Make your Workday equity work as hard as you did.
Devin Satterthwaite spent 15 years as a Workmate in Sales and Services. He know the Fidelity plan, the ESPP mechanics, the BrokerageLink window most Workmates never open, and the RSU withholding trap that hits every April. Devin now helps current and former Workmates turning their comp into actual wealth — before the tax decisions get made for them.
Three reasons standard planning falls short for Workday comp
Workday withholds federal taxes on RSU vests at the IRS supplemental rate — 22%. If you're filing jointly at a household income above $384K, you likely owe 32%. That gap on a single vest can mean a $1,800+ surprise check to the IRS every April. It's a five-minute W-4 fix most Workmates never make.
By the time your RSUs hit your E*TRADE account, most of the tax decisions are already locked in. The planning that actually moves the needle — ESPP hold vs. sell timing, capital gains sequencing — happens in the months before, not on April 14th.
Add it up: your vested RSUs, your held ESPP shares, your 401k index fund with 32% tech exposure, and any WDAY in a personal brokerage. For a Workmate with 4+ years of tenure who hasn't actively diversified, Workday stock can easily be 30-50% of liquid net worth. J.P. Morgan flags concentration risk at 30%. T. Rowe Price flags it at 10%. Most Workmates are somewhere in between and don't know it.
What changes when we plan together
Here is exactly how Devin translates your equity, taxes, and timeline into a strategy built around how you actually want to live.
RSU tax planning
Forward-looking strategies around your quarterly vest schedule, supplemental withholding adjustments, and capital gains timing. Before the vest lands, not after.
ESPP optimization
The hold vs. sell decision isn't just about tax treatment. It's about how much of your net worth is already tied to a single ticker. We build a plan that accounts for both.
Fidelity BrokerageLink
Most Workmates default to the 26-fund menu and never touch it. BrokerageLink opens a self-directed sub-account inside your active 401k — no rollover, no taxes, no impact on your company match. You go from 26 mutual funds to thousands of ETFs and individual securities. It's a 5-minute activation toggle in the Fidelity portal.
Concentration and diversification
A written plan for when, how much, and in what sequence to diversify out of WDAY, built around your tax bracket, vest schedule, and timeline.
Exit and sabbatical modeling
Whether you're planning your W2 exit, approaching your 10-year sabbatical, or just running the numbers — I'll show you exactly what financial independence looks like given your current comp, vest schedule, and savings rate.
Your complimentary 30-minute call includes:
No slides, no pitch deck. Whether or not we work together is entirely up to you.in this section
We'll add up your WDAY exposure across RSUs, ESPP, 401k, and brokerage and see where you
I'll flag the gap between what Workday withholds and what you likely owe before your next vest date.
