Head of New Markets

Alternative Payments • Toronto, ON

3d • $175,000 - $220,000 • Hybrid

About The Position

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!

Requirements

• 7–12 years across growth, strategy, or business development in B2B SaaS or fintech.
• You’ve taken at least one new market from “should we do this?” to “this is producing revenue.”
• You switch contexts fast: positioning doc on Monday, BDR sequence brief on Tuesday, product roadmap review on Wednesday, CEO presentation on Thursday.
• You test before you scale, you measure what matters, and you’re willing to say “this didn’t work, here’s what I learned” in a room full of people.
• You’ve worked at a company between $3M–$30M ARR that was figuring out how to go from one market to several.
• Strong communication skills to collaborate effectively across Product, Marketing, Sales, and executive stakeholders.

Nice To Haves

• Understanding of PE-backed business dynamics, the MSP industry, or payments/fintech.
• Familiarity with multi-product and multi-vertical go-to-market strategies.
• Experience working alongside performance marketing and design teams on launch campaigns.
• Comfort with Salesforce, Apollo, and marketing analytics tools.

Responsibilities

• Own the Accounting Services vertical and overall performance from soup to nuts, including quota target tied to team performance
• Run growth experiments: new acquisition channels, content-led approaches, partnership motions, event strategies. Measure honestly and document learnings.
• Evaluate new markets: vertical attractiveness, TAM, competitive landscape, billing and invoicing workflows, buyer differences. Deliver go/no-go recommendations with draft GTM plans.
• Build GTM plans for new verticals: positioning, ICP definition, channel strategy, messaging, and pipeline targets.
• Advise on conference strategy as a growth channel: which events justify the investment and what the commercial play is at each in these verticals.
• Keep sales, marketing, and product aligned on new-market work. You run the planning, set the priorities, and make sure everyone’s building the same thing.

Benefits

• Competitive salary tailored to your experience, skills, and expertise.
• The total compensation range for this role is $175,000 – $220,000 CAD (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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed