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Beyond the Checkbox:
October 2026 Highlights
October 8, 2026
- Fireside Chat: Callan Harrington, Insurance Growth Lab, Going Against the Grain
- On-Demand Webinar: Preparing for OSHA Season with Aclaimant
- On-Demand Webinar: Aclaimant × UKG, Streamlining Workers' Comp Claims
- From David's Desk: Two posts resonating with risk and safety leaders
- Champion Spotlight: Cassandra Geoghegan, Traffic Management
FIRESIDE CHAT: CALLAN HARRINGTON, INSURANCE GROWTH LAB, GOING AGAINST THE GRAIN...THE PLAYBOOK OF INSURANCE TOP PERFORMERS
If AI is making every piece of content cheaper to produce, the only durable advantage is doing something nobody else is willing to try. Callan Harrington has watched three Insurtech exits and three flops up close; and the common denominator among the winners is a willingness to go where everyone else refuses.
Callan, founder of strategy agency Flash Growth, breaks down the contrarian plays that moved the needle: Matic Insurance targeting loan servicing instead of fighting over home-sale leads, G&N Insurance replacing corporate gifts with custom bobbleheads for referral partners, and the B2B Insurtechs quietly driving 80% of their enterprise leads from paid media rather than six-figure trade show booths.
- Why AI saturation is about to put a premium on in-person relationships and proprietary data
- The one pattern across top performers: take the risk earlier, then bet the farm when something works
ON-DEMAND WEBINAR: PREPARING FOR OSHA SEASON WITH ACLAIMANT
OSHA 300A posting season is almost here — and February 1 is not the deadline you want to be scrambling for in late January. Aclaimant's Phillip Ching and Yelena Binkle walked through how to use Aclaimant to get ready now: clean data, defensible records, and the shortcuts that make 300, 300A, and 301 filing feel like a repeatable process instead of a fire drill.
- How to structure your incident data so OSHA filings generate themselves
- The pre-filing audit that catches gaps before an inspector does
ON-DEMAND WEBINAR: ACLAIMANT × UKG
STREAMLINING WORKERS' COMP CLAIMS MANAGEMENT
David Wald and Aclaimant's Alex Schillo sat down with the UKG team for a joint session on the operating model that eliminates the friction between HRIS, incident capture, and claims. The short version: when payroll data, OSHA records, and claims intake live in connected systems, workers' comp stops living in anyone's inbox.
- The handoff points where most WC claims lose time (and money)
- What a UKG + Aclaimant stack changes for mid-market programs
FROM DAVID'S DESK: WHAT'S RESONATING WITH SAFETY AND RISK MANAGEMENT LEADERS
Two posts from David Wald's LinkedIn that landed with risk and safety leaders this month:
1. "A claims analyst described part of her job to me as an 'arts and crafts project.'" On the hidden tax of manual spreadsheet work, the kind that doesn't show up on a dashboard but shows up eighteen months later as turnover you can't explain. "Most risk teams aren't understaffed. They're mis-deployed."
2. "Can you police a claim administrator for three-point contacts?" On the gap between what's written into every TPA service agreement and what any program is actually measuring: "You are paying for a performance obligation you have no instrument to measure."
CHAMPION SPOTLIGHT: CASSANDRA GEOGHEGAN, TRAFFIC MANAGEMENT
If you watched Cassandra's Fireside Chat earlier this year, you know how she thinks about field-first risk. This month we're making it official — Cassandra is our newest Aclaimant Champion.
In 2018, Cassandra was a paralegal with deep litigation experience when a recruiter called about a role that didn't exist yet: Traffic Management's first-ever risk manager. The CFO took a chance on her, and she's been building the program ever since — now as Sr. Manager of Compliance & Risk.
- The best risk leaders don't all come from the same place litigation experience translates
- Her motto: "Do everything with integrity, intention, and to the best of my ability."
Want to see a demo of the Aclaimant system for yourself?
ONE LAST THOUGHT…
The best risk programs we're seeing this month share one specific trait: they measure the work that doesn't show up on a form.
The three-point contact that was supposed to happen. The analyst's Thursday that got absorbed by assembly instead of analysis. The field crew that logged the incident because the software didn't gate them out of it. The contrarian channel the whole market overlooked.
That's the gap between the checkbox and the outcome. It's where the next decade of risk program performance lives.
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