Note: this hiring process is being managed by Hike's current Chief of Staff who is being promoted into a new role.

About Hike Medical

Hike Medical is reinventing musculoskeletal care, starting with feet. Our proprietary AI-vision platform turns a 30 second web-based (no sensors) foot scan into precision engineered, 3D-printed insoles that prevent pain before it starts. We're already protecting on-their-feet workforces at Fortune 50 leaders, major health systems, and middle America manufacturers.

Fresh off a stealthy round with top tier VCs, we run a fast, no BS, execution-first culture out of Boston’s Seaport as we sprint toward $100M ARR and standing with 10M Americans as they step into their shoes daily.

• First and only PDAC-approved 3D printed custom insole in the world 🌎

• 3 proprietary AI models that power the experience

• Two products: one for employers & health plans, one for clinics — creating a virtuous cycle of clinician-labeled data

• Expanded care access to 100,000+ Americans to date

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

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

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

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)