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 fast, 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 requiring a minimum of 4 days in office 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 New 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 - Market-competitive salary tailored to your experience, skills, and expertise.

📌 Head of Outbound (Canada)
🏢 Alternative Payments
📍 Canada