Strategic Fixer

About Clipboard

Our mission is to uplift as many communities as possible. We do this through our app-based marketplace that connects healthcare professionals with the workplaces that need amazing workers. This enables hundreds of thousands of people to achieve financial stability for themselves and their families while providing essential care to millions of people across the U.S.

Founded in 2016, we are a remote-first team of over 1,000 people building a top Y-Combinator company and have been profitable since 2022. We’re the leader in Long-Term Care staffing and are rapidly expanding into Home Health, Hospitals, and more, meaning we have more work to do than people to do it, and are growing our team to support millions more people and their communities.

The Role

Clipboard Health is a marketplace that connects healthcare facilities with professionals looking for shifts.

Our largest customers run complex operations, and when something isn't working, the problem rarely sits neatly within one team. A customer may be implementing a new product, dealing with a complicated integration, or facing an operational issue with no obvious owner or solution.

That's where you come in.

We're looking for a Strategic Fixer who can walk into ambiguous, high-stakes problems, quickly figure out what's actually happening, and drive the work required to fix them.

This role is particularly well suited to someone coming from a top-tier consulting environment who is ready to move from advising clients to owning outcomes. You should be comfortable taking an ambiguous problem, structuring it, getting into the details, aligning senior stakeholders, and driving execution across teams that don’t report to you.

This isn’t a role where you make a recommendation and hand it off. You own the problem until it’s solved.

You might spend one week diagnosing why a customer’s payroll integration is failing, the next coordinating an engineering fix, and the next working directly with a customer’s VP of Operations to get a complex implementation back on track.

The problems will vary. Your job is the same: figure it out, get the right people moving, and make the fix happen.

What you’ll do

• Own complex customer and product problems from diagnosis through resolution

• Work directly with enterprise customers and senior stakeholders, including VP and Director‑level leaders

• Structure ambiguous problems into clear hypotheses, workstreams, priorities, owners, and timelines

• Analyze data, customer feedback, and operational details to identify root causes and separate symptoms from the underlying problem

• Lead complex implementations, particularly involving time clock compliance, payroll, and integrations with systems like ADP and UKG

• Partner closely with Product and Engineering to investigate issues, define solutions, and drive execution

• Coordinate across Product, Engineering, Operations, and other teams to unblock work and keep critical initiatives moving

• Influence teams and stakeholders without direct authority

• Communicate clearly and directly when priorities shift, assumptions change, or things aren’t going according to plan

• Identify recurring customer problems and patterns, and turn those insights into improvements to our product and operations

• Travel to customer sites occasionally when being there in person will help move an important problem or implementation forward

What we’re looking for

• 2–6 years of experience at a top‑tier strategy or management consulting firm such as McKinsey, BCG, Bain, Deloitte, Strategy&, EY‑Parthenon, Oliver Wyman, LEK, Kearney, or a comparable firm

• Demonstrated experience solving ambiguous, complex problems for clients and senior stakeholders

• Strong structured problem‑solving skills. You can take a messy situation, develop a hypothesis, determine what information matters, and quickly get to the root cause

• Exceptional analytical skills and comfort working with data to make decisions

• Strong executive presence and communication skills. You can confidently work with stakeholders ranging from frontline operators to VP and C‑level leaders

• Strong stakeholder management skills and the ability to drive outcomes across teams without direct authority

• A high level of ownership. You don’t stop at the recommendation; you stay close to the problem until the desired outcome is achieved

• Highly organized and able to manage multiple workstreams, priorities, and stakeholders simultaneously

• Curious, resourceful, and persistent. You are comfortable getting into the weeds when that’s what it takes to solve the problem

• Willingness to challenge assumptions, ask uncomfortable questions, and push a problem forward when there isn’t an obvious path

The ideal candidate has spent the early part of their career learning how to solve hard problems in a demanding consulting environment and now wants to apply those skills with real ownership.

We’re especially interested in people who are excited to make the transition from advisor to operator: someone who can bring the rigor of consulting but is equally comfortable rolling up their sleeves and making the solution happen.

The Interview Process

At Clipboard, we don’t believe proxies are a reliable way to measure ability. We prefer to evaluate candidates by having them do work that closely resembles the actual job.

Our process is designed around that:

1. Preliminary Screen

2. Case Study

3. Case Study Interview

4. Hiring Manager Interview

5. Culture Interview

6. Reference Check

7. Offer!