Chief of Staff to CEO

Chief Of Staff Opportunity At Hike Medical

Hike Medical is building the defining company in musculoskeletal care. We sit at the intersection of AI, robotics, and healthcare, operating across three product lines: a proprietary AI-vision platform that turns a 30 second web-based foot scan into custom 3D-printed orthotics, an AI agent platform that automates the entire DME workflow from pre-visit processing to claims and revenue cycle, and SoleForge, our vertically integrated 3D printing factory producing custom medical devices at a scale the industry has never seen.

Our customers are both the largest employers on earth and the biggest companies in orthotics and prosthetics. On the clinical side, we're live across the industry's largest national providers. On the employer side, Fortune 50 companies trust us to protect their on-their-feet workforces.

But custom insoles are just the wedge. Our long-term vision is bionics: AI-designed, robotically manufactured orthotic and prosthetic devices at scale, replacing a fragmented, manual industry that hasn't changed in decades. Insoles today, full DME tomorrow, bionics by 2040.

We've stealthily raised $22M through Seed and Series A backed by top-tier investors who invested early in companies like OpenAI, Anduril, and Mercury. We run a fast, results first, high ownership culture out of our new SF Rincon Hill office. If you want to work on problems that sit at the frontier of AI, manufacturing, and healthcare, this is the place.

The Opportunity

We're hiring a Chief of Staff to serve as the CEO's force multiplier and operational backbone of the company.

This is not a coordination role. This is a high-autonomy, high-accountability leadership role designed for someone who thrives in ambiguity, prioritizes ruthlessly, and drives the most important initiatives across the company to completion.

You will operate at the center of Hike helping leadership focus on what matters most, identifying the highest-leverage problems before they become bottlenecks, and leading cross-functional efforts that unlock our next stage of growth.

This role sits at the intersection of strategy, execution, product, operations, and leadership alignment.

You will ensure:

• The most pressing company priorities are clearly defined and aggressively executed
• Leadership attention is directed at the highest-leverage issues
• Critical cross-team initiatives move forward without dropped balls
• Ambiguity turns into action plans
• Teams stay focused on what truly matters

This role is ideal for someone who:

• Can prioritize under uncertainty without waiting for direction
• Thrives in ambiguous, fast-moving environments
• Works with little instruction and high autonomy
• Leads high-priority, cross-functional initiatives end-to-end
• Identifies the most pressing issues and escalates appropriately
• Brings clarity, structure, and momentum to complex problems
• Operates with extreme ownership

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

We care more about ownership, clarity of thought, and execution velocity than perfect credentials.

Core Experience

• 510 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)