Director of Strategy & Operations

The Work

• - Own the student-counselor matching process end-to-end — optimizing it for quality, speed, and scale while staying close enough to spot when individual cases go sideways - Build and iterate on logic-based workflows in HubSpot that reduce manual effort without losing the human judgment that makes matches work - Instrument the process so performance is visible, measurable, and continuously improvable
• Counselor Supply Engine> - Lead the recruitment, onboarding, and quality management of our global counselor network — while personally setting the standards that define what great looks like - Oversee high-volume hiring pipelines and hold the bar on who makes it in and who doesn't - Design the infrastructure that lets us scale supply without sacrificing quality — and audit it regularly to make sure it's holding
• - Lead the escalation team while staying close to the hardest customer situations yourself — you'll know when to delegate and when to step in - Build the SOPs, protocols, and feedback loops that turn reactive fixes into systemic improvements - Own the metrics — NPS, CSAT, refund rates — and drive structural changes when the numbers tell you something is broken
• Operational Systems & Infrastructure> - Own HubSpot end-to-end: architecture, workflow configuration, automations, data hygiene, and reporting - Identify what to automate, what to keep high-touch, and build the connective logic between both - Create documentation and operational infrastructure that scales beyond any single person — including you
• Cross-Functional & Strategic Work> - Partner with founders and leaders across Sales and Marketing on new service launches — owning the operational planning and execution, not just the advisory input - Bring structure to ambiguous problems and a bias toward implementation over deliberation - Be the person in the room who not only identifies what needs to change but leaves with ownership of making it happen

What We're Looking For

• 5–8 years of experience in strategy, operations, consulting, or a high-growth startup environment — with a track record of moving from diagnosis to execution
• You've built things, not just recommended them — processes, systems, and workflows that actually ran in production
• A natural player-coach: you develop and lead people without losing touch with the details that determine outcomes
• Hands-on CRM experience — HubSpot or comparable — you know what a well-architected workflow looks like and you can build it yourself
• Background in consulting, investment banking, or a strategy role at a fast-scaling company is a strong plus
• Marketplace or service operations experience is a strong plus — counselors, coaches, contractors, or service providers at scale
• The range to go from a founder-level strategy conversation in the morning to getting your hands dirty in a workflow builder in the afternoon
• Deep comfort with ambiguity and a bias toward action over deliberation
• Low ego. High standards. The kind of person who finds the broken thing before anyone else notices it.

Why This, Why Now

• Direct founder access and real decision-making authority from week one
• A business with genuine mission — the students we serve are getting into schools that change their lives
• The kind of operational complexity that sharpens you — and makes your next role easier to get and better to have
• Competitive compensation commensurate with experience
• Health, dental, and vision — base plans 100% employer paid | Flexible PTO | 401(k) with match