Implementation Specialist

Role SummaryThe Implementation Specialist owns the post-contract onboarding lifecycle for every new Pearly account, regardless of segment — from Committed through Go-Live. This role is responsible for getting new practices fully configured, trained, and confident in the platform, then handing off a well-documented, “Adopted” account to the Account Management CSM for ongoing relationship management, retention, and expansion. Where the Account Management CSM owns the long-term customer relationship, the Implementation Specialist owns the critical first stretch: turning a signed contract into a live, functioning customer.This is a full life-cycle implementation role covering the entire book — SMB through Enterprise — rather than a single segment, and is a core seat in Pearly's CS model alongside the Account Management CSM. Time AllocationImplementation & onboarding delivery ~75%Kickoff through go-live, all segmentsCross-functional coordination ~15%Sales handoff, Product/Eng escalations, CSM handoffSupport queue coverage ~10%Support queue overflow + PTO backfill Key Responsibilities Onboarding DeliveryOwn onboarding for all newly signed accounts across every segment, managing pacing and prioritization across a mixed caseload.Lead structured kickoff calls that define scope, timeline, stakeholders, and success criteria with each practice.Configure the Pearly platform — PMS integration, payment setup, user permissions, and workflows — to match each practice's specific <needs.Run> live training sessions for practice staff and providers, ensuring functional competency before go-live.Track onboarding milestones and early account-health signals in Pylon, escalating risk early.Cross-Functional CoordinationValidate the automated HubSpot → Pylon handoff at Committed, confirming segment and account data are accurate before kickoff.Partner with the CSM on a documented go-live handoff once an account reaches “Closed Won” status.Surface technical or product gaps discovered during implementation to cross-functional stakeholders, with clear reproduction detail and proposed solutions (where applicable).Provide light Support queue coverage for overflow and PTO backfill, consistent with the team's shared coverage model.Process & DocumentationHelp build and maintain onboarding playbooks, templates, and segment-specific workflows as the customer base grows.Identify recurring onboarding friction points and propose process or tooling improvements.Success MetricsTime-to-go-live from Committed to Closed Won statusOnboarding CSAT / NPS% of accounts reaching “Adopted” status within target windowHandoff quality, based on CSM feedback on handoff completenessData hygiene at close (segment field populated and accurate on HubSpot deals)Ideal Candidate Profile2–4 years in SaaS implementation, onboarding, or technical customer successStrong project management skills with the ability to run multiple concurrent onboardingsOutcome/ROI orientedComfortable leading live software configuration and training sessions with non-technical end usersDetail-oriented and process-driven, with experience building or improving onboarding playbooksFamiliarity with tools like HubSpot and a support/CS platform (e.g., Pylon, Zendesk, Intercom)Technical background is a plus — comfort with integrations, APIs, or PMS/software configuration helps with platform setup and troubleshooting during onboardingDental or healthcare software experience is a plus, but not requiredPayment Services background a plusComfortable with startup ambiguity and evolving process