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Head of Design

Why be with company?

We all know what a great neighborhood feels like. The sad reality is that every day, our neighborhoods are losing their character, authenticity, and sense of community. From Main Streets to Manhattan, our beloved local businesses are being pushed out at unprecedented rates, replaced with corporate brands or empty storefronts. America is losing its small business backbone — its diversity, energy, and competitive edge.

All while there is a generational opportunity in commercial real estate directly ahead of us. We’ve been quietly and deliberately building withco to empower millions of small businesses to seize their opportunity to become their own landlords. And if we’re successful, we’ll have created not only the most financially impactful company of its time, but also neighborhoods that we’re proud to live in. Join our mission to make it exciting to be a small business owner in America.

We've raised $30M+ from the world's best investors, including Founders Fund, Canaan, NFX, BoxGroup, and angels like Ken Chenault, Danny Meyer, Venus Williams, Kevin Durant, and more.

Why we need you:

As our Head of Design, you’ll serve on the executive team as partner to our CEO and CTO.

Small businesses have been exploited and ignored — trust is broken. Your mission? Build a brand and product that arms America’s grittiest entrepreneurs with the tools, knowledge, and capital to take control — to buy back their buildings, rewrite the rules, and win a game that’s been rigged against them.

This isn’t just about visuals. Design here is holistic, strategic, and tangible, Your influence will go beyond screens to define what it means to buy — not a car, not a home — but an asset that fuels community, legacy, and generational wealth..

What you'll do:

  • Launch big. Lead the launch of our first digital app.

  • Move fast. Set our pace of innovation by rapidly prototyping designs that hit home for our customers.

  • Own it all. Shape every detail of new product features — ideas to pixels — and define our roadmap.

What makes you a great fit:

  • A born designer. Design isn’t just what you do; it’s who you are. People call you the best designer they’ve ever worked with. You take extreme ownership of your work.

  • Insatiably curious. Your optimism and curiosity drive you to understand people, solve problems, and create experiences that matter. You don’t wait — you call.

  • Fearless. You’re not here for titles or red tape. You’re here to swing for the fences and make an impact that lasts.

Our Culture

While small business is for everyone, withco’s culture is not for everyone. In fact, it’s for a very, very, very small group. What makes our culture so special is how much we value accountability and clarity in how we work and curiosity and obsession in how we build. We have a disproportionate number of craftspeople, athletes, ex-founders, PhDs and scientists.

Our Benefits

We’re building withco to create generational wealth not only for small business builders, but also our team of builders. We endeavor to make this the most meaningful career experience of your life. In addition, we offer:

  • Top decile all-in compensation for our stage

  • Eligibility for carried interest in our real estate vehicles

  • 100% company-paid medical, dental, and vision insurance

  • A beautiful office in SoHo

  • Unlimited PTO and WFH

  • Paid parental leave

  • 401(k), FSA/HSA, and commuter benefits

  • Weekly team lunch and regular team events, always at a small business

We’re proud to be an equal opportunity employer. We care about building a uniquely diverse, energetic, inclusive, and service-oriented team — one that understands, cares about, and represents the different small business communities we aim to serve.

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CEO of Withco
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Kevin Song
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Average salary estimate

$135000 / YEARLY (est.)
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$120000K
$150000K

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What You Should Know About Head of Design, Withco

At withco, we're on a mission to empower America's small businesses, and we're looking for a passionate Head of Design to join our team! In this crucial role, you'll serve on the executive team, collaborating closely with our CEO and CTO to revolutionize how small business owners reclaim their spaces and rewrite the rules of commercial real estate. If you're the kind of person who sees design as a holistic experience, this is your chance to make a real impact. Your role will go beyond the surface level visuals; you'll shape a brand and product that not only looks good but also provides the tools, knowledge, and capital for entrepreneurs to buy back their buildings and create lasting legacies. You'll lead the launch of our first digital app, move swiftly in your design process, and own every detail, from idea generation to pixel perfection. We’re searching for a truly exceptional designer – someone insatiably curious, fearless, and committed to producing experiences that matter. In return, we provide generous compensation, unlimited PTO, comprehensive health benefits, and a culture that thrives on accountability and clarity. Join us, and help breathe life back into neighborhoods across the country, transforming small businesses into thriving community pillars!

Frequently Asked Questions (FAQs) for Head of Design Role at Withco
What responsibilities does the Head of Design at withco have?

