Product Design Manager

About the Role

We are looking for a Product Design Manager to lead our product design team at Olly Olly. This is a player-coach leadership role — you are responsible for design outcomes, not just design output. You will spend the majority of your time managing and elevating the work of your team, with roughly 20-30% of your time contributing directly as a designer yourself on high-priority work.

Design at Olly Olly should be practical, fast, and thoughtful. We want someone who sees AI as part of the design workflow — not a side tool — and who can help the team use LLMs and prototyping tools to move faster, think more clearly, and test ideas earlier, while still maintaining a high bar for craft, usability, and clarity.

You will report to our CPO and work in close partnership with engineering and product to ensure great design ships — not just great mockups.

Three Direct Reports

• UX/UI Product Designer (in-app)
• UX/UI Product Designer (in-app)
• UI/Web Designer (marketing and brand-adjacent)

What You Will Own

• Day-to-day management of a three-person design team — running design reviews, unblocking work, giving direct feedback, and raising the bar on quality
• The design system and visual language for our core product, ensuring consistency across every screen and interaction
• UX flows, wireframes, and prototypes for new features — from early problem definition through to production-ready specs
• Design QA — making sure what gets built matches what was designed
• Improving how product, design, and engineering work together — ensuring design is involved early in problem definition, not just UI delivery
• Collaboration with engineering and product on sprint planning, roadmap prioritization, and tradeoff decisions
• Darko's output across UI and web — reviewing his work and ensuring brand and product design stay visually coherent
• A culture of prototyping and early validation — pushing the team to test ideas before they are fully built

How You Will Spend Your Time

• 60-70% — Managing the team: reviews, feedback, career development, process improvement, and cross-functional coordination
• 20-30% — Hands-on design: contributing directly to high-priority or complex features where your execution adds the most value

What Success Looks Like

• Design is involved earlier and more effectively in product development
• Product experiences become more intuitive, cohesive, and outcome-oriented
• The team ships faster with better alignment across product, design, and engineering
• Design quality rises across the product — not just within isolated features
• The design team becomes a force multiplier for product strategy and execution

What We Are Looking For

• 6 years of product design experience, with at least 1-2 years managing or formally leading other designers
• An exceptional eye for design — your taste shows up in your portfolio, your feedback, and the standards you hold your team to
• Strong product thinking — you understand user flows, information architecture, and how design decisions connect to business outcomes
• Experience designing and shipping B2B SaaS or workflow-heavy products
• Experience building or maintaining a design system in a fast-moving product environment
• Proven ability to ship — you have a track record of moving work from concept to production without losing quality
• Active use of AI tools such as Claude, ChatGPT, Cursor, or similar in your design workflow
• Fluency in Figma and modern design tooling
• Strong communicator who can translate design decisions into business rationale for non-design stakeholders
• Comfortable in a growth-stage environment where priorities shift and you need to make good decisions with incomplete information

Nice to Have

• Experience designing for SMB audiences or home services markets
• Background in SaaS or digital marketing platforms
• Familiarity with web and marketing design in addition to product

About Olly Olly

We are a $25M ARR company helping thousands of home service businesses get found, get calls, and grow. Design is central to how we deliver value — both in our product and how we show up in the market. This is an opportunity to own a small but high-impact design team at a company that is scaling fast and investing in getting the product right.

Portfolio Required

• Please include a portfolio with your application. Applications without one will not be considered.
• We want to see product design work — UX flows, shipped features, design systems — not just visual polish.
• Show us your thinking, not just the final output.