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For the 30-day window after you sign

You just signed a job offer with equity. Now the clock starts on six things nobody told you about.

Benefits enrollment closes in 30 days. The federal 401(k) cap counts across both employers. Your first RSU vest probably under-withholds. Clarity wires your accounts in, walks you through every deadline, and watches for the moves as they happen.

Get my new-job playbookTour the demo — no account needed

$1 for 7 days, then $19/mo or $179/yr. 30-day money-back guarantee.

Six time-bound things nobody tells you about

Each one is dateable, each one is expensive to miss, each one is invisible if you don't know to look. Clarity makes them all visible the day you start.

  • Benefits enrollment window

    Usually 30 days from start

    Health plan, FSA, HSA, dependent-care FSA, commuter, life insurance. Miss the window and most carry annual lockout. Clarity surfaces every deadline pulled from your offer.

  • 401(k) contribution cap progress

    Year-end matters

    Federal cap is per-person, not per-employer. Job change mid-year? You may already be closer to the cap than your new payroll knows. Clarity tracks YTD across employers and warns before over-contribution.

  • RSU vest tax setting

    Day of vest

    Default withholding is 22% federal — almost always too low for tech salaries. Clarity catches each vest as it lands and tells you how much extra to set aside before April.

  • ISO AMT clock

    Calendar year of exercise

    Exercise too many ISOs in a single year and you trigger AMT — a six-figure mistake hiding in plain sight. Clarity models the AMT line against your actual income and flags it before you exercise.

  • ESPP purchase window

    Typically every 6 months

    Most plans have a 15% discount + lookback that's free money — but only if you contribute the max before the purchase date. Clarity tracks contribution rate against the cap and the next purchase window.

  • HSA contribution cap

    April 15 of next year

    Triple-tax-advantaged and most people leave thousands on the table. Clarity tracks your YTD and reminds you before the cap closes.

Here's what the playbook looks like inside Clarity

Same component the app renders for real users — wired to demo data here. Each milestone row tracks status, due date, and the account it watches.

Active playbook

Starting a new job — Acme Corp

Day 3 · 2/7

Next move

Set 401(k) rate to 17% — gets you to the $23,000 cap by Dec without overshoot.

in 4d

  1. Connect new employer payroll account

  2. Confirm benefits enrollment deadline

    May 30 — Acme HR window

  3. Set 401(k) rate to hit $23,000 cap by Dec

    in 4d

  4. Decide on previous 401(k) rollover

    in 14d

  5. Confirm HSA + FSA elections vs IRS caps

    in 7d

  6. Watch for first payroll deposit

  7. Q4: AMT check before any ISO exercise

    in 145d

Watching Acme payroll · Chase ··1184 · Fidelity 401k · Carta RSU

Background watchers

Watching 6 things for this playbook

Next 60 days

  • Benefits enrollment closes

    Deadline

    Acme HR — Sat May 30

    in 11d

  • First RSU vest — Acme

    Vest

    84 shares, ~$3,420 to set aside

    in 25d

  • Quarterly estimate adjusts

    Tax

    New W-2 income changes Q3 estimate

    in 42d

  • ESPP enrollment window

    Deadline

    Next 6-month period opens Jun 15

    in 27d

Quiet by default. You only hear from us when something actually needs you.

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Common questions

How is this different from a financial advisor?

An advisor charges ~1% of assets and most won't touch you until you have $1M. Clarity is $19/mo, watches your real accounts continuously, and the playbook surfaces every deadline an advisor would walk you through — without you having to schedule a call to ask.

How is this different from asking ChatGPT?

ChatGPT will write you a generic checklist. It can't see your accounts, doesn't know your RSU schedule, doesn't catch a vest landing, doesn't track your YTD 401(k) across employers, and forgets the conversation tomorrow. Clarity holds the whole picture and updates as your accounts change.

How is this different from a retirement calculator?

Calculators take inputs and return one chart. Clarity reads your real synced balances, applies the event, and surfaces every deadline as it approaches — it's a continuous system, not a one-shot model.

Can Clarity see or move my money?

No. Plaid returns a read-only access token; brokerage and exchange connections use read-only API keys. There is no "send" or "trade" tool anywhere in the product. AES-256 at rest, TLS 1.2+ in transit. Full security overview at /legal/security.

What if I'm not at a tech company?

The new-job playbook works for any W-2 employer with benefits. The equity-specific milestones (RSU, ISO, ESPP) only fire if you actually have them — Clarity reads it from your offer letter or your broker connection. No equity, no AMT chapter.

Your offer letter has six clocks running. Start them right.

Set up Clarity once. The new-job playbook surfaces every deadline as it approaches and watches for the vests, contributions, and exercises as they happen.

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