Head of Product - AI-Driven Fintech for SMBs (Remote Canada)

Jobgether; Canada; Remote; CAD 240,000 - 270,000; Full time

Benefits offered by this job

Remote-friendly Canada-wide work

Competitive compensation

Professional development

Equity or long-term incentives

Health and wellness benefits

Job summary

Invoice Simple, a partner company listing this opportunity in Canada, seeks a hands-on Head of Product to define the product vision and drive the next generation of financial software for small businesses. You will own the roadmap, oversee AI-enabled features, and lead a team across engineering, design, data, and marketing in a remote, distributed environment.

You will shape product strategy, experiment rapidly, and deliver measurable improvements in acquisition, activation, and retention while

Qualifications

• Ten years in product management or development with five+ years leading PMs.
• Hands-on AI experience with prototyping or coding tools.
• Proven SaaS product launches, scale, and metrics.
• Experience in financial tech, payments, or accounting products.
• Strong mobile product knowledge including subscriptions and app-store distribution.
• Ability to translate business goals into strategy, roadmaps, and KPIs.
• Comfortable with AI-assisted development and collaborating with engineers.
• Experience recruiting, coaching, and developing PMs.
• Strong cross-functional collaboration and stakeholder management.
• Customer empathy for small business owners translating into simple experiences.

Responsibilities

• Define and communicate long-term product vision and strategy.
• Lead evolution of invoicing platform into a comprehensive financial OS.
• Develop AI-powered capabilities for tasks like invoice creation and payments.
• Champion rapid, AI-native product development with prototyping and experiments.
• Improve customer acquisition, activation, retention, and revenue through data-driven decisions.
• Enhance end-to-end customer journey across mobile and web.
• Set high standards for product quality, usability, transparency and security.
• Recruit and develop a high-performing PM team and maintain accountability.
• Collaborate with Engineering, Design, Data, Marketing, Payments and CX teams to meet roadmaps.
• Drive experimentation, performance measurement, and strategic investments.

Skills

Product leadership

AI prototyping

SaaS product management

Fintech/payments

Mobile product

Strategic analytics

Technical fluency

People management

Cross-functional leadership

Customer-centric

Job description

Invoice Simple, a partner company listing this opportunity in Canada, seeks a hands-on Head of Product to define the product vision and drive the next generation of financial software for small businesses. You will own the roadmap, oversee AI-enabled features, and lead a team across engineering, design, data, and marketing in a remote, distributed environment.

You will shape product strategy, experiment rapidly, and deliver measurable improvements in acquisition, activation, and retention while