Customer Success
Open to CSM, Enablement, and Onboarding roles.
I'm Jason Sheffield. As an early CS at 3Nickels I developed the journey map, health scoring, and renewal playbooks that produced 6x book growth across 20+ accounts. Everything on this site, including the Impact Assessment, I built myself.
Or ask my AI anything about my background, run your job description against my experience, or watch a short intro. I built all three.
Key highlights
6x
Grew annual contract value from $15.6K to $93.6K, anchored by a two-year agreement with my largest client.
0 → 1
Early CS hire. Wrote the handoff playbook, onboarding project plans, success plans, and CSAT workflows while running the book.
2x
Driven by kickoffs, product trainings, QBRs, and webinars across enterprise, SMB, and nonprofit accounts.
24%
Of webinar sign-ups went on to complete a profile, one of the company's key usage metrics.
10 years
Managed a donor portfolio in nonprofit leadership, growing revenue year over year and owning a $60K budget.
Operating systems, not titles
Customer Success runs on repeatable systems. These are the playbooks and workflows I've designed and shipped.
Structured transition from closed deal to kickoff that raised new-client activation.
Setup, training, and launch milestones that cut missed dependencies across concurrent rollouts.
Account goals tied to recurring QBRs, keeping key clients on track from adoption through renewal.
In-app and email surveys with post-ticket triggers and account mapping.
Kickoffs, Lunch & Learns, and webinars built for non-technical audiences.
UTM tagging and v1 dashboards in Kibana and Google Analytics to measure outcomes.
Built as an early CS hire at 3Nickels / GuidedChoice while running a book of 20+ enterprise, SMB, and individual accounts.
Featured work
3Nickels / GuidedChoice, early CS hire. A B2B2C fintech with a growing book and no playbooks, no structured handoff from Sales, and no customer feedback loop. I built them while running 20+ accounts.
B2B2C means two audiences: the employer who signs the contract and the employees who decide whether to use the product. I built relationships with both.
A large multinational construction and infrastructure employer had low participation in the middle of a post-merger rebrand. I took over as point of contact in April 2025.