Implementation Specialist

The 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.

Implementation & 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

• 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.

• Validate 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.

• 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.

• 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)

• 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