For most advisors and their clients, Q1 is synonymous with taxes — planning conversations compress around the April 15th deadline, and when it passes, the pace naturally slows. But for clients with equity compensation, there is no off-season.
Equity comp runs on its own calendar, driven by vesting schedules, blackout periods, enrollment windows, and tax deadlines that don't pause after filing season. If Q1 had you playing catch-up, Q2 is the window to get ahead. The prior-year return is filed, real numbers are available, and several time-sensitive planning events are already in motion.
Companies on a quarterly vesting schedule typically follow a February/May/August/November or March/June/September/December cadence — making May or June the first significant post-tax-season vest. Many ESPP programs run semiannual purchase periods ending in May and November, with enrollment decisions due now. And for clients approaching mid-year, now is the time to begin mapping the planning conversations that will carry through Q3.
Q2 is not a recovery period. For equity comp clients, it's one of the most active planning windows of the year — and the advisors who treat it that way are the ones who differentiate themselves.
Effective equity compensation planning starts with a clear, current picture of what your client actually holds. In practice, many advisors are working from incomplete information — a grant summary pulled during onboarding, a vague understanding that the client "has RSUs," or a compensation statement forwarded without context. Q2, with a major vesting window approaching and prior-year tax data now in hand, is the right moment to fix that.
Before any planning conversation can be productive, you need answers to four foundational questions.
What grant types does the client hold? RSUs, PSUs, ISOs, NQSOs, and ESPP participation each carry different tax treatment and different planning implications. A client holding both ISOs and RSUs requires a fundamentally different conversation than one with RSUs alone. Know what's in the mix before the vest hits.
What does the vesting schedule look like? The two most common quarterly cadences areFebruary/May/August/November and March/June/September/December — but your client's schedule may not follow either. Semi-annual vesting concentrates equity income into two large annual events. Annual cliff vests create a single high-stakes moment. Monthly vesting, increasingly common at post-IPO companies, produces a continuous stream of taxable income that requires ongoing monitoring rather than event-driven planning. Knowing the schedule tells you when to act and how much runway you have.
Cliff or graded? A client approaching a four-year cliff vest is about to receive a single large block of shares — a very different scenario than one receiving smaller grants each quarter. Cliff vests concentrate both income and risk into one event.Graded schedules spread the planning across the calendar but require consistent attention to prevent small vestings from accumulating into an unmanaged position.
What is vesting in Q2, and what is it worth? For each upcoming vest, you want the gross share count, estimated value at current price, projected net shares after withholding, and the resulting impact on the client's overall concentration. A working estimate is enough at this stage to determine whether a vest requires proactive planning or routine monitoring. Grantd is built to run this kind of grant inventory and net vest projection quickly, giving advisors a working picture of the full equity landscape before client conversations begin.
The Q2 Equity Compensation Audit Treat Q2 as the annual moment to conduct a full equity comp audit for every client in this category — pull all outstanding grants, confirm vesting dates, and map every equity event through year-end. If you built this inventory at onboarding, refresh it now. Plans change, grant agreements get amended, and clients change employers. An inventory that was accurate eighteen months ago may be meaningfully incomplete today.
Advisor takeaway: You can't plan around a vesting event you don't see coming. The first move in Q2 is building — or refreshing — a complete picture of every client's outstanding grants, vesting schedule, and upcoming equity events. Everything else in this guide depends on having that foundation in place.
For clients with equity compensation, the post-earnings trading window isn't simply the absence of a restriction — it's the primary planning window of the quarter. Understanding how these windows work, which clients have blackout exposure, and what the tax withholding implications are at vesting should be central to every advisor's Q2preparation.
How the Quarterly Trading Window Works For most calendar-year public companies,Q1 earnings are announced in late April or early May. The blackout window lifts shortly after, and for companies on a February/May/August/November vesting schedule, the trading window is deliberately structured to extend a few days past the May vest. This alignment gives participants a clean window to act on multiple fronts: selling newly vested shares, transacting on existing holdings, or executing a planned diversification. Clients who arrive at this window without a plan tend to make reactive decisions — or none at all. Clients who arrive with a framework in place can execute deliberately.
The Monthly Vesting Problem Clients on monthly vesting schedules — increasingly common at post-IPO technology companies — will inevitably have vest events that fall inside a blackout. Those positions can't be settled through open-market sales, which means net settlement or a pre-arranged sell-to-cover structure needs to be confirmed in advance. This is a direct output of the grant inventory work from the previous section — knowing the vesting cadence tells you which clients have blackout exposure before it becomes a problem.
Using the Open Window Intentionally For quarterly vesting clients, the post-earnings window is the moment when multiple planning actions can converge — executing sell decisions on the new vest, rebalancing existing company stock holdings, initiating diversification if concentration thresholds have been crossed, or establishing a 10b5-1 plan before the next blackout closes. That last point is worth flagging: the open window is also the window to put a systematic trading plan in place for future quarters, which we'll cover in the next section.
