Flexe is a team of technology entrepreneurs and logistics experts who are transforming the $1.5T logistics industry. We deliver technology-powered flexible warehousing infrastructure to the world’s largest Enterprise companies, creating unprecedented agility and flexibility in their supply chains. Our cloud-based software platform connects to 1300+ warehouse operators across North America, making the process of sourcing, operating and scaling logistics services fast and efficient. Flexe.com

As a Principal Product Manager, you will harness deep market insight, technical expertise, and strategic product vision to define, build, and scale high-impact enterprise solutions. In this role, you will lead cross-functional alignment, drive product innovation—including identifying and integrating AI and automation capabilities where they deliver actual value—and partner closely with Engineering, UX, and business leaders. You will translate ambiguous business and operational challenges into clear, customer-centric roadmaps that unlock top-line growth and measurable business outcomes. You will scale your influence and impact through your ability to mentor others.

What You’ll Do

Strategic Vision & Product Roadmap: Define the long-term vision, strategy, and multi-year roadmap across core product lines, ensuring alignment with market opportunities and overall business strategy + goals.
AI & Innovation Strategy: Identify and evaluate opportunities to integrate modern AI, machine learning, and intelligent automation into product workflows to optimize complex processes and drive operational efficiency.
Product Triad Leadership (UX & Engineering): Serve as a core partner alongside Principal UX Designers and Lead Engineers—engaging early in continuous discovery, prototyping, and technical architecture discussions to ensure solutions are intuitive, scalable, and technically sound.
Customer Obsession & Continuous Discovery: Spearhead user research and feedback loops across internal and external stakeholders, translating qualitative user research and quantitative data into high-value product capabilities.
Business & Data-Driven Outcomes: Own product success metrics (OKRs/KPIs). Conduct advanced data analysis to monitor metrics, forecast trends, and make high-stakes, evidence-based trade-offs that drive revenue and efficiency.
Navigating Ambiguity & Execution: Deconstruct complex, loosely defined market and business problems into structured, actionable execution plans across cross-functional delivery teams.
Leadership, Influence & Mentorship: Lead cross-functional alignment without direct line authority—building consensus among executives, commercial teams, and engineering leaders—while coaching mid-level and junior product managers to elevate team capabilities.

What We’re Looking For

Experience: 8+ years of product management experience delivering complex Marketplace, B2B SaaS, enterprise platforms, or technology products, with a proven track record of driving products from zero-to-one and scaling mature platforms.
Strategic & Business Acumen: Demonstrated capability in defining long-term product positioning, evaluating market dynamics, and aligning product outcomes directly with revenue targets and company objectives.
UX & Human-Centered Design Fluency: Strong history of partnering with UX research and design teams to simplify data-heavy, complex operational workflows into seamless, intuitive user experiences.
Technical Acumen: Strong understanding of modern software architecture, APIs, data pipelines, and agile development frameworks, with a proven ability to engage in technical trade-off discussions alongside engineering leads.
Applied AI & Automation Knowledge: Familiarity with identifying, evaluating, and applying modern AI/ML capabilities, GenAI, or algorithmic automation to solve enterprise operational challenges.
Cross-Functional Influence & Communication: Exceptional communication and stakeholder management skills, with a track record of building alignment across executive, technical, and commercial leadership.
Data Literacy & Analytical Skills: Proficiency using quantitative data, user telemetry, and business intelligence to drive decisions, model trade-offs, and prove product value.

Bonus Qualifications

Past experience as a Software Engineer, Engineering Manager, Data Scientist, or UX Researcher/Architect.
Proven experience consolidating fragmented enterprise tools in