Head of Design
Company shown to members 🔒 · Remote · US only
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First recorded by Psst: 12 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.
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The 20-second read
- Experience
- 15+ years required
- Where you can live
- US only
- Skills and tools
- b2b, saas, compliance, hipaa
- Job type
- Full-time
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Job details
- Where you can work
- United States
- Employment type
- Full-time
- Advertised pay
- $365K–513K/yr
- Experience
- 15+ years required
- Employer publication date
- 6 July 2026
- First recorded by Psst
- 12 October 2026
- Last checked at the source
- 10 November 2026
About the job
At the company, our mission is to help businesses earn and prove trust. We believe that security should be monitored and verified continuously, and we empower companies to practice better security and prove it with ease. The company has a kind and talented team, and while some have prior security experience, many have been successful at the company without it.
The company is hiring for a Head of Design (VP) to lead our design organization — setting direction for a ~40-person team, shaping the next generation of AI-native product experiences, and building the quality systems that let great design ship at scale.
The Design team at the company shapes how security and compliance teams experience the company — from a startup founder building their security program for the first time to an enterprise security team managing hundreds of controls. The org spans all areas of the company — GRC, Trust, Platform, Self-serve, and AI — and includes product designers, visual designers, design engineering, content designers, and a user researcher, led by experienced design directors. As AI fundamentally changes what products can do and how they get built, this team is at an inflection point: the right leader will define what it means for a design org to be genuinely AI-forward — enabling designers to move faster, ship more, and contribute to product direction and delivery in new ways.
This is the right role for a design leader who leads with AI fluency, brings strong taste and craft across interaction design and visual design, and has the operational instincts to build the systems that make quality a consistent property of the whole org.
What you’ll do as Head of Design at the company
- Lead a team of ~40 designers and design directors across GRC, Trust, Platform, Self-serve, and AI — setting org-wide direction and enabling each leader to do their best work
- Lead the team building the next generation of agentic, AI-native product experiences — defining what great design looks like as the company’s products are increasingly shaped by AI
- Establish an AI-native design practice: evolve agentic UX patterns, redesign team workflows around AI tooling, and define how design engineers and designers collaborate in an AI-first environment
- Bring a strong point of view to design decisions — engaging deeply on interaction design, visual quality, and product direction, and building the trust that allows design decision-making to scale
- Set a clear, shared standard for design quality across the company — spanning visual design, interaction design, and AI-enabled experiences — and build the systems that hold that bar consistently: design system, definitions of done, and launch review frameworks
- Drive design as a first mover: shape design direction proactively, establishing the taste and systems that set the pace for the product and the org
- Build strong partnerships with Product and Engineering, establishing shared quality frameworks embedded in how the whole org ships
- Recruit and grow the team — develop existing leadership, maintain a high bar for AI fluency and design craft across every hire, and close capability gaps as the org evolves
How to be successful in this role
- 15+ years of design experience, with 5+ years leading and scaling large design organizations, with director-level reports
- Deep fluency in interaction design and visual craft — enjoys getting into the weeds, providing precise direction, and holding a high bar for quality across design decisions
- Deep B2B SaaS experience — understanding the constraints of building for SMB and enterprise customers, complex workflows, multi-user products, and platform-level design challenges
- Org-level AI fluency: has built AI tooling, workflows, and cultural adoption into a design team’s practice, enabling teams to ship more and move faster; has a clear point of view on how AI changes design roles and team structure
- Proven track record building quality systems: design system ownership, definitions of done, launch review processes, and quality frameworks built in partnership with Product and Engineering
- Has led design through a company inflection point — navigates ambiguity, adapts the org, and maintains quality and momentum when the business is changing fast
- Strong XFN leadership — trusted by product and engineering counterparts, navigates fast-moving and opinionated exec environments, and drives alignment on shared outcomes
- Must be authorized to work in the U.S. without the need for current or future employer sponsorship.
- Responsible for protecting the company and customer data in how your team operates and delivers results.
- Open to using AI to amplify their skills and strengthen their work - demonstrating curiosity, a willingness to learn, and sound judgment in applying AI responsibly to improve efficiency and impact.
What you can expect as a the company’n
- Industry-competitive salary and equity
- Comprehensive medical, dental, and vision coverage, with 100% of employee-only benefit premiums covered for most medical plans
- 16 weeks fully-paid Parental Leave for all new parents
- Health & wellness stipend
- Remote workspace, internet, and cellphone stipend
- Commuter benefits for team members who report to the SF and NYC office
- Family planning benefits
- Matching 401(k) contribution with immediate vesting
- Flexible PTO policy, plus 80 hours of Sick Time
- 11 company-paid holidays
- Virtual team building activities, lunch and learns, and other company-wide events!
- Offices in SF, NYC, London, Dublin, Tel Aviv, and Sydney
To provide greater transparency to candidates, we share base pay ranges for all US-based job postings regardless of state. We set standard base pay ranges for all roles based on function, level, and country location, benchmarked against similar-stage growth companies. Final offer amounts are determined by multiple factors and may vary based on candidate location, skills, depth of work experience, and relevant licenses/credentials.
#LI-remote
At the company, we are committed to hiring diverse talent of different backgrounds and as such, it is important to us to provide an inclusive work environment for all. We do not discriminate on the basis of race, gender identity, age, religion, sexual orientation, veteran or disability status, or any other protected class. As an equal opportunity employer, we encourage and welcome people of all backgrounds to apply.
About the company
We started in 2018, in the wake of several high-profile data breaches. Online security was only becoming more important, but we knew firsthand how hard it could be for fast-growing companies to invest the time and manpower it takes to build a solid security foundation. The company was inspired by a vision to restore trust in internet businesses by enabling companies to improve and prove their security. From our early days automating security monitoring for compliance standards like SOC 2, HIPAA and ISO 27001 to creating the world's leading Trust Management Platform, our vision remains unchanged.
Now more than ever, making security continuous—not just a point-in-time check— is essential. Thousands of companies rely on the company to build, maintain and demonstrate their trust— all in a way that's real-time and transparent.
Referral Instructions
If you are being referred for the role, please contact that person to apply on your behalf.
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