It’s July, and if you work at a publicly traded tech company, you know what that means.

The quiet period is probably over (or ending soon). The quarterly earnings call has happened. The blackout window has lifted. And for the first time in weeks, you’re actually allowed to sell company stock.

Summer, particularly the window between earnings releases, is one of the best times of year for tech professionals to strategically sell and diversify their equity holdings.

But here’s what I see all the time. People know they should diversify. They know they’re overconcentrated in company stock. But they don’t have a plan for when and how to actually execute those sales.

So the quiet window opens, they think about it for a few days, and then the window closes again. And nothing happens. Again.

Let’s fix that. Let’s talk about how to strategically sell company stock during summer quiet periods without overthinking it, without trying to time the market, and without running into insider trading issues.

Understanding Trading Windows and Quiet Periods

If you’re new to equity compensation, the concept of trading windows might feel confusing. So let’s start with the basics.

Blackout Periods: These are times when you’re prohibited from trading company stock. They typically begin a few weeks before quarterly earnings and end a day or two after the earnings are released. This is to prevent insider trading, the idea being that employees might have access to material non-public information during this time.

Quiet Periods (or Trading Windows): These are the times when you’re allowed to trade. For most public companies, quiet periods last about six to eight weeks per quarter, usually starting right after earnings are announced.

Your Personal Trading Window: Some employees (executives, certain finance/legal roles) have additional restrictions beyond the company-wide blackout. If you’re in one of these roles, you need to check with your legal or compliance team before trading.

The summer months (July through early September, depending on your company’s fiscal calendar) often include one or two solid trading windows, making it an ideal time to execute planned stock sales.

Why Summer Is Prime Time for Strategic Selling

There are a few reasons why summer is particularly good for diversifying your company stock holdings.

Longer Trading Windows: Q2 and Q3 earnings are often spaced out in a way that gives you more trading flexibility than Q4 (when everyone is scrambling before year-end) or Q1 (when new equity grants and vesting schedules kick in).

Emotional Distance from Big Vests: If you had a major RSU vest earlier in the year, summer is far enough removed that you’re not caught up in the excitement (or anxiety) of the vest itself. You can make more rational decisions.

Tax Planning Opportunity: Selling in July gives you visibility into your income for the year and allows you to plan for any tax-loss harvesting or charitable giving strategies later in the year.

Less Year-End Pressure: Selling in summer means you’re not trying to squeeze trades into a compressed December window when everyone else is also trying to rebalance.

The Strategic Selling Framework

Okay, so you’re in a trading window. You know you need to diversify. How do you actually decide how much to sell?

Here’s the framework I use with clients.

Step One: Know Your Target Allocation

Before you sell anything, you need to know what you’re aiming for. What percentage of your total portfolio should be in company stock?

For most tech professionals, I recommend keeping company stock at 10% to 15% of your total investable assets. Some people are comfortable going up to 20%, but that’s pushing it.

If you’re currently sitting at 30%, 40%, or 50% in company stock, you need to sell enough to get back into that 10% to 20% range.

Step Two: Calculate the Gap

Let’s say your total portfolio is worth $500,000, and $200,000 of that is company stock. That’s 40%.

Your target is 15%, which would be $75,000.

That means you need to sell about $125,000 worth of company stock to hit your target allocation.

Step Three: Decide on a Selling Timeline

You don’t have to sell it all at once. In fact, I usually recommend spreading sales out over multiple trading windows.

Selling in tranches (say, $40,000 this quarter, $40,000 next quarter, and $45,000 in Q4) smooths out market volatility and makes the decision feel less dramatic.

Step Four: Execute During the Trading Window

Once you’ve decided how much to sell, place the trade during the quiet period. Don’t wait until the last day of the window. Give yourself a cushion in case there are any issues with your brokerage or compliance approval process.

The Psychological Barriers to Selling (and How to Overcome Them)

Knowing you should sell and actually doing it are two different things. Here are the mental blocks I see most often.

“But what if the stock goes up after I sell?”

It might. That’s the risk of any investment decision. But here’s the thing: you’re not selling because you think the stock is going to crash. You’re selling to reduce concentration risk and protect your overall financial plan.

If the stock does go up after you sell, you still own some of it (remember, you’re keeping 10% to 15% of your portfolio in company stock). So you still benefit from the upside. You’re just not betting your entire financial future on one company.

