Description

As a Strategic Initiatives Lead at Check, you'll tackle the company's most ambiguous and high-stakes problems, turning them into durable solutions. You'll partner with the COO and work across teams to drive strategic programs, leveraging product changes, AI workflows, and process design to redefine how payroll businesses operate.

Requirements

• Proven experience building a new team, function, or program from scratch in a high-growth environment
• Holds a high bar for quality and prefers getting it right over fast delivery
• Able to simplify messy, ambiguous problems and drive crisp recommendations
• Hands-on and willing to go deep into operational and technical details
• Strong analytical skills and comfort with data, AI tools, and system models

Responsibilities

• Understand problems from ground up by working support tickets, solving tax notices, and analyzing data
• Turn ambiguity into a structured plan with clear impact quantification and action sequence
• Own strategic programs end-to-end: problem definition, execution, measurement, monthly business reviews
• Launch and lead new teams: define mission, hire, build processes, develop leaders
• Design scalable workflows with AI-native solutions as default