Case study
How a GovTech provider automated government account follow-ups
An AI AR Collections Specialist that captures the date, the blocker, and the escalation contact on every overdue government account, and syncs it back to ConnectWise and QuickBooks.
Daily touch
on every overdue account, automated and consistent
Exception
management replaces manual daily chasing
Two-way sync
to ConnectWise and QuickBooks, no double entry
Overview
A U.S.-based GovTech software provider runs a cloud platform used by law enforcement agencies, district attorneys, and correctional facilities. The customer base is almost entirely public-sector, which means most invoices, despite being due on receipt, are slow to clear. Payments routinely sit through multiple approval levels inside agencies, and the AR team’s job is less about asking “will you pay?” and more about figuring out who in the agency to chase next. Roughly 20 customer accounts each month required this kind of daily, persistent follow-up, and a single AR lead was personally calling, emailing, and checking back to keep payments moving.
The company partnered with Squirrels.ai to deploy an AI AR Collections Specialist tuned specifically to the government-payment context. The agent now runs daily multi-channel follow-up across email, SMS, and phone after a configured 20-day grace period, asks the three questions that actually move government invoices (when will payment be made, what is holding it up, and who else should be contacted), and syncs every status, promise-to-pay date, and dispute flag back to ConnectWise and QuickBooks. The AR lead has gone from manually chasing every account every day to managing exceptions through a real-time dashboard.
Client at a glance
Industry
Government-focused software (cloud platform for law enforcement, district attorneys, and correctional facilities)
Payment terms
Invoices due on receipt, with a 20-day grace period before collections outreach begins
Customer base
Government and public-safety agencies across the United States
Existing systems
ConnectWise for day-to-day AR tracking and QuickBooks for accounting records
Overdue volume
~20 customer accounts per month requiring active follow-up
Use cases deployed
AI AR Collections Specialist with two-way sync to ConnectWise and QuickBooks
The challenge
Government AR is a different operating model than commercial AR, and the team’s existing workflow was running into the limits of what one person can do manually.
Multi-level approvals slow every payment
Government and public-safety agencies typically route every invoice through multiple approval layers: the requesting department, the finance office, sometimes a procurement officer, and finally the entity that actually cuts the check. Even invoices technically due on receipt routinely sit 30, 60, or 90 days while moving through that chain. The AR team’s job was less about collecting on disputed invoices and more about keeping otherwise-approved invoices visible inside slow-moving bureaucracies.
The questions that matter are not “will you pay?”
Standard collections scripts focus on getting commitment to pay. In the government context, that question is almost beside the point. The three questions that actually move money are: “when will the payment be made (with a specific date)?”, “what is currently holding it up?”, and “who else inside the agency should we be contacting?” An effective government AR motion has to ask those three questions, every single time, and log the answers.
Daily follow-up that one person could not sustain
Most overdue accounts needed a touch every day, or at minimum every couple of days, to keep moving. With 20 active overdue accounts running at any given time, that meant a stream of daily calls, statement sends, voicemails, and email replies, on top of the AR lead’s other responsibilities. Some accounts inevitably went days or weeks without contact, and those were the ones that drifted into the 60- and 90-day buckets.
Two systems, no live link
Daily AR tracking lived in ConnectWise. Accounting records lived in QuickBooks. Updates from a conversation, a promise-to-pay date, a dispute flag, a corrected contact, all needed to be entered manually in one or both systems. The result was either double entry or missing entries, and the records were rarely as up-to-date as the conversations they were supposed to reflect.
Additional constraints
- Tone had to stay professional and respectful. These are government and law-enforcement customers, and the relationship matters.
- A grace period was required. The team did not want any outreach happening before 20 days past due, to give agencies time to process invoices internally.
- The system had to honor promises to pay. Once a payment date was captured, follow-up cadence needed to pause until that date passed.
- Daily AR work was being measured in time saved, not in dramatic recovery numbers; the agency payment cycle is what it is.
The solution
Squirrels.ai deployed an AI AR Collections Specialist configured around the realities of selling to government. The agent does not try to negotiate; it executes the daily follow-up motion the team was already running, every day, on every account, and logs the answers cleanly.
Government-aware outreach cadence
- 20-day grace period built in: outreach simply does not start until an invoice is 20 days past due, giving agencies the internal processing time they need.
- Daily-touch cadence: configurable outreach days, for example day 1, day 3, day 5, and day 10 past the grace period, keep accounts visible without becoming hostile.
- Multi-channel by design: the agent rotates across email, SMS, and phone so an agency contact who ignores email might pick up the call, and vice versa.
- Respectful tone tuned for public-sector relationships: scripts were configured to match the company’s existing voice with government customers, never aggressive, always professional.
