Olly Olly is building software and services that help small businesses grow. We operate at the intersection of product, AI, local business growth, and operational execution, helping customers improve visibility, generate demand, and get more value from their digital presence. We work in an environment where speed matters, but quality matters too. The work is not about producing polished artifacts in isolation. It is about understanding real customer problems, shaping the right solutions, and shipping experiences that drive measurable outcomes for the businesses we serve. About the Role The Head of Product Design will own the visual language, product experience, design culture, and standard of craft that defines how Olly Olly shows up for clients and in the market. As Head of Design, you will lead design across the product experience, helping define where we are going, how we get there, and how design raises the quality of the product at every stage. 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 The role design plays in improving customer experience, product adoption, usability, retention, and customer value Stronger systems, standards, and collaboration patterns across product, design, and engineering What You’ll Do Build and lead the design organization: hire, coach, and develop designers while defining what great design looks like at Olly Olly Stay close to the work as a player‑coach, partnering with product managers, engineers, and company leadership to shape product direction, make trade‑off decisions, and raise the quality of shipped experiences Partner with the CPO on product strategy and roadmap, translating strategy into well‑executed design and contributing to roadmap conversations as the voice of design Improve how product, design, and engineering work together by ensuring design engages early in problem definition, stakeholder input, validation, refinement, and launch readiness Lead UX research and discovery: define user flows, identify friction, run usability testing, and advocate for the end user in every product conversation Lead with an AI‑forward workflow, encouraging and operationalizing the use of LLMs and AI tools across the design process Raise the bar on UX, interaction quality, and consistency by establishing standards for interaction design, content hierarchy, visual consistency, and usability Create a culture of prototyping and validation, pushing the team to test ideas earlier through lightweight prototypes, internal feedback, and customer validation Drive design QA and shipping quality by establishing design QA standards and partnering closely with engineering to maintain a high bar through implementation How You’ll Collaborate Shared ownership of brand direction with Head of Marketing Close partnership with CPO on product priorities, roadmap alignment, and experience strategy Deep collaboration with engineering on implementation quality and product development process Cross‑functional work with sales, customer success, content, and marketing as design needs arise What We’re Looking For 10+ years of design experience, with at least 3 years in a leadership role Strong track record working in fast‑moving startup or growth‑stage environments Experience designing and shipping B2B SaaS, workflow‑heavy, or systems‑oriented products Strong portfolio spanning both product design 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 Demonstrated ability to connect design work to product and business outcomes Strong product thinking, interaction design, and systems thinking Experience partnering deeply with product and engineering leaders Ability to move between high‑level strategy and hands‑on work Comfort working in ambiguity and helping create clarity where process is still evolving Active use of AI tools such as ChatGPT, Claude, Cursor, or similar in your workflow Fluency in Figma and modern design tooling Strong communication skills and ability to influence cross‑functional teams and executive stakeholders An exceptional eye for design quality and high standards A clear point of view and confidence to defend it, advocating design as a strategic function Comfortable in a fast‑moving, growth‑stage environment where priorities shift and speed matters Nice to Have Experience building or maturing a design function at an early‑stage or growth‑stage company Experience designing for SMB audiences Familiarity with local business, SMB software, marketing technology, or operational tools Background in SaaS or digital marketing platforms Familiarity with agency or marketing‑facing web design contexts Comfort prototyping in code or working closely with engineers on implementation details Experience introducing better design processes, critique, and standards into organizations that are scaling quickly Exposure to motion design, interaction design, or mobile‑first experiences 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 Customers have a clearer, simpler, and more valuable experience Design quality rises across the product, not just within isolated features The company builds stronger internal standards for usability, craft, and consistency The design team becomes a force multiplier for product strategy and execution 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. Design is central to how we deliver value and how we compete. 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. #J-18808-Ljbffr