Y Combinator 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.
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.
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