Head of Design

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.

ABOUT THE ROLE

We are looking for an exceptional Head of Design to grow our design team and function. In this role, you will be the first design leader at Topline Pro, joining to lead and grow our design team as we scale the company. Upon joining, you will lead two direct reports, a Sr. Product Designer and a Product Designer, as well as assist in growing the design team. In the coming year, you will grow 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. You will report directly to the Chief Product Officer, Erik Ornitz, and partner together to chart the strategic path for design at Topline Pro for years to come. In addition to craft, strategy, and team leadership, a big part of your role will be hands-on design, leading the team by doing the work alongside them. You get to help shape the product, build systems, and create great user experiences.

This is an opportunity to step into a true player-coach role in a rapidly growing startup. You will design product flows, evolve our brand, and set the creative direction, as well as hire, mentor, and support a growing design team. You will be a key partner across internal teams, helping ensure everything we ship feels simple, clear, and high quality.

If you’re energized by mission-driven AI-powered SMB SaaS; leading, growing, and enabling great design teams; and owning design end-to-end while staying close to the work, we’d love to see you apply. We’re excited about leveraging great design and AI horsepower to enable SMBs to grow their businesses - we hope you are too!

WHAT YOU’LL DO

Design hands-on

• Design product experiences from start to finish

• Ship work that is clear, thoughtful, and high quality

• Set a high bar through direct contribution and critique

Build the design function

• Define the vision for design at Topline Pro

• Hire and mentor a small team across product and brand

• Create strong team rituals and support a healthy design culture that champions invention, experimentation and delivering impact for our users

• Build upon our existing design system to support velocity within the growing organization

Lead cross-functionally

• Serve on our leadership team, an ongoing working committee comprised of our CEO, COO, CPO, and 5 heads of department to steer company direction as we scale
  Partner with product, engineering, customer success, sales and marketing

• Shape the product roadmap and bring a design lens to company strategy

• Make sure design is integrated across every part of the business

Own the creative direction

• Build and evolve our visual and interaction standards

• Connect product and brand into one cohesive experience

• Lead internal and external partners to support design at scale
  

WHAT WE’RE LOOKING FOR

• 10+ years of experience in product and brand design

• 4+ years leading small teams in high-growth environments

• A strong portfolio showing both product thinking, visual design, and systems thinking

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

• Proficiency with AI and how it shapes product design

• Direct experience building AI-powered products

• High standards for clarity, usability, and execution

• A strong communicator who collaborates well across functions

• A leader who still loves doing the work and wants to stay close to it

• An ownership mindset, with deep commitment to our overall product and company success

WHO YOU ARE

• Focused on impact and solving real user problems

• Sees design as a growth lever for the business

• Comfortable with ambiguity and fast-moving teams

• Gives clear feedback and receives it well

• Takes ownership and follows through

WHAT WE OFFER

• Competitive cash compensation+ equity package

• Work 4-days in office from our new office in Boston / 1 day remote

• 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 can change the lives of home service pros