Director of Design at Propel

Propel builds technology that strengthens the social safety net in America, aiming to provide every American with the tools and resources needed to thrive. The company focuses on improving how government benefits are delivered, ensuring experiences like checking an EBT balance or choosing a D-SNP plan feel seamless and dignified.

Propel has grown significantly, serving over 5 million Americans and achieving a 35% YoY revenue increase. They are reinventing entire benefit categories, including Medicare, around the real needs of low-income Americans.

About the Role

Propel is seeking a Director of Design with strong taste who can tie design decisions to revenue, retention, and company priorities. This role involves defining what design means at an AI-native company and reporting to the Head of Product. The Director will be a core member of the EPD leadership team.

Key Responsibilities

• Lead a senior, autonomous design team of seven designers, including five at the Staff or Principal level, with backgrounds at companies like Figma, Facebook, Uber, and Duolingo. The team covers product design, content design, and design research. Responsibilities include team coaching, growth, performance management, hiring, and maintaining high standards for craft and judgment.

• Address and reduce design debt by defining its importance to users and the business, prioritizing fixes, and securing investment. This involves making trade-offs clear to product and engineering leads and finding ways to progress without solely relying on other teams' roadmap time.

• Improve product development processes by collaborating with product and engineering leadership to enhance organizational decision-making. The ideal candidate will challenge existing frameworks, systems, and roadmaps to make them more user-centric and modern, stepping outside the design lane when necessary for collective improvement.

• Redefine design as an AI-native function, addressing questions about design processes in an era of nearly free prototyping, the role of tools like Figma, and ensuring consistent design decisions with an increasing number of people shipping code. This requires a strong perspective on how leading consumer companies are deploying AI.

• Elevate Propel’s product experience to move key metrics. This includes focusing on visual design, copy, information architecture, consistency, and loading latency to ensure users understand their benefits and engage effectively.

Requirements

• Experience managing a product design team at a consumer software startup or a scaled pro-sumer startup.
• Has worked at the Staff or Principal IC product designer level in the last 3 years.
• Has managed a team of at least five designers, including hiring, performance management, and promotions.
• Fluency in consumer software patterns, including growth loops, churn and retention, behavior-based monetization, and A/B testing.
• A considered perspective on AI-native design practice, with evidence of active development through personal use of LLMs, code generation, and generative design tools.
• The ability to tie design work to company strategy in a high-priority, resource-constrained environment.
• Exceptional organizational skills and strong communication abilities, particularly in writing project plans and strategic concepts.
• Composure when priorities shift, as the roadmap and tooling are evolving rapidly.

Bonus Points

• The ability to perform design work independently when necessary.
• Experience with native Android and iOS apps.
• Work on a product used by millions of people.
• Experience with content design, user research, or brand and visual design.
• Experience with government programs or safety net services.
• Prior experience on a leadership team.

Why Join Propel?

• Propel addresses a generational challenge in the social safety net, where design plays a crucial role in simplifying complex rules for users.
• Inherit a highly autonomous, mission-motivated, senior-leaning team with extensive experience.
• Propel combines maturity with startup attitudes, operating profitably while continuously reinventing itself around AI and creativity.

This Role May Not Be For You If...

• You expect craft investment to be justified solely on its own merits, as Propel focuses on solving a challenging business problem with inventive revenue and product models.
• You prefer a settled operating model, as Propel is committed to reinventing itself, including design processes, as an AI-native organization.

Benefits and Compensation

• Meaningful work with a strong sense of mission.
• Remote-friendly work environment with a dog-friendly office in Downtown Brooklyn, including optional in-person retreats.
• 20 days of PTO.
• 4% 401K match.
• $10,000 lifetime spend towards Carrot Fertility.
• Excellent Medical, Dental, and Vision options.
• A strong equity package reflecting the role's level and anticipated impact.
• Expected cash compensation is $240,000 - $280,000, based on internal leveling.