My best thing about manager

Managers know nothing. Either a Buyback should have happened previously to trust him. Or he's just lowballing you.

Apart from founders nobody else can guarantee

Self explanatory

Managers don't know anything about buybacks. Dilasa Dene ke liye bol rha hai. To do buybacks you need approval from the board of directors. And normally investors are more interested in getting their returns than giving it to junior or mid management

See, betting on ESOP vs hike is always risky. See if your situation allows you the risk in the first place. Food on the table, 50% salary in investments, other responsibilities have to be taken care of. If it doesn't, don't even consider it.

If you can take the risk, then consider the next few points

1. Is your company doing really really well? Nobody is going to buy secondaries when they don't need to. If the company desperately needs money, they are going to do a primary investment.

2. Have they bought back shares before? The Indian ecosystem is littered with examples of folks not honouring esops.

3. Are they going to stick vesting into it? Standard vesting is 25% over 4 years with a 1 year cliff. In that case, if the buyback happens before that, you don't have esops to vest (I don't know if you already have esops, if you do then this is different)

4. If it has a vesting period, then you have to consider if you plan to give the next 4-6 years of your life to the same company. Career mobility, managers, toxic environments, b school plans - Everything changes. If you don't see yourself here for that long, don't consider it.

Remember ESOPS are the easiest thing to dangle for them at this point since money is tight at most places. If you are good at what you do and the work is in demand, you have leverage.