Customer Success Lead (SMB, Tech Touch)

Join ContactMonkey as the SMB Customer Success Lead, where you'll own the Small & Medium Business book of business and drive retention and product adoption through a tech-touch engagement strategy. This individual contributor role focuses on automation, systems building, and direct customer management, with a primary metric of Gross Dollar Retention (GDR). You'll design and operate the tech-touch motion, lead churn diagnosis, and own customer communications at scale. This position offers a hybrid work environment, employee stock options, personal development budget, health and dental coverage, and extended vacation days.

• Design and operate a proactive, tech-touch engagement motion that drives retention and product adoption across a large portfolio of SMB accounts.
• Own customer retention (GDR) as your primary metric, and build the infrastructure that makes that number move.
• Lead churn diagnosis for the segment, maintain a data-backed, documented picture of why SMB accounts leave, and use those insights to continuously improve the playbook.
• This role is ideal for someone who has personally built and run a scaled CS motion before, someone who thinks in process & systems, acts on data, and understands how to keep a large, diverse book of business healthy without manual hand-holding on every account
• Experience in an early-stage, SMB-focused SaaS company where efficiency was a necessity, not a nice-to-have
• Directly owned a GDR or NDR number and can speak to how you moved it
• Comfortable being the primary point of contact for a portfolio of accounts, not just the system behind the scenes
• Background as a Customer Success Manager, with direct experience owning a book of business, including renewals, upsell conversations, and account escalations
• Personally built and executed a tech-touch or low-touch CS motion — not just supported someone else's
• You solve problems by automation and/or building systems, not by solving the same thing twice
• Comfortable with Salesforce, Pendo, Gong, or equivalent tools to instrument health, productivity, and risk
• Able to self-generate reporting and insights independently
• Have instrumented CS health and risk on a CS platform (Gainsight, Vitally, ChurnZero) or a homegrown stack (Salesforce + product analytics + automation)
• You don't just use AI tools, you build with them. You've shipped workflows or agents that do real work autonomously
• Sharp judgment on where automation earns trust and where a human still has to own the call
• You treat AI as infrastructure for the motion, not a productivity hack on the side
• Comfortable wiring AI into a stack: retrieval over a knowledge base (e.g. surfacing the right save play from a playbook library based on account signals), chaining steps, automating against APIs — not just prompting in a chat window
• You are a systems thinker who treats every manual task as a process waiting to be automated
• You enjoy the direct customer-facing side of CS as much as the systems side; you don't see relationship management and automation as a tradeoff
• You're comfortable owning a large book of business directly, building genuine relationships with customers even when the primary engagement model is tech-touch
• You understand the difference between SMB and Enterprise Customer Success — and you know why that matters
• You thrive in ambiguity and are energized by building something from the ground up
• You are data-driven and comfortable pulling your own analysis to inform decisions
• You are proactive by default — you engage customers before problems surface, not after