Site-by-site health and expansion agent for healthcare software success teams serving multi-site provider groups on HubSpot

What The Retention Specialist does

A 120-person company sells clinical workflow software to multi-site provider groups and outpatient networks. A typical customer buys for two clinics, goes live, and then either spreads to ten more sites or quietly stalls. The six-person success team manages these accounts from HubSpot, but health is judged by gut feel at the account level, so one struggling site hides behind a healthy average, and expansion only happens when a clinic manager happens to mention a new location on a call. The Retention Specialist works for the success managers and the head of customer success. It owns a health score at two levels (account and site or department), risk alerts routed to the right owner, a defined save play for each risk level, and an expansion watchlist that pairs proven sites with untouched sites, departments or modules in the same network. It works only from de-identified operational data, and it is built, monitored and tuned on an ongoing basis so the score stays honest as the product and customer base change.

Built on HubSpot

The team already runs accounts, tickets and renewals in HubSpot Service Hub, so the score, alerts, tasks and expansion deals belong there where success managers work every day, using custom site objects and the customer success workspace. HubSpot alone cannot safely strip PHI from upstream product and ticket data or reason about site-level patterns, so a self-hosted n8n pipeline handles de-identification and a custom Claude build running under a BAA writes explanations and drafts from clean data. Breeze features can assist with record summaries and internal tasks once the team has confirmed their HubSpot tier's HIPAA coverage and kept PHI out of the properties those features read.

What starts it

• Nightly refresh of de-identified usage counts and admin activity from the product, rolled up per site
• A site misses an onboarding or go-live milestone date recorded on its HubSpot record
• A known champion, clinic manager or IT contact changes role, leaves, or bounces email
• A HubSpot ticket is tagged with a high-severity or repeat theme at a given site
• A renewal, fiscal-year budget window or new-location announcement (logged by a rep or found in a contact update) lands within the next 120 days

What it reads

• HubSpot Service Hub (companies, custom site objects, tickets, renewal deals, contact roles, customer success workspace)
• Product analytics export of aggregate, de-identified counts only (active staff users, modules used, workflows completed per site), passed through a self-hosted n8n pipeline
• Onboarding and training records (go-live dates, staff training completion per site)
• Zonka Feedback NPS and post-ticket CSAT responses, with free-text redacted before scoring
• Contract and billing data synced into HubSpot (licensed sites, modules purchased, renewal date)
• Databox dashboards for team-level health trends and portfolio rollups

When a person takes over

• Any critical score on an account renewing within 120 days goes to the head of customer success, who decides whether to run the executive recovery play or adjust commercial terms. The agent does not offer discounts or credits.
• When a ticket theme suggests a possible patient safety or clinical workflow issue, the agent stops all automated outreach to that site and routes it to the clinical lead and the support manager, who own the response.
• Expansion deals move to the account executive once the success manager confirms the proving site's champion is willing to be a reference internally. The agent never pitches a new site directly.
• If the de-identification step detects a field it cannot classify, the pipeline quarantines the record and alerts the maintenance owner instead of passing it through.

Rules it follows

• Protected health information never enters a prompt, model context or log. Only aggregate, de-identified counts and categories reach the model, every vendor in the data path (HubSpot tier, model host, automation runtime) must have a signed BAA or never touch PHI, and logs are reviewed during each maintenance cycle.
• No clinical claims. The agent may not state or imply outcome, safety or efficacy benefits in any draft. Anything resembling a clinical claim is routed to the clinical and regulatory reviewer before sending.
• All customer-facing messages are drafts that a success manager sends. No autonomous sending at the at-risk or critical levels.
• Scores always show their inputs and reasoning on the record. If a site has fewer than 30 days of data, it is labeled 'insufficient data' rather than scored.
• Meeting recordings and call transcripts are excluded from scoring unless the recording tool is covered by a BAA and the call is known to contain no PHI.

How you know it works

• Gross revenue retention and logo retention for accounts tracked by the agent versus the prior period
• Share of licensed sites live and active within the agreed onboarding window
• Number of expansion deals opened from the watchlist, and the share that close, versus expansions sourced informally
• Median days from a site entering 'at risk' to the save play starting
• Score accuracy: share of churned or downgraded accounts that were flagged at risk at least 90 days earlier

From pilot to live

1. Pilot (first 6 to 8 weeks)Map the data, sign or confirm BAAs, build the n8n de-identification pipeline and site object in HubSpot, and back-test the model against the last two years of renewals and site launches. Run it in shadow mode for two success managers, who compare alerts to their own read of each account.
2. Team rolloutTurn on alerts and save plays for the whole success team, launch the approved message library, and activate the expansion watchlist with AE handoff. Weekly review of false alarms and missed risks for the first month.
3. Run and maintainOngoing ownership by the build team: monitor pipeline health and data drift, run the monthly accuracy review, propose weight changes for approval, update save plays as products and modules change, and audit logs and vendor BAAs each quarter.