Head of Product

This is a fully remote position, open to applicants in Canada.

📋 Description

• Take charge of the product vision, organization, and measurable outcomes for Invoice Simple, both for customers and the business.

• Develop the next evolution of Invoice Simple, branching out from invoicing to encompass payments, financial management, and decision support.

• Establish a focused product strategy, set priorities, and create a roadmap with clearly defined outcomes and timelines.

• Lead AI-driven workflows that facilitate invoice creation, payment follow-ups, expense organization, and opportunity identification.

• Implement quality standards, transparency, and safeguards for AI interactions that involve customer finances.

• Form smaller, agile, AI-focused product teams where Product Managers can prototype, analyze, experiment, and deliver results.

• Collaborate with the General Manager and other functional leaders to enhance acquisition, activation, conversion, retention, and revenue.

• Refine the customer journey through app-store discovery, onboarding, subscriptions, payments, and sustained engagement.

• Design user-friendly, consumer-grade experiences across mobile platforms, web interfaces, languages, and markets.

• Attract, nurture, and motivate product talent.

• Work alongside Engineering, Design, Data, Marketing, Payments, and Customer Experience teams.

• Make challenging trade-offs, eliminate obstacles, and ensure timely delivery.

⛳️ Requirements

• Over 10 years of experience in product management or development, with at least 5 years in a leadership role managing product managers and a significant product portfolio.

• Recent, hands-on experience with AI-assisted prototyping or coding tools; readiness to showcase a personally developed project.

• Proven history of successfully launching consumer, SMB, or self-serve SaaS products at scale, demonstrating measurable improvements in activation, conversion, retention, or revenue.

• Experience in building and scaling complex, trusted products in payments, fintech, accounting, or financial services is highly preferred.

• Strong judgment in mobile products, including iOS or Android UX, subscriptions, app-store distribution, and experimentation.

• Demonstrated capability to hire and mentor Product Managers, make tough trade-offs, and consistently deliver results alongside Engineering and Design teams.

• Legally authorized to work in Canada.

• Technically proficient with high standards for simplicity, product quality, speed, and follow-through.

• Comfortable challenging assumptions, making decisions with incomplete information, and taking ownership of results.

• Possess a low ego and a strong sense of ownership; direct, kind, and effective in cross-functional collaboration.

• Eager to assist solo entrepreneurs in achieving success without introducing complexity.

🏝️ Benefits

• Flexible remote working options.

• Health and wellness benefits.

• Support for professional development.

• Retirement savings program with company match, subject to plan terms.

• Generous paid time off.

• Employee Stock Purchase Program, subject to eligibility.

• Bonus and long-term incentives, where applicable, in addition to base salary.