Alternative Payments is building the financial operating system for SMBs, consolidating the disconnected tech stack that holds service-based businesses back. Starting with MSPs, we’ve spent five years perfecting accounts receivable, and we’re now expanding into accounts payable, AI-powered analytics, and beyond. We’re at an inflection point: closing the loop on money movement and laying the foundation for a platform that will reshape how service businesses operate financially.

We’re growing rapid, thinking big, and building a global team that wants to be part of something that lasts. We believe the best solutions come from diverse perspectives, deep collaboration, and a shared obsession with customer impact. If you’re energized by real problems, real customers, and real impact, we want to hear from you!

What We’re Looking For We’re seeking a Head of Outbound to own the strategy, execution, and accountability of our outbound sales motion across the MSP and Accounting segments. You’ll design the BDR outbound architecture — signal-based targeting, sequence strategy, cold call frameworks, and email positioning — then build rigor and accountability throughout the team to make sure it runs at a high level every day.

Our BDR team operates in segment-specific pods (SMB, Mid-Market, Accounting), each led by an AE team lead who handles coaching and deal-level training but isn’t directly responsible for day-to-day outbound accountability. Your job is to fill that gap: build what the AE leads teach, set the standard for outbound quality, and drive efficiency improvements that show up in the numbers.





This is a hybrid position based in Toronto, ON and is available to candidates who are eligible to work in Canada.

What You’ll Do

- Improve outbound efficiency across MSP and Accounting segments: diagnose what’s working, redesign what isn’t, and raise the bar on BDR output.

- Design BDR outbound playbooks for each segment: signal-based targeting, sequence architecture, cold call scripts, and email positioning tailored to different buyer personas.

- Build rigor and accountability across the BDR team — daily/weekly operating cadences, activity standards, pipeline inspection, and performance management.

- Collaborate across Marketing, Partnerships, and Events to drive a strategic approach to outbound efforts.

- Work with Head of Current Markets to build GTM plans for new verticals: define the buyer, the pitch, the outbound motion, and the pipeline targets.

- Build the mid-market and enterprise outbound motion alongside the existing SMB process.

What You’ll Bring

- 5–10 years in B2B SaaS or fintech sales, including time where your job was building or running outbound programs across multiple segments.

- Experience building outbound playbooks: signal-based targeting, cold sequences, call frameworks.



You know the difference between a sequence that books meetings and one that gets ignored.

- A track record of improving BDR performance through better process, accountability, and outbound strategy — not just managing reps, but raising the standard.

- You’ve worked at a company in the $3M–$20M ARR range where not everything was built yet.

- Working knowledge of Salesforce, Apollo, Instantly.

- Proven ability to leverage AI to drive team efficiency and prove outcomes with tangible results.

Nice to Haves

- Familiarity with the MSP / Accounting ecosystem, PE-backed roll-ups, or payments/AR automation.

- Experience building outbound motions across multiple verticals simultaneously.

- Comfort with outbound tooling beyond Apollo — intent data platforms, enrichment tools, deliverability monitoring.

- Track record coaching or mentoring BDRs into AE roles.

- Deals you personally closed in markets your company hadn’t sold into before.

What We Offer

- Competitive salary tailored to your experience, skills, and expertise.

- The total compensation range for this role is $185,000 – $225,000 CAD (OTE), plus equity . The range displayed on each job posting reflects the approximate total target compensation for the position. Within the range, individual pay is determined by factors including relevant skills, experience, education/training.

- Equity opportunities so you can share in our growth and success.

- Unlimited PTO and flexibility when you need it the most.

- Yearly learning & development stipend to help you grow and do your best work.

📌 Head Of Outbound (Toronto)
🏢 Alternative Payments
📍 Toronto