Head of Product

Responsibilities

• 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.

Requirements

• 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.
• 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.
• 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.

Benefits

Additional Information

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!

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