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7 questions to ask your future employer before accepting an offer

Inside Upflow

Alex Louisy

Aug 29, 2022


1. Understand and find meaning in the long-term vision2. Understand the founders’ motivations3. Understand the company’s product-market-fit dynamics4. Understand the company’s culture, values, operating principles5. Understand the company's financial health6. Understand investors’ or external stakeholders’ perspectives (if you can)7. Understand your offerKey Takeaways

Accepting a job offer is a very important decision. Whether it’s full remote, on-site, or anywhere in-between, this is where you’ll spend most of your time and energy in the next couple of years. And yet, the process of coming to this decision is quite short, only meeting with a couple of people in a short time frame. How to make the best decision?

Making the right choice and landing at the right place is unique to everyone. Changing jobs isn’t much about finding a “good” company, but one that is good for you - and vice versa. That’s one of the reasons why we have spent a lot of time clarifying our operating principles at Upflow, as we know it’s not a fit for everyone!

Beyond operating principles, at Upflow, we highly encourage future team members to “reference check us” as we truly believe hiring is a two-way process and ensuring alignment is key to mutual success. The more you know, the better it is.

Yet, we are very surprised to see how many candidates would accept an offer to join a company for the next 3 years of their life, without checking who or what this company really is.

Here are some pieces of advice on how to best inform your decision about your next job.

Are you ambitious and looking for a challenge? Check out our career page!

1. Understand and find meaning in the long-term vision

💡 Make sure there is a solid and consistent long-term vision, and that you find it inspiring and meaningful.

Ask your manager, or a founder, about the vision for the company. Where does she see her company ten years from now?

Look for a solid answer, consistent across the entire process and different team members.

Remember, if the founder is not inspiring, you won’t be inspiring — keep it in mind if you decide to join and need to hire a team.

2. Understand the founders’ motivations

💡 Founders will have a very important impact on your job, even if indirectly. Make sure you understand why they are on that journey.

Is she a first-time founder? Second-time founder? Dig into their previous life, and motivation to become a founder.

Why is she doing this? How did it all start? Dig into the path to ideation, and creation.

What outcome is she expecting from the company? Look for early indicators of success, meaning impact, rather than lagging indicators such as the company valuation or how much they raised.

Are there multiple founders? If so, try to talk to each of them. Look for alignment and consistency in their narrative.

3. Understand the company’s product-market-fit dynamics

💡 If it is an early-stage company, you need to get a good understanding of where you are landing in terms of risks.

What’s the company stage, 0 to 1 or 1 to 10? That is the question. Your day-to-day will be very different. For example, scaling is stronger in phases 1 to 10 than in phases 0 to 1, and that’s a very different job to be in.

Towards the end of the process, and in early-stage companies only, ask simple questions about the metrics of the company to assess (1) if they are willing to share them, and (2) which metrics matters to them. Clarity is key here. Metrics will depend on the type of business, but watch out for vanity metrics instead of real metrics.

  • What’s the north star metric of your company? If it’s not revenues, watch out.

  • What are your revenues?

  • How many customers/users do you have?

  • What’s your main distribution channel?

  • What’s your target price? Is this consistent with their distribution channel? You may refer to this P9 article to identify gaps.

  • What is your objective for the next 12 months?

4. Understand the company’s culture, values, operating principles

💡Each company is different, not only in its product or market but also in how people work together. There is not necessarily a right or wrong answer, but you want to make sure this team’s way of working fits you.

What are the company’s operating principles, and values? Ask for examples of behavior that are fits and misfits. Unclear answers are not a great sign.

How does the company operate? Understand the rhythmics, and the methodology they use to plan, prioritize, divide and do the work - for instance, the OKR.

Reach out to people in similar positions at the company who you haven’t met yet, thanks to LinkedIn. Generally be curious about the organization, its structure, and dynamics.

If you’re unsure, you may talk to people who left the company. They are easy to find on LinkedIn and their feedback will probably be helpful.

5. Understand the company's financial health

💡The company can look really great, but you are not going far away if you are running out of cash. Make sure they have solid foundations to grow.

What’s our financial path? Is the company bootstrapped or VC-backed? What does that mean for the company trajectory, and my job?

If the company raises money from VC to grow, you may ask:

  • When was the last raise? Why did they raise?

  • What’s the company's cash runway? Understand how long they have before running out of cash.

