S&O Senior Associate

Clipboard Health LLC; Northern (KY); Hybrid; USD 90,000 - 120,000; Full time

Job summary

Clipboard Health LLC is seeking a Strategy & Ops Senior Associate to join the Billing team. This generalist role offers exposure to a range of problems and opportunities, from predictive analytics to vendor onboarding and payment method redesign.

You’ll work on projects to maximize profitability, speed revenue recognition, and maintain customer experience, with a startup mindset and responsibility across initiatives.

Qualifications

• Insatiably curious and able to identify non-obvious clues and patterns.
• Willing to go to the source, test features, listen to customers, and validate ideas.
• Tenacious with problem-solving and able to persist through ambiguity.
• Bounce back quickly from mistakes and maintain momentum in feedback loops.

Responsibilities

• Build an internal predictive analytics model and underwriting process to inform contracting decisions.
• Research and onboard a vendor to embed AI agents in collections.
• Redesign payment methods to accelerate cash conversion with eCheck options.
• Manage a team of Billing Account Managers.

Skills

Curiosity

Source truth

Tenacity

Resilience

Job description

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.

About this Role

The Strategy & Ops Senior Associate role is an experienced generalist role at Clipboard suited for the “all-around athlete” type who can do it all and wants exposure to a range of problems and opportunities.

You’re likely someone who’s interested in and capable of solving different problem types – you’re resourceful, adaptable, and confident you can figure it out if you can sink your teeth in deep enough.

Your first “tour of duty” will be on the Billing team (see more below). The specific projects you take on will depend on your strengths and what we learn during the recruiting process and your first days at Clipboard; that being said, here is a list of example initiatives to give you an idea:

• Build an internal predictive analytics model and corresponding underwriting process to catch bad payers early with high accuracy to inform our contracting decisions and risk mitigation tactics

• Research, vet, and onboard a new vendor that embeds AI agents into our customer-facing collections efforts

• Redesign our process for converting workplaces to new methods of payment, such as getting customers who send checks to start paying us via eCheck to speed up the cash conversion process

• Manage a team of Billing Account Managers

First Tour of Duty – Quick background on Billing

Our most immediate need right now is on the Billing team. The TLDR is that we want to maximize our profitability by collecting money as fast as possible and minimizing losses, while preserving the customer experience, all in service of reliably converting revenue into cash (the lifeline of a capital-intensive business like ours). This in a way is “ensuring high-quality growth” for the company.

Although Clipboard provides a service where workplaces can find qualified professionals to fill shifts, we are in many ways a lending company at our core since we pay professionals immediately after they work a shift. For illustrative purposes: a nurse works a shift → we pay the nurse $100 immediately with our cash → the workplace pays us $120 a month later. We extend debt to workplaces using cash we borrow, with interest, from an Asset-Backed Line (ABL) of credit – workplaces use that debt to pay their staffing costs, and we expect to be paid back by the workplaces at a later date based on agreed-upon net terms.

Billing is doing the critical work of converting our revenue into cash that we put in the bank. Otherwise, money we cannot collect is money we’ve already burned. With thousands of customers operating in different regulatory environments, under different conditions, with nuanced capital structures and corporate setups, and using varied complicated processes…this can be hard to do at scale. We consistently fight a multi-faceted battle: a battle wherein we must maximize the speed at which we recognize revenue, maximize the margin associated with each shift, and maximize the customer experience, all without letting one unduly impact the other.

Optimizing collections is critical to make sure Clipboard is generating sustainable, high-quality growth and turning top-line revenue into cash that we use to service or grow other parts of the business, and you will help us do that.

Who we’re looking for

We find those who are most successful in this type of role:

• Are insatiably curious and notice non-obvious clues and patterns: Curiosity sits atop our company values. Understanding something from first principles and getting to the root cause of the problem will often reveal the best solution, and a natural and unwavering curiosity to keep asking questions and digging will take you most of the way.

• Roll up their sleeves and go to the source: There are multiple ways to say this: touching reality, dogfooding, seeing for yourself, going to the front-lines, etc. Don’t just take someone’s word for it – go find out yourself by testing the feature, or listening to the agent call, or calling the customer, or executing the workflow. This is how you seek truth.

• Bring a tenacity and persistence to problem-solving: You’ll hit walls and find yourself in uncertain and unfamiliar situations. If you can sit with the uncertainty, look at the problem from new angles, and keep applying pressure to a problem – you’ll position yourself for breakthroughs.

• Bounce back from failure quickly: You’ll make mistakes, move in the wrong direction, and stumble from time‑to‑time. Just avoid big mistakes and don’t make the same mistakes twice, and learn from them quickly. Worry less about failing and more about losing momentum in your feedback loop. If you fail cheaply and quickly, that's worth the lesson/learning you get in return.

While performance on your case and interviews during the hiring process is the most important aspect of your candidacy, your years of relevant working experience will be taken into consideration for both (a) the work you’re placed into once hired and (b) compensation.

Why Join Clipboard?

• 100% Remote – Always. Work from anywhere in the world.

• 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 workplace customers.

Hiring Process

1. Application

2. Case Study 1

3. Interview 1

4. Case Study 2 [OPTIONAL]

5. Interview 2 [OPTIONAL]

6. Interview with Head of Operations

7. Interview with Head of People

System Requirements

To succeed in this role, you must have:

• A reliable laptop/desktop (no Chromebooks or Linux OS).

• Minimum 20 Mbps wired internet connection.

• Wired headset for clear communication.

• A quiet, distraction-free workspace.

• Stable power and internet connectivity