Head of Customer Success

ABOUT US

Scalestack is the AI infrastructure for autonomous enterprise GTM. We built an AI-native platform trusted by companies like Harvey, Profound, and Astronomer. With presence in New York, Miami, London, and Buenos Aires, we are backed by strong investors including the Zapier Fund.

We build the infrastructure layer that makes enterprise AI agents actually work in production: reliable, data-rich, and deeply integrated into existing systems. The results speak for themselves: $19M in recovered pipeline for MongoDB, 2x CRM fidelity for Redis, and a 92% match rate powering Typeform at 250K+ form records/month.

ROLE DETAILS

Type: Full-time
Location: New York (Hybrid)
Level: Senior / Director
Reports to: CEO

THE ROLE

We are looking for a Head of Customer Success to build and lead the function that turns Scalestack from a platform into a long-term strategic partner for our enterprise customers. You will still own a small, strategic portfolio of important accounts, but the majority of your time will go into strategy, coaching, and raising the bar of the team.

You will define how we run Customer Success at Scalestack: playbooks, QBR standards, escalation protocols, renewal forecasting, and the commercial motion for retention and expansion. You will be the executive our enterprise customers reach for when they need to know someone senior at Scalestack is paying attention. And you will grow a team of CSMs who do not need to be told what to do.

WHAT YOU WILL WORK ON

LEADERSHIP & TEAM DEVELOPMENT

Lead, coach, and grow the Customer Success team, starting with a small team in New York and scaling from there
Set clear goals, define scorecards, and hold the team to a high bar without micromanaging
Run 1:1s, skip-levels, and performance reviews that actually develop people
Recruit and hire exceptional CSMs: raise the bar on every hire, never settle
Build a team culture that is ownership-driven, outcome-focused, and allergic to mediocrity

STRATEGY & OPERATIONS

Define and own the CS strategy: segmentation, coverage model, staffing ratios, and how CSMs scale with the business
Build the playbooks, QBR templates, onboarding frameworks, and standard customer communications that the team runs on. Documentation is not optional, it is how we scale
Forecast GRR and NRR with precision and own the operating cadence that surfaces risk early
Partner with Sales, Product, and Leadership to translate customer signals into pricing, packaging, and roadmap decisions
Instrument the function: health scores, usage metrics, renewal funnels, and dashboards that drive action

COMMERCIAL OWNERSHIP

Own GRR and NRR for the full customer base, with quarterly visibility and monthly review
Personally own the renewal and expansion strategy for top-tier accounts
Lead complex renewal and expansion negotiations when the deal requires executive weight
Maintain a small, strategic account portfolio (roughly 30 to 40 percent of a standard CSM load) to stay close to customers and to the work

ESCALATIONS & EXECUTIVE PRESENCE

Be the senior face of Scalestack for enterprise customers: run executive QBRs, handle escalations, and own difficult conversations with VP and C-level stakeholders
Step in when a customer is at risk and bring calm, structured thinking that turns the situation around
Build trusted-advisor relationships with economic buyers and executive sponsors across the portfolio
Represent Scalestack externally with the credibility our enterprise customers expect from a strategic partner

TECHNICAL FLUENCY

Operate fluently in our space: APIs, AI agents, LLMs, agentic workflows, enrichment and orchestration pipelines
Know the Scalestack platform deeply and stay close enough to the work that you can review team output with authority
Understand the modern data stack and adjacent AI tooling (Claude Code, MCP, agentic frameworks) well enough to hold your own in a technical room
Handle enterprise security and compliance conversations independently (data residency, PII handling, access controls)

WHAT WE ARE LOOKING FOR

REQUIRED

7+ years in Customer Success, Solutions, or Post-Sales at B2B SaaS or enterprise data companies, including 3+ years managing a CS team
Proven track record owning GRR and NRR at the portfolio or function level, with clear, quantifiable results
Executive presence and credibility with VP and C-level buyers: you run enterprise rooms without breaking stride
Strategic thinker who can zoom from a renewal spreadsheet to a three-year CS roadmap and back inside the same meeting
Coach, not commander: you develop people by raising the bar and giving them room, not by telling them what to do
Technical fluency with APIs, AI agents, LLMs, and modern data infrastructure. Not surface-level familiarity
High-ownership operator: you build the system, you do not wait for it
Absolute master of English language, written and spoken. Clear, direct, convincing and warm communicator
Comfort and experience working across the Americas

PREFERRED

Experience scaling a CS function from early stage through growth stage
Background in RevOps, data enrichment, or GTM tooling
Familiarity with Salesforce, HubSpot, and workflow platforms (Asana, Notion)
Prior experience in a founder-led, fast-moving startup environment

WHAT SUCCESS LOOKS LIKE

30 Days: Deeply understand the platform, the team, every active account, and our top 5 customers. Sit in on every major customer touchpoint. Identify the top 3 strategic gaps in the function.

60 Days: Publish the CS operating model: coverage ratios, QBR cadence, escalation protocol, renewal forecasting. Run your first executive-level escalation or QBR independently. Ship at least 2 reusable assets (playbooks, templates) the team is actively using.

90 Days: Lead the renewal motion for the quarter. Have a calibrated view on every CSM and a development plan for each.

6 Months: Hit GRR and NRR targets for the quarter. Hire at least one CSM against a clear bar. Run a full QBR cycle across the top accounts with zero slippage.

12 Months: Own a CS function the company trusts to deliver. GRR above industry benchmark, NRR above 115%. Team scaled with quality. CS is a reliable source of revenue and a strategic partner to Sales and Product.

OUR VALUES

Ownership & Commitment: We take full responsibility for our work, see it through, and hold ourselves accountable to the outcome.
Deliver Results: We focus on outcomes. We ship things that matter, on time and at the right quality.
Insist on the Highest Standards: We refuse to accept mediocrity. We raise the bar constantly and push each other to do the same.
Learn and Be Curious: We ask why, challenge assumptions, and treat every mistake as a chance to get better.
Collaboration: We win as a team. We share context freely and make decisions that are good for the whole.

INTERVIEW PROCESS

We move quickly and tell you where you stand at every step.

Screening call — 15 min. Mutual fit check.
Culture fit calls — 45 min each (2 calls, optional third if needed). Alignment on working style and values.
Skills and technical conversation — 45 min. Deep dive on your experience, past deals, and how you think.
Take-home or live exercise (optional) — 3–4 hours. A practical problem that reflects what you'd actually be doing here.
Decision

COMPENSATION & BENEFITS

Competitive salary and equity benchmarked to your experience and location
Flexible and unlimited PTO
Equipment reimbursement
Hybrid: in-office once a week in New York
Significant opportunity to build a function from the ground up and shape how Scalestack scales