Head of Product

About the role

This role owns the end to end product strategy and execution for the Alternative Payments platform, guiding how AR, AP, and analytics work together as a unified system. The hire will act as the primary product authority across the suite, defining what gets built and why it matters to customers and the business. They will partner deeply with engineering and design to translate complex requirements into clear, executable product outcomes. This position requires comfort with ambiguity and the ability to lead through influence in a fast moving, data informed environment. Success will be measured by the coherence of the product portfolio, the quality of delivered experiences, and the long term trust built with our customers.

Key facts

What you'll do

• Own the product roadmap across accounts receivable, accounts payable, and analytics, mapping how these products intersect and identifying where 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 and ensuring consistent standards.
• Work closely with product managers to sharpen product requirement documents 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, long term roadmap.
• Implement AI thoughtfully across the product organization, not just for workflow efficiency, but as a genuine product capability that creates measurable value for partners and customers.
• Propose and establish best practices for how the product team operates, including discovery, prioritization, documentation, and cross functional collaboration.
• Partner with data and analytics to validate hypotheses, measure outcomes, and iterate on product decisions based on evidence.
• Represent the product organization in high level discussions with key partners and stakeholders, aligning on strategic priorities and product direction.
• Translate complex technical and business constraints into clear product guidance that engineering teams can execute against with confidence.
• Drive alignment across teams by facilitating structured decision making, clarifying trade offs, and ensuring shared ownership of product outcomes.
• Build and maintain strong relationships with customers and internal stakeholders to uncover needs, validate solutions, and ensure product value is realized.
• Continuously assess the competitive landscape and emerging technologies, feeding insights back into the product strategy to keep the platform ahead of the curve.
• Establish metrics and feedback loops for product performance, using results to refine processes and prioritize the next set of improvements.
• Mentor product managers and designers, elevating the quality of thinking and execution across the product team.

Requirements

• 10+ years of product experience, with meaningful time in financial technology such as 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, setting direction while enabling autonomy.
• Technical enough to read a system design document, challenge an engineering estimate, and help product managers write PRDs that engineering teams trust and can implement.
• Fluency with AI as a product capability, including experience implementing AI within a product organization beyond team tooling, but as a core product surface.
• Conceptual depth with AI technology, including familiarity with embeddings, retrieval augmented generation, and agent based architectures at a level that earns engineering credibility.
• Strong written and verbal communication skills, with the ability to write clean strategy documents and run tight, focused leadership reviews.
• Comfortable working in a fast paced, high ownership environment where the roadmap evolves quickly and priorities must be clarified under uncertainty.
• Eligible to work in New York or Toronto, hybrid, with reliable access to the necessary tools and systems.

Nice to have

• Experience managing design across an organization, spanning product design, marketing design, and sales collateral.
• Prior experience transitioning product ownership from a founder, navigating the trust building and handover process successfully.
• 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.

Practical notes

• This role is available to candidates eligible to work in New York or Toronto, hybrid.
• 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 are provided so that team members can share in the growth and success of the company.
• Unlimited PTO and flexibility are offered to support focus and wellbeing when it is needed the most.
• Yearly learning and development stipends are provided to help team members grow and do their best work.
• Alternative Payments is building the financial operating system for SMBs, consolidating the disconnected tech stack that holds service based businesses back.
• The company has spent five years perfecting accounts receivable and is now expanding into accounts payable, AI powered analytics, and beyond.
• The role is based in a fast growing, thinking big environment that is building a global team committed to making an enduring impact.
• Success in this role requires a deep obsession with customer impact, collaboration, and the ability to synthesize diverse perspectives into coherent product strategies.
• The position involves significant responsibility in shaping how money moves for service businesses, influencing both product and engineering decisions at scale.
• The candidate should be prepared to own outcomes end to end, balancing strategic vision with hands on execution alongside the product and engineering teams.