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CheckCheckSan Francisco, CA

Strategic Initiatives Principal

Leads strategic initiatives by diagnosing ambiguous operational problems, designing AI-first solutions, launching teams, and driving end-to-end execution across functions. Requires 7+ years experience, 2+ years management, SQL proficiency, and hands-on AI deployment in operations.

169k – 226k
Remote7+ YOEBusiness Operations

About the role

Responsibilities

  • Get deep before you build: understand issues by working support tickets, solving tax notices, updating configurations, filing with agencies, and analyzing data.
  • Turn ambiguity into a plan: structure problems, quantify impact, identify root causes, and build sequenced action plans with crisp recommendations.
  • Own strategic programs end-to-end: from definition through execution and measurement, across engineering, product, operations, and revenue teams; stand up monthly business reviews.
  • Launch and lead new teams: define mission, hire first people, build processes, and develop leaders for self-sustaining teams.
  • Design workflows and processes: write SOPs, build playbooks, create scalable operating models with AI-native solutions as default.
  • Develop people: set expectations, give feedback, build environments for high performers.

Requirements

Must have:

  • 2+ years of management experience
  • 7+ years total in business operations, strategy, consulting, or adjacent
  • Demonstrated 0→1 experience scoping and launching new teams/programs
  • Comfortable with data: SQL proficiency or equivalent
  • Experience deploying AI tools (LLMs, agents, copilots) into operational workflows

Nice to have:

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

Compensation & Benefits

  • Expected salary: $205,000 - $225,500 (San Francisco, New York, Los Angeles, Seattle); $168,500 - $185,350 (other locations)
  • Medical, dental, vision, disability, life insurance
  • Stock options, flexible PTO/sick leave, 16 weeks parental leave, 401(k), $100/mo stipend for internet/phone

Skills

SQLAI ToolsLLMsAI AgentsCopilotsData AnalysisProcess EngineeringBusiness OperationsStrategyProgram Management
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