“I feel disloyal selling my company’s stock.”

I get it. You work there. You believe in the mission. You helped build this thing.

But holding company stock is not a test of loyalty. Your compensation package already ties a significant portion of your financial well-being to the company’s success (salary, bonus, future equity vests, career trajectory).

Diversifying your already-vested stock is just smart risk management.

“I’m going to owe a ton in taxes if I sell.”

Yes, you will owe capital gains tax on the appreciation. But you know what’s worse than paying taxes on a gain? Watching the stock tank and not having any gain left to tax.

Taxes are the cost of making money. If your shares have appreciated significantly, paying taxes means you won the game. Celebrate that.

Tax-Smart Selling Strategies

Since we’re talking about taxes, let’s talk about how to minimize them.

Sell Shares with the Highest Cost Basis First

If you’ve been accumulating company stock over time through multiple RSU vests, you likely have shares with different cost bases.

Selling shares with the highest cost basis (the shares that have appreciated the least) will minimize your capital gains tax.

Most brokerages let you specify which “tax lots” you want to sell. Choose “highest cost” or manually select the lots with the smallest gains.

Pair Sales with Tax-Loss Harvesting

If you have other investments sitting at a loss, you can sell those in the same year to offset the capital gains from your company stock sale.

This is called tax-loss harvesting, and it’s a smart way to reduce your overall tax bill.

Consider Donating Appreciated Shares

If you’re charitably inclined, donating appreciated company stock directly to a charity or donor-advised fund is one of the most tax-efficient moves you can make.

You get a tax deduction for the full fair market value of the shares, and you avoid paying capital gains tax on the appreciation.

For example, if you bought shares at $50 and they’re now worth $150, donating them saves you capital gains tax on the $100 gain plus gives you a $150 charitable deduction.

What to Do with the Cash After You Sell

Okay, you sold some company stock. Now you have cash sitting in your brokerage account. Don’t let it just sit there.

Reinvest it into a diversified portfolio that aligns with your risk tolerance and values.

This might include:

• Broad market index funds (domestic and international)
• Bond funds for stability
• Real estate investment trusts (REITs)
• Socially responsible or ESG-focused funds

The goal is to spread your wealth across different asset classes, geographies, and sectors so that no single company’s performance makes or breaks your financial plan.

Common Mistakes to Avoid

Let’s talk about what not to do.

Mistake #1: Trying to Time the Market

Don’t wait for the stock to hit some arbitrary price target before selling. The “I’ll sell when it hits $200” strategy usually backfires because the stock either never gets there or you move the goalposts when it does.

Stick to your allocation targets and sell based on those, not on price predictions.

Mistake #2: Selling Too Much Too Fast

If you’re massively overconcentrated (like 70% company stock), it can be tempting to sell it all and rebalance in one shot.

But that can trigger a huge tax bill and might not be the best use of your trading windows. Spread the sales out over a year or two for smoother tax management.

Mistake #3: Forgetting About Estimated Taxes

If you’re going to realize significant capital gains from stock sales, you might need to make estimated tax payments to avoid underpayment penalties.

Talk to a tax professional about whether you need to adjust your withholding or pay quarterly estimated taxes.

Your Summer Stock Sale Action Plan

Let’s make this concrete. Here’s what to do in the next 30 days.

This Week:

• Check when your company’s next trading window opens
• Calculate your current company stock as a percentage of your total portfolio
• Decide on your target allocation (10% to 20% is a good range)

Before the Trading Window Closes:

• Calculate how many shares you need to sell to hit your target
• Decide whether to sell all at once or spread over multiple windows
• Place the sell order (use highest cost basis shares to minimize taxes)

After the Sale:

• Reinvest the proceeds into a diversified portfolio
• Update your financial plan to reflect the new allocation
• Set a reminder to rebalance again in six months

And if you’re not sure how much to sell, or you want someone to review your equity compensation strategy, let’s talk.

Let’s Build a Diversification Plan That Works

If you’re sitting on a concentrated position in company stock and you know you need to diversify but you’re not sure where to start, I can help.

We’ll review your full financial picture, calculate your optimal allocation, and build a strategic selling plan that reduces risk without triggering unnecessary taxes.

Schedule a consultation at wovencapital.net/schedule and let’s make sure this summer trading window doesn’t pass you by.