Real Estate Technology, Artificial Intelligence, SaaS

VP, Customer Success

New York, NYOnsiteFull Time$200,000–$250,000 /yrPosted 1 month ago

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Required skills

Customer Success
Enterprise SaaS
Retention
Expansion
ARR
Strategic Partners
Growth Analysts
AI
Playbook building
Executive Relationships

Nice to have

Industrial Distribution
Manufacturing
Automotive
Healthcare
Pilot
POC

Role summary

InstaLILY is seeking a VP of Customer Success to lead their customer SWAT team and manage Strategic Partners and Growth Analysts. This role focuses on driving retention and expansion outcomes, owning executive-level customer relationships, and anticipating future customer success needs. The ideal candidate will have 10+ years of experience in enterprise SaaS Customer Success leadership, a proven track record of moving retention and expansion metrics at scale, and a strategic, commercial mindset. Experience building retention and expansion motions is crucial. The role requires hands-on engagement, comfort with ambiguity, and a forward-thinking approach to AI's impact on Customer Success. Industry experience is a plus, with a willingness to deeply understand customer operations. This is a full-time, onsite position in New York City.

About InstaLILY

InstaLILY is an AI products and infrastructure company that puts execution at the frontier of enterprise AI. That work begins with Lily™, the world's first AI Forward Deployed Engineer, which learns how a business works, builds the software it needs, and goes live in days. It does not leave when the work ships; it stays and keeps the software working as the business changes. Lily runs wherever the work happens, in the cloud, on-premise, or at the edge, through InstaLILY's Small Data Center, built with NVIDIA technology. Founded in 2023 by Amit Shah and Sumantro Das, InstaLILY has raised nearly $100 million from Energize Capital, Insight Partners, and Home Depot Ventures. Headquartered in New York, with offices in San Francisco, London, and Toronto, InstaLILY serves leading companies across construction, industrial distribution, logistics, healthcare, and other operationally intensive industries. Learn more at https://instalily.ai/.

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

You'll be our VP of Customer Success, extending the reach of our Chief Growth Officer as the senior InstaLILY presence across our largest customer relationships. You'll lead our customer SWAT team — the function that gets customers stood up, keeps them successful on the platform, and steps in wherever needed: pilot workshops, post-POC escalations, complex account decisions. You also lead a team of Strategic Partners who own the day-to-day customer relationships across their portfolios, and senior Growth Analysts who lead pilot-to-production delivery alongside junior analysts.

The role is highly adaptable and evolving. It will change over time and won't strictly stay within these responsibilities. You'll bring your playbook and optimize ours — you're not starting from zero, but you're not stepping into a defined machine either. Expect the unexpected.

You'll report to our Chief Growth Officer.

What You'll Do

Personally show up on customer calls. You hold the executive-level relationships across our accounts, and step in whether that's a pilot workshop, a post-POC escalation, or a complex account decision.

Own retention and expansion outcomes. Retention and expansion are the metrics that matter most; you drive them through how you run the customer relationships and the operating rhythm.

Think ahead of the product. You anticipate what CS looks like 6 to 12 months out and prepare the team for it.

Pattern recognition, judgment, and an anticipatory mindset. You read where accounts are going before the numbers confirm it, and you act on it rather than wait.

Coach the team. You develop the team's judgment through feedback on their accounts, coaching in customer conversations, and modeling the standard yourself.

Lead your Strategic Partners and Growth Analysts. Hire, coach, and grow the team that owns customer engagement day-to-day and pilot-to-production delivery.

What You'll Need

10+ years in Customer Success leadership at enterprise SaaS.

Ongoing, multi-year enterprise contracts. You've owned relationships where success is measured over years and renewals, not one-time sales.

You've moved the numbers at scale. You can point to specific gross retention, net retention, and expansion ARR you've moved across a portfolio of enterprise accounts, not just individual account wins.

Strategic and commercial. You see 2-3 moves ahead on where an account is going and know how to shape a conversation into an expansion opportunity when the timing is right.

Bring your playbook. You've built the retention and expansion motion at least once before. You can bring it, optimize what we already have, and take it further.

Pattern recognition, judgment, and mindset. You've caught things others missed on accounts, and you can help newer team members develop that same instinct.

Hands-on with the work. You're in a C-suite QBR and in the weeds of an account plan the same week.

Tested through friction. You've held accounts through rocky implementations, executive turnover, and pricing pushback. Delivering outcomes matters more than keeping every conversation comfortable.

Concise and structured. You think in structure and hold a clear point of view under pushback.

AI-native, and thinking ahead of the product. You use AI seriously in your own work and have a view on where AI reshapes CS itself over the next 12 to 24 months.

Comfort with ambiguity. You build the playbook as you go, and the role will evolve as we scale.

Industry curiosity. You'll work with customers in industrial distribution, manufacturing, automotive, healthcare, and similar verticals. Industry experience is a plus; a willingness to deeply understand a customer's operations matters more.

In-office availability. 5 days/week in our New York 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.

Deep partnerships. Backed by Insight Partners with deep ecosystem partnerships across Google, NVIDIA, and Microsoft.

Customer impact. You'll drive measurable operational change inside the customers you own.

Stage. Early enough to shape how InstaLILY runs customer relationships and expansion at scale.

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: $200,000–$250,000 base, commensurate with experience, plus variable compensation.

Equity. Generous stock option 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.

We use AI to assist with parts of our application review process. If you’d like to opt out, please contact our recruiting team (lily.hiring@instalily.ai).

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