Disclaimer: I am an amateur. I did spend a few hours researching and modeling this. But there is always the possibility I used bad information or, more likely, made a mistake.
My current employer is the first with an Employee Stock Purchase Plan (ESPP). As is typical with such plans, it offers a 15% discount, and up to 10% of one's base salary can be directed to the ESPP. So even if you are generally disinclined to invest in specific stocks, as opposed to broadly diversified mutual funds, this is too good a deal to pass up.
However, what I didn't realize until recently, when I had reason to sell some of the stock, was that it is better than a 15% discount. Considerably better, for several reasons.
First, getting to allocate 10% of your base salary to stock, and buying it at a 15% discount, sounds like a 1.5% bonus. But the benefit is actually the reciprocal of 1.00 - 0.85, or 17.6%. So noticeably better than a straight 15%.
Then there are the tax effects. Two considerations here. First, Qualified ESPPs are not subject to payroll taxes[1]. So no 7.65% FICA. Second, so long as you hold the stock long enough[2], that discount is taxed as long-term capital gains, rather than ordinary income. Your mileage will vary, depending on tax bracket, but a typical scenario would be a 15% rate, rather than 28%. The state's bite, in my state of MN, is unchanged at about 8%. So instead of a total FICA + Fed income tax + State income tax bite of 42%, your rate is only 23%. That means your take home is .77/.58, or 32.7% greater.
So the 17.6% discount, multiplied by a 32.7% benefit from the tax treatment, gives you an effective benefit of 2.34% of your total income, assuming you invest the max 10%. More than a 50% increase in the apparent 1.5% benefit. Most 401k matching is 3%, so one way to view that 2.34% gift is that is almost doubles your 401k match.
But Wait, There's More!
There is more to that 401k parallel. Just as a 401k gives you the opportunity for tax-deferred compounding, so does ESPP compensation--so long as you hold the stock. (That does have a downside, though. Over time, you will accumulate a very large position in a single stock--the non-diversified anti-pattern. Worse yet, it is the stock of your own employer. So my preference is to flip the stock. Hold it long enough to get favorable tax treatment, but then sell it--even as you continue to buy more to get that discount on the new purchase.
One More Thing
Some ESPPs have a "look-back" provision. This establishes the purchase price as the lower of the price at the first day of the period or the last day of the period. This has a couple of benefits versus the last day of the period. In ordinary circumstances, the first day price would be a few percent lower than the last day price. So getting the first day price is more than ample compensation for having your contributions tied up for 6 months, earning no interest. Moreover, if the stock does particularly well, the value of the lookback is greatly increased. On the other hand, in the event of a downturn, you are still protected, receiving the last day price.
Notes
[1] I'm pretty sure this is true. I found websites that say this, but I had to look really hard, and some seemed to suggest that this might change.
[2] The holding period is tricky. Many people will know there is a 1-year holding period to receive the very favorable long-term capital gains rate. But it turns out there is a 2-year-from-grant-date for the discount to be treated as a capital gain, rather than ordinary income.
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