Head of Outbound

Responsibilities

• 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.

Requirements

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

Benefits

Additional Information

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!

Your Match

How well this role fits your profile.

Company Intel

What employees say

Worked at alternativepayments? Share your experience