Director of Design

US, Remote

About Gladly:

Gladly, the customer-centered, AI-powered customer support platform is built around people, not tickets. Unlike traditional ticket-based customer support solutions, our software helps brands deliver radically personal service at scale by integrating every channel—voice, email, SMS, chat, social messaging, and self-service—into a single, lifelong conversation stream. Companies like Allbirds, Bombas, Crate & Barrel, and Warby Parker use Gladly to create exceptional customer experiences, transforming everyday customer interactions into lasting connections. 

Gladly is a fully distributed company that embraces remote work and believes in flexibility, innovation, and inclusivity. We foster a collaborative, inclusive culture that prioritizes growth, DEIB, and meaningful connections. At Gladly, people are at the heart of everything we do.

About Gladly

Gladly, the customer-centered, AI-powered customer support platform is built around people, not tickets. Unlike traditional ticket-based customer support solutions, our software helps brands deliver radically personal service at scale by integrating every channel—voice, email, SMS, chat, social messaging, and self-service—into a single, lifelong conversation stream. Companies like Allbirds, Bombas, Crate & Barrel, and Warby Parker use Gladly to create exceptional customer experiences, transforming everyday customer interactions into lasting connections. 

Gladly is a fully distributed company that embraces remote work and believes in flexibility, innovation, and inclusivity. We foster a collaborative, inclusive culture that prioritizes growth, DEIB, and meaningful connections. At Gladly, people are at the heart of everything we do.

The Opportunity

We're looking for a visionary Director of Design to lead, inspire, and grow our talented design team, shaping the future of customer service. Design is already part of what sets Gladly apart, and you’ll continue to drive that differentiation forward. 

You'll be a key strategic partner to the Product, Engineering, and Marketing leadership, ensuring that design—both in the product and how we tell our story—remains a core part of our company's mission and success.

You’ll be leading a team of impressive designers and championing our brand principles in everything we build. Our product takes inspiration from the best consumer experiences, and customers rave about how the intuitive design helps them drive better and faster results. You'll be a player-coach, both guiding the team and contributing directly to design efforts, fostering a culture of collaboration, innovation, and continuous improvement. You will oversee both Product Design and Brand Design, creating a cohesive design language across all aspects of Gladly. 

If you're passionate about building products that people love, crafting a compelling brand narrative, and leading a team to do their best work, we want to hear from you!

What You’ll Do

  • Lead, mentor, and grow a team of product and brand designers, fostering a culture of creativity, collaboration, and continuous learning.
  • Contribute to product and brand strategy, often exploring new areas of opportunity.
  • Establish and maintain design systems, processes, and tools to ensure consistency, efficiency, and scalability across both product and marketing design.
  • Stay plugged in to industry trends and best practices in both product and brand design, fostering fresh perspectives and innovative ideas to the team.
  • Act as a player-coach, contributing directly to key projects and initiatives, and helping team members bring their best to each project.
  • Oversee the user research process, ensuring that design decisions are informed by user insights and data, and that brand messaging resonates with our target audience.
  • Drive the evolution of the Gladly brand identity and its expression across the product, marketing materials, website, and all other touchpoints.

What We’re Looking For

  • 10+ years of experience in design, with at least 4 years in a leadership role, managing and mentoring design teams.
  • A strong portfolio showcasing a track record of designing and leading the design of successful, user-centered products and impactful marketing campaigns, ideally in the SaaS or enterprise software space.
  • Exceptional leadership and communication skills, with the ability to inspire, influence, and collaborate effectively with team members and stakeholders at all levels.
  • A deep understanding of design principles and methodologies, as well as brand strategy and marketing principles.
  • A strong visual design aesthetic and a keen eye for detail.
  • Experience building and scaling design systems and working with modern design and prototyping tools.
  • Experience conducting and interpreting user research and quantitative inputs.
  • A strategic mindset, ability to connect design choices to broader company strategy and goals, and ability to prioritize for outcomes.
  • A drive for innovation, creativity, emerging technologies, and pulse on design trends and user behaviors.
  • Experience working in companies with very high design standards is a plus.
  • Exceptional problem-solving and communication skills, with a collaborative mindset.
  • The ability to navigate ambiguity and manage multiple priorities effectively.
  • A willingness to learn and contribute to a fast-paced team fueled by underdog grit and a shared passion for excellence.

Why Join Gladly?

At Gladly, we’re not just building software—we’re transforming an industry. We take a people-first approach, both in our product and our culture. When you join us, you’ll enjoy:

  • Competitive salaries, stock options, and comprehensive benefits
  • Generous paid time off, parental leave, and home office stipends
  • A fully remote work environment with opportunities for in-person team gatherings
  • A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive

At Gladly, we believe in challenging the status quo, celebrating grit, and striving for excellence. We thrive as a team by embracing transparency, collaboration, and a customer-first mindset. If this role excites you but you don’t meet every qualification, we still encourage you to apply. Diverse perspectives and experiences are the cornerstone of our success.

Estimated Salary for this role: $173,000-$249,000

The cash compensation above includes base salary, and is not reflective of potential commission for employees in eligible roles, or annual bonus targets under Gladly's bonus plan for eligible roles. In addition to cash compensation, all Gladly's employees are eligible to participate in Gladly's equity incentive plan to receive stock options per the terms of the agreement. Individual compensation packages are based on a few different factors unique to each candidate, including their career level, skills, experience, specific geographic location qualifications and other job-related reasons.

Why Join Gladly?

At Gladly, we’re not just building software—we’re transforming an industry. We take a people-first approach, both in our product and our culture. When you join us, you’ll enjoy:

  • Competitive salaries, stock options, and comprehensive benefits
  • Generous paid time off, parental leave, and home office stipends
  • A fully remote work environment with opportunities for in-person team gatherings
  • A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive

At Gladly, we believe in challenging the status quo, celebrating grit, and striving for excellence. We thrive as a team by embracing transparency, collaboration, and a customer-first mindset. If this role excites you but you don’t meet every qualification, we still encourage you to apply. Diverse perspectives and experiences are the cornerstone of our success.

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