How to ditch Microsoft and join a great startup

Guest Commentary: The last few months have not been great for Microsoft. First, the Surface turned out to be a flop. Then, Ballmer resigned without a successor in sight and admitted he missed the boat with smartphones. And two weeks ago, he held a company meeting where he bawled that Microsoft was still the best company in the world. He must have left his flight suit and “Mission Accomplished” banner backstage.

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Microsoft CEO Steve Ballmer at his final company meeting

There’s always been a steady stream of talent leaving Microsoft, but after recent events, we’re certain to see more of an exodus. Picture this. You’re a young and ambitious Microsoft employee who joined out of college a few years ago. Some of your friends from school run startups, and every once in a while you see Facebook posts about them getting funded, getting their hundred-thousandth user, or maybe even exiting. Many of your other friends work at small companies where they enjoy huge scope and very little politics. They get to take advantage of the latest technology stacks and give back to open-source along the way. You read articles about quitting your job and starting your own company. You begin to wonder if the race to climb from level 59 to 65 is really the one worth winning.

Luckily, it’s never too late to get out and find a more fulfilling role, especially in today’s startup-rich landscape. Here are a few tips I’ve gleaned from my own experience and that of my friends on how to leave Microsoft and join the startup scene.

The first thing to do is to ask yourself what you really want. Starting a company may seem like the glamorous path but it’s a huge leap. If you are passionate about solving a big problem, have found an amazing cofounder and are willing to live without a safety net then please don’t wait for anyone’s permission. Just go for it. If that’s not quite the case then joining a startup (ideally early-stage & fast-growing) will undoubtedly give you the crucial experience necessary to build your own business someday.

Like all great experiences, joining a startup is risky. Life at Microsoft may be slow and full of politics, but it’s simple. Your annual review tells you how you’re doing, and there are mentors who can steer your career because they’ve seen every path through the organization. However, join a startup and you’ll work with little guidance and be measured on hard results – users and revenue. Your company might run out of cash five months after you join. And the way Microsoft is doing right now, you may not be able to go back to it. If you’re not willing to take this risk, you might be better off making the switch to Google or Amazon.

borispullIf you’re still set on the startup path, get a resume together. Make every point in it as concrete as possible. Don’t write that you “contributed” to a part of the Visual Studio code base, write exactly what you built and why it was important. More importantly, make sure to wipe all references to your Microsoft review scores. Outside of Microsoft, mentioning these things will only bring you pain. When you have a first draft, get your friends at startups to review it, and take their feedback seriously. You’ll often discover that their expectations for interviewing and hiring are quite different from what you’ve seen.

As you’re working on your resume, start putting together an online portfolio. The technical interview is dying, which is not something Microsoft and other major players have adapted to yet. Many startups won’t even screen a developer or designer who doesn’t have a portfolio of projects they can talk about, so if you’re a dev, make sure you have some good work on GitHub. At the very least, find a way to show your creativity and talent. Put your designs on Dribbble, write on a blog, or post a video of yourself giving a talk. Having side projects shows that you can’t help making things, even when you’re not paid to. This passion for creation is the cultural fuel of all startups.

If you’re an engineer, there’s another, more practical reason to have a presence on GitHub. It shows that you’re adept with more than just Microsoft technology. For example, if you’re thinking about data science, you should be versed in Hadoop, NOSQL, and MapReduce. It’s a turn-off for companies to meet you only to find out you’ve never left the Microsoft C# bubble.

Once you have a reviewed resume, material in your portfolio, and you’ve brushed up on the state of the art, it’s time to turn into a networking animal. Everyone knows a warm intro is worth 100 cold applications, so tell your friends and old colleagues that you’re on the market. You should even tell your friends of friends because weak ties score the most jobs. You want to be the person that someone says this about: “I know a really good engineer annoyed with Microsoft, and he’s looking around.”

Beyond your direct network, there’s a great way to connect with startups: get to know investors in the area. They are always open to networking (it’s a huge part of their job after all) and act as de-facto headhunters for their portfolio companies. It doesn’t hurt to cold-contact people at companies, but make sure you sound like you have something to offer. Generic sounding ‘I came across your jobs page’ emails go directly into spam. Instead, get on Google, figure out what the company’s biggest challenge is for the next six months, and suggest three ways to overcome it.

As you start to talk to acquaintances, investors, and interviewers outside your circle of friends, you should watch out for some of the biases you’ve probably picked up at Microsoft. Here are some things to keep in mind:

  • Never mention your review scores.
  • Know what job you want. It goes without saying that no one wants to hear that you just want to leave Microsoft.
  • If you’re a PM, be very concrete about what you’ve done. There’s a tendency to think that PMs at Microsoft don’t do anything useful.
  • Show that you’re eager to contribute, not manage. Managing may have been the end game at Microsoft, but it’s not at a startup.

Finally, be vision-driven instead of constraint-driven when discussing an idea or product. It’s a common stereotype that a Microsoft engineer’s first reaction to a new idea it to poke holes in it. Startups don’t operate on this type of thinking. They have bold, even crazy, visions and find ways to realize them. Think SpaceX.

