Director, Office of the CEO

The Traction

Revenue grew 5x over the past year, and Lily has driven over $200M in new annual sales for a single customer. We serve some of the largest operators in our industries, including SRS Distribution (part of The Home Depot family), United Rentals, and Henry Schein, and we work closely with the Google DeepMind and NVIDIA ecosystems.

How We Work

We work in small teams with real ownership: clear problems, direct access to the customers whose work you're changing, and room to ship. Your code runs in live production systems inside billion-dollar operations, so you see your impact directly. People who do well here want that proximity to the work. We're growing fast, and the people who join now shape what this company becomes. Everything runs on three principles: Customers, Culture, and Code.

The Role

This role exists to extend the COO's capacity across his priorities: customer engagements, PE and portco partnerships, deals that drive ARR, and the internal cadence that keeps everything moving. You'll work directly with Sumo on the priorities he's driving, translating strategic direction into executable plans and driving them to completion. You'll operate alongside him, in his absence, and in front of the stakeholders and teams he can't always be with.

You'll move across customer engagement, deal execution, internal execution, 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 across customers, PE partnerships, revenue, and internal execution. Drive them to completion across functions.
• Operating cadence ownership: Build and run the cadence that keeps Sumo in front of the right accounts and priorities with the right context at the right time. Turn what's currently ad-hoc into repeatable structure.
• Strategic thought partnership: Be a credible thought partner to Sumo on commercial priorities, customer strategy, and internal decisions. Bring patterns across accounts and teams into focus for leadership.
• Execution behind the scenes: Prep for deals, escalations, customer conversations, and internal decisions as if you were leading them. Own the follow-through end-to-end.

What You'll Need

• 6-10 years of operator, strategy, or founder experience: Chief of staff, consulting, PE, VC, startup founder, or senior operator backgrounds. Comfort with both internal ops and external commercial surfaces. Bonus if you've worked with or inside PE firms or portfolio companies.
• Executive presence: You hold your own with senior operators (internal leadership, customers, or PE) when the moment calls for it.
• Operator and commercial instinct: You read deals, customers, teams, 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: You can hold many threads at once and identify what matters across them.
• Detail-oriented: Sumo runs many accounts and priorities 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 office.

What You'll Get

• Real traction: The product works, customers are live, and Lily has driven over $200M in new annual sales for a single customer. 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, London, and Toronto. Sharp, low-ego team moving fast.
• Growth: The learning curve is steep.

Compensation and Benefits

• Salary Range: $160,000 - $200,000 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!

Quality Over Quantity

• To ensure a focused, high-quality hiring experience, we kindly ask candidates to limit their applications to 3 open requisitions at any given time.
• Applying strategically to roles that best align with your skills and career goals gives you the highest chance of standing out.
• Have you interviewed with us in the past 12 months?
• We encourage you to reach out directly to your previous interviewer rather than submitting a new application.

InstaLILY is committed to providing an inclusive and barrier-free recruitment process. If you require an accommodation, please let us know, and we will work with you to meet your needs.