Customer Success Manager - Freelance, Remote

About the Client Our client is a fast-growing SaaS company building an AI-powered operating and decisioning platform for regulated industries, with 40-50 client accounts and growing. Their platform automates complex operational workflows — from client onboarding to document processing and data intake — for enterprise and mid-market customers who depend on high-touch, reliable support. As a boutique, high-growth team, the founder currently manages Customer Success personally and needs a dedicated professional to take primary ownership of the client relationship function. Why does this role exist? As the client base has grown to 40-50 accounts, one person can no longer give every client the proactive attention needed to drive renewals, adoption, and growth — the founder needs a dedicated Customer Success partner to take that responsibility off his plate immediately. This role exists to build real, lasting relationships with enterprise clients: tracking usage, running recurring syncs, managing renewals, and spotting expansion opportunities before they're missed. This is not a support or ticket-response role — it requires someone who proactively drives the relationship forward rather than reactively waiting for clients to raise issues. The Impact you’ll make Client Relationship Management Own day-to-day relationships across a portfolio of 40-50 enterprise and mid-market accounts. Conduct regular client check-ins and proactively monitor product usage and adoption. Follow up with clients consistently to keep engagement and momentum high. Renewals & Account Health Track renewal timelines and manage the renewal process across all assigned accounts. Monitor usage trends to flag at-risk accounts before they become churn risks. Maintain accurate, up-to-date account records and health tracking spreadsheets. Recurring Client Syncs Set up and independently run recurring client syncs and check-in calls. Prepare talking points and follow-up actions for each client conversation. Ensure meeting notes and next steps are documented and tracked to completion. Growth & Expansion Identify upsell and expansion opportunities within the existing client base. Partner with leadership to develop and pitch account growth strategies. Track and report on expansion pipeline across the portfolio. Reporting & Organization Create and maintain spreadsheets covering account status, usage, renewals, and outreach cadence. Provide regular status updates to leadership on portfolio health and key account risks or wins. Skills, Knowledge and Expertise Required: Strong English communication skills, both spoken and written — this is critical given direct enterprise client interaction Background in SaaS or software companies, with the ability to understand the platform, client use cases, and technical context Prior experience specifically in Customer Success (relationship management, renewals, adoption, growth) — not Customer Support (ticket resolution, reactive troubleshooting) Proficiency with spreadsheets (Google Sheets/Excel) for tracking accounts, usage, and renewals Comfort managing relationships across enterprise accounts independently Your superpowers are... Technical: Familiarity with HubSpot or similar CRM tools on the Customer Success side Spreadsheet fluency for building and maintaining tracking systems Comfort working across Google Workspace, Slack, and Microsoft Teams Ability to quickly learn a SaaS product deeply enough to speak to it confidently with clients Soft Skills: Proactive, articulate communicator — doesn't wait to be asked, initiates outreach and follow-up Confident enough to independently lead client calls without founder involvement Relationship-builder with a growth mindset — naturally spots opportunities to expand accounts Highly organized, able to juggle 40-50 accounts without letting details slip WFH Set-Up: Computer with at least 8GB RAM, an Intel i5 core processor/AMD Ryzen 5 Processor and up. Internet speed of at least 40MBPS Headset with an extended mic that has noise cancellation and a webcam Back-up computer and internet connection Quiet, dedicated workspace at home You should apply if... You think of yourself as a relationship-builder, not a ticket-closer — you get energy from proactively checking in on clients rather than waiting for them to reach out with a problem. You're comfortable being the primary point of contact for enterprise clients and can run a client call with confidence, without needing someone else in the room. You're naturally organized and love building systems (trackers, cadences, follow-up routines) that keep dozens of relationships running smoothly. You see renewals and upsells not as sales tasks, but as a natural outcome of doing right by the client consistently over time. What to expect... Work Setup: Remote position Must have a reliable internet connection and a quiet workspace Required to provide own computer with Intel Core i5 or something similar or higher operating system Working Hours: 40 hours per week M-F from 9 am to 5 pm Eastern Time Compensation: $7 per hour No benefits package included Benefits