Cherry Park
Advisory Group
317-605-3688
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Cherry Park Advisory Group is a boutique compliance practice built around the proposition that the Form 5500, when read carefully, is one of the most candid public documents an employer produces about its benefits program. Our work begins there.
We built Cherry Park to do the work that gets deferred — the careful, document-driven, source-reconciled work that surfaces exposure before it becomes a finding.
Form 5500 reporting is the most quantitatively detailed window into an employer's benefits program — and one of the most commonly mis-prepared. The schedules describe carrier and broker compensation, plan structure, participant counts, and operational details that, when read together, frequently reveal compliance gaps invisible from inside the company.
Most providers treat the filing as a once-yearly transaction. We treat it as the public record it is. The result is a different kind of engagement — one designed to identify and remediate exposures before the regulator, the audit committee, or the broker raises them.
The practice is built around health & welfare plans specifically. Other firms make Form 5500 one item on a long service menu; we make it the focus. That clarity informs how we staff engagements, what we accept, and how we deliver.
"After years of watching the Form 5500 reduced to a transactional output, I built Cherry Park to do the harder, quieter work — the kind that protects an employer before the regulator ever picks up the file."
David Skinner is the founder and principal of Cherry Park Advisory Group, where he leads the firm's health & welfare plan compliance practice. He spent his earlier career inside the brokerage and TPA communities — preparing, peer-reviewing, and remediating Form 5500 filings across regional employer groups and multi-state plan sponsors — before establishing Cherry Park to bring that work under a single, dedicated discipline.
His engagements concentrate on the matters most providers will not take: late or omitted filings under the DFVC program, contested Schedule A reporting, plan structures inherited from acquisitions, and the operational gaps that emerge between the carrier, the broker, and the employer. He works directly with HR leadership, and on a co-counsel basis with brokers, audit firms, and ERISA counsel when an engagement warrants a dedicated practitioner.
Particular engagements have included Form 5500 reconstruction for plans inherited through acquisitions, factual development for sponsors under DOL investigation, Schedule A reconciliation for multi-state employer groups, and welfare-plan diligence on behalf of strategic acquirers and their counsel. David is a regular contributor to professional publications on welfare plan compliance, Form 5500 reporting, and the implications of CAA §202 for plan sponsors.
A 60-minute conversation with a senior compliance practitioner — focused on your current filing, your current carrier compensation disclosures, and the questions you have not yet been able to put to your existing providers. There is no charge for this initial review.
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