About Olly Olly

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 are 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.

We are looking for people with high ownership, strong judgment, and a bias toward action. At Olly Olly, leaders are expected to work across functions, stay close to the customer, and help build the systems and culture that allow the company to scale.

About the Role

Most design leadership roles at a company our size are execution roles dressed up as leadership roles. This one is not.

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, and 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: someone 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.

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

Lead design as a product and business function

Own the role design plays in improving customer experience and business results. Ensure design is focused on solving meaningful problems and contributing to product adoption, usability, retention, and customer value.

Build and lead the design organization

Hire, coach, and develop designers over time while defining what great design looks like at Olly Olly. Set clear expectations for quality, pace, collaboration, and ownership.

Stay close to the work

Operate as a player-coach. Partner directly with product managers, engineers, and company leadership to shape product direction, make tradeoff decisions, and raise the quality of shipped experiences.

Partner on product strategy and roadmap

Work closely with our CPO to translate product strategy into thoughtful, well-executed design, not just at the feature level but at the experience level. Contribute to roadmap conversations as the voice of design, not just executing on decisions, but helping shape them.

Improve how product, design, and engineering work together

Help create a stronger product development rhythm by ensuring design engages early in problem definition, stakeholder input, validation, refinement, and launch readiness, not just UI delivery.

Lead UX research and discovery

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

Lead with an AI-forward workflow

Encourage and operationalize the use of LLMs and AI tools across the design process, from clarifying requirements and exploring flows to generating prototypes and identifying edge cases. Help the team use these tools in a practical way that improves speed and thinking.

Drive clarity in complex workflows

Olly Olly’s products often sit across operational, marketing, and growth workflows. Simplify complexity for customers while preserving the depth needed for real-world use cases.

Raise the bar on UX, interaction quality, and consistency

Establish standards for interaction design, content hierarchy, visual consistency, and usability across the product. Build stronger patterns and reusable approaches so the product feels more cohesive as it grows.

Create a culture of prototyping and validation

Push the team to test ideas earlier through lightweight prototypes, internal feedback, and customer validation. Treat learning as part of velocity, not as a separate phase.

Build systems, not just screens

Help evolve design systems, reusable patterns, and team practices that improve speed without sacrificing quality. Ensure consistency scales with the product.

Drive design QA and shipping quality

Establish design QA standards so what ships matches what was designed. Partner closely with engineering to maintain a high bar through implementation.

Use insight to raise the bar

Use data, customer feedback, and usability insights to continuously improve the product experience and raise the quality bar over time.

Be the voice of the customer in the room

Bring strong user empathy and practical judgment into prioritization and design decisions. Help the company balance customer needs, operational realities, and technical constraints.

How You’ll Collaborate

Shared ownership of brand direction with our Head of Marketing
Close partnership with our 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 the ability to influence cross-functional teams and executive stakeholders
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 do not let good be enough.
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 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

In this role, success means:

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. 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.

Head of Product Design