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Hello,

I have just been offered a job from a former manager who is now at a new startup company. There are only 35 employees and no IT staff. He wants me to be the IT manager over the infrastructure and also the main endpoint support. My background is primarily endpoint support with some Sys Admin and network support. The environment has an Azure AD domain and Web Root for AV. Not much else has been established as far as the infrastructure. He is really pushing me to get in on this opportunity. It does seem like it could be great but I’m not sure if I’m getting in over my head. He said I’m fully qualified and would have the help of himself and several vendors but I’m with a really good and stable company. I am married with three children so it won’t be an easy decision. I haven’t got the official offer yet but was told the pay would be better and have stock options. Any advice or ideas on the setting things up with the infrastructure if I take it? Would you go for it? I have wanted to move up in my career but not at the expense of the well being of my family.

Thanks,

Joe

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Go for it. What’s the worst that could happen?

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Well for starters, talk it over with your family. Startups can provide some great opportunities, but they can also go bust pretty quickly. What’s the size of your current company vs the startup? Your former manager thinks you can do the job which is good, and it will obviously be a learning experience, but you have to plan for the possibility of it going belly up. Can you weather something like that if it happens? The offer itself will also be a big factor. What’s the percentage increase over what you make now. Make sure there are benefits included (insurance).

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Setting up the infrastructure won’t need advice from here. There are plenty of documented resources available out in the wild that’ll depend completely on your details.

As for the move, compare the whole compensation package, not just pay. How did health insurance plans compare? Time off? On-call expectations? The commute?

If they’re all favorable and your spouse doesn’t have immediate concerns, then take the extra pay you receive plus any cost savings in reduced expenses like the commute and chuck it into savings. Build your Employer Went Belly Up safety fund. Keep your resume up to date, especially as you document your infrastructure build.

Write the details for your office, summarize for LinkedIn or your profile here, then summarize that more for your rez.

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Patrick makes a great point; talk it over with your family. They need to be aware of what you have been offered and as they will be affected by your decision, should at least have some input.

If you have a difficult decision like this, try and do a pro / con analysis. What the are arguments for and against making the decision (both for going and staying, not always quite the same). Sometimes, it’s worth looking at the money (bird in the hand), other times it’s more about opportunity (grass is greener).

I would say that most people will agree that at the end of your life, you will regret more the things that you didn’t do, than the things you did do. Just throwing that out there.

It’s also worth highlighting something that has stood me in good stead. If ever I have a tough decision to make, and I get stuck, I toss a coin. It’s not about how the coin lands, but about how you feel at the instant you see which way it has fallen. If you are pleased, then you know that you are happier with the result; disappointed means that you really wanted it to go the other way. That will tell you which is really the more important choice and the one that you really want.

Best of luck

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Really good point here. I’ve found myself already knowing which decision I want and just want the responsibility for making it (and therefore, possibly regretting the other) out of my hands. I’ve created quick little randomizer programs before, and since the computer will spit out a result instantly, it felt too fast (especially if the result was one that I didn’t really want).

I’d modify it to appear like it was going through all the choices and give me a result after visually showing a flipping of numbers. I’d have it calculating like a roulette wheel so that I’d stop it on a number. No matter what, I was typically displeased with the result so I kept tinkering.

All while ignoring the fact that I’d already made my decision and was just seeking validation. :slight_smile:

We’ve seen that here in numerous topics. Someone will believe themselves to be conflicted over a job decision, but the writing reveals how they really feel. “It’s a great job and I love the people but…” or “I’ve been offered a great job with lots of potential but…” Those “buts” are often 12x longer than the rest.

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To go back to the OP, it’s natural to be cautious or even apprehensive. The more comfortable you’ve gotten with your routine, the more difficult it is to leave. And when there’s a family to support, it becomes even more scary. I’ve been there. Just this year, in fact. Granted, I didn’t go to a start-up so my level of risk was much, much lower. I moved to an organization in the same industry that’s twice the size of where I’d left, and one that not even 5 years ago was going through some massive internal conflicts.

But there were sweeping changes that had happened from the top down. When I received the offer, it was a raise enough to where I would have had to stay at my then-current job for another 10 years to match (I work for public school, so that multiplier isn’t nearly as impressive as it sounds! At my level, I got maybe an annual 1% COL increase, as I’ve long tapped out my steps). Benefits were naturally identical, as I was moving from one K-12 to another. So on paper, everything sounded great.

