How to ask an AI chatbot about your vesting schedule and exercise history
Mike’s a CPF® at Secfi. He specializes in helping clients make the most of their stock options and integrate equity compensation into their broader financial plans.
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Mike’s a CPF® at Secfi. He specializes in helping clients make the most of their stock options and integrate equity compensation into their broader financial plans.
You can ask an AI chatbot about your vesting schedule and exercise history by using Maeve, Secfi’s AI equity assistant, connecting ChatGPT to Secfi’s MCP, or manually uploading your equity documents.
Maeve is built for equity planning inside Secfi, while Secfi’s MCP brings that data and calculation tools into external AI chatbots like ChatGPT. Regular AI chatbots can be helpful for basic questions, but have limitations that you may have already experienced, like confidently sharing answers that are slightly off, or giving different answers with similar prompts and context.
In this article, we’ll compare approaches to accessing your vesting schedule and exercise history in AI chatbots.
| Approach | Best for | Main limitation |
|---|---|---|
Maeve, Secfi’s AI equity assistant | Asking equity planning questions inside Secfi using Secfi’s data and tools, such as visualizations | Requires using an additional app rather than staying on your AI assistant of choice |
Secfi MCP for ChatGPT | Bringing Secfi’s equity data and calculation tools into the AI assistant you already use | Requires a Secfi account, authorization, and relevant equity details in Secfi |
Manual upload or copy-paste into an AI chatbot | One-off explanations, term definitions, or quick document summaries | Data can be incomplete, LLM may provide inconsistent or incorrect answers based on predictive text instead of calculations. |
An AI chatbot can explain equity terms without a connector. It can explain vesting or help you understand how stock options are taxed. If you upload PDFs or paste text directly into the chatbot, it can summarize and make inferences based on what you’ve provided.
But when the question becomes more complex, the chatbot needs accurate data and reliable calculation logic.
For example, to estimate the cost of exercising vested options, it may need your number of vested options, strike price, grant type, current fair market value, and exercise history. To estimate AMT exposure, it may also need income, filing status, state, deductions, dependents, and other tax inputs.
Without that data, a general chatbot may fill in gaps with assumptions that sound reasonable but do not match your situation. It may also make calculation errors, especially when several moving parts interact at once.
A connector gives the chatbot a way to request relevant data from another system instead of relying only on what you paste into the chat. Depending on the connector, it may also let the chatbot use dedicated calculation tools to help answer your questions.
Secfi’s Model Context Protocol (MCP) helps connect external AI chatbots like ChatGPT to Secfi’s equity data and planning tools.
This approach is useful if ChatGPT is already where you think through work or broader life planning, and you want your equity data included in that conversation.
“We’re bringing quality and precision into their AI experience,” says Robin Stordeur, Head of Product & Design at Secfi.
That means Secfi’s MCP can help external AI assistants use Secfi data and tools for questions such as:
How many vested options remain unexercised?
What would it cost to exercise my vested options?
What AMT exposure should I model if these are ISOs?
What tax withholding might apply if these are NSOs?
What might my shares be worth across different exit scenarios?
Could non-recourse financing help me exercise without using as much cash upfront?
A connected session stays active for 30 days before requesting re-authorization. Secfi’s MCP can only use personal data saved in your Secfi profile, so you may need to connect Carta where supported, upload your grant agreement, or add grant details manually first.
Secfi’s MCP gives the AI assistant a way to request structured data and use Secfi’s dedicated equity planning tools instead of relying only on manually copied details.
Maeve is Secfi’s AI equity assistant. It’s an AI chatbot in the broad sense because you can ask it questions in natural language and get conversational answers, but it’s built specifically for equity planning rather than general research.
Maeve can be useful when you want to ask questions about your stock options, vesting, exercise costs, AMT, taxes, exit scenarios, and financing inside the Secfi platform. Within the Maeve app, you also get tools and visualizations built with our custom UI for helping you to better understand your equity.
You can ask Maeve the same questions you’d ask Secfi’s MCP in ChatGPT.
For illustrative purposes only. Actual results may vary and there is no guarantee of any particular outcome.
Your company’s equity platform is still important. Depending on your company, that might mean Carta, Pulley, Shareworks, Capable, or another stock plan system. These platforms are usually where employees confirm official records, such as grant details, vesting schedules, strike prices, exercise history, and post-termination exercise deadlines.
Some equity and private-capital platforms are also building AI experiences on top of company data. Carta, for example, has Claude connectors packaged workflows that use MCP connections to access Carta data and support private-capital tasks.
That’s useful if you manage equity for your company, but it’s different from employee-side equity planning. For most employees, the equity platform is best understood as the place to confirm official records.
AI outputs can provide helpful educational context, but high-stakes financial decisions require verification against official records.
Confirm grant details against official records. Verify your grant type, share count, strike price, vesting schedule, and exercise history against your official equity platform or company documents.
Verify that your data is current. Tax estimates can change when your company’s fair market value or 409A valuation changes.
Check option types and exercise deadlines. Confirm whether your grants are Incentive Stock Options (ISOs) or Non-Qualified Stock Options (NSOs), and check your post-termination exercise window if you are leaving or recently left your startup.
Review tax calculations with a tax advisor. AMT exposure, NSO withholding, state tax residency, and equity sale timing can all depend on your individual situation.
Treat AI outputs as educational context rather than formal advice. Review major exercise, sale, financing, or investment decisions with the appropriate legal, tax, or financial professional before acting.
You can ask an AI chatbot about your vesting schedule and exercise history in a few different ways. Now you know that:
If you want a one-off explanation, uploading a document may be enough, as long as you do not look for precise numbers and calculations.
If you want a dedicated Secfi-native equity planning experience, use Maeve.
If you want to ask equity planning questions in ChatGPT, use Secfi’s MCP.
Give Secfi’s MCP or Maeve a try next time you have complex questions about your equity.
The tool shown here uses artificial intelligence and is for illustrative purposes only and not necessarily indicative of future results and there is no guarantee that similar results can be achieved. The information provided by the tool is not professional advice and is not intended by Secfi, Inc., its affiliates, and Secfi representatives, to be deemed as investment, legal, tax or other professional advice or recommendations of any kind, or to form the basis of any decision to do or to refrain from doing anything. Secfi does not review the accuracy or completeness of the information provided to us within the tool.