Product Design Manager

Olly Olly is a $25M ARR company focused on helping home service businesses grow through effective design. They are seeking a Product Design Manager to lead a three-person design team, ensuring high-quality design outcomes while also contributing hands-on to critical projects.

Responsibilities:

• 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
• 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

Requirements:

• 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
• 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
• 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