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 development and user experience, including iOS or Android design principles, subscriptions, app-store distribution, and product experimentation.

- Strategic and Analytical Capabilities: Ability to translate business objectives into effective product strategies, prioritize investments, interpret performance data, and make informed decisions in evolving environments.

- Technical Fluency: Comfortable working with AI-assisted development tools, understanding technical concepts, and collaborating closely with engineering and design teams to turn ideas into functional products.

- People Management and Team Development: Proven ability to recruit, coach, motivate, and develop product managers while establishing high standards for ownership and execution.

- Cross-Functional Leadership: Strong collaboration and communication skills, with the ability to influence stakeholders, challenge assumptions constructively, and manage complex trade-offs.

- Customer-Centric Mindset: Deep empathy for small-business owners and the ability to transform complex financial processes into simple, intuitive, and reliable experiences.

- Personal Attributes: A hands-on builder with high standards for product quality, simplicity, speed, and accountability. Demonstrates curiosity, adaptability, sound judgment, low ego, and a strong sense of ownership.

- Location and Work Authorization: Must be legally eligible to work in Canada and available for occasional travel for team and leadership meetings.

Benefits:

- Competitive Compensation: Expected annual base salary ranging from CAD $240,000 to $270,000 , depending on experience, location, skills, and internal equity.

- Performance Incentives: Additional bonus opportunities and long-term incentive compensation, where applicable.

- Flexible Remote Work: Remote working arrangements within Canada, with flexibility to support work-life balance.

- Health and Wellness Benefits: Access to health and wellness programs designed to support employees' overall well-being.

- Retirement Savings: Participation in a retirement savings program with employer matching contributions, subject to applicable plan terms.

- Paid Time Off: Generous paid leave to support personal commitments, rest, and work-life balance.

- Employee Stock Purchase Program: Opportunity to participate in an employee share purchase program, subject to eligibility.

- Professional Development: Support for ongoing learning, skill development, and career advancement.

- Collaborative Environment: Opportunity to work with talented professionals across multiple disciplines and contribute to innovative, AI-driven financial products.

- Leadership Impact: Significant ownership and influence over product strategy, team development, and the future direction of a growing global software platform.

How Jobgether works:

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Why Apply Through Jobgether?

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

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