How to choose between job offers from very different companies

Hi Elphas!

Long time reader but first time poster, and I really need some advice.

My role was recently made redundant (or I was laid off, I think that's the same thing in the US?), and I have been looking and applying for jobs for about 5 weeks. It's taken a lot of applications and interviews but I've got to a point where I have an offer on the table, with a couple more companies giving strong indicators that an offer is imminent (confirmed final round short interviews with leadership unrelated to the team I'd be in, 15-30 mins that they've framed as an informal opportunity for me to ask any final questions and come to the offices/get to chat to more people before any decision is made).

I'm aware I shouldn't count my chickens before they've hatched and all that, but I've never been in a situation where I've had to choose between multiple job offers before, and with this offer now on the table there is a time limit within which I will have to accept/decline. I am letting the other companies know that I have received one so they can schedule these interviews ASAP, but in the meantime I'm starting to think about who would be the best option to go with in such a turbulent time in the Tech industry, particularly having come from a company that just halved it's headcount and let almost 1000 people go.

My dilemma lies in that my role is one that isn't specific to a certain field/industry or company size, so I've been applying to any and everything that sounds interesting or a good place to learn (I have worked in multiple tech companies in some very different environments and love to push myself beyond my comfort zone in a new domain to gain more technical knowledge). Subsequently, the companies I'm at final stages with are very different in terms of size, industry and reputation.

The job offer I have on the table currently is in the tech team at a very large chain of grocery stores, which also has a few other businesses, as well as a bank, although that's seperate from the team I'd be in. I would be working across one of a large portfolio of projects (valued in the £ms) and I believe would be the first in the role on these newer portfolios (they are hiring 4x of my position across multiple teams and portfolios, so I would not be the only new hire).

It is long established, publicly listed, is a nationally (and maybe internationally?) recognised name, and I would hope be able to offer some stability and work/life balance, as well as round out my CV with a very large company, as I've been so far working in startups and scale ups so can see it would be useful to demonstrate that I can work across extremely large organisations as well as the smaller more agile ones. However, because of that, I'm wary of the extra red tape, slower comms and maybe slightly more dinosaur ways of working in place currently (one of the interviewers asked why, when I've been at startups and rapidly growing companies in the past, I'd want to work at 'a great lumbering giant' like this company).

The second company is also well established (about 11 years), however very recently pivoted to a new field, which is extremely innovative and complex, and while it could be a super cool challenge, I'm unsure if the market has been proven yet. They closed Series B in 2017, with about $500m raised, and haven't started fundraising for Series C from my understanding, but also because of the pivot I don't know if they're profitable yet as much of the tech is in the R&D phase. It is closer to the scale of the company I'm in now, and has a similar energy and drive from the teams I've met so far which I've loved, as well as some extremely enticing perks (insurance, holiday allowance, tax free monthly 'bonus'). However, I don't want to be blinded by this, as my current company clearly hasn't been doing things in the right way (we had a super innovative product, and great perks too, which in hindsight they could have cut back on to save money vs rinsing investment and having to cut headcount).

The third company is a small startup (c. 140 employees), which just closed a Series B fundraise. There is only one person doing the role across the company at the moment and I would be joining them to support and take over part of their workload so they can try and focus on the strategic planning that is now happening to help them become profitable. I have really really liked the people I met so far, it is very similar in size to a startup I worked at in the past which I absolutely loved because I got to meet or work alongside almost everyone, as well as be exposed to far more than you usually would in my role so the learning was through the roof, however I am aware that stability, work/life balance, and the general risk of joining an earlier stage startup at the moment makes this option less sensible in the long term, and doesn't necessarily add breadth of experience to my CV.

It's so tricky, because I have my head telling me one thing, my heart telling me another, and I feel guilty in general that I'll potentially have to turn offers down that I would have taken if other interview processes hadn't started at the same time (I would have said yes to any of these companies if they had come through individually).

Help! What are the main factors you have considered when choosing between offers, and how can I phrase a rejection email for offers that I don't want to take up, but without burning bridges in case any future roles came up where I might want to be considered?

Thanks, and sorry for the long post!

You need to follow your gut. That’s the only way.Judging from your writing, the series B start up sounds like the best option for you because you sound very excited about it.There is no right or wrong answer. Even if you choose A and you end up not being happy you can always leave and get a new job.
3 things1- culture of each company - does that shoe fit your workstyle? Startups tend to be manic unfocused and fast fast fast but sometimes pivoting and creating busy work because things and processes don't yet exist. If you like planned organized work this isn't for you. Big companies tend to take longer to make decisions but have more money and resources and plan ahead to get to the end of projects. If they are public they also have the stock market to please so its all out there. 2- Content of the job. Do you want to do what the company wants you to do and vice versa?This definitely needs alignment in your head. Write out what each company gives you and then use that to whittle down the options. Add in to that recipe- who you report to- the rapport you feel, level of the role, opportunity for advancement, etc.3-compensation- How much is this a part of your choice? Don't necessarily take the one that pays the most it might not be the right choice given the items above. Though, if you are in sales you are likely coin operated! If you produce revenue or help the companies bottom line is there a bonus for hitting a target? Stock options? RSU's - value it all out. This is certainly a champagne problem to have. Unless you are not likely to take that first job. Call/email the other 2 places let them know you have an offer that has a time limit. Let them know you have to decide by X date (give them the day before the deadline) let them know that deadline is firm from the other company. Don't share who it is but let each suitor know you would choose them if things were aligned. Ask them to let you go if they are no moving forward with you - this may seem brave but its the right move and is the best way to not burn the bridge if things do not work out with your first choice. Don't let them make offers if you truly given what you mapped above have any concerns. Its better to not get an offer than to turn down one that you just don't want. One last thing, think about how you felt when the first company made the offer, that could also be a good predictor of long term success, remember they did not struggle to tell you they wanted you. They just made that call. How you are treated during the process is often how you will be treated when you come on board. Have one more conversation with that hiring manager, keep in touch until decision day you definitely don't want them to think they were a default option no matter what.
One thing I often consider is 'where does this role take me' - ie how does it set me up for the future. It's very demoralising to be not just stuck in a job but to also realise that your CV/future prospects are being sabotaged by it. Each job is just a step into the future - none of them are the future and none of them are perfect. Jobs that give you more options, make your 'story' bigger, and expand your horizons are often very fulfilling and can be the start of great things!
That's a great point about considering the long term goals and career path.