Strategic Finance Associate

Payroll is broken. It's still running on decades-old infrastructure. We're rebuilding it.

We don't run payroll ourselves — we power the businesses that do. As the inventors of embedded payroll, we're redefining how people get paid and making it easier for those 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 is far more than just API infrastructure. We’re a springboard for building and scaling payroll businesses.

The team and role

The Finance and Business Operations team helps Check turn insight into action. We combine curiosity, data, and operational context to develop a deep understanding of how the business works, get to the root of problems, and identify opportunities for improvement.

We pressure-test decisions, help drive change and measure outcomes so we can learn and iterate. We’re a lean and curious team who all practice deep ownership over our domains, but none of us exists in a narrow lane. We stretch across surface area to ensure the entire team provides the level of partnership and analysis needed to propel the business forward.

Check is looking to hire a Strategic Finance Associate. This person will support Check’s financial model and annual planning process, design analytical and financial frameworks to optimize decision-making and provide our leadership team, Board, and employees with insights about our performance.

The ideal candidate is highly analytical and strategic, and can seamlessly navigate between complex details and the big picture.

In this role, you will:

• Own Check’s financial model including both revenue and cost drivers
• Support annual and quarterly financial planning and target-setting processes
• Support decision-making across the org with ad-hoc analyses (e.g. new product pricing, cost optimization, capital allocation)
• Prepare Board presentations and update investors on company performance
• Support equity and debt fundraising processes
• Support deal negotiations with key vendors and partners
• Apply AI tools and agents to analysis and reporting as a core part of how you operate

Many backgrounds could fit this role, but ideal candidates will have some or all of the following:

• Strong financial modeling, analytical, and presentation skills
• Ability to distill complex issues into structured frameworks and action plans
• 3+ years of work experience including: 2+ years in investment banking or similar role
• Familiarity with AI tools/agents to accelerate workflows

Bonus points if you have:

• Experience in fintech, payments, or embedded/vertical SaaS
• SQL proficiency or equivalent analytical depth
• Prior experience in a Strategic Finance or Business Operations team
• Prior experience in high-growth technology startups