Principal Product Manager, Trilogy (Remote) - $200,000/year USD

Tired of being a roadmap custodian? Ready to be a product visionary instead? As a seasoned product leader who's navigated the zero-to-launch journey, you understand that true product excellence is an ongoing pursuit—not a checkbox exercise.

At Trilogy, we've reimagined product management. Forget managing endless backlogs or completing template specs. Here, you'll own a singular, meaningful business outcome. Your mission? Make it happen. With AI as your ally and user feedback as your compass, you'll translate deep domain knowledge into actionable insights, driving rapid product iterations until your target metrics sing.

Join a team that values impact over process theater. We're building a culture where decisions flow from user data, quick feedback cycles, and razor-sharp insights—not meetings about meetings. If you're ready to transcend traditional product management and create something that genuinely moves the needle, we want to talk. This is product leadership as it was meant to be.

What You Will Be Doing

• Craft and evolve BrainLifts—structured repositories of expert knowledge that enhance AI capabilities, inform strategic decisions, and demonstrate your domain mastery
• Deliver weekly product enhancements driven by data insights, continuously steering toward defined success metrics
• Cultivate comprehensive domain expertise, enabling high-caliber decision-making, precision-tailored outputs, and authoritative communication across the organization
  
  

What You Won’t Be Doing

• Orchestrating month-long feature development cycles—we embrace a weekly ship cadence to maintain momentum
• Creating verbose product requirement documents, maintaining endless backlogs, or over-specifying every UI element and edge case
• Delving into technical implementation details or architectural design—focus on outcomes, not code
  
  

Basic Requirements

Principal Product Manager key responsibilities

• 4+ years in product leadership positions where you personally crafted product vision, established strategic roadmaps, owned core problem-solution hypotheses, and refined products based on metrics or customer insights
• Proven track record of successfully launching at least one complete software product (beyond features or modules) that reached external users in real-world scenarios
• Substantial enterprise software product management experience
• Genuine passion for integrating AI tools into your workflow (research, analysis, synthesis, strategy formulation)
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5623-CA-Toronto-PrincipalProdu