Tax Withholding: The Gap Most Clients Don't See Coming Every vesting event triggers a tax obligation — and default withholding mechanics routinely fall short for higher earners. Federal supplemental withholding defaults to a flat 22%, which leaves a meaningful gap for clients in the 32%, 35%, or 37% bracket. That gap widens when equity income layers on top of base salary and prior supplemental wages already recognized in the year. Once cumulative supplemental wages exceed$1 million, the rate jumps to 37% on the excess — a threshold that can catch clients and employers alike off guard when a large vest hits mid-year. State apportionment adds further complexity for clients who have changed their primary work location since the grant date.
Modeling Withholding Adequacy Now Post-tax-season is the one moment advisors have everything needed to model withholding adequacy properly: the prior-year return is filed, YTD payroll data is available, and the upcoming vest value can be estimated with reasonable precision. The framework is straightforward — project total income for the year, calculate expected tax liability, subtract what's been withheld YTD, and compare that to what will be withheld on the upcoming vest. Any gap needs to be addressed through a W-4 adjustment or an estimated tax payment. The June 15th Q2 estimated tax deadline is the action trigger. Grantd makes it straightforward to layer vest income onto YTD data and flag withholding gaps before they become underpayment penalties.
Advisor takeaway: The post-earnings trading window is the most consequential planning moment of the quarter for equity comp clients. Advisors who map these windows in advance, identify blackout exposure, and model withholding adequacy before the vest —not after — are the ones who prevent surprises and deliver real planning value when it matters most.
For clients who are corporate insiders —officers, directors, and certain employees with regular access to material non-public information — a 10b5-1 plan is the primary tool for executing planned stock sales without running afoul of insider trading rules. The plan is established during an open trading window, specifies in advance the price, volume, and timing of future sales, and then executes automatically — including during blackout periods when the client otherwise couldn't trade.
The Q2 open window, following the lift of the post-Q1 earnings blackout, is one of only a few opportunities during the year to establish, modify, or renew these plans. That makes it time-sensitive.
The 2023 SEC rule changes added meaningful complexity. All participants are subject to a cooling-off period between the date the plan is adopted and when the first trade can execute — meaning there is an intentional waiting period built into every new or modified plan before it becomes active. This makes liquidity timing an important planning consideration. For clients with near-term cash flow needs, one practical approach is to execute a single discretionary sale during the open window while it's available, address the immediate liquidity need, and then establish the10b5-1 plan to handle the remainder of planned trading systematically. This allows the client to meet short-term needs with intention while still putting a structured, delegated trading program in place for the period ahead.
Advisors don't execute these plans in isolation. Coordination with the client's corporate counsel and compliance department is required, and plan documentation needs to meet the updated SEC requirements to qualify for the affirmative defense. The advisor's role is to identify which clients need a plan or have one approaching expiration, model the trading parameters that align with the client's financial plan, and ensure the conversation with legal happens before the window closes again. The Grantd 10b5-1 Planning Hub gives advisors a centralized place to build, track, and monitor trading plans across their entire client base — so nothing falls through the cracks when the window closes.
Advisor takeaway: The Q2 open window is one of a handful of opportunities each year to put a systematic trading plan in place for insider clients. Know which clients need one, have the parameters ready, and get legal coordinated before the window closes.
Q2 historically sees elevated employee turnover. Annual performance reviews wrap up, bonuses are paid out, and many employees use the post-filing season as a natural reset point to make a move.For clients with meaningful equity compensation, a job transition is one of the highest-stakes planning moments they'll face — and one where bad decisions or missed deadlines can be extremely costly.
The first thing to establish is what happens to unvested awards. RSUs are typically forfeited at termination unless the plan document includes retirement-eligible provisions, pro-rata vesting, or change-in-control protections. PSUs may have different treatment depending on where the client sits in the performance period. These details live in the individual award agreement — not the summary plan description — and need to be reviewed before a departure decision is finalized.
Stock options carry the most urgent deadline. For ISOs, the post-termination exercise window is typically 90 days from the last day of employment. Miss that window and the options are forfeited. For NQSOs the window is often longer but varies by plan. Clients sitting on meaningful in-the-money options need to understand their timeline and the capital required to exercise before they hand in their notice.
One often overlooked planning angle: for clients considering a job change, timing the departure thoughtfully relative to upcoming vest dates can preserve significant value. Mapping exactly what unvested awards are at risk and when the next vesting events occur gives clients the information they need to make an informed decision rather than an emotional one. Grantd's equity award inventory and analysis tools make it straightforward to model forfeiture value and surface upcoming vest dates — so advisors can walk into that conversation with a clear picture of what's at stake before the client makes a move.
Advisor takeaway: Clients in job transition have a narrow and often unforgiving window to make decisions about their equity. The advisor who can map out forfeiture risk, expiring exercise windows, and tax timing in the first conversation after a departure announcement becomes indispensable at exactly the right moment.
