Chief of Staff

Hike Medical

About The Position

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 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

Requirements

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
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

Responsibilities

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
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