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 segments
Cross-functional coordination ~15%
- Sales handoff, Product/Eng escalations, CSM handoff
Support queue coverage ~10%
- Support queue overflow + PTO backfill
Key ResponsibilitiesOnboarding Delivery- Own 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 Coordination- Validate the automated HubSpot 12 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 & Documentation- Help 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 Metrics- Time-to-go-live from Committed to Closed Won status
- Onboarding CSAT / NPS
- % of accounts reaching "Adopted" status within target window
- Handoff quality, based on CSM feedback on handoff completeness
- Data hygiene at close (segment field populated and accurate on HubSpot deals)
Ideal Candidate Profile- 2-4 years in SaaS implementation, onboarding, or technical customer success
- Strong project management skills with the ability to run multiple concurrent onboardings
- Outcome/ROI oriented
- Comfortable leading live software configuration and training sessions with non-technical end users
- Detail-oriented and process-driven, with experience building or improving onboarding playbooks
- Familiarity 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 onboarding
- Dental or healthcare software experience is a plus, but not required
- Payment Services background a plus
- Comfortable with startup ambiguity and evolving process
