Head of Client Success

Head of Client Success
Remote | Full-Time | $3,000–$5,000+/month USD | Mexico · Colombia · Canada

Overview
At Lupa, we're hiring for a Head of Client Success for a confidential AI-native Loan Origination System (LOS) backed by top-tier Series A investors, with over $25M raised, headquartered in New York City. Our client partners with US finance companies, credit unions, and banks to transform their lending operations through intelligent automation.
This is a build-the-machine role, not a white-glove role. You'll own the full client relationship from post-sales handoff through every phase of the partnership — implementation, go-live, support, and expansion. You'll lead a team of Account Managers and a growing Support function, and your success will be measured by net revenue retention, gross revenue retention, expansion revenue, and the per-client efficiency of the CS function as the company scales toward serving 10x its current portfolio.

What You'll Do
Client Relationship & Commercial Ownership

Own the enterprise client relationship from post-sales handoff through implementation, go-live, support, and expansion
Run structured kickoff and intake conversations that diagnose real hiring problems and set realistic expectations
Proactively identify expansion and upsell opportunities across all service lines
Map key stakeholders at every account; build relationships at multiple levels
Drive reactivation strategies for dormant accounts
Track account health proactively — catch deteriorating relationships before the client goes quiet
Negotiate contract renewals and expansion agreements; partner with Legal on complex deals

Team Leadership & Function Building

Build and lead a team of Account Managers responsible for individual client relationships, commercial ownership, and renewals
Build and scale the Support function — design tiered service models, escalation paths, and AI-native tooling
Codify playbooks, engagement models, and best practices that let the function scale from N clients to 10N without 10x headcount
Scale the team — own recruiting, onboarding, coaching, and organizational strategy for Client Success

Voice of the Customer

Gather and synthesize customer feedback into structured product themes
Serve as the voice of the customer back into Engineering and Product
Partner with Services through implementation; at go-live, CS picks up the drive and Services becomes the technical escalation path

Reporting & Operations

Own commercial outcomes: NRR, GRR, expansion revenue, renewal rates
Maintain clean CRM records of client interactions and strategic intelligence
Use AI tools as a genuine operational advantage

Who You Are
Must-haves

6+ years in enterprise Client Success, Account Management, or related commercial roles; 2+ years managing teams
Fluent English — required to work effectively with US clients
Proven commercial track record: personally owned NRR/GRR targets, closed expansion deals, navigated renewal negotiations with enterprise customers
Strong client leadership: managed senior executive relationships, navigated high-stakes situations, turned at-risk clients into champions
Fintech/Banking/SaaS experience — or ability to quickly learn the loan origination process and lending industry

Nice-to-haves

Experience in RPO, staffing, or recruiting agency environments
Spanish proficiency for internal collaboration
Familiarity with AI-native tools (Claude Code, Lovable, or similar)

You'll thrive here if you:

Communicate exceptionally — equally comfortable in a CFO's office and pushing back internally on engineering trade-offs
Embody extreme ownership — you don't let "that's a product issue" become an excuse
Think like a builder — you design CS as a system, not a service
Have commercial DNA — expansion, renewal, and account growth are instinctive for you
Are a natural coach and leader

What's in It for You
💰 $3,000–$5,000+/month USD · Competitive salary
🏠 100% Remote · Mexico, Colombia, or Canada
🚀 High-impact role at a Series A AI-native fintech
🌱 Build and lead the CS function as Lupa scales toward 10x portfolio
🤝 Work at the intersection of fintech, AI, and enterprise client strategy

👉 Apply Here: https://app.lupahire.com/lupa-apply/81924a2e-a97f-4c62-867a-acacff923147?source=inbound-candidates