Design Director, Core Insurance & Design Systems

Headway

$249K — $312K *
Finance & Insurance
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 3+ years leading design system or product design teams.
  • Extensive experience building and shipping design systems.
  • Proven ability to build and scale design teams.
  • Strong communication skills to simplify complex technical details.
  • Eye for high-quality visual design with meticulous attention to detail.

Responsibilities

  • Lead and advocate for design systems across products.
  • Oversee foundational customer experiences including insurance and support.
  • Manage internal tooling for operational efficiency.
  • Hire, lead, and coach a diverse design team for product and content development.

Benefits

  • Equity compensation
  • Medical, Dental, and Vision coverage
  • HSA / FSA
  • 401K
  • Work-from-Home Stipend
  • Therapy Reimbursement
  • 16-week parental leave for eligible employees
  • Carrot Fertility annual reimbursement and membership
  • 13 paid holidays plus a Holiday Break
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development opportunities
Full Job Description
As the Product Design Director for this team, you will help contribute to our mission by making Headway's operation more efficient, by building a powerful design system, strategic content design, wildly predictable insurance experience and robust internal tools. In this role, you will lead and continue building a talented team of product designers, design system designers and content designers. You'll be a key partner to other teams, ensuring our design systems empower teams to build cohesive, high-quality experiences at scale.

In this role, you will:
  • Lead the design systems across our products, as well as lead the team defining these systems. You will also be an advocate of design craftsmanship across our product, design, and engineering organizations.
  • Oversee the foundational experiences including insurance experiences, support experiences and security experiences for our customers.
  • Manage the internal tooling experiences that helps Headway operate efficiently.
  • Hire, lead, and coach a team of design system designers, content designers, and product designers responsible for design systems and foundational experiences.

Experience we're seeking:
  • 3+ years of experience leading successful design system or product design teams.
  • Extensive experience in building and shipping design systems across a variety of systems.
  • Experience building and scaling a design team.
  • Great communication and excel in making complex technical details easy to understand.
  • Value high quality visual design with attention to detail.

Compensation and Benefits:

The expected base pay range for this position is $249,600 to $312,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.
  • Benefits offered include:
    • Equity compensation
    • Medical, Dental, and Vision coverage
    • HSA / FSA
    • 401K
    • Work-from-Home Stipend
    • Therapy Reimbursement
    • 16-week parental leave for eligible employees
    • Carrot Fertility annual reimbursement and membership
    • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
    • Flexible PTO
    • Employee Assistance Program (EAP)
    • Training and professional development

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