Head of Outbound

About the role

At Alternative Payments, you will own the end-to-end strategy and execution of outbound sales for the MSP and Accounting verticals. You will design the architecture of our BDR outbound motion, from signal-based targeting to cold call frameworks and email positioning. You will build the daily, weekly, and monthly operating cadences that create accountability and visibility for the entire team. You will partner with AE team leads to translate their coaching into scalable outbound behaviors that raise quality and predictability. You will measure, analyze, and iterate on every touchpoint to ensure the motion delivers predictable pipeline at a high efficiency.

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.
• Own the coaching and development of BDRs so they consistently hit activity and pipeline targets.
• Define and track leading and lagging metrics for the outbound motion to ensure continuous improvement.
• Partner with RevOps to maintain clean data hygiene, accurate forecasting, and reliable funnel insights in Salesforce.
• Test and iterate on messaging frameworks to ensure they resonate with high intent buyers in each segment.

Requirements

• 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.
• Eligible to work in Canada and available to work from Toronto, ON a minimum of 3 days per week in the office.
• Comfortable operating in a fast growth environment where processes are evolving as the business scales.
• Strong written and verbal communication skills to articulate complex ideas to both executives and practitioners.

Nice to have

• 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 $225,000 - $260,000 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.

Why choose Alternative Payments?

At Alternative Payments, you'll do work that truly matters.

• Own your impact: Lead meaningful, high-impact projects and collaborative initiatives that are shaping the future of FinTech and redefining how businesses get paid.
• Collaborate: Work with a diverse, innovative team where every voice is heard and great ideas come from anywhere.
• Grow with us: Your career journey is top of mind. We prioritize internal growth and give you the space to shape your path based on your goals.