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VP of Product

Canada - Remote; United States - Remote

Ready to accelerate your career?

Cardata is where driven people make an outsized impact. We’re a small but mighty team transforming how businesses manage vehicle reimbursement — replacing outdated programs with smart, automated solutions.

Our vision is bold: to provide the most comprehensive, intelligent, and automated software and services for creating ideal vehicle programs. And we’re building toward that vision every single day.

Join us and you’ll find challenge, growth, and the chance to deliver real impact — helping hundreds of companies and thousands of drivers across North America focus on the work that matters most to them.

As the VP of Product, you will be a trusted voice with executives, customers, and cross-functional leaders: translating strategy into real results while advancing how we apply AI, automation, and modern discovery to scale our product and organization. You will set the vision, strategy, and execution cadence that drive measurable customer and business impact, owning the full product lifecycle: deeply understanding our users, markets, and data; defining clear priorities and outcomes; and partnering closely with Engineering and Design to deliver high-quality, scalable solutions. You’ll lead and develop a high-performing product organization, make decisive tradeoffs on scope and sequencing, and ensure teams are focused on solving the right problems.

**The role is remote-first, with occasional travel to Canada for in-person collaboration, not a mandated weekly hybrid schedule. There may be select periods of the year with increased travel to support planning cycles, launches, or key initiatives.**

What You’ll Do:

  • Own the product vision and strategy, translating company goals into clear priorities, outcomes, and tradeoffs that are aligned with customer needs and market demands
  • Develop and maintain deep, first-hand expertise in our product, customers, and users (how they actually work, where they struggle, and how they derive value) through interviews, deal support, escalations, and ongoing feedback loops
  • Lead competitive and market intelligence analysis to inform roadmap decisions and prioritizations
  • Pressure-test product strategy by regularly reviewing discovery insights, usage data, and delivery signals
  • Partner tightly with Engineering and Design to ensure high-quality delivery
  • Ensure backlogs are well-formed, outcomes are clear, and teams are solving the right problems 
  • Make decisive calls on scope, sequencing, and resourcing to keep momentum high 
  • Lead, mentor, and develop Product Managers and/or Product Owners, setting a high bar for ownership and product judgment.
  • Establish clear expectations for product quality, discovery rigor, and delivery accountability
  • Step into the weeds when needed, clarifying requirements, unblocking decisions, shaping scope, or helping teams navigate complexity
  • Hold teams accountable for outcomes, not just output, using data, customer impact and revenue as the yardstick
  • Identify execution gaps early and intervene constructively to get initiatives back on track
  • Foster strong cross-functional trust by being decisive, transparent, and consistent
  • Act as a credible, hands-on product voice with executives, customers, and internal stakeholders
  • Clearly communicate roadmap decisions, progress, risks, and tradeoffs—especially in moments of constraint
  • Proactively identify and drive opportunities to apply AI and automation to improve customer outcomes, internal efficiency, and product scalability
  • Help shape how the company thinks about product, execution, and customer value

What We’re Looking For:

  • 10+ years of Product Management experience, with significant time in B2B SaaS environments
  • Prior experience leading and scaling Product teams, specifically developing Product Owners
  • Demonstrated success building and evolving multi-persona B2B products with complex workflows
  • Experience supporting or leading products through a growth phase of approximately $10M to $100M+ ARR
  • Strong track record of translating strategy into execution and measurable outcomes
  • Deep familiarity with Agile product development and modern product discovery practices
  • Demonstrated experience applying AI, automation, or workflow intelligence to real product problems, with a strong sense of where these approaches create leverage and where they don’t
  • Strong product judgment and strategic thinking, paired with pragmatic execution instincts.
  • High technical fluency (APIs, systems, architecture tradeoffs)
  • Excellent product sense and UX intuition; comfortable collaborating deeply with Design leadership
  • Strong business acumen, with a track record of translating product decisions into measurable outcomes (e.g., GRR, NRR, ARR growth, expansion, efficiency)
  • High sense of urgency and ownership, driven to move from insight to action and from roadmap to real-world impact
  • Proven ability to establish and maintain strong cross-functional relationships built on trust, reliability, and consistent follow-through
  • Clear, compelling communicator with executives, teams, and external stakeholders
  • Highly organized, accountable, and decisive, with a bias toward action

Bonus items: 

  • Experience with M&A 

Compensation

The compensation range for this full-time position is $260,000–$300,000, reflecting base salary plus bonus, with actual earnings based on experience, skills, and performance. This is an approved, budgeted hire, and we are actively seeking a leader who will bring new perspective and contribute meaningfully to the team.

Why you’ll love working at Cardata:

We’ll be honest — Cardata isn’t for everyone. If you thrive in a fast-paced environment, take extreme ownership, and constantly push yourself (and your work) to be the best, you’ll fit right in.

You’ll be surrounded by driven teammates who genuinely care — about the work, about our customers, and about helping each other succeed. Together, we take on ambitious goals and celebrate the wins along the way.

What we offer in return for you bringing your best:

  • Remote work and flexible working hours
  • Mentorship and development opportunities (to help you achieve your career goals!)
  • Extended medical & dental benefits
  • Healthcare spending account
  • $3,000 annual Health and Wellness Spending Account to support your overall wellbeing
  • Employee assistance program (EAP)
  • Flexible (Unlimited) Time Off: No annual cap on vacation, supported by a trust-based, flexible approach to time away.

Cardata is an equal opportunity employer. All candidates will be equally considered without regard to race, ancestry, place of origin, colour, ethnic origin, language, citizenship, creed, religion, gender/gender identity, sexual orientation, age, marital status, physical and/or mental handicap or financial ability. We are dedicated to creating an inclusive environment where everyone feels welcome to bring their authentic selves to work.

If you require accommodations during the recruitment process, please let us know.

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