Head of New Markets

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 New Markets to figure out where Alternative Payments grows next — and prove it with revenue, not slide decks. You’ll evaluate new verticals, build GTM plans, run growth experiments, and own product launch strategy from the commercial side.

First priority: Accounting services vertical growth experimentation. We launched in the Accounting Services vertical and we’re looking to accelerate growth. Test acquisition motions that don’t exist yet — content-led plays, partnership funnels, event-based approaches. Run them, measure them, and kill what doesn’t work without getting attached.

Second priority: market expansion. Evaluate 2–3 candidate verticals, pick the best one, build the GTM plan, and get it producing pipeline.

You’re not writing outbound sequences or coaching BDRs on calls. You’re deciding whether we should be in a market at all, what the pitch should be, and what success looks like — then handing execution to the people who run the pods.

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

What You’ll Do

• 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.

What You’ll Bring

• 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.

What We Offer

• Competitive salary tailored to your experience, skills, and expertise.

• The total compensation range for this role is $200,000 – $240,000 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.