The three questions, every time
The agent’s knowledge base was specifically structured around the three questions that move government invoices forward. Every conversation surfaces and captures the answers.
- When will the payment be made? the agent asks for a specific date, not a vague “soon,” and records the promise-to-pay date for follow-up timing.
- What is holding it up? the agent surfaces blockers like “waiting on the finance director’s sign-off,” “PO has not been issued,” or “check run is monthly,” and flags them for the AR lead.
- Who else should we be contacting? when the current contact is not the decision-maker, the agent asks for an escalation contact and adds them to the next round of outreach.
- Promises drive cadence: when a contact commits to a payment date, the agent automatically pauses outreach until that date passes, instead of continuing to chase.
Two-way sync with ConnectWise and QuickBooks
- API integration with ConnectWise: overdue invoice data flows out, and status updates, notes, promise-to-pay dates, and escalation contacts flow back in, so the daily AR tracking system stays current.
- QuickBooks accounting sync: payment status and dispute flags are pushed into the accounting record, so the books match what is actually happening on the calls.
- No double entry: the AR lead no longer transcribes every call into ConnectWise and then again into QuickBooks. The agent’s summarized notes land in both systems automatically.
- File-transfer fallback: where API access is limited, file-based data flow is supported, so the integration never becomes a blocker.
On-demand payment links and dispute capture
- Payment links sent in real time: during a call or text, when a contact says they are ready to pay, the agent can send a payment link immediately instead of routing back through the AR lead.
- Invoice details resend on request: if a contact says “I never received that invoice” or “can you send me a copy?”, the agent handles it inside the same conversation.
- Disputes captured cleanly: any contact who challenges a charge or asks for clarification is logged, flagged, and pulled out of the automated cadence for human review.
- Auto-stop on engagement: the moment a customer pays, promises to pay, or disputes the invoice, all further outreach stops automatically.
Real-time dashboard for exception management
- Live view of every overdue account: contact attempts, responses, promises to pay, disputes, and payments received.
- Filter views surface the accounts that need the AR lead’s attention today, instead of dumping the entire list every morning.
- Conversation transcripts and call recordings available on demand for any account that needs deeper review.
- Departmental blockers (“waiting on finance director,” “awaiting PO”) are tagged so the team can spot patterns across multiple agencies.
Pilot-first deployment
- Free implementation: API integration, knowledge base setup, and cadence configuration were all included in onboarding.
- Modest monthly subscription matched to the actual volume of ~20 monthly contacts, with no multi-month lock-in.
- Dry-run testing of every call script and email template let the AR lead preview the agent’s tone and content before going live.
- Squirrels.ai positioned the platform as a time-saver, not a payment negotiator, which matched the team’s actual needs.
Results and impact
The collections motion went from a daily, manual, one-person chase loop to a continuous, automated process that the AR lead now supervises through a dashboard.
What changed in the business
- Every overdue account gets touched, every day. What used to depend on the AR lead having time to call now happens automatically across email, SMS, and phone, on every account, every single business day after the grace period.
- The right questions actually get asked. Promise-to-pay dates, current blockers, and escalation contacts are now captured on every conversation, not just on the calls the AR lead happened to make personally.
- AR work shifted to exception management. The AR lead spends time on disputes, departmental blockers, and the harder agency conversations, while the agent handles the daily check-in calls and reminders.
- ConnectWise and QuickBooks finally agree. Status updates, notes, and promise-to-pay dates flow back into both systems automatically, so the records match the conversations.
- Patterns across agencies became visible. Tagging blockers (“waiting on finance director,” “awaiting PO”) surfaced patterns across customers that the team can use to refine outreach and educate agencies on faster payment paths.
- Tone and relationships stayed protected. Government customers continue to hear a professional, respectful voice, never an aggressive collections script. Relationships intact, payments moving.
- ROI tracks to time saved, not to dramatic recovery. The platform delivers on the metric that actually matters in government AR: hours of AR-lead time reclaimed and consistency of follow-up across every overdue account.
TESTIMONIAL
Why Squirrels.ai
Squirrels.ai deploys AI agents that handle calls, emails, and texts at scale, trained on a company’s own scripts, FAQs, and SOPs. For this GovTech provider, the platform delivered:
- An AI AR Collections Specialist purpose-tuned for government payment cycles, with a 20-day grace period and respectful professional tone.
- A conversation model built around the three questions that actually move government invoices: when, what is the blocker, and who else.
- Two-way API sync with ConnectWise and QuickBooks, so promise-to-pay dates, dispute flags, and notes flow back to both systems automatically.
- Real-time dashboard analytics that turn daily AR work into exception management instead of routine chasing.
- On-demand payment links, invoice resends, and dispute capture, handled inside the same conversation.
- Free implementation, volume-based pricing, and a pilot-first rollout so value could be validated before any longer commitment.