I was still scared.

I’d spent 17 years at my previous org. I had complete ownership of several responsibilities and I was the go-to guy for them all. The networking I was doing was paying off and and and…

All great reasons to stay. But I couldn’t ignore the pay increase, the closer commute, and a type of professional-growth opportunity I wouldn’t have had if I’d stayed. Six months after taking the job, I’ve grown my professional network in ways I couldn’t have predicted. One trade-off is the slightly worse insurance benefits (my new org is with some barely-known dental and optical providers)…but comparatively speaking, what I gained makes up for those minor inconveniences.

My family is still covered, and with special-needs kids, that’s a big deal. It took us forever to find a dentist who’d even give us the time of day; it was heartbreaking to be told “no” by so many pediatric dentists. When I switched jobs, I was prepared to go complete out-of-pocket just to stay with the kids’ dentist. Luckily, they accept our new insurance as well. But it was a risk.

Ultimately, what stuck out to me was the growth opportunity. If I was going to advance in public school technology management, I needed more experience on the instructional and administrative sides, rather than only tech. That’s why I was sitting where I was for 18 years (including the 1 year I spent at a district prior to my last one), with only the last 5 being any significant growth.

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Thanks so much for the advice! A few details about the startup. They are a startup pharma company that has a promising drug. Benefits sound great as far as health, vacation, etc… My former manager thinks the pay increase should be at least 10-15% with stock options. The commute would be longer by about 15 - 20 minutes. If they are successful they could be purchased by a larger company which is the trend with pharma companies. If they do offer stock options, being bough out could be good as far as the options but that may mean I’d have to look for work again in 2 or 3 years. So good or bad in a few years I may be looking for work. The experience would look good on my resume though. There may be a lot of long hours until things settle down. They are anticipating growing by a few dozen employees in the next year or so.

This will be the first time I have helped setup an infrastructure and that is a little intimidating. I’ve supported various parts of an infrastructure but never made the decisions in designing one. There is so much involved with security, networking, DR, backups, servers, and even PCs and printers. There is a lot that can be outsource and hosted via cloud services but wow, being the only employed IT guy to be responsible for all of that. My former manager is a consultant for the company but he may eventually become a full time employee also.

I have had problems with my manager at my current company over the years but things have been great in the last year or so. He has a temper and sometimes just goes off on people over little things. Everyone is entitled to a bad day once in a while but it is a little more than that. The company I am with has been in business for 50 years and has a great owner. Other than the issues with my manager I love it there.

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One thing to consider is being purchased by a larger company as you mentioned. What happens to your job? The larger company will have an existing I.T. department. There is a significant chance that you will not be needed.

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So that pretty much guarantees that the company will either be bought out for the IP or fold for failure of the product to catch hold in the market. You at least know it’s going to be a 2-3 year gig going in.

Which means that after your pay increase covers the longer commute, everything extra you make should go into savings, and that once the two year mark hits, your eyes should start looking elsewhere.

As for being responsible for creating everything, don’t. :slight_smile:

Your role will be that of a manager, not a line worker. You bring in and oversee the consultants and vendors who’ll be doing the heavy lifting for you. You frame these contracts in terms of ROI: the vendors have the expertise you don’t, and they can mitigate the risks while creating value that you can’t because you’d have to learn from Step 1 whereas they can hit the ground running. But you have the best interests of the company at heart and you know enough to be able to spot BS; you therefore protect your company’s interests as the project manager while keeping the vendors on track with timely deliverables.

This will also look awesome on your resume.

However, as you mention, there is a bunch of risk involved here. You know it’s going to be a temporary gig; you’d be naive to think otherwise, and I think deep down, you know that.

As for your current employer, think bigger and broader. Your current supervisor has a history, and you say they have a great owner…but how long is that owner going to be around? An organization existing for 50-60-90 years is irrelevant. What matters is how an organization stays current.

Ask Kodak and Polaroid how their longevity worked to their benefit.

I’m not trying to push you toward this new gig. Only you can make that decision for yourself. I’m only trying to pick out a few aspects you may not have considered.

