What 20,000 Benefits Professionals Are Looking For. The Operating System Behind Benefits Vendor Selection
Benefits professionals on BenefitPitch run seven to eight thousand vendor searches every month, yet no standard mechanism exists to measure whether a selected vendor actually delivers on what was promised.
Dave Kerrigan spent 25 years inside benefits before building BenefitPitch, and the problem he kept watching was downstream of selection. An employer runs a thorough RFP, chooses a vendor, and three years later learns the claims reduction never came. Both sides produce reasons. The vendor points to low employee engagement. The employer points to missed benchmarks. Neither had agreed, at the start, on how performance would be tracked in real time. That absence of a shared measurement framework is what Kerrigan describes as the next unsolved layer in the vendor relationship.
His search data adds a separate signal: categories like COBRA, TPA services, and FSA or HSA administration rank consistently in the top ten searched, not because employers are discovering them for the first time, but because the current solutions are leaving enough unmet need that buyers are actively looking for something better.

What we discuss

• Why a father's death and a layoff within the same year forced an entrepreneurial decision
• How the two-sided marketplace problem was broken by licensing a vendor knowledge management system to brokerage firms first
• What broker consolidation through acquisition does to institutional knowledge of vendor performance
• Why brokers running seven to eight thousand searches per month on a single platform reveals structural demand, not curiosity
• How BenefitPitch approaches vendor questionnaires at the RFI level rather than vertical-specific depth
• Why Kerrigan resisted building an RFP product and what customer demand eventually forced
• How a shared, donated question bank changes where broker value actually sits in the procurement process
• What consistently top searched categories, including behavioral health, EAP, wellness, and legacy admin services, signal about employer dissatisfaction
• Why real-time, mutually agreed performance measurement between employer and vendor is the gap Kerrigan believes the industry has not yet solved

Referenced in this episode

1. Wellness360: Enterprise wellness platform — wellness360.co
2. BenefitPitch: Vendor marketplace and knowledge management system for benefits brokers, consultants, and HR leaders — benefitpitch.com
3. Smart RFP: RFI and RFP sister product to BenefitPitch, featuring a shared public question bank and annual vendor panel reviews
4. Claude: AI assistant cited by Kerrigan as a present-day example of prompt-driven RFP generation — claude.ai
5. Road2Wellbeing Podcast: Wellness360 podcast series in which this conversation appears
6. EAP: Employee assistance programs, listed as a distinct top-searched category from behavioral health on BenefitPitch
7. TPA services: Third-party benefit and claims administration, cited as a consistently top-searched category suggesting buyer dissatisfaction with current solutions
8. FSA, HSA, HRA: Tax-advantaged financial account administration, cited alongside TPA and COBRA as legacy categories with persistent search demand
9. COBRA: Federal continuation health coverage administration, cited as a top-ten searched category despite its decades-long presence in the market
10. Dependent eligibility audits: Verification services for benefit plan eligibility, cited among the top-searched categories that surprised Kerrigan given their maturity