Meet CaddiLegal AI ROI webinarReplayADVISE AIOct 20–22AI for Mid-Sized LawNov 5Legal InnovatorsNov 17–18

AI-native automation

Automate work acrossBill.com and Sentrywith Caddi AI Agents.

Automate anything you do across Bill.com, Sentry, and the rest of your tools. Sign in, show or tell Caddi what you want, and it runs end to end. No workflow builder.

Free for one user.

How to connect Bill.com and Sentry

  1. Connect Bill.com to Caddi

    Allow

    1Sign in to Bill.com

    One click with your own Bill.com login. No API keys.

  2. Connect Sentry to Caddi

    Allow

    2Sign in to Sentry

    The same click again. Both tools are connected.

  3. Resolve issue in Sentry when new bill in Bill.com.

    Type it

    3Show or tell it

    Screenshare the job, or type it in chat. Change it any time.

  4. Running

    14 done1 for review

    4Watch it run

    Caddi does the work and flags anything unsure for review.

  • The Planning Center
  • Beveridge & Diamond
  • Palace
  • Portner & Shure
  • Knight Law Group
  • Ervin Cohen & Jessup
  • Burney Wealth Management
  • JFS Wealth Advisors

What Caddi is and how it works

An AI teammate that runs your back-office loops.

  • Doesn't break. Caddi reads intent, so when fields move or UIs change, your loop keeps running.
  • Taught like a new hire. Walk Caddi through the work once. Tweak it later by chat, with no workflow builder to re-architect.

SOC 2 attested · Human-in-the-loop · Full audit trail · 150+ tools across legal, finance, and operations

Practical ways to use Bill.com and Sentry together

  • 01

    Resolve issue in Sentry when new bill in Bill.com.

    Caddi watches Bill.com for new bill and resolve issue in Sentry. No copy-paste, no missed records.

  • 02

    Create vendor in Bill.com when new issue in Sentry.

    Caddi watches Sentry for new issue and create vendor in Bill.com so the two systems stay in lockstep.

  • 03

    Assign issue in Sentry from Bill.com events.

    When bill approved happens in Bill.com, Caddi assign issue in Sentry with the right context attached.

Actions Caddi can take across Bill.com and Sentry

  • Bill.com

    New bill

    Triggers when a bill is created in BILL.

  • Bill.com

    Bill approved

    Triggers when a bill clears its approval workflow.

  • Bill.com

    Payment sent

    Triggers when a vendor payment is sent.

  • Bill.com

    Invoice paid

    Triggers when a customer pays an invoice.

  • Bill.com

    Create vendor

    Add a vendor with remittance details.

  • Bill.com

    Create bill

    Create a bill against a vendor, with line items.

  • Bill.com

    Create invoice

    Create and send an invoice to a customer.

  • Bill.com

    Look up payment status

    Fetch the status of a bill or payment.

  • Sentry

    New issue

    Triggers when Sentry groups a new error into an issue.

  • Sentry

    Issue regressed

    Triggers when a resolved issue starts happening again.

  • Sentry

    Alert fired

    Triggers when a Sentry alert rule's threshold is crossed.

  • Sentry

    Resolve issue

    Mark an issue resolved, optionally in the next release.

  • Sentry

    Assign issue

    Assign an issue to a person or team.

  • Sentry

    Fetch issue details

    Pull the stack trace, tags and event counts for an issue.

Common questions

How does Caddi connect Bill.com and Sentry?

Bill.com and Sentry just run together. You teach Caddi the way you'd teach a new hire: walk it through how you use them today, with no workflow builder to wire up. Caddi turns that walkthrough into a verified loop and runs it against Bill.com and Sentry end-to-end.

Do I need engineering help?

No. Whoever does the work today walks Caddi through it on a call, the same way they'd train a new hire. Caddi builds the loop. No code, no IT ticket.

Is my data safe?

Yes. Caddi is SOC 2 attested. The AI watches and builds the automation, and once the loop ships it runs as deterministic code, repeatable and logged, with any model step scoped and reviewable.

Can Caddi connect Bill.com and Sentry to other tools too?

Yes. Most Caddi loops span 3–6 tools. Once the first Bill.com + Sentry loop is live, Caddi suggests other tools and other workflows to fold in.

How fast can it go live?

Typical first loops ship within a week of that first walkthrough. The Caddi team reviews every loop before it runs in production.

Ready to automate Bill.com and Sentry?

Drop your work email and we'll show you Caddi running end-to-end against Bill.com, Sentry, and the rest of your stack.