15Five is looking for a Director of Product to lead product and design, reporting directly to our CTO. This role sits at the center of 15Five's push to be AI-native across product, ops, and go-to-market. You'll partner with the CTO to bring our strategic vision to life through a team of Product Managers and Designers. This is a hands-on leadership role where you are both an active coach of your team while staying close to lead our product work, sell the roadmap to customers, guide technical tradeoffs with engineering, and embed AI into how your org builds product day to day.

You'll thrive here if you're obsessed with customer outcomes over shipped features, want to build AI+Human led work intelligence rather than just manage people, and are energized by fast-paced, high-accountability environments. If you've led a product for complex B2B SaaS (HR tech or AI-first a plus), have real hands-on AI product and tooling experience (not just awareness of it), and can influence execs while still rolling up your sleeves then this is the role for you.

We're fully remote and looking for candidates in the central or eastern US time zones.

RESPONSIBILITIES

• Lead and develop a team of Product Managers and Product Designers, serving as both a coach and an hands-on product leader.

• Partner with the CTO and executive team to define and execute product strategy aligned with company goals.

• Own multiple strategic initiatives from discovery through customer adoption, ensuring successful execution and business impact.

• Drive product prioritization and decision-making using customer insights, data, technical considerations, and company strategy.

• Champion selling the roadmap and future vision directly to customers.

• Collaborate closely with Engineering, Design, AI, Data, Sales, Marketing, Customer Experience, Account Management, and other business leaders to deliver exceptional customer outcomes.

• Foster a high-performing product organization with a culture of ownership, innovation, collaboration, and continuous improvement.

• Stay at the forefront of AI technologies, tools, and best practices, championing AI-first product development and embedding AI into daily product management practices.

• Maintain a strong understanding of technology and architecture to effectively partner with engineering and guide technical product decisions.

REQUIRED EXPERIENCE /COMPETENCIES / ATTRIBUTES

• 5+ years of experience managing Product Managers and building high-performing product teams.

• Proven success leading product strategy and execution for complex B2B SaaS products.

• Experience in HR technology, enterprise SaaS, AI-first, or data-centric companies.

• Strong strategic thinking with the ability to balance customer needs, business objectives, and technical constraints.

• Solid understanding of modern software architecture and the ability to collaborate effectively with engineering leaders.

• Extensive hands-on experience using AI tools and frameworks as part of daily product management, with a passion for staying current on emerging AI trends and technologies.

• Excellent communication, collaboration, and stakeholder management skills, with experience influencing executive-level decisions.

Signs You’re the Right Fit for this Role

• You are obsessed with creating amazing experiences for customers
• You want to be hands-on with product development and people development
• You want to build and be part of human + AI agent teams
• You understand that releasing a feature is the midpoint of ensuring that it’s adopted
• You want to work in a fast-paced, startup environment
• You enjoy iterating product development with customers to maximize value
We encourage you to apply if the role is a fit or if it’s something you could grow into in the next 1-2 years - we’re open to considering a Senior Manager level for the right candidate.

Salary Range Details

This role's Total Rewards package includes annual base salary along with participation in an annual discretionary company bonus program, new hire equity awards, and comprehensive benefit and wellbeing offerings.
This role has an base salary range of $160,000 - $220,000/annually.
Final compensation decisions will be evaluated at the time of offer and may vary based on level and geographic location, in alignment with 15Five's Compensation Philosophy.