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 Product to join our Product team and own the full product vision across our growing AI platform, spanning accounts receivable, accounts payable, and analytics.

This role is ideal for someone who thrives on cross-functional ownership and technical depth, and wants to take a hands-on role in shaping product strategy, raising the bar for the PM team, and driving innovation that connects data, AI, and payments into a coherent product experience.

This role is available to candidates eligible to work in New York or Toronto, hybrid.

What you’ll do

Own the product roadmap across AR, AP, and analytics: understanding how these products intersect and where the gaps create friction for customers and engineering.

Manage and grow a team of product managers and product designers, overseeing product design scope across the organisation.

Work closely with PMs to sharpen PRDs and bring technical rigour to requirements, acting as the bridge between product and engineering when needed.

Define and own the future product vision for Alternative Payments, synthesising market signals, customer insight, and company strategy into a coherent roadmap.

Implement AI thoughtfully across the product organization, not just for workflow efficiency, but as a genuine product capability that creates value for partners.

Propose and establish best practices for how the product team operates: discovery, prioritization, documentation, and cross-functional collaboration.

What you’ll bring

10+ years of product experience, with meaningful time in financial technology (payments, lending, or money movement) or a vertical SaaS company with large payments revenue contribution.

Proven experience managing product managers and designers across a multi-product portfolio.

Technical enough to read a system design doc, challenge an engineering estimate, and help PMs write PRDs that engineering teams trust.

Fluency with AI as a product capability: you can articulate how you’ve implemented AI in a product org, not just team tooling, but as a product surface.

Conceptual depth with AI technology: familiarity with embeddings, RAG, and agent-based architectures at a level that earns engineering credibility.

Strong written and verbal communication skills; able to write clean strategy docs and run tight leadership reviews.

Nice to have

Experience managing design across an organization (product design + marketing design + sales collateral).

Prior experience transitioning product ownership from a founder — navigating that trust-building and handover process.

Track record of raising the technical floor in a PM team through coaching, process changes, or targeted hiring.

Comfort working in a fast-paced, high-ownership environment where the roadmap evolves quickly.

What We Offer

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

The base salary range for this role is $160K–$250K, 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.