Strategic Initiatives Principal

About Check

Payroll is broken. Come fix it alongside a team that’s as passionate as you are!

At Check, we’re not just building our own business — we’re building payroll businesses together with every one of our partners. As the inventors of embedded payroll, we’re redefining how people get paid and making it easier for payroll businesses to launch, grow, and thrive.

On our team you'll use creative problem-solving, critical thinking, and grit to simplify the complexity of payroll for thousands of employers of every size, across all industries. We ignore conventional role boundaries in favor of the unique strengths and values each builder brings to our mission: **make paying people simple. Check out our origin story!

Check is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses. See how it works for our partners.

About the Role

Check is hiring a Strategic Initiatives Principal to run at our most important, ambiguous problems and turn them into durable solutions.

This role is about getting to the heart of a problem quickly, cutting through noise and defining what actually matters. We’re looking for someone who approaches problems creatively, seeking out the simplest solutions and pulling on a variety of tools to get the job done: product changes, engineering fixes, operational processes, AI workflows and skills, or process design from scratch.

You’ll partner closely with our COO and work across the company on problems that don’t fit neatly into a single function: from how we plan and forecast our operational teams, to rethinking complex, operationally heavy workflows through an AI-first lens. Many of these problems have a technical edge — analyzing data, working with AI tools, and understanding the underlying data models and systems you’re operating on. Some problems will require building from first principles, others will require connecting dots across teams and systems that don’t yet speak clearly to each other.

The problems on our team don't come with playbooks. They come with real stakes, messy edges, and teams counting on you to figure it out. This is a role for a leader, but it’s also hands-on by design. You'll get to own things end-to-end: the strategy, the people management, and the work itself. You’ll be expected to operate with a high level of autonomy and willingness to get deep into the weeds to build real domain understanding. You’ll toggle between strategy and execution, helping the organization move faster, operate more simply, and adapt as priorities evolve. And as you solve each hard thing, new ones will emerge for you to take on. The scope here grows as you do, which means there's plenty of interesting territory ahead.

What you’ll do

• Get deep before you build — before proposing a path forward, you'll be expected to understand the mechanics of an issue from the ground up. That means working support tickets directly, solving tax notices, updating configurations, filing with agencies, and getting into the data until you know what's actually broken and why.
• Turn ambiguity into a plan — structure the problem clearly, quantify the impact, identify root causes, and build a sequenced action plan. You'll write the brief, run the analysis, and make a crisp recommendation — not just flag that something is hard.
• Own strategic programs end-to-end — from problem definition through execution and measurement, working across engineering, product, operations, and revenue teams. That includes standing up a monthly business review for your initiative: the right metrics, the right decisions surfaced, stakeholders aligned.
• Launch and lead new teams — define the mission, hire the first people, build the processes, and develop leaders so the team eventually runs without you. You're building something to last.
• Design how the work gets done — own workflow design and process engineering for your initiatives. Write the SOPs, build the playbooks, and create operating models that scale. You'll reach for AI-native solutions first — not as an add-on, but as the default starting point when you're designing how a team or process should work.
• Develop your people — set clear expectations, give real feedback, and build an environment where strong performers grow. You're accountable for the output of your team, not just your own.

What We're Looking For

• You've built something from nothing — stood up a new team, function, or program in a high-growth environment and made it self-sustaining
• You hold a high bar — for yourself, your team, and the work. You'd rather slow down and get it right than ship something half-baked
• You simplify — you can take a messy, ambiguous problem and distill it into a clear problem statement and action plan
• You're deeply curious — you ask "why" five times, you dig into the data, you talk to the people closest to the problem before forming an opinion
• You've actually shipped AI into team operations — not just talked about it. You’re familiar with modern AI tools (LLMs, agents, copilots) and deploying them.
• You're a strong people leader — you hire well, develop people, set clear expectations, and create environments where high performers thrive
• You're comfortable working across engineering, product, ops, and business teams without needing a formal mandate

Must have

• 2+ Years of management experience
• 7+ years of total experience in business operations, strategy, consulting, or a closely adjacent function
• Demonstrated experience scoping and launching net-new teams or programs (0→1)
• Comfortable working directly with data — SQL proficiency or equivalent analytical depth
• Experience deploying AI tools into operational workflows (not just familiarity)

Nice to have

• Experience in payroll, fintech, or infrastructure/platform businesses
• Background in management consulting, business operations, or program management

Travel & Office Policy

The Check team is distributed across the US. Roles can be remote, hybrid, or based in one of our offices in New York City or San Francisco. We offer ample opportunities and encourage employees to attend team offsites, events, and hackathons throughout year. All Checketeers gather in the spring for our annual 3-day company retreat.

For our in-office and hybrid employees, our offices are open all week. We provide meals on Tuesdays and Thursdays and there are regular happy hours, game nights, and other in-person events.

Remote work at Check requires the ability to perform all responsibilities without distraction or disruption, while maintaining quality, effective communication, and productivity.

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Check is proud to be an Equal Opportunity employer. We do not discriminate based on race, religion, color, national origin, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender, gender identity, gender expression, transgender status, sexual stereotypes, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. We also consider qualified applicants with criminal histories, provided they are consistent with applicable federal, state, and local laws. Check is committed to providing reasonable accommodations for candidates with disabilities in our recruiting process.

Check participates in E-Verify and will provide the federal government with Form I-9 information from all new employees to confirm that they are authorized to work in the U.S. Check does not use E-Verify to pre-screen applicants.