Head of Product, Invoice

Position: Head of Product, Invoice Simple
This position is listed on behalf of a partner company, which manages all applications and next steps. Our partner is looking for a Head of Product, Invoice Simple based in Canada.

We are seeking an experienced, hands-on product leader to define and drive the next generation of intuitive financial software for small businesses and independent entrepreneurs. In this strategic leadership role, you will own the product vision, roadmap, team development, and measurable business outcomes. You will lead the evolution of invoicing into a comprehensive financial platform encompassing payments, bookkeeping, and intelligent automation.

With a strong focus on AI-powered innovation, you will transform complex administrative tasks into seamless experiences that save customers time and help them grow. Working closely with engineering, design, data, marketing, and business leadership, you will accelerate product development and deliver meaningful improvements in customer acquisition, engagement, and retention. This is an opportunity to combine strategic vision with hands-on building in a fast-paced, collaborative, and remotely distributed environment.

Accountabilities:

Define Product Vision and Strategy:  Own and communicate the long-term product vision, translating business ambitions into a focused strategy, actionable roadmap, clear priorities, and measurable delivery commitments.

Drive Product

Innovation:  Lead the evolution of an established invoicing platform into a comprehensive financial operating system that helps independent businesses manage invoices, payments, expenses, bookkeeping, and financial decisions.

Lead AI-Powered Experiences:  Develop intelligent product capabilities that go beyond answering questions to completing meaningful tasks, including invoice creation, payment follow-ups, expense organization, and financial insights.

Accelerate Product Development:  Champion AI-native product development practices, encouraging product managers to prototype, analyze, experiment, and deliver working solutions quickly rather than relying exclusively on traditional documentation and processes.

Improve Customer and Business Outcomes:  Partner with the General Manager and cross-functional leaders to improve customer acquisition, activation, paid conversion, retention, payment adoption, and overall revenue performance.

Optimize the Customer Journey:  Enhance the complete user experience, from app-store discovery and onboarding to subscriptions, payments, and long-term engagement across mobile and web platforms.

Ensure Exceptional Product Quality:  Establish high standards for simplicity, usability, reliability, transparency, and security, particularly when developing products involving financial information and transactions.

Build and Lead a High-Performing Team:  Recruit, develop, mentor, and inspire talented product managers while establishing a culture of accountability, curiosity, customer empathy, and continuous improvement.

Collaborate Across Functions:  Work closely with Engineering, Design, Data, Marketing, Payments, and Customer Experience teams to align priorities, remove obstacles, make informed trade-offs, and deliver products on schedule.

Drive Experimentation and Continuous Improvement:  Promote data-driven decision-making, rapid experimentation, rigorous performance measurement, and strategic investment based on customer value and measurable business impact.

Simplify Complex Experiences:  Ensure that increasingly sophisticated financial tools remain intuitive and accessible to everyday business owners across different devices, languages, and markets.

Requirements:

Extensive Product Leadership

Experience:

At least 10 years of experience in product management or product development, including a minimum of 5 years leading product managers and managing a substantial product portfolio.

Hands-On AI

Experience:

Recent, practical experience using AI-assisted prototyping or coding tools, with the ability to demonstrate a product, prototype, or solution personally developed using these technologies.

Proven SaaS Product Expertise:  Demonstrated success launching and scaling consumer, small-business (SMB), or self-service SaaS products, with measurable improvements in activation, conversion, retention, or revenue.

Financial Technology

Experience:

Strongly preferred experience developing and scaling complex, trusted products in payments, fintech, accounting, or financial services.

Mobile Product Expertise:  Strong understanding of mobile product…