CA$200,000 – CA$240,000/yr

Head of New Markets

Torontofull-timeexecutive
OtherHead
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Quick Summary

Overview

Alternative Payments is building the financial operating system for SMBs, consolidating the disconnected tech stack that holds service-based businesses back.

Technical Tools
salesforceab-testingb2bfintechroadmap-planningsaas

Responsibilities

~1 min read
  • 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.

  • 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 Have

~1 min read
  • 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

~1 min read
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.

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.

  • 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.

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.

Location & Eligibility

Where is the job
Toronto
Hybrid — some on-site time required
Who can apply
Same as job location

Listing Details

Posted
May 4, 2026
First seen
May 5, 2026
Last seen
May 6, 2026

Posting Health

Days active
0
Repost count
0
Trust Level
66%
Scored at
May 6, 2026

Signal breakdown

freshnesssource trustcontent trustemployer trust
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alternativepaymentsHead of New Markets$200k–$240k