The Tool Desk
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Start with the downside you can afford
A startup job is both a career move and exposure to a young business with uncertain prospects. A polished pitch or recent funding announcement does not establish that the company will reach its next milestone, raise more money, or remain solvent. Early-stage businesses may not have the mature revenue and income record of established companies, and their future is uncertain. The U.S. Securities and Exchange Commission explains that startup securities differ from publicly traded securities in ways that affect risk and liquidity: SEC: What You Need to Know About Startup Investments.
Before comparing offers, write down your household’s fixed costs, savings buffer, dependents’ needs, and any income interruption you could manage if the new role ended sooner than expected. Then assess the startup offer under an adverse scenario: the job ends, the equity cannot be sold, and it provides no cash to replace lost income. This is not a prediction; it is a way to test whether the downside is acceptable.
Evaluate the company’s prospects
Ask for the reasoning behind the company’s outlook, not just the headline version. Questions to raise with the hiring manager or leadership include:
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- Who pays for the product, and what evidence shows customers continue to pay or use it?
- What are the next product, customer, revenue, or cash-flow milestones?
- What financing or revenue assumptions support the plan to reach those milestones?
- What could break those assumptions, and what would leadership change if growth is slower or financing takes longer?
- When the company discusses runway, what cash, current net burn, planned spending or hiring changes, and next financing milestone does that estimate assume?
Runway is meaningful only in context: the same estimate can depend on very different spending plans or financing assumptions. No particular number of months is a universal guarantee of safety. Treat the answers as evidence to weigh, not proof that the company will succeed.
Check whether the role is worth the career risk
A promising company can still be the wrong job. Clarify the work you would own in the first six to twelve months, who you would report to, what authority you would have, how success would be measured, and what people and tools would be available. Ask how priorities could shift if the company misses a milestone or changes its strategy.
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If practical, speak with prospective teammates about how decisions are made and how the role interacts with other teams. Compare the startup’s learning opportunities, responsibility, and likely next career step with what your current job offers. These factors help structure the choice, but they cannot predict an individual career outcome.
Compare guaranteed compensation, not headline totals
Put your current and prospective packages side by side, separating guaranteed cash from uncertain or conditional value. A bonus target is not the same as a guaranteed bonus, and equity that cannot be sold is not take-home pay.
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| Compare | What to establish |
|---|---|
| Base salary | Written annual amount, pay schedule, and any conditions. |
| Bonus | Whether it is guaranteed or discretionary, how it is calculated, and what conditions apply. |
| Signing or relocation payment | Amount, payment date, and any repayment condition. |
| Equity | Instrument, award terms, exercise cost if applicable, vesting, dilution exposure, and realistic access to liquidity. |
| Health benefits | Employee and dependent costs, coverage, providers, and the date coverage can begin. |
| Retirement benefits | Eligibility, employer contributions, vesting, and what you give up by leaving your current plan. |
| Other terms | Severance, paid leave, work location, and expected hours; do not assume an unwritten promise is guaranteed. |
Use the written offer and plan documents as the basis for the comparison. If a benefit, subsidy, or severance arrangement matters to your decision, ask whether it can be included in writing.
Understand the equity before assigning it value
First identify the exact instrument and request the governing plan and grant documents. Options, restricted stock, restricted stock units (RSUs), SAFEs, and convertible notes are not interchangeable. A SAFE is not ownership until its conversion is triggered; other instruments have their own terms and rights. The SEC’s overview explains that an option gives its holder the right, but not the obligation, to buy shares at an agreed strike price after vesting, and that securities can carry different terms: SEC: What You Need to Know About Startup Investments.
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If the offer includes stock options
Ask for the share count and how it compares with the company’s fully diluted capitalization. Confirm the strike price, vesting schedule and cliff, expiration date, post-termination exercise window, and treatment if the company is acquired. Ask about the cash needed to exercise and potential tax consequences; those depend on the award, timing, jurisdiction, and your circumstances. Consider qualified legal or tax advice before making decisions based on the documents.
If the offer uses another equity instrument
Ask what rights the instrument gives you, what event or conditions affect ownership, what documents govern it, and what it could cost or require of you. Do not treat an advertised grant value as cash compensation. Ask what assumptions produced any estimated value, which class of stock is involved, and what the company can explain about capitalization and restrictions on selling.
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Account for liquidity and dilution
Private-company shares may be difficult or impossible to sell when you want to. Potential exits can include a public offering, acquisition, merger, or liquidation, but neither an exit nor its timing or value is assured. A grant’s share count can also be diluted by future issuances. The SEC describes startup investments as carrying distinct risks and potential illiquidity: SEC: What You Need to Know About Startup Investments. Treat equity as a contingent possibility, not a substitute for salary you need to pay expenses.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Plan health coverage and retirement before giving notice
For U.S. workers, changing jobs can create a gap between leaving one health plan and becoming eligible for another. The Department of Labor says a new plan may have a waiting period of up to 90 days after eligibility. Confirm the startup plan’s enrollment date, premiums, dependent coverage, and in-network providers before resigning. See the Department of Labor’s guidance on changing jobs and benefits: Changing Jobs and Job Loss.
In qualifying circumstances, COBRA can provide temporary continuation of group health coverage. Participants generally pay the full premium plus up to 2 percent. Depending on eligibility and timing, a spouse’s or dependent’s plan, Marketplace coverage, Medicaid, or CHIP may be alternatives. Check the rules, costs, and deadlines for your circumstances rather than assuming COBRA is the only option. The Department of Labor outlines these choices at Changing Jobs and Job Loss.
Review your current retirement plan’s vesting schedule and identify any unvested employer match or other benefits you would forfeit. Then compare the startup’s eligibility date, contributions, and vesting terms. The Department of Labor recommends understanding retirement-plan effects when changing jobs: Changing Jobs and Job Loss.
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Questions to get answered before accepting
- What financing position and cash-flow assumptions underpin the next company milestone?
- Which customer, revenue, retention, or product evidence supports the plan, and what remains uncertain?
- What would change if growth slows or financing takes longer than expected?
- What outcomes are expected from this role in the first six and twelve months, and what authority and resources come with it?
- What exact equity instrument is offered, and can I review the plan and grant documents before accepting?
- For options, what are the strike price, vesting schedule, post-termination exercise period, expiration, and acquisition treatment?
- When can I enroll in health coverage, what are the employee and dependent costs, and which providers are in network?
- What retirement benefits or unvested compensation would I leave behind, and when would I qualify for the startup’s plan?
- Which compensation, benefits, and severance terms are guaranteed in writing?
Make the comparison using your own priorities
Compare the two jobs across six dimensions: guaranteed after-tax cash and bonus certainty; equity terms, dilution, exercise cost, and liquidity; company financing and business evidence; role scope, manager, and skill growth; health and retirement benefits; and your household’s ability to handle a downside. Decide which dimensions matter most to you rather than applying a universal weighting formula. The right choice depends on the company’s actual facts and documents, the contract terms, local benefit rules, and your own tolerance for risk.
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