Jordan spent three days negotiating a Head of People offer at a 90-person Series B.
They pushed the base up $15K. Got another 0.1% in equity. Traded a signing bonus for double trigger equity acceleration.
By the time Jordan signed, it felt like a win.
Four months in, Jordan realized they'd never gotten the job they interviewed for.
The CEO had described a role that would "build the People function from scratch and sit on the leadership team." The offer letter, which Jordan read mostly for the comp terms, had them reporting to the VP of Finance and no reference of them being at a leadership level (E7+).
It also turned out that they weren't allowed to get visibility into the budget... at all. Jordan had negotiated a great package for a job that didn't really exist.
The mandate is a different document than the offer
βPart II of the Land the Role Playbook covered how to answer interview questions like a business leader and secure a job offer offer.
This is what happens after: Most People leaders have negotiated comp on behalf of businesses for their entire career and rarely (if ever) negotiate for their own total rewards.
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Here are three things to check on before you sign any offer:
1. Where you sit. The reporting structure and the standing meetings, ideally put in writing, not just implied in conversation.
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Reporting to the CEO isn't a nice-to-have here, it's the norm, even at Jordan's stage. Per Pave's Data Lab, at companies with 51β100 employees, about 82% of People/HR leaders report to the CEO, 12% report to a CFO or COO, and 6% report to someone else.
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A People leader not reporting to the CEO is a yellow flag because it can signal the level of respect and influence afforded to the function. If your offer has you reporting anywhere else, that's not automatically disqualifying, but it's a conversation to have.
Similarly, make sure you'll have appropriate visibility. "I'll loop you into leadership" is not a permanent seat on the leadership team's agenda.
2. What you own. Who is reporting to you, what metrics are you expected to move the needle on, and what level of visibility and input will you have to the company-wide budget.
In a perfect world, budget and headcount authority should stated as numbers, not adjectives. "Autonomy" isn't a number. $50K without sign-off is. While many startups don't have tiered budget sign-offs by level figured out early on, at least make sure you can see the budget. This is a personal choice, but for me, as the senior-most people leader at a startup, not being able to see the budget is a reason to decline an offer.
3. The comp package. Most first-time Head of People candidates under-negotiate because base salary is the only line they're used to thinking about. If you're doing this job right, you're helping build enterprise value, not just running a function. Your package should treat you like someone with a stake in that value, not just a salaried hire.
Before you decide what to push hardest on, it's worth being honest with yourself and the people in your life about what you actually value right now. There's no universally correct mix.
My own answer has changed over time. Earlier in my career, when I was living pretty lean, I negotiated hard on equity and was glad to trade cash for a bigger stake in the upside.
After being lucky with some early career success and introducing a mortgage into the mix, my preference shifted toward more of a blend: solid annual cash comp alongside long-term upside, instead of betting everything on equity.
Neither version was wrong. It matched the season. Use what follows as a menu to weigh against your own life right now, not a checklist you need to max out on every line.
Equity amount. Don't anchor to the company's first number. Ranges shift fast by stage and how much has already been diluted, so pressure-test whatever they offer against real data (Pave, Carta, or a direct comparison to what a peer got at a similar stage) instead of taking it on faith.
If you can't get comparable data, ask directly: "How does this compare to the equity you gave the last VP-level hire?" Also consider negotiating for grants tied to performance milestones or tenure, not just your initial grant.
Equity terms. This is where executives lose real money without realizing it, because most people never read past the grant size.
- Vesting: while this is shifting, most common is still 4 years with a 1-year cliff and monthly vesting after the cliff.
- Acceleration: the term to know is single-trigger vs. double-trigger. Single-trigger means your unvested equity accelerates the moment one trigger is hit (e.g., the company is acquired), regardless of what happens to your job. Double-trigger means it accelerates only if two things happen (e.g., the company is acquired and you're terminated without cause or your role is materially diminished within a set window after the deal). Boards and acquirers resist single-trigger because it creates a "vest and walk" risk right when they need you to stay. Double-trigger is the more standard, reasonable ask for an executive.
- Exercise window: the default is 90 days to exercise vested options after you leave, which can force you to either pay a large tax bill fast or forfeit equity you earned. Executives increasingly negotiate an extended post-termination exercise window, sometimes years instead of days.
- ISO vs. NSO vs RSU: know which you're being granted, and loop in a tax advisor before you sign, especially around early exercise, 83(b) elections, Qualified Small Business Stock (QSBS) tax benefits, and potential Alternative Minimum Tax (AMT) exposure. Those are all tax questions, not HR ones (and this newsletter is my opinion, not official or legal advice), and it's worth paying someone to get right. If your company has a successful exit, it could cost you tens to hundreds of thousands of dollars to get it wrong.
If equity is new or overwhelming to you, this Carta 101 course is great.
Bonuses, two kinds. A sign-on bonus should make you whole for real money you're forfeiting: unvested equity, an unpaid bonus, a relocation cost. Ask for the number tied explicitly to what you're leaving on the table, and read the fine print. Many sign-on bonuses are structured as forgivable loans you owe back pro-rata if you leave within 12β24 months. A performance bonus should be tied to outcomes you actually influence and can point to later: successful fundraise readiness, retention of key leaders, a clean audit. Not vague "goals" the CEO sets after the fact. If the role is pivotal to a specific milestone (a Series C close, $50M ARR, an acquisition, an IPO), it's fair to ask for a one-time success bonus tied to that event, since that's the moment the value you helped build actually gets realized.
Guaranteed severance. Because you have no tenure or relationship capital yet if the board or a new CEO decides to make a change, some execs ask for a defined severance package on termination without cause: months of base salary continuation, COBRA covered for that period, and a pro-rated bonus. This one is harder to secure, but can be very valuable. If you do manage it, get it in writing. Verbal promises often don't survive a change in CEO, board composition, or company strategy, and those are exactly the moments this protection exists for.
The Four-T Playbook
Every edition, I share a proven tip, trick, tactic, or template. This time, it's a:
π Tip: Don't verbally accept an offer on the phone, even out of excitement. Always take the time to review the terms in writing.
Final thoughts
That closes out The Land-the-Role Playbook. Part I helps you position yourself as a credible candidate, Part II helps you succeed in interviews, and Part III gives you tools to negotiate your offer like someone who's about to help build real enterprise value, because you are.
Which part was most helpful? Hit reply and tell me Part I, II, or III.
Until next time,
Melissa