"Are we reserving appropriately? If we have a bad year next year, what's it going to cost the partners?"

It's the question Richard Silberstein heard from a CEO at a coffee shop, and it's the same question CFOs of self-insured employers are asking across the country right now.

In this episode of Benefits Redefined, Richard is joined again by Prabal Lakhanpal, National Practice Leader for Alternate Risk and Captives at Alera Group, to unpack how to actually answer it.

They cover:

→  How to evaluate whether your medical claims reserves are appropriate, using Monte Carlo simulation and confidence level analysis

→  Why most auditors will not accept reserves above the 70-80% confidence threshold, and what that means for partnership tax planning

→  The difference between being a buyer of insurance and a trader of insurance, and why captives change the math

→  Why medical stop loss is priced like a 1-in-1 year event when the coverage is built for 1 in 5

→  How combining short tail risks like stop loss with long tail risks like workers comp creates a diversified, more stable portfolio

→  The 500 employee, $2 million premium threshold where alternate risk strategies start to make sense

→  How adding employee benefits to an existing property and casualty captive can drive admin cost efficiency straight to the bottom line

→  Group captives as the solution for smaller employers who want access without the infrastructure build

→  Where fiduciary duty intersects with captive strategy, and why CFOs and HR leaders should be in the same conversation

Whether you're a CFO weighing alternate risk, an HR leader trying to bring enterprise thinking to your benefits strategy, or a benefits committee member wrestling with reserve adequacy, this conversation gives you a working framework.

GUEST Prabal Lakhanpal, National Practice Leader, Alternate Risk and Captives, Alera Group | https://www.linkedin.com/in/praballakhanpal/

Want to learn more? Connect with Richard via our website: www.benefitsredefined.com 

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Most CFOs believe their health plan is under control. They shop it every year. They have a trusted broker. Then they score the plan — and come back a 50 out of 100.

Richard Silberstein talks with Tina Wilt, GBA — Charter Health Rosetta Advisor with nearly 30 years employer-side experience and the architect of a community-owned health plan — about the Plan Grader™, the 40-question assessment that scores employer health plans on a 0–100 scale.

Tina explains what the score actually means, what separates a 50 from a 70, and why she has seen up to 40% savings between a legacy plan and a fully optimized one. We also cover direct primary care, the LOCAL framework, and what employers can do off-renewal to move the needle.

CHAPTERS

0:00 Intro

1:39 Meet Tina Wilt 2:50 Community-owned health plans

3:31 Direct primary care

5:10 What is Health Rosetta?

7:39 The Plan Grader™

13:24 The question that surprises every CFO

17:23 The $1,200 vs. $3,000 MRI

18:37 What a 50 vs. 70 score is worth

21:15 Up to 40% savings — real-world examples

25:17 The LOCAL framework

30:16 Close

GUEST Tina Wilt, GBA — Alera Group | https://www.linkedin.com/in/tina-wilt-gba-64507612/

LEARN MORE Health Rosetta: https://healthrosetta.org

Connect with Richard: www.benefitsredefined.com

Want to learn more? Connect with Richard via our website: https://www.benefitsredefined.com

PBM reform is gaining attention — but what does it actually change for employers?

Wellbeing is evolving from a program to a strategic priority. Richard speaks with Gretchen Day about how organizations are rethinking workforce health.

Connect with Gretchen: https://www.linkedin.com/in/gretchenday/

Want to learn more? Connect with Richard via our website: https://www.benefitsredefined.com

Captives are gaining attention — but many employers misunderstand how they actually work.

As interest grows, so does the need to separate common assumptions from real-world application.

In this episode of Benefits, Redefined, Richard speaks with Don Balla about how captives fit into today’s market.

You’ll learn:

Connect with Don: https://www.linkedin.com/in/donballa/

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Want to learn more? Connect with Richard via our website: https://www.benefitsredefined.com

Employee benefits are no longer just an HR expense — they are becoming one of the largest and fastest-growing line items on an organization’s P&L.

In this episode of Benefits, Redefined, Richard Silberstein sits down with Prabal Lakhanpal, National Practice Leader of Alternative Risk and Captives, to explore how employers are rethinking the way they fund and manage healthcare risk.

