The tactical playbook for getting 20-40% more comp (without sounding greedy) | Jacob Warwick (Executive Negotiator)

Warwick separates two numbers that are easy to blur. The first is what a plain, non-aggressive pushback produces: ask whether there is any chance of a little more, and he says he sees a 20% improvement almost every time. His illustration is a $100,000 offer holding another $20,000 from the ask alone.

Almost always see a 20% improvement on that

The 40% is a different kind of number: his target when calculating for clients, not an observed average. Above it sit outliers he cites at 100 to 400% and broken salary bands, which the industry treats as gospel. The evidence is his own practice, with a senior-skewed clientele and no denominators, so 20% is the floor to test and 40% a ceiling of ambition.

The argument on top of those numbers is asymmetry, not entitlement. Companies extract value at ratios he puts at 5 to 1 up to 100 to 1, and near-infinite scalability means the product person is a large part of that take even though product is already paid well. Set against the company's share, the ask reads as arithmetic rather than greed, which is where the confidence comes from.

He also names who is bad at this: product leaders, engineers and designers negotiate worse than the obnoxious marketers and revenue leaders, an irony given product's role in defining the tech generation. On overreaching he takes a side: being a tall poppy is risky, and he would still rather clients over-negotiate and get slapped down, because that is failing forward.

Lenny puts the uncomfortable question directly: founders listening to advice about negotiating harder are unlikely to be thrilled. Warwick relocates rather than softens it. Given the pace of innovation, how important is top talent, and keeping it? If you want a chance you must retain it, because replacing it is expensive. Compensation stops being a concession and becomes a retention cost.

He then attacks the framing he says poisons these conversations, the belief that negotiation is adversarial. His alternative is a request for information: as a founder, help me understand what matters to you and what value this work drives, and fairer terms follow. It is the same collaborative posture he uses against the greed objection, aimed at the other side of the table.

His proposal is rarely a bigger base or bonus percentage. It is performance incentives and milestone triggers: if the company reaches $100 million ARR and I contributed this much, what does that outcome look like, another tranche of stock or cash? The structure doubles as a screen, since people confident enough to push toward performance pay tend to have more skin in the game and to stay to see it happen.

when everyone thinks they're top talent, somebody's got to be lying

He concedes the resistance is legitimate, grounding it in his own history as a CEO: the difficulty is a sorting problem, since everyone believes they are top talent and no company can pay everyone at the top of the market. He now advises Fortune 500 compensation committees so they stop losing people. A top performer leaving in 10 months costs the recruiter performance pay and the company hundreds of thousands, or in his examples millions in lost IP. The unnamed case: $10 million-plus across a handful of people, against losing them to a competitor and a stock drop after public earnings commitments, a pay-10-to-save-300 trade. He notes the company may not know it cost them $10 million today.

His operating model explains why his clients' negotiations do not look like confrontations. He calls it fingerprintless: he is never in the room, and correspondence passes through him before reaching the recipient, as an attorney's would. You call before you talk to the CEO, prepare, perform, debrief; when the CEO emails, the draft comes to him and you write the reply together.

He locates the reason in market norms rather than secrecy. Hollywood has agents as middle mediators, corporate America mostly does not, and an agent in the room can dilute an executive's presence. The structural consequence is deliberate slowness: days to respond, not to manufacture urgency but to signal scarcity and thought while collecting information.

Haste equals risk.

Asked for the biggest mistake, he names no phrase and no tactic. People do not understand when the negotiation starts, and it starts far earlier than they think. A profile and a resume are a snapshot of the past that does nothing forward; if that is all a counterparty sees, they stamp you as the role you last held. His sharpest version is the headshot, which he claims predicted income with almost frustrating consistency. Narrative becomes reputation, and reputation becomes the price.

If you are positioned as a commodity, you will be treated like a commodity.