Head of Outbound

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.

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. This is a hybrid position requiring a minimum of 3 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

• Competitive salary tailored to your experience, skills, and expertise.
• The total compensation range for this role is $185,000 – $225,000CAD (OTE), plus equity.
• 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.