Anthropic 10b5-1 Trading Plan Guide

By Joe Forish, CFA, CFP®|Published On: Oct 5, 2026|Categories: Financial Planning|

For most of your career at Anthropic, an Anthropic 10b5-1 trading plan probably sounded like something executives worried about — not you. You had options and RSUs. There was no public market. Nobody was watching your trades, because there were no trades to watch.

That changes with the IPO.

Once Anthropic goes public in November 2026, a new regulatory reality kicks in. If you’re an officer, director, or an employee Anthropic designates as a restricted person under its trading policy, insider trading rules will govern when you can sell your shares. The Anthropic 10b5-1 trading plan is the primary tool that gives you flexibility to sell outside of narrow trading windows — and it comes with rules and timing constraints that are already more compressed than most employees realize. There’s a newer wrinkle: according to Reuters, Anthropic is considering requiring even rank-and-file employees — not just senior leadership — to sell shares through preset 10b5-1 trading plans. If that policy is adopted, it would be an unusual step, and it means this guide is relevant to far more Anthropic employees than it might appear.

What Is a 10b5-1 Trading Plan?

Rule 10b5-1 of the Securities Exchange Act creates an affirmative defense against insider trading liability. The rule lets insiders — executives, directors, and employees with access to material non-public information (MNPI) — sell company stock on a pre-scheduled basis, provided they set up the plan at a time when they weren’t aware of any MNPI.

The mechanics are straightforward. You work with a financial advisor to create a written agreement that specifies exactly when and how your shares will sell. The plan can set exact dates (“sell 500 shares on the first trading day of each month”), price thresholds (“sell 1,000 shares if the stock exceeds $X”), or a formula combining both.

Once adopted and the required cooling-off period passes, your custodian executes the trades automatically — without any further input from you. That’s the key feature: you’re out of the loop. The trades happen mechanically, which is precisely why the 10b5-1 defense works. Your plan existed before you knew anything that could have influenced it.

What the 2023 SEC Rule Changes Mean for Your Anthropic 10b5-1 Trading Plan

In December 2022, the SEC adopted significant amendments to Rule 10b5-1, which took effect in 2023. Older guides can give you a false sense of security about what the rules actually require.

Cooling-Off Periods: The Rule That Trips Up First-Timers

Under the amended rules, insiders must wait through a mandatory cooling-off period between adopting the plan and executing the first trade. The length depends on your role.

Officers and directors (Section 16 persons): The cooling-off period is the later of 90 days after adoption or the first quarterly or annual filing date after adoption — capped at 120 days total.

Other employees (non-officer/director): 30 days after plan adoption.

This distinction matters significantly for Anthropic employees. An engineer without officer status faces a 30-day wait. A VP-level officer, however, faces at least 90 days. Senior employees should confirm their classification before making any timing assumptions.

Who Needs a 10b5-1 Trading Plan at Anthropic?

Officers and Directors

If you’re a C-suite executive, a named officer in Anthropic’s public filings, or a board member, an Anthropic 10b5-1 trading plan is not optional — it’s the primary mechanism for selling shares in an orderly way after the IPO and lockup expiration. Your trading windows will be narrow, typically a few weeks after each quarterly earnings release. Any off-window sales without a plan will attract regulatory scrutiny.

Employees Named Under Anthropic’s Trading Policy

Anthropic will publish an insider trading policy when it goes public. That policy will name which employees qualify as “restricted persons” subject to trading window limitations. Employees in finance, legal, business development, and corporate development — essentially anyone with access to forward-looking financial information — commonly end up on this list. If you’re on it, a trading plan is likely the right vehicle for any planned liquidation.

Employees Who Want to Diversify Systematically

Even if Anthropic does not ultimately require rank-and-file employees to use a 10b5-1 plan, the structure offers real behavioral benefits. A pre-committed, automated selling schedule removes the temptation to time the market — a discipline most individual investors consistently fail to maintain on their own. And if the company does require it, you’ll already be prepared.

The Timeline Problem: November IPO, May 2027 Lockup

The IPO targets November 2026. Under a standard 180-day lockup, that means lockup expiration falls around May 2027. The instinct is to think: fine, I’ll set up the plan before the lockup ends.

But the problem with that instinct is that you can only adopt a 10b5-1 plan when you’re not in possession of MNPI — and for most of the period between the IPO and lockup expiration, you will be in possession of MNPI. Quarterly earnings, product announcements, regulatory developments: the ordinary flow of information inside a newly public company creates ongoing exposure. Lockup expiration doesn’t clean your information slate.

When Is the Right Window to Adopt Your Trading Plan?

