James
Fortune 500 Senior Vice President
Stock Options & Executive Planning
Their World
James is a Senior VP at a Fortune 100 company with 22 years of tenure. His equity accumulation is substantial: hundreds of thousands of shares across options and restricted stock. He's three to five years from retirement and needs to figure out how to convert decades of equity compensation into a sustainable retirement income stream without triggering unnecessary taxes.
The Complexity
James has options at six different strike prices with varying expiration dates. Some are deep in the money, others are underwater. His restricted stock vests quarterly, creating regular taxable events. He needs to coordinate exercises and sales around quarterly blackout windows, 10b5-1 plan rules, and his company's insider trading policy. His golden parachute provisions add another layer if there's a change of control before he retires.
The Tesseract Way
Your Personal CFO creates a multi-year equity liquidation plan optimized for tax efficiency: which options to exercise first, how to layer sales across tax years, and when to trigger NUA treatment on company stock in his 401(k). James sees a year-by-year roadmap from today to retirement with projected cash flows at every stage.
Your Dashboard View
A glimpse of what James's Personal CFO dashboard looks like.
Tesseract Dashboard
James
Total Net Worth
$28,000,000
Projected Annual Tax Savings
$610,000
Through optimized strategy
Action Items
- 1Review option exercise priority by expiration date
- 2Update 10b5-1 plan for Q3
- 3Model retirement income scenarios at ages 60, 62, 65
Upcoming Deadlines
Option Lot Expiration
Aug 15, 2026
Blackout Window Starts
Jun 15, 2026
This Could Be Your View
See your complete financial picture in one place.