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The Wellness Stipend Playbook: What to Include, What to Exclude, and What Your Employees Won’t Tell You

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  • Last Updated on September 17, 2026
  • 10 mins
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Table of Contents

A conversation with Samantha Levin, Wellness Program Manager 

Wellness stipend is one of those benefits that can go either way. Done well, it uplifts your employee population, motivates them, and has a genuinely significant effect on their health outcomes. Done poorly, it’s either abused or just an inefficient waste of money. The delivery mode has enormous potential — but more often than not, it isn’t implemented as effectively as it should be. 

This piece comes out of a conversation with Samantha Levin, a wellness program manager who has helped hundreds of employers roll out employee wellness programs. We covered a lot of ground, and the collation of it is what you’ll find below. 

Watch the full conversation with Samantha Levin below for the primary source behind this piece. 

What a wellness stipend actually is 

A wellness stipend is a monetary benefit given by an employer to employees, redeemable for certain wellness-related activities and expenditures. In most cases, the eligible categories are defined upfront by the employer. In some cases, employees have complete freedom to spend it however they choose — but that’s the rarer setup. 

One thing people often ask: is it taxable? Yes, it is. It’s treated as any other form of monetary income and taxed accordingly.   

Why most wellness stipends are inefficient

When employees are given free will over how to spend their stipend, they tend to spend it on things they want rather than things they need. Samantha has seen this play out in some pretty absurd ways — hot tubs, wine subscriptions, purchases that are more desire than genuine wellness investment. These might give a short-term dopamine hit, but the long-term effect is marginal. They don’t help employees lead a better life. 

So the obvious question becomes: is the answer to design the entire program from an organizational level and roll it out unilaterally? No, that’s not the right approach either. And I’ll come back to why. 

What to include — and what to exclude

There’s a lot of content out there on “25 ways to spend your wellness stipend.” What I want to cover here is different: both sides of the equation — what belongs in a well-designed program and what doesn’t. 

I asked Samantha directly: what do you include, and what do you exclude? Her answer was clearly shaped by a lot of experience across a lot of different organizations and population groups. 

Include: 

  • Mental health — therapy, mindfulness, meditation, stress management. The basics, but essential. 
  • Physical health — gym memberships, yoga classes, anything that keeps employees physically active and fit. 
  • Financial health — this one gets excluded far too often, and that’s a significant blind spot. Financial stress is one of the biggest drivers of poor health outcomes. Something as simple as allocating a portion of the stipend toward tax preparation assistance or financial planning can make a real difference. 

Exclude: 

Big desire-driven purchases — the hot tubs, the home improvement, the wine subscriptions, the vacation spending. These eat into the budget without delivering meaningful, lasting wellness outcomes. Samantha put it well: the stipend should go toward things employees wouldn’t typically spend on themselves, not things they simply want. 

The survey step people skip 

Here’s the tension: if you give employees complete freedom, they’ll spend on things that don’t move the needle. But if you design the entire program top-down without any input, you risk building something that doesn’t actually reflect what your population needs — and employees won’t feel ownership over it. 

The answer is to gather insight before you finalize the program. Engagement surveys and pulse surveys are the right tool here. They help you understand the general tone of what your employees actually want, so you’re designing with them rather than at them. Wellness360 can help with this, as can a number of other platforms — the point is that the data should inform the design. 

The things employees need but won't say out loud 

This was the most interesting part of the conversation with Samantha, and it’s the piece most organizations completely miss. 

There are things employees genuinely need that they’ll never raise their hand and ask for — not because they don’t want them, but because they’re afraid of being judged, or they don’t know how many others feel the same way, or it simply feels too personal to bring up at work. These unspoken needs are often the things that, if addressed, would make the biggest difference. 

Samantha brought up relationship building as a prime example — couples counseling, communication skills classes, fellowship opportunities with colleagues. These are things people know they need and want, but rarely ask for in a professional context. Another one she flagged: addiction recovery support. Employers may see signals in aggregate HRA data that a percentage of their population is at risk, but employees aren’t going to volunteer that information or ask for help unless there’s a clear, safe channel to do so. 

The way to surface these needs is through anonymous feedback collection. Even a simple anonymous survey can reveal what people need but aren’t willing to say publicly. Wellness360 supports this, but any anonymous collection tool will do the job. What it unlocks is a layer of insight that can completely change the effectiveness of your stipend program.

The fundamentals, summarized 

If you’re responsible for designing or rolling out a wellness stipend program, here’s what this comes down to: 

  1. Cover the full spectrum of wellness — mental, physical, and financial. Financial wellness in particular is underinvested and high-impact. 
  2. Exclude desire-driven purchases that deliver short-term satisfaction but no lasting health outcome. 
  3. Don’t design in a vacuum — use surveys to understand what your population actually wants before you finalize the structure. 
  4. Go one level deeper — anonymous feedback will surface the needs employees are hesitant to voice, and addressing those is where you can make a real difference. 

 

A wellness stipend done right isn’t just a perk. It’s a signal to your employees that their health — all of it — actually matters to the organization. 

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