Job Description
LeanData helps the world’s fastest-growing companies automate, simplify, and accelerate revenue. Trusted by over 1,000 customers including OpenAI, Snowflake, Shopify, Siemens, and Palo Alto Networks. LeanData sits at the center of the modern revenue stack.
We are building a next-generation Customer Success organization — one where AI does the monitoring, pattern detection, and routine outreach, so our people can focus entirely on outcomes and relationships. The Digital CSM role is the leading edge of that model.
As a Digital CSM, you will own a portfolio of 250–300 smaller commercial accounts and will be the architect and operator of a scaled, AI-augmented coverage model. This is not a traditional CSM role. You won't be meeting and defining outcomes, driving adoption and engagement, educating on the product, solving issues or advising - the agents will. AI agents handle health scoring, risk detection, opportunity identification, and call prep (as needed). You handle the moments that machines can't: re-engaging at-risk customers, spotting expansion opportunities, and translating LeanData's value into language that sticks and inspiring customers to do more with LeanData.
This role is ideal for someone who is energized by scale, comfortable building and operating AI tools, and motivated by the challenge of building something new — not inheriting a playbook.
Open to remote
■ What You'll Own
Portfolio Health & Retention
Own retention outcomes across a 250–300 account digital portfolio, with AI agents as your first line of monitoring and customer engagement
Triage AI-surfaced risk signals and determine when human engagement is required vs. when an automated playbook is sufficient
Intervene on churn risk, silent accounts , and adoption drop signals before they become losses
Partner with Account Management on expansions
Adoption & Value Delivery
Automate the guidance given to customers to get them towards deep adoption of LeanData's core workflows — routing, matching, and orchestration — as the primary retention lever
Use AI-generated summaries and in-product benchmarks to help customers see their value without requiring a live EBR
Identify customers who have plateaued in adoption and design targeted re-engagement sequences
Expansion & Growth Signals
Monitor AI-ranked expansion signals and convert top opportunities through self-serve or light-touch engagement
Surface multi-threading opportunities in single-stakeholder accounts and introduce LeanData to additional personas
Partner with AEs on accounts showing expansion readiness above a defined ARR threshold
Digital Program Design
Contribute to the design and iteration of automated touchpoint sequences, playbooks, and nurture programs for the digital tier
Identify gaps where AI coverage is insufficient and flag for human escalation or program improvement
Experiment with in-product messaging, video outreach, and community-led engagement as low-cost, high-scale channels
■ What We're Looking For
Required
1-3 years of Consulting, Customer Success, Account Management, or related experience in B2B SaaS
Analytical mindset: able to interpret health score trends, usage data, and risk signals to prioritize action
Comfort operating with AI tools, automation platforms, and data-driven workflows; enhance and build new agents that are needed
Strong understanding of RevOps, Marketing Ops, and GTM Ops, key workflows, and empathy for the challenges faced by the people running these operations
Strong written communication: you'll do more via email, video, and async channels than on live calls
Experience with running a book of business in a data driven manner through a CS platform
What Sets You Apart
Demonstrated ability to manage a high-volume account book (100s of accounts) with strong retention outcomes
You've worked in a scaled or digital CS model before and know the difference between coverage and connection and when to apply the appropriate touch
You're excited about AI as a force multiplier and have used AI to build things to make yourself more efficient and or to improve the customer experience
You think in portfolios, not individual accounts — you make triage decisions, not just relationship decisions
You have a bias for building: you'll improve playbooks, flag gaps, and contribute to a model that doesn't fully exist yet
Salesforce proficiency
Why work at LeanData:
LeanData covers employee insurance premiums up to 90%
Stock options in LeanData for all full-time employees
Flexible PTO
401K plan