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My former manager thinks the pay increase should be at least 10-15% with stock options

What can make that bazillion shares in stock worthless?

Vesting - Options typically vest over time. If you quit or are fired before all the options vest, you forfeit your unvested options.

If the company is bought before your options vest, you may get options in the acquiring company, but that will depend on the details of the stock agreement

Low Exit Value - The company could IPO for less than the strike price of the option.

The way 409A valuations work this isn’t especially likely with early stage start ups (it is far more likely the company will just fail), but it is possible.
In that case, if you haven’t exercised your options you would just not exercise them. If you have exercised your options, you would face a capital loss as you paid more for the stock than it is now worth.

Preferences - Even if your options have already vested, even if you’ve already exercised them and now own stock, the investors will likely get at least the value of their investment back before your stock becomes worth anything. This is because their “preferred stock” has a “liquidation preference”.

How much money the company has raised and what multiplier the investor has will determine how much the company must sell for before common stock has value.

Participation Rights - Investors may have “participation rights” that mean they would get both their liquidation preferences and then also get the value of their shares.

Dilution - When the company’s owners raise money or offer stock options to employees, they do so by printing new stock. You own the same number of shares, but the total number of issued shares is larger and so you hold a smaller percentage of the company.

Repurchases - There may be language in one of the option plan documents that lets the company decide to repurchase the stock you’ve already been granted.

Unlike the option to voluntarily sell stock back, compulsory repurchases are a bad deal for employees as the price to be paid is set by the board

Clawbacks - Some plans may have clawbacks, where even vested options are forfeited under certain circumstances, such as termination.

There are many different documents where repurchase or clawback language can be included; if you are concerned, it’s best to consult a lawyer.

High Valuations - You often have a limited amount of time after leaving a company to exercise your options. Additionally, options expire after some number of years, often five or ten.

If your company has a high valuation but is still private when you have to exercise your options, you could get stuck needing to raise a large amount of cash to pay for the stock and cover the tax liabilities.

Taxes - Profit from options and shares can count as income.

A tax professional can give you advice on how to plan for your taxes and the possible value of early exercise.
IPO Lock-Ups - When a company goes public on a stock exchange, insiders usually can’t sell for the first 90 to 180 days.This is referred to as the “lock-up period”.It prevents the market from being flooded with shares, reducing the supply and inflating the IPO price.
Unfortunately, by the time you can sell so can all your coworkers. The valuation employees are able to sell at is usually lower than the immediate valuation.

A Great simulator for estimating what an offer is worth can be found @ https://tldroptions.io

Lets talk about compensation.

There’s a LOT more than Salary and comute to look at.

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There really normally isn’t work life balance as the only IT guy at a startup growing 500% year over year. I’ve worked with a lot of these guys in a previous life. A good MSP should be running day to day stuff for you, but it’s still a ton of work.

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I agree with John’s assessment on this. I am on a similar job the OP is going through but the staff and business is growing 300 % to 400 %, I am the only IT there and it takes time and effort to keep it running efficiently and properly. Healthcare is crazy to maintain around the clock.

Even with an MSP (which was turned down by management) there is a lot of work and projects to do. It is almost a 24/7 job .

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If the family is on board, jump on it as it sounds like a fantastic offer.

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Thanks! All good points. The life balance is one of my biggest concerns. Things are good in that regard where I currently work. I guess the offer would have to be really good for me to move. I%u2019ll post what happens. No guarantees that I%u2019ll get an offer but I think chances are good.

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I didn’t notice this mentioned yet (but then, I didn’t really read everything word for word, either) but there is something else to be worried about with the job you mention - losing it fairly quickly to someone else. As an MSP, I would go in there and snatch them up as a client and put the IT person out of work. I do this regularly. There are very few arguments that I am not able to overcome regarding why a company this size even has an onsite IT person.

No matter how much guarantee they give you, if it’s not in writing (and sometimes, even if it is) then there is no guarantee your job will be around in 6 months.

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Are you happy where you currently are?

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Love the company and if I had a different manager I would probably never leave.

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Risk vs Reward. Weigh the options carefully when you have a family. You need to make sure you have the financial security for them, and if you are already happy at your current job then you can’t use quality of life as a determining factor.

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Talk with your family before taking some action.