As the Head of Design at withco, you'll have the responsibility of launching our first digital app and guiding the innovation pace by rapidly creating designs that resonate with our customers. This role involves shaping every new product feature's details, from concept to pixel, and defining our design roadmap in conjunction with the executive team, ensuring that design is not only visually appealing but also aligns with our mission to empower small businesses.

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What qualifications are needed for the Head of Design position at withco?

For the Head of Design role at withco, we expect you to have a solid background in design, showcasing a portfolio that reflects your exceptional skills. You should possess an insatiable curiosity and a willingness to understand user needs deeply, solve problems, and create impactful experiences. Furthermore, we value a strong sense of ownership and the ability to work autonomously without waiting for permission to drive projects forward.

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What is the company culture like at withco for the Head of Design?

The culture at withco is driven by a strong emphasis on accountability, clarity, and curiosity. It's a unique environment suited for those who value craftsmanship and are passionate about making a difference. As our Head of Design, you'll find yourself amongst a team of former founders, scientists, and athletes who share a common goal: to uplift small businesses and make an impact in their communities.

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What can a Head of Design expect in terms of benefits at withco?

The Head of Design at withco can expect top decile compensation, eligibility for carried interest in our real estate ventures, and comprehensive health insurance that covers medical, dental, and vision. We also offer unlimited PTO, paid parental leave, a 401(k) plan, and regular team lunches, ensuring a supportive work environment that values work-life balance and team bonding.

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How does withco define design beyond visuals for the Head of Design?

At withco, design transcends mere aesthetics; it is seen as a strategic and holistic process that influences how small business owners engage with their assets. For our Head of Design, this means crafting experiences that empower entrepreneurs, creating interfaces that facilitate these transactions, and developing a brand narrative that resonates with their mission to reclaim spaces and build generational wealth within their communities.

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Common Interview Questions for Head of Design
Can you describe your design philosophy as the Head of Design?

When answering this question, focus on your approach to creating user-centered designs that prioritize functionality, accessibility, and engagement. Discuss how your design principles reflect the mission of empowering small businesses, emphasizing holistic design strategies that create lasting impressions and positive experiences.

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How do you approach collaboration with cross-functional teams?

Share examples of successful collaborations in your previous roles as a Head of Design. Highlight your communication skills, ability to incorporate feedback, and your experience in leading discussions that bridge design with product management and engineering, ensuring that everyone is aligned towards a common goal.

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What methods do you use for rapid prototyping?

Discuss specific tools and processes you rely on for rapid prototyping, like Sketch or Figma, and how you leverage user feedback to iterate quickly. Explain how this approach allows you to fine-tune designs to meet customer needs while staying aligned with company objectives.

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How do you ensure that your designs are aligned with the brand's mission?

Talk about your strategies for integrating brand values into your design work. This may include reviewing brand guidelines, collaborating closely with leadership, or establishing a clear design process that includes brand narrative as a key component in your projects.

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Can you provide an example of a project where you took extreme ownership?

Share a specific project that showcases your leadership in design. Discuss the challenges faced, the strategies you implemented, and how your ownership resulted in a successful outcome for the product or brand, reflecting your commitment to making an impact.

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What is your experience with user-centered design?

Outline your understanding of user-centered design principles and how you've implemented them in your work. Mention any methodologies you've applied such as user research or usability testing to ensure your designs truly meet the needs of the target audience.

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How do you measure the success of your design decisions?

Explain how you go about establishing key performance indicators (KPIs) for design initiatives, using metrics to evaluate user engagement, satisfaction, and conversion rates. This demonstrates your ability to tie design work directly to business outcomes.

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How do you handle constructive criticism in your work?

Describe your openness to feedback and how you view it as an opportunity for growth. Discuss how you’ve successfully integrated feedback into your design iterations, and how this approach ultimately led to stronger results.

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What strategies do you use for keeping the design team inspired and motivated?

Talk about fostering a positive culture of creativity and collaboration within your team. Mention initiatives like design workshops, brainstorming sessions, or team-building activities that you have implemented to inspire innovation and maintain enthusiasm for projects.

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In your opinion, what are the biggest trends in design today?

Stay informed about current design trends and discuss how they can influence designs at withco. Be prepared to offer insights on trends that align with the company’s vision for supporting small businesses, such as sustainable design or inclusive design practices.

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Full-time, remote
DATE POSTED
March 17, 2025

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