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Hike MedicalHike MedicalSan Francisco, CA

Chief of Staff to CEO

Serves as the CEO's force multiplier, leading high-priority cross-functional initiatives, strategic prioritization, and operational execution in a fast-growing AI-healthcare startup. Requires 5-10 years in high-growth tech/ops with extreme ownership and autonomy.

150k – 200k
On-site5+ YOEBusiness Operations

About the role

What You’ll Own

Strategic Prioritization & Focus

  • Partner directly with the CEO to identify and sequence the company’s highest-leverage initiatives
  • Continuously assess what matters most — and redirect attention when needed
  • Surface risks, bottlenecks, and emerging opportunities early
  • Ensure leadership conversations translate into clear execution plans
  • Protect company focus by driving ruthless prioritization

High-Priority Project Leadership

  • Independently lead mission-critical cross-functional initiatives
  • Drive alignment across Product, Engineering, Sales, Ops, and Clinical
  • Frame ambiguous problems into structured workstreams
  • Model trade-offs and make data-informed recommendations
  • Push projects to completion with speed and accountability

Operating in Ambiguity

  • Bring structure where none exists
  • Build lightweight systems that scale
  • Clarify decision rights and accountability
  • Operate effectively without full information
  • Make forward progress while details are still forming

Cross-Team Collaboration & Alignment

  • Act as connective tissue across departments
  • Identify misalignment before it becomes friction
  • Ensure handoffs are clean and execution velocity remains high
  • Facilitate high-quality decision-making across teams
  • Help leaders stay focused on outcomes over activity

Leadership Leverage

  • Prepare internal, board, and investor materials
  • Synthesize complex data into clear insights
  • Ensure the right conversations happen at the right time
  • Hold teams accountable to commitments
  • Increase the output and effectiveness of the CEO and leadership team

Customer & Market Immersion

  • Spend time in clinics, factories, hospitals, and warehouses
  • Stay deeply connected to customer pain points
  • Translate frontline insights into strategic initiatives
  • Support high-stakes partnerships and enterprise relationships

What We’re Looking For

Core Experience

  • 5–10 years in high-growth tech, venture, consulting, banking, product, operations, or similar high-performance environments
  • Experience leading complex, cross-functional initiatives
  • Proven ability to operate in ambiguous environments
  • Demonstrated success working with little direction and high autonomy
  • Experience supporting senior leadership or founders is a plus
  • Healthcare, hardware/software, or AI exposure is a plus

Strengths

  • Elite prioritization skills
  • Structured thinker who can decompose messy problems quickly
  • High agency and extreme ownership mentality
  • Calm under pressure
  • Exceptional communicator (written and verbal)
  • Able to zoom from 30,000-foot strategy to tactical execution seamlessly
  • Strong cross-functional collaborator
  • Biased toward action

Nice-to-Haves

  • Experience at a venture-backed, high-growth startup
  • Exposure to product development cycles
  • Financial modeling or analytical background
  • Experience working directly with executives or boards

Primary Responsibilities

  • Serve as CEO’s right hand across strategic and operational initiatives
  • Identify and prioritize the most pressing company issues
  • Lead high-impact cross-functional projects from start to finish
  • Bring clarity and structure to ambiguous initiatives
  • Ensure leadership focus remains on highest-leverage opportunities
  • Drive accountability across teams
  • Strengthen cross-team communication and collaboration
  • Increase organizational velocity and execution quality

What You’ll Get

  • Competitive cash compensation + meaningful equity
  • Full medical, dental, and vision coverage
  • Relocation bonus (if needed)
  • Direct partnership with founders and leadership
  • Exposure to Fortune 50 executives, investors, and healthcare leaders
  • A front-row seat — and steering wheel — to scaling a category-creating company
  • Free custom insoles (of course)

Skills

Cross-Functional Project LeadershipStrategic PrioritizationFinancial ModelingAnalytical SkillsProduct DevelopmentAi ExposureHardware/Software ExperienceBoard Materials PreparationInvestor RelationsExecutive Communication
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