Strategic Initiatives Lead

About the Role

Check is hiring a Strategic Initiatives Lead 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

What we offer:

For full-time employees, Check offers company-sponsored medical, dental, vision, short-term/long-term disability, and basic life insurance coverage, effective on their first day of work. We also offer stock options, flexible PTO and sick leave, up to16 weeks of fully paid parental leave for all new parents, flexible return-to-work arrangements, 9 annual holidays, a 401(k) retirement plan, and a $100 monthly stipend for home internet and mobile phone expenses.

The actual annual salary for this role depends on each candidate's experience, qualifications, and location of work. Most new hires are placed near the midpoint of this range to ensure fairness with our existing team's compensation.

• The expected range in San Francisco, New York, Los Angeles, and Seattle is between $205,000 - $235,000.
• The expected range for all other locations is between $174,500 - $200,000.

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