Cherry Park is a boutique advisory practice built around a single discipline: the compliance, integrity, and strategic value of employer health & welfare benefit plans. We prepare and review filings, but our work begins where most providers stop — interrogating the data for risk, inconsistency, and missed opportunity before they reach a regulator.
Most firms treat the Form 5500 as one item on a long service menu — a once-a-year filing, prepared from whatever the broker and TPA happen to send over. We treat it as something different. The practice rests on three principles.
The Form 5500 is the most candid public document an employer produces about its benefits program. We read it accordingly.
Every filing that leaves the practice is reviewed by a senior preparer. There is no second tier of staff, and no junior-to-partner handoff at deadline.
Reconciliation against source is the work, not a courtesy. We surface discrepancies — and the recommendations they warrant — before the regulator does.
Each engagement draws on a defined set of capabilities developed expressly around health and welfare plan compliance. We do not staff generalists, and we do not subcontract the work that bears our name.
A structured review of plan documents, SPDs, wrap arrangements, and operational data — surfacing the gaps between what the plan says, what the carrier reports, and what the employer is actually administering.
Capability brief →Original-year preparation, peer review of in-flight filings, and DFVC-program remediation for late or omitted returns. Every filing is reviewed by a senior preparer before it leaves the practice.
Capability brief →A line-by-line examination of broker, consultant, and carrier compensation disclosures — reconciled against CAA §202 requirements and the plan's own service-provider agreements.
Capability brief →Pre-audit document organization, response drafting, and on-the-record support during DOL or IRS examination. We prepare employers for inquiry, and we answer the inquiry itself.
Capability brief →Specialist support engaged through your broker, audit, or legal team — preserving the client relationship while extending technical depth on the questions that warrant a dedicated practitioner.
Capability brief →"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.
Confidence that the filing reflects the plan, that the plan reflects current law, and that the next inquiry from the DOL — or from the audit committee — will not be the first time you hear of a problem.
Compliance depth your firm can stand behind without expanding headcount. We work white-label or co-branded; the client relationship remains yours throughout.
Operational and filing-level competence to complement counsel work — Form 5500 reconstruction, factual development, and quantitative analysis for matters under examination.
A referral relationship, or a behind-the-scenes preparer for clients whose health & welfare filings sit outside your firm's defined practice area.
A close reading of the Department of Labor's most recent guidance on welfare plan compensation disclosure, the questions it answers for filers, and the larger questions it leaves to interpretation by the regulated community.
Patterns we see in third-party filings — and the corrective approach we take when remediation is preferable to amendment.
From the first letter through the on-site interview, the documentation the employer should have already assembled — and the documentation it almost certainly has not.
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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