Case Study: How Chicago Cook Workforce Partnership automated insurance certificate reviews with Gatekeeper Agents

The Partnership uses Gatekeeper's Insurance Certificate Review Agent to automate compliance in 20 seconds with a full audit trail.

The Chicago Cook Workforce Partnership is a non-profit organisation that manages one of the largest public workforce systems in the U.S. It serves as the designated administrator of federal workforce development funding for Chicago and Cook County. The Partnership oversees a network of about 70 community-based organisations, including American Job Centers and Career Centers, supporting both youth and adults. Its mission is to help career seekers build meaningful careers and empower employers to strengthen their teams. Alongside federal funding, The Partnership manages a diverse portfolio of initiatives funded by corporate and philanthropic sources.

Following a NetSuite implementation, the team built a sophisticated set of processes inside Gatekeeper, including a custom invoicing workflow that handles payments to partner organisations.

The Challenge: insurance compliance at federal funding standards

Every sub-grantee partner working with The Partnership is required to submit valid insurance certificates that meet a strict set of requirements. Coverage types, policy limits, named insureds, and effective and expiration dates all have to be checked before any work begins. As a largely federally funded organisation, The Partnership has clear compliance obligations on each one.

The reality on the ground was harder. Dave Swanson, The Partnership’s Senior Project Manager, estimated that around 95% of certificates submitted by partners did not meet requirements on the first attempt. Reviewing each one manually meant opening the document, extracting coverage details, comparing limits to requirements, checking expiration dates, writing back to the partner with detailed feedback, and tracking the back-and-forth until the certificate passed.

The workload was too high to manage consistently. Volume spiked during renewal periods. Review standards risked varying between reviewers. Expiration dates were easy to miss when stacks of certificates were waiting. Important compliance checks were at risk of being missed because there were simply not enough hours in the week.

The solution: Insurance Certificate Review Agent To Automate Insurance Compliance

During a Discovery Session, the Gatekeeper team configured the Insurance Certificate Review Agent to The Partnership's specific coverage requirements. The agent reads every certificate the moment it arrives. It validates coverage types, checks policy limits against minimum thresholds, confirms named insureds and insurer details, and flags expired or expiring dates. Compliant certificates progress automatically. Non-compliant submissions are rejected on the spot, and the partner receives a detailed breakdown of which fields are missing or incorrect and what they need to fix.

Total time from submission to partner response was around 20 seconds.. Only compliant certificates ever reach the compliance team. Routine rejections never need a human reviewer, which frees the team to focus on the small number of certificates that genuinely warrant judgement and on broader compliance work.

“Watching a certificate get rejected, with a detailed breakdown sent back to the partner inside 20 seconds, was the moment it clicked. The agent is doing work we never had hours in the day to do, and our partners are getting clearer, faster feedback than they ever did from us manually.”
Kendall Griffin, Business Applications Specialist, Chicago Cook Workforce Partnership

Implementation timeline:

• Short Discovery Session to map insurance compliance requirements and configure the Insurance Certificate Review Agent
• Insurance Certificate Review Agent deployed into the certificate review workflow using The Partnership's compliance rules
• First certificate reviewed in around 20 seconds, automatically triaging compliant and non-compliant submissions

“Federal funding doesn’t forgive missed compliance checks. Coverage requirements are strict, and we have to demonstrate we are enforcing them on every partner. Having an agent that reviews every certificate to the same standard, every time, gives us a compliance position we did not have before.”

Dave Swanson, Senior Project Manager, Chicago Cook Workforce Partnership

See it in action

The results: Insurance Certificate Review Agent Reduces Manual Reviews By 95%

Every partner submission is now reviewed against the same criteria, every time. Coverage gaps are identified immediately. Expiry risks surface before they become onboarding delays. Renewal-period spikes that previously created backlogs now resolve as quickly as partners can resubmit compliant certificates. Every decision the agent makes is logged with a full audit trail, which matters for an organisation reporting to federal funders.

Beyond the certificate agent, The Partnership has turned on Gatekeeper’s Obligations capability to surface internal and external commitments across their contracts. With general service agreements being brought into Gatekeeper over the next six months, contract risk and vendor risk will sit alongside each other within a single platform.

The Agent toolkit:

• Gatekeeper Insurance Certificate Review Agent to validate insurance certificates against coverage requirements and automate compliance decisions.
• Gatekeeper Obligations to surface internal and external contract commitments.
  

What's Next: Insurance Certificate Review Agent Proves The Value Of AI In Compliance

The Partnership has transformed a high-volume compliance bottleneck into a 20-second automated workflow. Insurance certificate reviews now run to the same standard every time, without consuming team hours, while every decision is logged with a full audit trail for compliance reporting.

With that success established, the team is already expanding its use of AI. The next agent on the roadmap will automate invoice support reviews, helping the Finance team reduce the audit risk of manually checking documentation submitted alongside partner spend. The Partnership is also exploring how MCP can connect Gatekeeper data into broader workflows, while Gatekeeper's unlimited agent model lets the team deploy AI across workflow boards wherever it delivers the greatest operational value.

“What works about Gatekeeper’s approach is that agents fit the way we already operate. We didn’t have to change our process to suit a new tool. The Insurance Certificate Review Agent picked up the volume of routine work no one realistically had time to do manually, and runs it consistently against our requirements. Adding more agents across our workflow boards without re-pricing every interaction means the platform can grow with us.”

Dave Swanson, Senior Project Manager, Chicago Cook Workforce Partnership