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.

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 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 $170,000 – $210,000 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 — whether that’s deepening your expertise in your domain or exploring something new.

• Thrive in a supportive culture: As a scaling start-up, there’s a lot to be done and initiative is key. We believe in shared learning, open communication, and building each other up. When one of us grows, we all do.

Our Values

• Transparency & Honesty: We communicate openly and truthfully with partners, investors, and each other so everyone understands where we stand and where we’re headed.

• Resourcefulness & AI: We stay scrappy, find creative solutions, and make progress even when the path isn’t obvious. We have a bias for action and seek out the information and resources necessary to make decisions and move quickly.

• Partnership: We win and lose together. We collaborate with our partners, investors, and teammates to tackle big challenges and reach shared goals.

• Revolutionary & Boldness: We challenge conventions, take calculated risks, and build better, stronger solutions that move our business and the industry forward.

• Accountability: We take ownership of our decisions and results. We follow through on our commitments knowing our work directly impacts our partners, our team and our business.

Applying to Alternative Payments

We’re looking for candidates who are ready to step in and make an impact from day one. We know that sometimes people hold back unless they meet every requirement, but if you’re excited about the role, bring relevant experience, and are ready to contribute, we want to hear from you!

All resumes are reviewed by our small but mighty talent team. While we may use AI tools to help prioritize applications, real people are behind every resume review and hiring decision. We’re also committed to an inclusive and accessible process. If you need any accommodations during your application or interview experience, please let us know — we’re happy to help.