For most employees, the right time to adopt is during an open trading window — the brief period after each earnings release when information is fully public and trading restrictions temporarily lift. These will likely occur in the near future:

Q4 2026 earnings release: Probably February or March 2027
Q1 2027 earnings release: Probably April or May 2027

If you’re an officer subject to the 90-day cooling-off period and you adopt during the Q4 earnings window in February 2027, your first eligible trade date lands in May 2027 — right when the lockup is also expiring. That’s threading a very specific needle, with zero room for delay.

The cleanest timeline for most employees: adopt the plan during an open trading window after the lockup has expired. This avoids the complexity of the lockup overlay entirely and gives you a cleaner, simpler setup.

How to Set Up Your Anthropic 10b5-1 Trading Plan

Setting up a plan is not a DIY project. Start by confirming your classification — officer, Section 16 reporting person, or designated insider under Anthropic’s trading policy — since that determines your cooling-off period and certification requirements. Once Anthropic is public, you’ll need pre-clearance from the company’s general counsel before adopting any plan, so don’t skip that step.

Engage a financial advisor and securities counsel early: the plan documentation requires legal review, and your trading schedule needs to be designed alongside your tax situation, not in a separate silo. Adopt only during an open trading window when you have no MNPI, then do nothing until the cooling-off period clears. Don’t modify the plan — amendments can restart the cooling-off period or undermine the 10b5-1 defense entirely. After that, your financial advisor handles everything automatically, and your securities counsel files the required Form 4 disclosures if you’re a Section 16 reporting person.

Coordinate Your Anthropic 10b5-1 Trading Plan With Your Tax Strategy

An Anthropic 10b5-1 trading plan sets your selling schedule. It doesn’t change how your shares get taxed. But your plan needs to be designed alongside your overall tax strategy — not as a separate document that exists in its own vacuum.

ISO shares carry more complexity. If you exercised ISOs before the IPO, you likely triggered AMT on the spread. Shares that meet the holding period requirements — two years from grant, one year from exercise — qualify for long-term capital gains treatment federally. California, however, taxes all capital gains as ordinary income regardless of holding period. Your plan needs to respect the ISO holding period calendar to avoid wasting favorable treatment you’ve already earned.

QSBS shares require separate consideration before you include them in any trading plan. In the rare event that you are an Anthropic employee that qualifies for QSBS, confirm your federal exclusion amount and California tax position first. California doesn’t conform to QSBS, so the state-level gain is fully taxable regardless of the federal outcome. Selling in the wrong order or at the wrong time can waste a meaningful federal exclusion.

AMT liability timing matters more than most employees anticipate. If you exercised ISOs in 2026, that tax bill comes due in April 2027 — one month before lockup expiration. Your trading plan and your AMT cash flow need to be designed together. Discovering in April that you’re illiquid with a six-figure tax bill is exactly the kind of problem a good advisor prevents.

Frequently Asked Questions: 10b5-1 Plans for Anthropic Employees

When can I adopt a 10b5-1 trading plan?

If you’re an officer or director, the cooling-off period is the later of 90 days or the first quarterly or annual filing date after adoption, capped at 120 days. Non-officers face a 30-day cooling-off period. Also, any material modification to an existing plan can trigger a new cooling-off period — so get the plan right before you adopt it.

Does a 10b5-1 plan let me sell shares during the lockup period?

No. The lockup agreement is a separate contract with the underwriters that prevents all share sales during the lockup period, regardless of any trading plan. An Anthropic 10b5-1 trading plan adopted during the lockup would not begin executing until after the lockup expires.

Can I cancel or modify my trading plan?

You can terminate a 10b5-1 plan at any time. Modification, however, is more restricted. Amending material terms typically triggers a new cooling-off period and may undermine the 10b5-1 defense if it appears the modification was influenced by MNPI. The SEC’s 2023 amendments increased scrutiny of plan modifications significantly. In general, adopt a plan you’re comfortable holding to completion.

Do I need a lawyer to set up a 10b5-1 plan?

Possibly. According to Reuters, Anthropic is considering requiring rank-and-file employees — not just officers and directors — to sell shares through preset 10b5-1 trading plans after the IPO. This would be an unusual policy; most public companies only impose plan requirements on senior leadership. The proposal is still under discussion as of this writing. If it is adopted and you receive any equity as an Anthropic employee, you should assume you will need a plan in place before you can sell any shares.

The Clock Is Already Running

Lockup expiration is May 2027. The first open trading window after the IPO is probably February or March 2027, at the earliest. An officer subject to a 90-day cooling-off period who adopts in February gets a first eligible trade date in May, threading the needle, for sure.

That timeline requires knowing your classification now, having Anthropic’s trading policy in hand the moment it’s published, and adopting on the first available day of the first open window. The employees who pull this off have been thinking about their Anthropic 10b5-1 trading plan since before the S-1.

The employees who start thinking about it in April 2027 have to wait until at least August 2027 to act upon it.

Schedule a free consultation with Fortrove Partners →