Brand Design Lead
About Olly Olly
We're on a mission to transform local marketing for the businesses that actually keep America running - the contractors, plumbers, roofers, and home service providers who built this economy one job at a time.
At Olly Olly, we combine technology and hands-on expertise to help 17,000+ small businesses dominate their local markets. We're building an intelligent growth operating system that makes marketing automatic, not accidental.
Our platform handles everything local businesses need to win online: local SEO, Google Business Profile optimization, review generation, and competitive intelligence that shows them exactly how to beat their rivals. We deliver results in plain English, without the jargon that makes business owners' eyes glaze over.
We've scaled to $25M ARR serving small businesses that hate marketing but love customers. Now we need a design leader to build the brand that champions these underdogs and earns their trust.
The Mission
You'll own the visual identity and web experience for a brand that stands up for America's small businesses - the ones who get overlooked, underestimated, and overcharged by traditional marketing agencies.
Your design challenge: marry clean, crisp, straightforward visual design with content that's genuinely easy to understand. Our site needs to feel professional enough that a skeptical contractor trusts we know what we're doing, while being so clear that someone who hates marketing can actually follow along.
Think Apple's clarity meets a brand that actually gives a damn about plumbers. No marketing jargon. No confusing tutorials. Every page, every visual element should make a busy contractor think "finally, someone who speaks my language."
Your primary responsibility is designing and evolving our corporate brand and website - the face of Olly Olly that convinces contractors we're different, trustworthy, and actually on their side. You'll also design the scalable theme system for our client websites, ensuring the sites we build are as excellent as the brand we present.
Key Responsibilities
Company Website Ownership (Primary Focus) - Maintain and elevate our corporate website. Design new features, high-impact landing pages, educational tutorials, and improvements that reinforce our position as the champion for small business. Make complex marketing concepts instantly understandable.
Brand Identity That Champions Small Business - Create a visual language that's clean, professional, and refreshingly straightforward. Your work should make a roofer feel understood and a skeptical electrician feel like we're not trying to snow them.
Clarity-First Design System - Build a system where every component is optimized for understanding first, aesthetics second. Design educational content that breaks down marketing concepts visually so a contractor can actually grasp what matters.
Scalable Theme Architecture - Design a modular, customizable website theme system (primarily WordPress) that becomes the foundation for thousands of client websites across 50+ service industries.
Visual Excellence & Conversion - Create visually diverse, industry-leading themes that are modern, professional, and tailored to our clients' industries. Every design choice must drive visitors toward conversion - getting the phone to ring is what matters.
SEO & Performance by Design - Integrate SEO best practices, site speed principles, and accessibility standards into everything you design.
Production-First Thinking - Design themes that are intuitive for our internal teams through flexible modular blocks and layout options. Your system must make building 50+ sites per month seamless and error-proof.
Marketing & Educational Asset Creation - Design sales presentations, one-pagers, email templates, tutorial graphics, and campaign materials that reinforce our brand promise: straightforward, no-bullshit help that actually works.
Iteration & Improvement - Use data, competitor analysis, and design trends to continuously improve effectiveness, aesthetics, and usability. A/B test landing pages, analyze conversion metrics, and evolve designs based on what actually works.
What Makes You the Right Fit
This is a senior role with high expectations. The ideal candidate lives at the intersection of breathtaking visual clarity and rigorous systems-level thinking.
Must-Haves:
7+ years of professional UX/UI design experience, with heavy focus on web design
World-class portfolio demonstrating: marketing websites that are beautiful AND easy to understand; scalable design systems; educational/tutorial design that makes complex topics accessible; multi-site, multi-brand, or theme-based web design
Strong foundation in conversion-centered design (CRO) and data-driven decisions
Work for service industries, small businesses, or "blue-collar" audiences (huge plus)
Expert-level proficiency in Figma
Deep understanding of WordPress architecture and page builders (Gutenberg/Block Editor)
Mastery of user-centered design, responsive design, typography, and color theory - with talent for making information clear and scannable
Pragmatic understanding of front-end technologies (HTML, CSS) and how they influence design
Exceptional communication skills - articulate design decisions to leadership and provide crystal-clear documentation for production teams
Pixel-perfect attention to detail
Foundational understanding of on-page SEO principles
Ability to design for skeptics and the marketing-averse - you earn trust and create clarity when your audience starts from doubt
Bonus Points: Experience designing educational content or tutorials; portfolio showing before/after redesigns that improved accessibility; experience with home services industries; familiarity with heatmaps and A/B testing; track record of improving conversion rates AND user comprehension; understanding of local search; experience designing sales enablement materials.
What You'll Love About Working at Olly Olly
Salary: Competitive, commensurate with your expertise
Schedule: 100% remote, Monday-Friday 8 AM - 5 PM CST with excellent work-life balance
Time Off: 15 vacation days + U.S. holidays
Champion the Underdog: Your work determines whether thousands of small businesses trust us. You're designing for the people who built America.
Design-First Leadership: You'll report to a CEO who believes design quality and clarity are the difference between earning trust and losing it.
Autonomy & Ownership: This is a foundational role. You'll own our brand presence and have authority to shape how America's small businesses see us.
High-Performance Culture: Work with smart, driven colleagues who care about craft and aren't satisfied with "good enough."
Real Impact: When your designs work, contractors understand what we do. When your tutorials are clear, plumbers can actually use the tools. When you get it right, small business owners finally feel like marketing isn't a black box designed to rip them off.
How to Apply
Submit your resume and portfolio link.
Portfolio requirements: We need to see marketing websites prioritizing clarity, scalable design systems, educational/tutorial content, and design that drove conversion. Show us work that demonstrates you understand how to earn trust through straightforward, honest design - especially with skeptical audiences who hate complexity.
Portfolios without clear examples of design systems or scalable web/theme projects will not be considered.
Diversity and Inclusion at Olly Olly
We celebrate differences in background, culture, abilities, and perspectives because diversity drives innovation and creativity. Your voice matters here - really matters. Your unique perspective will help us shape the future of small business growth.
