Strategic Initiatives Principal

About the role

Check is hiring a Strategic Initiatives Principal to tackle our most challenging, ambiguous problems and transform them into sustainable solutions. This role involves diving deep into issues, structuring them clearly, and developing actionable plans. You'll work closely with the COO and collaborate across various departments to address complex workflows through an AI-first lens.

What you’ll do

• Understand the mechanics of an issue from the ground up before proposing a path forward.
• Structure problems clearly, quantify impacts, identify root causes, and create sequenced action plans.
• Own strategic programs end-to-end, from problem definition to execution and measurement, involving multiple teams like engineering, product, operations, and revenue.
• Stand up monthly business reviews for your initiatives, ensuring the right metrics, decisions, and stakeholder alignment.
• Launch and lead new teams, defining missions, hiring, setting processes, and developing leaders.
• Design how work gets done, owning workflow design and process engineering, writing SOPs, building playbooks, and creating scalable operating models.
• Develop your team, setting clear expectations, giving feedback, and fostering an environment where high performers thrive.

What We're Looking For

• 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, including SQL proficiency or equivalent analytical depth
• Experience deploying AI tools into operational workflows (not just familiarity)
• Nice to have: background in management consulting, business operations, or program management; experience in payroll, fintech, or infrastructure/platform businesses; travel & office policy details