• Shape overarching UX strategy and inform prioritization for high-impact, cross-cutting design initiatives
• Drive MVPs from concept through successful launch, ensuring design quality, cross-functional alignment, and readiness for validation and iteration to MLP
• Ensure modular design solutions and workflows connect across customer segments and internal teams
• Advocate for coherent, high-quality user experiences across distributed design efforts
• Partner closely with PM, Engineering, and Ops leadership to align design strategy and external partner requirements with roadmap and sequencing decisions
• Guide teams through early-stage, high-ambiguity initiatives, turning uncertainty into clear design strategy
• Coach and unblock design ICs, enabling them to audit workflows, anticipate systemic design challenges, and proactively align complex stakeholder groups
• Occasionally travel for in-person planning, research, validation, and business partner collaboration with Payors and benefits managers (~2x per quarter)

• Manage up to five direct reports, supporting growth goal definition, skill development, and performance management
• Foster a collaborative, growth-oriented design culture by mentoring designers, providing clarity on decisions, and encouraging autonomy while maintaining alignment
• Support learning and skill development through intentional work assignments and regular 1:1s, ensuring every designer has visibility into their growth and impact
• Ensure designers’ work aligns with broader strategic goals and maintains consistency across projects, teams, and systems

• Leadership & Strategic Expertise: Proven experience leading design teams, shaping strategy, and coordinating cross-functional design work
• Full Lifecycle Experience: Demonstrated contributions across the product lifecycle, with ability to balance strategy and execution at a high level
• Complex B2B Experience: Experience designing for complex B2B, regulated, or operationally dense industries (eg. healthcare, fintech, government, enterprise SaaS), with comfort navigating related ambiguity, constraints, and multi-actor workflows
• Collaboration Skills: Track record of working effectively with PMs, Engineers, Operations, and leadership stakeholders to align design decisions with business goals
• Adaptability: Comfortable operating in high-ambiguity, fast-moving environments, particularly in 0→1 or complex cross-cutting initiatives
• Systems Thinking: Experience tackling cross-functional design problems, auditing workflows, and aligning multiple stakeholder groups around complex problems
• Human-Centered Design: Portfolio demonstrating strong critical thinking, problem-solving in complex domains, and user-centered design principles
• Technical Proficiency: Proficient in design and collaboration tools (Figma, Notion, Miro) with an understanding of technical constraints and possibilities

• You lead with optimism and balance, turning ambiguity into solution-oriented design strategy while listening empathetically, communicating clearly, and building trust across teams
• You excel in cross-cutting design challenges, guiding 0→1 initiatives and foundational capabilities with a systems-level perspective
• You are data-informed, leveraging both qualitative and quantitative insights alongside user empathy to guide decisions
• You prioritize simplicity in structures, communications, and processes, keeping focus and alignment at the core of your leadership approach, even when project conditions are ambiguous
• You value distributed leadership, empowering ICs and peers to own outcomes while defining escalation paths and alignment points
• You are comfortable designing within an established, robust design system, leveraging shared components and patterns to move quickly while partnering with our design systems team to thoughtfully evolve the system over time.

• You aren’t seeking a highly structured work environment. Comfort with ambiguity is essential as Parachute scales and design work spans multiple initiatives
• You are not looking for a management-only role focused solely on administrative duties. This role combines management, strategic design leadership, and hands-on craft coaching to enable designer success
• You aren’t seeking a purely individual contributor role. You may still roll up your sleeves to drive high-quality execution, but this position requires balancing hands-on design guidance with team leadership and coaching
• You aren’t looking to focus exclusively on small, isolated feature work. This role requires a systems-level perspective across multiple initiatives
• This role may not be a fit for designers whose experience has been primarily in consumer-facing products with limited exposure to complex B2B solutions or regulated environments.

Benefits

• Medical, Dental, and Vision Coverage
• 401(k) Retirement Plan
• Remote-First Company with a NYC office, offering a physical workspace for our greater New York City area employees.
• Equity Incentive Plan
• Annual Company-Wide Bonus (up to 15%)
• Flexible Vacation Policy
• Summer Fridays - 5 Fridays Off During Summer (Separate From PTO)
• Monthly Internet Stipend
• Annual Home Office Stipend
• Co-Working Space Reimbursement
• Annual stipend for education and development

Base Salary (based on level and experience)

$170,000 - $210,000