fintech.

Here is a preview of some of the amazing benefits here at Puzzle:

• Competitive compensation
• 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
• 401K so you can save for your future
• And much more

Visa Sponsorship Notice: Puzzle does not provide visa sponsorship for new hires at this time. We can only consider candidates who are legally authorized to work in the U.S. or Canada without requiring new visa sponsorship or transfer of an existing visa.

Candidates should be currently residing in the U.S. or Canada to be eligible for this position. If hired, you will be required to present proof of work authorization. This employer is a participant of the E-Verify program.

Puzzle is an equal opportunity and affirmative action employer. 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.