Sell your employee stock options — the full journey, handled.

Stage one: the exercise decision

Exercising converts vested options into shares by paying the strike price. That payment is only part of the bill — the perquisite tax on the difference between fair market value and strike is usually the larger number, and your employer typically withholds it through payroll in the exercise month. Between the strike and the withholding, employees are frequently surprised by how much cash exercising consumes before a single rupee comes back.

Because of that cash gap, the smartest sequencing is usually offer-first: get a firm purchase offer (or at least a grounded valuation) before exercising, so you know the proceeds that will refill the gap and roughly when. Exercising into the unknown is how people end up holding an illiquid position and a tax bill at the same time.

The exercise window is the hard deadline

While employed, you can generally exercise vested options at your convenience. After leaving, most schemes give a fixed window — commonly between one and six months, though schemes vary widely — after which vested options lapse worthless. No negotiation, no extension in most cases.

If you are serving notice or have recently left, work the timeline backwards: the transfer takes days, the ROFR or approval process can take weeks, and arranging exercise funds takes however long it takes. Starting the sale process early is the difference between a planned exit and a fire drill.

Buyback vs secondary sale: the real comparison

Company buybacks and secondary sales get you to the same place — cash for equity — by different roads, and the trade-offs are worth understanding:

• Timing: buybacks happen when the company chooses, often once every few years and sometimes never. A secondary sale happens when you choose, if demand exists.
• Quantity: buyback programmes are usually capped — a percentage of your vested holding. A secondary can cover any quantity a buyer will take.
• Price: buyback prices are set by the company, generally around a recent round's terms. Secondary prices are negotiated and can sit above or below that reference depending on demand.
• Tax shape: proceeds from a company buying back its own shares are taxed under a different mechanism than a sale to a third party, and the rules have changed over the years — this is precisely where a CA earns their fee.
• Effort: a buyback is administratively effortless for you. A secondary needs documentation and process — which is what a platform is for.

Stage two: selling the exercised shares

Once exercised, you are an unlisted shareholder and the sale mechanics are standard: KYC, a Client Master Report proving your demat details, any scheme-mandated transfer notices, an agreement where warranted, then an off-market demat transfer. The gain between your sale price and the fair market value at exercise is a capital gain — long- or short-term by holding period, counted from exercise, not from grant or vesting. Keep your exercise records; they are your cost-basis evidence at filing time.

One under-appreciated detail: because the perquisite leg was taxed at FMV, selling soon after exercise at a similar price can mean minimal additional gains tax — the heavy tax lifting already happened. Holding longer restarts a genuine investment decision: you are choosing to keep capital in a single illiquid stock.

What a structured desk changes

Doing all this alone means finding a credible buyer, agreeing a price with no reference data, drafting documents, chasing company approvals and trusting a stranger's bank transfer. A structured sale compresses it: valuation against live secondary demand, a firm offer you accept online, scheme-compliant transfer mechanics, and settlement into your verified bank account within T+2 working days of the transfer. The option holder's job reduces to two decisions — whether to exercise, and whether the net number is good enough.