Customer Success Operations Engineer

About the Role

We're looking for a Customer Success Operations Specialist to build and run the operating engine behind our Customer Success organization — and to make AI tools and AI-driven workflows the core building block of how that engine works, not an add-on to it. This isn't a traditional "reporting and process" ops role. You'll be expected to design CS workflows around AI from the ground up: using AI to synthesize customer signals, draft and route communications, automate health scoring and QBR prep, and surface insights that used to take a CSM hours to find. You'll partner closely with CS leadership to identify where AI can replace manual, repetitive work and where it should augment human judgment — then build, test, and own those workflows end to end. This is a great fit for someone who's naturally curious about AI tooling (LLM-based assistants, automation platforms, AI features inside CRM/CS platforms), comfortable prototyping quickly, and excited to shape how a growing CS org operates in an AI-first way.

Responsibilities

• AI-Driven Operations (Core Focus)
  • Design and own AI-powered workflows across the customer lifecycle — onboarding, health scoring, renewal risk detection, QBR prep, and escalation triage
  • Evaluate, pilot, and implement AI tools (e.g., AI features within Gainsight/Salesforce, LLM-based assistants, automation platforms like Zapier/Workato) to reduce manual work for CSMs
  • Build AI-assisted reporting and insight generation — using AI to summarize account activity, flag churn risk, and generate customer-facing or internal-facing drafts (renewal emails, QBR decks, health summaries)
  • Create and maintain prompt libraries, playbooks, and guardrails so AI tools are used consistently, accurately, and safely across the team
  • Continuously test new AI capabilities against real CS use cases and make recommendations on what to scale, adjust, or retire
• Systems, Process & Reporting
  • Own and maintain the Customer Success tech stack (CRM, CS platform, automation/AI tools), including configuration, data hygiene, and integrations
  • Build and maintain dashboards that track health scores, renewals, churn/retention, NPS/CSAT, and the performance of AI-assisted workflows themselves
  • Design, document, and continuously improve CS workflows and playbooks with AI as the default first step, not a bolt-on
  • Partner with CS leadership to define and track key metrics (NRR, GRR, churn, time-to-value, AI-driven efficiency gains)
  • Support CS forecasting, capacity planning, and account segmentation as the customer base grows
• Cross-Functional & Enablement
  • Act as the liaison between Customer Success, Sales, Product, and Data/IT on tooling, integrations, and AI adoption
  • Train and enable CSMs on new AI tools and workflows, and gather feedback to iterate quickly
  • Maintain data integrity across systems, since clean data is the foundation every AI workflow depends on

Requirements

• 2–5 years of experience in Operations, Business Operations, Revenue Operations, Sales Operations, or Customer Success Operations (SaaS/tech environment preferred)
• Genuine hands-on experience using AI tools in a work context — e.g., building workflows with LLM-based assistants, using AI features inside a CRM/CS platform, or automating tasks with AI-enabled platforms (Zapier, Workato, Make, etc.)
• Comfort experimenting with new AI tools quickly, evaluating what works, and turning a rough idea into a repeatable workflow
• Hands-on experience with a CRM (Salesforce or HubSpot) and, ideally, a Customer Success platform (Gainsight, Totango, ChurnZero, Vitally, or similar)
• Strong analytical skills — comfortable building reports/dashboards and translating data into clear recommendations
• Advanced Excel/Google Sheets skills; SQL experience is a plus
• A process-improvement mindset — you naturally look for ways to make things faster, cleaner, and more scalable, with AI as your default lever
• Strong project management skills and the ability to juggle multiple workstreams independently
• Excellent written and verbal communication skills; comfortable working cross-functionally with Sales, Product, Data/IT, and CS leadership
• A high level of ownership, curiosity, and attention to detail

Nice to Have

• Experience building or configuring AI agents, custom GPTs, or automation flows for a business function
• Familiarity with prompt engineering basics and AI governance/guardrails in a business setting
• Experience with BI/visualization tools (Tableau, Looker, Power BI)
• Familiarity with customer health scoring models and renewal/forecasting methodologies
• Experience supporting a Customer Success org through a period of growth or scaling

Pay

Base Salary Range: $128,000—$134,000 USD

Benefits

• 95% premium coverage for employee medical insurance, and 77% premium coverage for dependents
• Health Savings Account (HSA) with employer contribution
• Dental, Vision, Short/Long term Disability, Basic Life, Voluntary Life, and AD&D insurance plans
• Flexible Spending Account (FSA) options: Health Care, Limited Purpose, and Dependent Care
• Well-being benefits including:
  • Full subscription to Headspace
  • Gympass+ membership with access to physical gyms
  • One Medical membership
  • Counseling services with an Employee Assistance Program