Product Design Manager

About the Role

Most design roles at a company our size are execution roles dressed up as leadership roles. This one isn't.

We're looking for a Product Design Manager who wants to own something — the visual language, the product experience, the design culture, and the standard of craft that defines how Olly Olly shows up for clients and in the market. You'll lead a team of three, partner directly with our CPO and Head of Marketing, and have a real seat at the table in how this product grows.

This is a player-coach role. You'll lead and you'll do. The best candidates will be energized by both.

What You'll Own

• The end-to-end design system and visual language across product and brand

• In-app UX/UI for our core platform, used daily by thousands of SMB clients across the country

• External-facing design including our website, digital collateral, and marketing assets

• Day-to-day leadership of a three-person team: two product designers focused on the app, and one web and marketing-focused designer handling client-facing creative

• Design quality, consistency, and velocity across all workstreams

Product Design Responsibilities

• Partner with our CPO to translate product strategy into thoughtful, well-executed design — not just at the feature level but at the experience level

• Lead UX research and discovery: define user flows, identify friction, and advocate hard for the end user in every product conversation

• Own and evolve a scalable design system that supports rapid development without sacrificing quality

• Drive wireframing, prototyping, and iteration in close collaboration with engineering and product

• Establish design QA standards so what ships matches what was designed

• Use data, customer feedback, and usability insights to continuously raise the bar on the product experience

• Contribute to roadmap conversations as the voice of design — not just executing on decisions, but helping shape them

How You'll Collaborate

• Shared ownership of brand direction with our Head of Marketing

• Close partnership with our CPO on product priorities and roadmap alignment

• Cross-functional work with sales, CS, and content as design needs arise

What We're Looking For

• 10+ years of design experience with at least 3 years in a leadership role

• An exceptional eye — your taste is immediately evident in your portfolio, your feedback, and the standards you hold your team to. You know the difference between good and great and you don't let good be enough

• Strong portfolio spanning both product design (UX/UI, systems, user flows) and brand or marketing design

• Deep experience leading UX research, usability testing, and translating insights into real product improvements

• Proven ability to build and maintain design systems that scale with a growing product

• A track record of shipping polished, user-centered experiences — not just beautiful mockups, but thoughtful flows that actually work in the real world

• Experience leading and mentoring small, high-output teams

• Fluency in Figma and modern design tooling

• A clear point of view and the confidence to defend it — someone who can advocate for design as a strategic function, not just a delivery layer

• Comfortable in a fast-moving, growth-stage environment where priorities shift and speed matters

Nice to Have

• Experience designing for SMB audiences

• Background in SaaS or digital marketing platforms

• Familiarity with agency or marketing-facing web design contexts

• Exposure to motion design, interaction design, or mobile-first experience

Why Olly Olly

We're at $25M ARR, growing, and helping thousands of home service businesses across the country get found, get calls, and grow their livelihoods. These are real small business owners — plumbers, roofers, HVAC techs — and the product we build directly affects whether their phone rings.

Design is not an afterthought here. It's central to how we deliver value and how we compete. We're investing in getting it right, which is why this role exists.

If you want to inherit a mature design org and manage process, this probably isn't it. If you want to build something, set the standard, and do work that actually matters to the people using it — we'd like to talk.