Head of Design Job at Topline Pro in Boston

About Topline Pro

We’re building AI powered Shopify for service businesses. We help service pros (e.g., roofers, landscapers, painters, cleaners) acquire direct business, fast. Up and running within minutes using Gen AI, our digital storefront products help pros get discovered, trusted, and booked repeatedly.

Topline Pro is co-founded by Nick Ornitz (CEO) and Shannon Kay (COO) with an excellent team of 70+ rockstars with plans to expand more in 2025. We serve thousands of local service businesses and were named as one of the 2023 and 2024 top 50 Tech Companies building for SMBs .

We're YC-backed and well funded with several years of runway, and we’ve experienced rapid growth in the past year. We're in a phenomenal position to scale—with the financial foundation, product-market fit, and momentum to go big. You’ll be joining at an inflection point—where the groundwork is laid and the path to massive impact is clear.

We are seeking an exceptional Head of Design to lead our growing design team and function. This leader will report directly to the Chief Product Officer and partner together to chart the strategic path for design at Topline Pro for years to come. They will build and manage a high-performing team of product and brand designers, lead user research, and serve as a key partner to product, engineering, marketing, and leadership to deliver exceptional, AI-powered user experiences. They’ll work closely across functions to ensure our design craft is world class, user centric, and highly impactful.

We believe “great candidates” do not come about through simply a checkmark next to past experiences. We believe in hiring people not just skills. Even if you do not check every box but find excitement at the prospect of working with us in this capacity, please apply.

What you'll do Strategic Design Leadership

Define and drive the overall product design vision and strategy, ensuring alignment with company goals and product roadmap.

Build a design culture that champions user empathy, invention, rapid experimentation, and world class execution.

Act as a thought partner to product and engineering leadership to shape product strategy and influence the broader company strategic roadmap.

Team Building & People Management

Recruit, develop, and retain top-tier product and brand designers.

Provide ongoing mentorship, performance feedback, and career growth opportunities for the design team.

Foster a collaborative and inclusive design environment where great ideas can come from anywhere.

Execution & Craft

Oversee the end-to-end design process, from discovery through execution and iteration.

Ensure the team delivers elegant and intuitive experiences across web and mobile (UI / UX), including thoughtful approaches to AI powered interfaces (NLX).

Implement scalable design systems and processes that support velocity without compromising quality.

Brand Cohesion

Oversee visual branding, voice, and storytelling across the product and marketing surfaces.

Champion a cohesive visual identity that is aspirational yet deeply connected to our customer base of Pros.

Collaborate with Marketing to help ensure our brand communicates our value clearly and effectively.

Cross-functional Influence

Collaborate closely with product managers, engineers, marketers, data scientists, and other team members to define and deliver impactful products.

Partner with research and data teams to deeply understand our users and continuously improve product-market fit.

What we're looking for 10+ years of experience in design roles across product design and brand, with at least 4+ years leading design teams scaling from Series B and beyond.

Demonstrated success building 0→1 products and evolving 1→100 systems in a startup or high-growth environment.

Strong portfolio across product UI / UX and brand creative, with a refined eye for visual and interaction design.

Experience building AI powered products that leverage generative models to deliver customer value

Experience setting creative direction and leading both in-house and external design partners.

Deeply user-centric, with high standards for quality and storytelling.

Natural collaborator with excellent communication and influence skills.

Thrives in ambiguity, embraces iteration, and moves quickly with intention.

Owner mindset, continually contributing to our overall product and company strategy.

Who you are Customer obsessed designer who champions user impact and outcomes

Strategic thinker who believes design has the power to dramatically accelerate company success

Team player with a passion for learning

Self-starter who finds comfort progressing through ambiguity

What we offer Competitive cash compensation + equity package

Work 4-days in office from our new office in Boston (1 remote day)

Full Medical, Dental and Vision Health Coverage

Computer and workspace enhancements

Monthly stipend for mental and physical health

401(k) plan (non-matching)

Unlimited vacation, 9 company holidays, and 1 personal volunteer day a year

Opportunity to take on significant responsibility and ownership in scaling a product that changes the lives of thousands of small business entrepreneurs across the country

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