Confidential advisory services for mid-market employers

Before You Hire Another Benefits Leader,
Confirm the Problem You’re Actually Trying to Solve.

I run a short, confidential assessment that helps mid-market leadership determine whether hiring alone will actually stabilize their benefits operations — or whether structural issues will persist regardless of who fills the role.

Who this is for

This is designed for organizations with 500–1,500 employees who are:

  • Planning to hire a Benefits Program Manager or senior benefits leader
  • Experiencing repeated enrollment issues, escalations, or system strain
  • Carrying unresolved operational or compliance risk tied to benefits execution

If none of the above apply, this assessment is likely unnecessary.

Why Hiring Alone Often Doesn’t Work

Most benefits problems don’t originate with individual performance.

They originate with:

  • Unclear ownership
  • Fragile handoffs between systems and vendors
  • Informal governance and exception-based work
  • Risk that compounds quietly until it escalates

When those conditions exist, hiring a capable leader often absorbs the chaos rather than resolving it. This assessment exists to surface those conditions before a long-term hire is made.

What the Assessment Covers

The engagement is a time-bound, non-disruptive review of how benefits operate today, focused on decision clarity — not implementation.

It examines:

  • Leadership intent and decision context
  • How benefits work in practice (not on paper)
  • HRIS and benefits governance patterns
  • Operational and execution risk exposure
  • Whether hiring alone can realistically stabilize conditions

The output is an executive-level decision brief, not a task list.

What This Is Not

This assessment does not include:

  • System configuration or implementation
  • Vendor audits or RFP support
  • Legal interpretation or compliance remediation
  • Tactical process redesign

Its value is in synthesis, framing, and consequence mapping — not execution.

How the Engagement Works

  1. Short leadership interviews (confidential, de-identified)
  2. Synthesis across systems, people, and risk
  3. Executive decision brief outlining viable paths forward

The engagement is intentionally scoped to minimize disruption and internal friction.

Timing & Investment

The assessment is typically completed within 3–4 weeks, depending on availability. Investment varies based on organizational complexity and scope, and is confirmed after a brief fit check to ensure relevance. Work begins only once scope and terms are mutually agreed.

Discretion Matters

This work is conducted quietly and is designed for leadership decision-making, not internal broadcasting. Findings are context-specific and not intended for reuse outside the organization without continued advisory support.

Request a Fit Check

A short exchange to confirm whether this assessment is appropriate for your situation.

Let's Fit Check →

© All About the Benefits

Confidential advisory services for mid-market employers