[Hiring] Head of Product Design @Olly Olly

Role Description

We are looking for a Head of Product Design 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.

As Head of Design at Olly Olly, you are responsible for design outcomes, not just design output. 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.

This is a hands-on player-coach role . You will be expected to lead the function while also staying close to the work:

• Partnering with product and engineering on strategy
• Improving how ideas move from problem definition through launch
• Coaching designers
• Stepping directly into important projects when needed

You will 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. The best candidates will be energized by both leadership and execution.

Design at Olly Olly should be practical, fast, thoughtful, and increasingly AI-enabled. We want a leader who sees AI as part of the design workflow, not as a side tool.

Qualifications

• 10+ years of design experience
• 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 the ability to influence cross-functional teams and executive stakeholders
• An exceptional eye for design
• A clear point of view and the confidence to defend it
• Comfortable in a fast-moving, growth-stage environment where priorities shift and speed matters

Requirements

• Build and lead the design organization
• Hire, coach, and develop designers over time while defining what great design looks like at Olly Olly
• Stay close to the work as a player-coach
• Partner on product strategy and roadmap
• Improve how product, design, and engineering work together
• Lead UX research and discovery
• Lead with an AI-forward workflow
• Raise the bar on UX, interaction quality, and consistency
• Create a culture of prototyping and validation
• Drive design QA and shipping quality

Benefits

• Opportunity to shape the design culture and standards at Olly Olly
• Work closely with leadership and cross-functional teams
• Engage in meaningful work that impacts small business owners

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