Insights

The math often says max it out. But the right contribution rate depends on your cash flow, your concentration in company stock, and how this benefit fits your bigger picture.     You understand what your ESPP is. You know how the discount and lookback work. You know the tax rules. Now comes the question

Your broker sends a 1099-B when you sell ESPP shares. But the cost basis on that form is often incomplete or understated, and filing without adjusting it often means paying tax twice on the same income.     Tax season is when ESPP mistakes become expensive. The most common one is not a decision error.

When you sell your ESPP shares matters more than most people realize. The timing alone can change how your gains are taxed and how much you actually keep. When you sell your ESPP shares matters more than most people realize. The timing of your sale relative to your purchase date and your original enrollment date

The discount is just the starting point. Here is how the lookback provision amplifies it and what that means for your decision to participate.     The discount is why people enroll in an ESPP. But understanding how that discount is calculated, and what a lookback provision adds to it, is what separates employees who

You opted in to your ESPP. Here is exactly what happens between enrollment and the purchase date and what you need to know to make the most of it.     You decided to participate in your company’s ESPP. Now what? The enrollment process seems simple on the surface. You pick a contribution percentage and

What is an ESPP, and why does it matter? ESPPs are one of the most underused benefits in tech compensation. This post breaks down exactly how they work and why they are worth paying attention to.     If you work in tech, you have probably seen ESPP in your benefits enrollment portal. Maybe you