Implementation Specialist

Pearly; Santa Barbara (CA); On-site; USD 90,000 - 120,000; Full time

Job summary

Pearly is seeking an Implementation Specialist to own the end-to-end onboarding lifecycle from contract to live deployment across SMB to Enterprise. You will configure the Pearly platform, run trainings for practice staff, and ensure a smooth handoff to the Account Management CSM for ongoing success.

The role emphasizes structured kickoff, data hygiene, and cross-functional collaboration with Sales, Product, and Support to address gaps and optimize onboarding plays.

Qualifications

• 2–4 years in SaaS implementation, onboarding, or technical customer success.
• Strong project management with ability to run multiple onboardings.
• Outcome/ROI oriented mindset.
• Comfort leading live software configuration and training for non-technical end users.
• Detail-oriented with experience building onboarding playbooks.
• Familiarity with HubSpot and CS platforms (e.g., Pylon, Zendesk, Intercom).
• Technical background is a plus — integrations, APIs, or PMS/configuration helpful.
• Healthcare software experience and payment services background a plus.
• Comfort with startup ambiguity and evolving processes.

Responsibilities

• Own onboarding for all new accounts across every segment, managing pace and prioritization across a mixed caseload.
• Lead structured kickoff calls defining scope, timeline, stakeholders, and success criteria.
• Configure the Pearly platform — PMS integration, payment setup, user permissions, and workflows.
• Run live training sessions for practice staff and providers.
• Track onboarding milestones and early account-health signals in Pylon, escalating risk.
• Validate the HubSpot → Pylon handoff at Committed.
• Partner with the CSM on a documented go-live handoff after Closed Won.
• Surface gaps to cross-functional stakeholders with clear reproduction details.
• Provide light support queue coverage for overflow and PTO backfill.
• Help build onboarding playbooks and templates.

Skills

SaaS onboarding

Project management

Process improvement

Non-technical training

HubSpot familiarity

Tools

HubSpot

Pylon

Zendesk

Intercom

Job description

• Sales handoff, Product/Eng escalations, CSM handoff

Role Summary

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.

Time Allocation

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

Key Responsibilities

Onboarding 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 → 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