Vice President of Product

Team: Product

Location: Canada

Commitment: Full-time

Workplace Type: remote

Accountabilities

• Own and continuously refine the product strategy and roadmap in response to market developments, customer needs, and business priorities.

• Establish clear quarterly priorities, focus resources on high-impact initiatives, and make informed trade-offs to prevent competing work from diluting execution.

• Develop a deep understanding of the last-mile delivery ecosystem, including shippers, carriers, couriers, dispatchers, drivers, and recipients.

• Lead quarterly and annual product planning with Engineering and go-to-market teams, aligning roadmaps and company objectives with measurable business outcomes.

• Establish effective processes for collecting, prioritizing, and responding to feedback from customers and internal stakeholders.

• Coordinate execution across product squads, proactively managing dependencies and risks while maintaining a transparent, company-wide roadmap.

• Define product success metrics before launch, connect them to broader business goals, and use adoption and usage data to guide improvements.

• Represent Product in executive planning, board discussions, customer advisory boards, and strategic customer engagements.

• Build a collaborative product culture, continuously improving team structure, workflows, processes, and tools.

• Recruit, coach, and develop Product Managers, Designers, and User Researchers, establishing clear expectations and career growth opportunities.

Requirements:

• 10+ years of experience in B2B SaaS product roles, including 5+ years leading product teams and at least 3 years at Director of Product level or above.

• Experience leading Product at a Series B or later company generating tens of millions of dollars in annual recurring revenue (ARR).

• Demonstrated success guiding a product organization through an expansion into the enterprise market.

• Proven ability to hire, manage, mentor, and develop Product Managers, Designers, and User Researchers.

• Strong UX and product design expertise, including experience overseeing usability testing, user interviews, and experimentation.

• A collaborative approach to Engineering, including joint scoping, disciplined scope management, and iterative product delivery.

• Experience conducting market research to evaluate opportunities within existing customer segments and adjacent markets.

• Strong product judgment, balancing customer evidence, usage analytics, strategic priorities, and business impact when making roadmap decisions.

• Analytical thinking and a data-driven approach to decision-making, performance measurement, and accountability.

• Experience building or managing Product Operations, with working knowledge of tools such as Jira, Productboard, and Amplitude.

• Excellent written and verbal communication skills, strong organizational abilities, and a consistent focus on outcomes.

• Experience in last-mile logistics or delivery is an advantage.

Benefits:

• Remote-first work environment, with quarterly domestic travel.

• Generous employee stock options.

• Comprehensive health, dental, vision, life, and disability insurance.

• 401(k) retirement plan.

• Flexible paid time off (PTO).

• Compensation for the Canada-based role is listed at CAD 225,000–275,000 per year. Final compensation and employment terms should be confirmed during the hiring process.