Lead PM / Head of Product

Location: NYC - in office 3 days/week
Reports to: CEO
Growth Path: Lead PM → Head of Product → CPO

Wayward is a well-funded (Series B stage), profitable, and high-growth AI-technology company transforming how brands connect with creator audiences. We’ve built a marketplace that turns editorial and creator content into scalable media, giving brands a powerful new channel to deploy ad budgets with precision and impact.

With 10x year-over-year growth and proven product-market fit, we are reshaping the future of performance marketing and unlocking an entirely new path for global ad spend.

We’re looking for a foundational Product Manager to own and scale Wayward’s product. This will be our first and only PM initially, working directly with the CEO, engineering, sales, and operations to define what we build next, why we build it, and how it creates value for customers and the business. This role will sit on the Executive Leadership Team.

This role is ideal for a PM who thrives in ambiguity, wants real ownership, and is excited by the opportunity to grow into a Chief Product Officer as the company scales.

• Own the end-to-end product lifecycle: discovery, strategy, roadmap, execution, and iteration

• Translate company goals, customer needs, and market insights into clear product direction

• Partner closely with engineering to ship high-quality product quickly and pragmatically

• Work with sales, growth, and operations to ensure the product drives revenue and customer success

• Define and track success metrics; use data (and intuition) to make smart tradeoffs

• Talk to customers constantly — validating problems, testing solutions, and uncovering new opportunities

• Establish product processes and rituals that scale with the company

• Help shape Wayward’s long-term product vision and category strategy
  

• 4–8+ years of product management experience (startup or high-ownership environments strongly preferred)

• Experience owning products from early stages through growth

• Strong product intuition paired with analytical thinking

• Ability to operate comfortably in fast-paced, ambiguous environments

• Excellent communication skills - you can align technical and non-technical stakeholders

• A builder mindset: scrappy when needed, opinionated but open, and biased toward action

• Interest in ad tech, marketplaces, creator platforms, or performance marketing is a plus

• Strong AI acumen

• Be the sole PM with real influence over product direction

• Direct line to leadership and meaningful impact on company outcomes

• Opportunity to help define a new product category

• Clear path to growing into a Head of Product / CPO role

• Join an early team shaping a trillion-dollar industry
  

We’re a small, tight-knit team where every individual makes a meaningful impact on both the product and the business. Our culture is fast-moving, collaborative, and ambitious. We value creativity, ownership, and speed - and we leverage AI to accelerate our work without losing sight of critical thinking and craft.

At Wayward, big ideas are encouraged and bold execution is celebrated.