What should I ask for when negotiating a CTO position in a funded start up?

Start with the real question: are you a “CTO” or the “head of engineering”?

In funded startups, the title CTO can mean two very different jobs:

• Company-level CTO: sets technical strategy, owns architecture, security, reliability, hiring plan, and often represents tech to investors/customers. You have decision rights across product/engineering tradeoffs.
• Head of Engineering / VP Engineering: executes delivery, manages engineers, ships roadmap, but product strategy and key technical calls may be shared or owned by the CEO/founder or a separate product leader.

Before negotiating numbers, negotiate scope and authority. If you accept “CTO” without the decision rights, you’ll be held accountable for outcomes you can’t control.

Ask for: a written role definition that answers: What do I own? What do I influence? What do I not own?

Equity: ask for the structure, not just the percentage

Equity is usually the biggest lever in a funded startup, but it’s also the easiest to misunderstand. You want clarity on how much, what kind, when it vests, and what happens if things go sideways.

1) How much equity (and in what form)?

Most startup employee equity is stock options (the right to buy shares later at a fixed “strike price”). Sometimes senior hires get restricted stock (actual shares that vest over time). Options are common; restricted stock can be better tax-wise but depends on jurisdiction and company policy.

Ask for:

• Equity grant size as a percent of fully diluted shares (meaning including the option pool and all convertible instruments), not just “number of options.”
• Current cap table summary (who owns what) and option pool size. You don’t need every name, but you do need the structure.
• 409A valuation (or local equivalent) and your strike price for options.

2) Vesting schedule and cliff

Standard vesting is 4 years with a 1-year cliff (you earn nothing until month 12, then vest monthly/quarterly). That’s normal, but you can negotiate details.

Ask for:

• Vesting start date (ideally your start date, not board approval date).
• Acceleration terms. “Acceleration” means you vest faster under certain events.

Two common acceleration types:

• Single-trigger acceleration: you vest some/all equity if the company is acquired.
• Double-trigger acceleration: you vest if the company is acquired and you are terminated or materially demoted afterward. This is more common and more acceptable to investors.

3) What happens if you leave (or they let you go)?

Options typically expire quickly after you leave (often 90 days). That can force you to either pay a large amount to exercise or lose the equity.

Ask for:

• Extended post-termination exercise window (e.g., 12–24 months) especially if you’re joining as a true executive-level CTO.
• Clear “good leaver / bad leaver” definitions if the company uses them (common in some regions). “Good leaver” typically means you keep vested equity if you’re terminated without cause.

Cash compensation: base, bonus, and risk-adjusted guarantees

Funded doesn’t mean “safe.” Your cash package should reflect the company’s runway and the market for your skillset.

Ask for:

• Base salary aligned to your location and seniority. If they can’t meet market, push for more equity and protections (below).
• Sign-on bonus (useful if you’re giving up unvested equity elsewhere). If they resist, ask for a sign-on equity grant that vests over 12–18 months.
• Performance bonus tied to measurable outcomes you control (e.g., “hire 6 engineers,” “ship v1 by date,” “achieve 99.9% uptime”), not vanity metrics.
• Severance: for a CTO, a reasonable ask is 3–6 months of salary if terminated without cause, plus continued benefits where applicable.

Runway check: ask “What is our current runway in months at the current burn rate?” (Burn rate = net cash spent per month.) You’re not being nosy; you’re pricing risk.

Authority and operating model: what you need to succeed

Many CTO failures are not technical—they’re governance failures. You need explicit decision rights and resources.

Ask for written clarity on:

• Reporting line: Do you report to the CEO? If not, why?
• Decision rights: Who decides architecture, cloud spend, security posture, hiring, vendor selection, and release criteria?
• Budget authority: What can you approve without CEO/CFO sign-off (tools, contractors, cloud, recruiting)?
• Hiring plan: headcount targets for the next 2–4 quarters and who owns recruiting execution.
• Product interface: how roadmap is set, how tradeoffs are resolved, and what happens when product wants speed over quality (or vice versa).

If the company is already funded, there should be a plan. If there isn’t, your first “deliverable” becomes inventing the plan—so negotiate time and authority accordingly.

Board and investor expectations

Ask what the board expects from the CTO in the next 6–12 months. Examples:

• Build an MVP and prove retention
• Scale from 0 to 50 customers
• Pass security reviews for enterprise sales
• Reduce cloud costs by X%

You want alignment early because board-level expectations can override internal priorities.

Legal and practical terms that protect you (and reduce future conflict)

These items are less glamorous than equity, but they prevent painful surprises.

1) Title, level, and future dilution

• Title and level in writing (CTO vs VP Eng) and whether you are considered an officer of the company (varies by jurisdiction).
• Refresh grants: ask whether the company has a policy for additional equity grants after 12–24 months based on performance.
• Dilution reality: your percentage will likely shrink in later rounds. That’s normal. What matters is whether the company grows value faster than dilution reduces your slice.

2) IP, inventions, and side projects

Most startups require an IP assignment (you assign inventions created on the job to the company). That’s standard. The risk is overly broad language that claims your prior work or unrelated side projects.

Ask for:

• A schedule of excluded inventions (a list of what you built before joining that remains yours).
• Clear rules for open-source contributions and whether you can maintain existing projects.

3) Non-compete / non-solicit / confidentiality

Rules vary widely by location. Non-competes may be unenforceable in some places and strict in others. Regardless, you should understand the practical impact on your career.

Ask for:

• Exact duration and scope of any non-compete (if present).
• Non-solicit terms (limits on recruiting former colleagues/customers).
• Standard confidentiality is expected; ensure it doesn’t block you from using general skills and know-how.

4) Change-of-control and role changes

“Change of control” means acquisition/merger. Clarify what happens to your role and equity if the company is acquired and the acquirer wants a different org structure.

Ask for: double-trigger acceleration, and a definition of “materially diminished responsibilities” (e.g., losing budget authority, losing direct reports, or being moved under a new manager).

What to do next

1. Request a one-page “CTO charter”: responsibilities, decision rights, reporting line, and 6–12 month goals—then negotiate against that document.
2. Get the equity details in writing: % fully diluted, vesting start date, cliff, acceleration, strike price, and post-termination exercise window.
3. Run a runway + resourcing check: current runway (months), hiring plan for the next two quarters, and your budget authority for tools/cloud/recruiting.
4. Negotiate downside protection: 3–6 months severance (without cause), and double-trigger acceleration tied to termination or material demotion after acquisition.
5. Sanity-check the offer with a structured review using /finances and pressure-test your role expectations with /roast.