We used to find out about renewals the way you find out about a parking ticket: too late to do much. An account owner would open HubSpot, spot a contract ending in three weeks, and begin from scratch. Dig up usage. Try to recall what had shipped since the last call. Take a guess at upsell room. Write the email that same afternoon. The renewals that went well were the ones somebody happened to check in time. The ones that slipped away quietly were mostly the ones nobody opened until all that was left was an apology.

Now an agent on Machine watches the renewal date on every HubSpot deal and moves early, at 90, 60 and 30 days out, with the packet built and the email drafted. It never sends anything and never touches pricing. The account owner gets a running start instead of a looming deadline.

The problem

A renewal date on a HubSpot deal is just a number on a calendar. It can't tell you if the account is in good shape, if the customer really uses what they paid for, if there's an obvious upgrade to bring up, or if the deal has gone silent in a way that ought to worry you. That story is spread across old notes, someone's memory of the last QBR, and whatever the owner can piece together in a hurry.

The usual backstop is a calendar reminder, or a pipeline report sorted by close date. It's a bare list with no homework behind it. By the time the owner digs in, the renewal is near, there's no packet, and the email gets dashed off instead of built around what this customer actually needs to hear.

What we built

Once a day, a cron on Machine starts an agent that reads the renewal date on every HubSpot deal and picks out the ones hitting 90, 60 or 30 days to go. For each, it assembles a renewal packet: the usage and value the customer has had since they last renewed, plus one or two specific ideas for growing the account. It looks at Google Calendar to see if a renewal call is already booked, and it drafts the outreach email. Accounts that seem stuck, silent or shrinking get their own at-risk flag. The packet and draft wait for the account owner. Nothing leaves by itself.

How it works

The pattern

Once a day a cron opens a session with reading connectors into HubSpot and Google Calendar. A skill holds the renewal playbook. The agent builds the packet and drafts the outreach, and the account owner reviews, edits and sends.

Guardrails

These accounts carry revenue, so what the agent may do is spelled out and kept small:

• It prepares and drafts, that's all. It never sends the renewal email, and it never makes or moves a calendar event. The email sits as a draft in the owner's inbox until the owner sends it.
• Pricing is off limits. It never applies, offers or suggests a specific discount or credit. Anything about price is for the account owner to discuss, not for a draft to state.
• Tiny writes. All it writes back to HubSpot is which renewal window a deal has been flagged for. The stage, the amount and the pipeline stay untouched.
• Kept apart. Each run gets its own sealed-off sandbox. The HubSpot and Google Calendar credentials are stored encrypted in the Secrets Manager, added at run time, and only handed to the agents you grant them to.
• All of it lives in code. The renewal playbook, the at-risk rules and what each system lets it do are files in the repo. They're versioned, and you change them with a reviewed change request, not a setting on a dashboard.

The outcome

Renewals no longer begin with an empty page. They begin with the packet assembled and the email drafted, so the owner's first job is reading, not rushing. The agent keeps an eye on every deal and does the legwork. A person still chooses what to say and when to hit send.