Director, Office of the COO

The Role

This role exists to extend the COO's capacity across InstaLILY's most critical commercial surfaces: customers, PE and portfolio company partnerships, and the deals that drive ARR. You'll work directly with Sumo on customer engagements and operational priorities — translating his strategic direction into executable plans and driving them to completion. Sumo operates at the front line with customers, PE firms, and portco executives. You'll operate alongside him, in his absence, and in front of the stakeholders he can't always be in the room with.

You'll move across customer engagement, deal execution, commercial strategy, and operating cadence for the COO's office. The core stays constant: extending Sumo's capacity, operating with his full trust, and getting things done.

You'll report to the COO.

What You'll Do

• COO leverage: Take ownership of strategic and operational priorities tied to customers, PE partnerships, and revenue. Drive them to completion across functions.
• Customer and PE force multiplier: Step into PE and portco meetings, customer conversations, and escalations on Sumo's behalf. Prep for every meeting as if you're leading it.
• Commercial execution: Drive deals forward across stages. Translate ambiguous direction into structured plans and own them to close. Bring patterns across accounts into focus for leadership.
• Operating cadence ownership: Build and maintain the cadence that keeps Sumo in front of the right customers with the right context at the right time. Codify the structures where ad-hoc no longer scales.
• Strategic thought partnership: Be a credible thought partner to Sumo on commercial priorities and customer strategy.

What You'll Need

• 7–10 years of operator, strategy, or commercial experience: Strategy, consulting, chief of staff, BD, or operator roles. 
• Executive presence in customer rooms: You can be put in front of a Fortune 500 customer or PE operating partner and hold your own. 
• Commercial instinct: You read deals, customers, and rooms. You know when to escalate and when to handle it yourself.
• First principles thinking: You strip problems down and rebuild from the ground up.
• Pattern recognition across accounts: You can hold many threads at once and identify what matters across them.
• Detail-oriented: Sumo runs many accounts in parallel and moves fast. You can stay on top of all the details.
• AI-native: You use AI seriously and want to keep pushing what's possible.
• Comfort with ambiguity: You're handed open-ended, high-stakes problems and trusted to figure out the path forward. You're energized by that, not unsettled.
• Acceleration: You accelerate decisions and execution. You're outcome-oriented for yourself, for Sumo, and for the people and functions your work affects.
• Move fast, close loops: You finish what you start, flag problems early, and don't need to be asked twice.
• Clear communication: Your writing lands and you can hold the room. You translate complexity without losing what matters.
• In-person availability. 5 days/week in our New York or San Francisco office.

What You'll Get

• Real traction: The product works, customers are live, and we've already driven over $200M in incremental revenue for customers. This isn't a bet on an unproven thesis.
• Direct COO partnership: You'll work alongside Sumo on the strategic and operational priorities he's driving.
• Stage: Early enough to shape how the company scales.
• Hands-on from day one: You own outcomes.
• Culture: Offices in New York, San Francisco, and London. Sharp, low-ego team moving fast.
• Growth: The learning curve is steep.

Compensation and Benefits

• Salary Range: $160,000 – $180,000 per year, commensurate with experience
• Equity: Generous stock options awards and refreshers for top performers
• Benefits: Medical, Dental, Vision, 401K, Well-being stipend, In-office lunch reimbursement, PTO and 10 US Federal Holidays, and more!