  • What objective are you pursuing to get to the next round? Look for operational and go-to-market signals, not numbers.

  • What if they miss this objective? **Look for an honest answer. Remember that at the seed-stage, there is a 90% chance you are not getting to the next stage. It’s ok to talk about it.

If the company is bootstrapped, you may ask:

  • How does hiring look like? Understand if funding will be a constraint for hiring a team in the future. Make sure you are fine with the answer.

6. Understand investors’ or external stakeholders’ perspectives (if you can)

💡For senior roles, you may be able to talk to the board or some investors. It is a great way to get external, yet honest feedback on the company's health, team, management, and trajectory.

If you get a chance to talk to investors, be smart about the questions you are asking and be prepared, their voices will probably weigh in a lot in the final decision.

Here are some questions you may ask:

  • Why did you invest in this company?

  • What do you like the most about the founder(s)? How often do you interact with them? Do they come to you for help or advice?

  • What would be the biggest challenge for the company in the next years to come?

  • How would my role make a difference in the company’s trajectory?

  • How do you see the next round of funding dynamics?

7. Understand your offer

💡 It may seem like the most obvious, but you don’t want to discuss this last minute.

Your offer will include four main components: title, cash, benefits, and hopefully, equity. Each of them needs to be carefully assessed.


Ask for the career path you may benefit from. Great companies will usually have a very standardized leveling (eg. L1, L2, L3, L12, or Manager, Director, VP, C-), and they would know what to expect from each level.

Ask what is expected from your level and the next. Beware of companies giving fluffy titles, or very senior titles, too early. It could be a blocking point later as it makes future hiring more complex.


Your compensation will be a fixed salary, plus a potential variable. If there is one, ask how the KPIs are expected to be set, and how often.

Ask if the variable will be guaranteed for the first few months to ensure you land correctly, or if there will be a “ramp” — which is standard for sales roles.)

If the company does not use a formula “yet” because they are too early-stage, ask about the variable philosophy. Is “normal” expected to get you to 100% of your variable, or is this a stretch goal? Is your variable compensation capped or uncapped? This can have a significant impact.

Ask about the foreseen compensation evolution. Ask if the company has salary grids tied to career paths. Great companies usually have a clear and transparent path of evolution.


Don’t be too picky about this part, but don’t wait for the last moment to enquire about those. Health, retirement benefits, meal allowance, travel allowance, and home stations are often under-estimated perks but can make a significant difference on your final “net in the pocket”. Your personal status here can have a huge impact (full remote, family, children…)


This one is often misunderstood. Ask if you will get equity. Maybe yes, maybe no. Whether your package includes equity or not, it’s usually a good sign when new joiners ask for equity, as it shows long-term interest and commitment to the company.

After series B, it is quite common to stop granting equity to every new team member. Whether you have some equity or not, ask about the general guidelines. Founders unwilling to share any equity with anyone is generally not a great sign.

Don’t let the recruiter fool you with vague formulas such as “$X worth of equity, detailed to be provided later” or even worth “You will get Y units of stock option”. The recruiter must give you clarity on:

  • The timing of the grant, meaning when you will be granted your stock options. Ask about the vesting schedule, ask if and how long the cliff is.

  • Which instrument you are granted (ISO, NSO, BSPCE, RSU)

  • The company: make sure the stock options are on shares of the parent company, where investors also invest, not in a subsidiary.

  • The strike price, meaning how much you will pay to exercise the stock option

  • The underlying value, meaning the underlying value of shares or the current fair market value (FMV) of shares you will get. That is the estimated current value of the share you could buy. Hopefully, this number will go up as the company grows but remember that it may also go down, especially after a bubble / high valuation cycle as we have seen over 2021/22. If the FMV goes below the strike price, your options are worth nothing. Be particularly careful with companies who raised significant amounts early on: this usually means high valuations and, therefore, a high strike price.

Key Takeaways

We encourage you to ensure all those questions are answered before accepting a job offer — at Upflow, or anywhere else! Sometimes, you will not have 100% clarity on everything, and that’s fine. Simply make sure you are not missing a key item.

At Upflow, we not only encourage future team members to ask those questions but try to provide answers to those questions proactively. We also work hard to provide great answers to those so that the best people want to join us in our journey! We are not perfect, but we always go by our operating principle: we invest in communication, with transparency and honesty. That’s it!

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