The conversation covers:

This episode is particularly relevant for CFOs, CHROs, and executives looking to better understand how to bring more control, transparency, and long-term strategy to their health plans.

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Connect with Prabal: https://www.linkedin.com/in/praballakhanpal/

Want to learn more? Connect with Richard via our website: https://www.benefitsredefined.com/

Are your healthcare costs secretly out of control?

Most employers are paying way more than they should—and you can fix it.

In this episode, we talk about clinical oversight and advocacy—how companies can prevent huge medical bills and save money. Richard talks with Julie Kueppers, Vice President of Clinical Analytics and Advocacy, about creative ways employers and employees can save on their benefits by implementing clinical review.

You’ll learn:

If you work in HR, finance, or benefits, this episode is packed with simple tips and real-world examples to help your company save money and keep employees healthy.

Comment below: What’s your biggest challenge with employee healthcare costs?

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Connect with Julie: https://www.linkedin.com/in/juliekueppers/

Want to learn more? Connect with Richard via our website: https://www.benefitsredefined.com

PBM reform is gaining attention — but what does it actually change for employers?

While legislation continues to evolve, many organizations are still left with the same question: what should we be doing differently today?

In this episode of Benefits, Redefined, Richard speaks with Kevin Gregory about the practical implications of PBM reform.

You’ll learn:

Subscribe to stay up to date with the latest episodes.

https://www.linkedin.com/in/kevin-gregory-a217691/

Want to learn more? Visit our website: https://www.benefitsredefined.com

Pharmacy spend is quickly becoming one of the largest and least understood drivers of employer healthcare costs. Many employers assume these costs are unavoidable—but that’s often not the case.

In this episode of Benefits Redefined, Richard speaks with Jennifer Perlitch, Clinical Pharmacist, about what employers are missing when it comes to pharmacy benefits and why looking “under the hood” of your PBM and drug data can reveal significant savings opportunities.

Jennifer works directly with employers reviewing pharmacy claims, contracts, and utilization patterns to uncover hidden costs, missed rebates, and opportunities to improve both outcomes and spending.

If you’re responsible for benefits strategy, healthcare budgets, or financial planning, this conversation will help you understand where pharmacy costs are really coming from—and what smart employers are doing differently.

In this episode, you’ll learn:

- Why many employers are unknowingly overpaying for GLP-1 medications and what alternatives may dramatically reduce costs.

- How PBM rebate structures actually work—and why shrinking rebates and “rebate credits” could significantly impact employer budgets in 2026 and beyond.

- What specialty drugs and biosimilars mean for your plan’s future costs, and how the right strategy can prevent unexpected spikes in spend.

- The single biggest mistake employers make during PBM reviews—and the critical questions CFOs and HR leaders should be asking instead.

For many organizations, pharmacy spend is increasing faster than any other part of their health plan. The employers who manage it well are the ones who actively analyze their data, challenge their PBM contracts, and bring clinical expertise into the decision process.

If you're a CFO, CHRO, or HR executive responsible for healthcare costs, this episode will give you a clearer picture of where risks—and opportunities—may exist in your current pharmacy strategy.

If you'd like to explore whether similar opportunities exist in your plan, you can connect with Richard through the Benefits Redefined website above.

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Connect with Jennifer: https://www.linkedin.com/in/jennifer-perlitch-0357923/

Comment below:

What has been the biggest challenge managing pharmacy costs in your organization?

Want to learn more? Visit our website: https://www.benefitsredefined.com

Fiduciary responsibility in employee benefits is evolving — and many employers may not fully understand their exposure.

In this episode of Benefits, Redefined, Richard Silberstein sits down with ERISA attorney Stacy Barrow to discuss how fiduciary risk is expanding beyond retirement plans into health plans, PBMs, and even voluntary benefits.

Topics include:

The growing wave of fiduciary litigation

How PBM arrangements are being scrutinized

Risks tied to voluntary benefits and vendor relationships

What employers should be doing now to mitigate exposure

This conversation is essential for CFOs, CHROs, and executives responsible for governance and oversight. Subscribe to stay up to date with our latest episodes.

Connect with Stacy: https://www.linkedin.com/in/stacy-barrow-21a9133/