Strategic Fixer

Department: Product

Location: Remote (Canada)

Compensation: $78K – $160K

Employment Type: FullTime

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.

Overview

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 wants exposure to a wide range of problems and is ready to own outcomes. You will take ambiguous problems, structure them, dig into the details, align senior stakeholders, and drive execution across teams that don’t report to you.

This isn’t a role where you make a recommendation and hand it off. One week you might be diagnosing a failing payroll integration, the next coordinating an engineering fix, and the next working with a customer’s VP of Operations to get an implementation back on track. The problems might vary, but your job stays the same: figure it out, get the right people moving, and own the problem until it’s solved. This role opens doors to a range of growth paths across Clipboard!

What youll do

• Analyze operational data to spot trends and bottlenecks, and turn your findings into clear recommendations that guide business decisions.

• Research and evaluate new tools, including AI, automation, and internal systems, and drive their adoption to make operations more effective.

• Design processes, workflows, and operating procedures that improve efficiency, quality, and customer experience

• Lead cross-functional projects and strategic initiatives from planning through execution, partnering with Operations, Product, Engineering, Customer Success, and other teams.

What were looking for

• 2–6 years of experience in a problem-solving role, such as strategy or management consulting, operations, strategy & operations, implementation, customer strategy, or program management.

• Experience solving operational problems by improving processes, designing workflows, or building scalable systems, while juggling multiple priorities in ambiguous, fast-moving environments.

• Strong analytical skills, with comfort using data (e.g., SQL, Python) to diagnose problems and support decisions.

• Clear written and verbal communication, with the ability to explain complex problems simply and align stakeholders across teams, from frontline operators to senior leaders.

• A high level of ownership. You don’t stop at the recommendation; you stay with the problem until it’s solved.

• A deep curiosity that drives you to reason from first principles and dig until you find the root cause.

• A habit of going to the source: testing the feature, listening to the agent call, calling the customer, or running the workflow.

Why Join Clipboard?

• We are remote-first, giving you the flexibility to work with us from many places.

• Fast-paced startup environment. Join a company that values curiosity, independence, and growth.

• A hiring process that rewards skills, not just experience. Every applicant gets a fair shot, our selection is based on real-world problem-solving ability, not just credentials.

• Opportunity to make a significant impact with our customers on both sides of the marketplace.

The Interview Process

At Clipboard, we dont 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. We are hiring for several teams through this one posting, so the process also helps us find the team where you’ll fit best. Here is how it works:

1. Application Review

2. Case Study

3. Case Study Interview

4. Hiring Manager Interview (s)

5. Offer!

Quick Note on Scammers:

Clipboard would never ask you for money or your bank details to participate in our hiring process. Report any scammers impersonating the Clipboard hiring team members here.