It can take a few months to find the right job, but eventually you’ll find a company you like. You’ll discover that compensation at a startup is considerably different and you should learn how to negotiate offers effectively (hint: know about “shares outstanding”). When you finally accept an offer, pour yourself a drink, look forward to the adventure to come, and smile as you think about never having to eat in those soulless Redmond cafeterias again.

One more thing. When you give notice, do it gracefully. Be honest about why you’re leaving but also positive. Chewing out your coworkers in the exit interview won’t do you any good. Your relationships at Microsoft will likely come in handy. You might get a note from your manager a few months after you leave asking if he can ditch Microsoft, too.

borisBoris Jabes is the CEO of Meldium, a Y Combinator-backed portal designed for teams to securely access their web apps. He worked as a PM and Lead at Microsoft for seven years. 

Editor’s Note: Want more advice on joining the startup world? Get your tickets for GeekWire Startup Day, Oct. 25. Early bird rates end Friday.

  • aaronbrethorst

    “Like all great experiences, joining a startup is risky” – Agree with everything (especially building a portfolio on GitHub) except for this. Unless the economy completely tanks, you should be able to bounce back from a failed startup with very little effort especially if you get into mobile development.

    • Boris Jabes

      I think that’s a fair counter-argument. The market sure would agree: the demand for good devs far outweighs the supply right now.

  • Sacha Sarieddine

    Very Good article. As a 12 year IT recruiting vet Boris hits on some very valid points. I’ve had great success helping MS folks get out and find new and exciting jobs at local start-ups and we’ve done it by using many of the suggestions Boris outlines. In my experience the biggest hurdle for most folks dying to get out of MS is the compensation piece. Softies are well compensated, so for those mid-career pro’s it can be quite a hit to leave a nice L63 IC role making 130K + annual cash bonus + stock to join a startup offering 110K + equity…….and the risk associated with a startup.

  • Sacha Sarieddine

    @aaronbrethorst:disqus – couldn’t agree more about the trajectory of Mobile Development…………..If you’re an engineer hoping for job security get into Mobile Development!

  • http://www.linkedin.com/in/merydith Will Merydith

    I had the opposite reaction to Ballmer leaving – I just signed up at Microsoft. MS has an incredible pool of talent, and a huge audience, they just need an updated vision and leadership and that wasn’t Ballmer/Windows.

    • Boris Jabes

      I whole-heartedly concur on what it takes to start a company. This was primarily aimed to people looking to join rather than build a startup from scratch.

      I have the utmost respect for the smart & talented people inside Microsoft. I think the integration of Nokia is going to be a rough ride, especially given the company’s dismal track record with large acquisitions (i.e. aQuantive).

      I truly hope a great, visionary leader comes in to replace Ballmer but that doesn’t change the fact that his announcement to depart without a succession plan in place smells bad; imagine if Schmidt had left Google this way, or Jobs retiring from Apple.

      • Mark

        Why point out aQuantive while ignoring the even larger Skype deal? Working pretty well so far, no? Agree with some of the other commenters. You have a lot of good advice here. The cheap shots just detracted from that. I’m kind surprised GW let it run as is. But aside from that it was still useful So thanks.

        • Boris Jabes

          You’re right, so far it seems as though Skype is going better but it’s still early. aQuantive was a larger acquisition in terms of people and we have more data about it. I don’t think anyone can argue that merging organizations of this size is difficult under any circumstances (including Google acquiring Motorola). When you add that this is happening in the midst of a CEO change and I think it’s safe to have some doubts.

          In any case, I appreciate the feedback and I’m glad you got some value out of the article anyway!

          • BrendynA

            I think a key difference between aQuantive and Skype is that Microsoft doesn’t viscerally get (and shouldn’t be in, IMO) the ad business. It knows what to do with telecommunications software, and Skype itself is a software company. Integrating an ad agency into a software company was culturally harder, but that wasn’t ultimately why the acquisition failed. It chased the wrong prize and lost the game. (To that I also say, make Bing ad-free! Pull a Google and provide a prime competitor’s core product a zero cost to consumers. Such a great opportunity.)

            I don’t take much solace in being self-righteous, since a certain segment will benefit from this advice no doubt, but it’s also possible talented people are staying because being at Microsoft now is like being there at its beginning. I’ve worked on v1 products for 6 years now. It’s been transforming for a while.

            Plus, it’s an awkward underdog, and I like those. Especially ones with vast resources and reach. Anyway, that’s appealing to some; as is leaving to join a great startup. But I think you can make your point without dissing one group or the other.

  • Anon Startup Developer

    I’ll add a “don’t”: “Don’t act like God’s gift to the startup”. Just because something worked at Microsoft, doesn’t mean it works in other more dynamic and less forgiving circumstances. Don’t act like any technology you haven’t encountered isn’t worthy of respect and understanding on its own terms. Startups require a lot of learning, in terms of adjusting the product to the changing business strategy and reacting to customer engagement or lack thereof.

  • SilverSee

    Respectfully, I think the jury is still out on a few things you deem failures in your first paragraph. Your article would have been better without this type of intro–it’s self-serving and sounds like sour grapes.

    • Boris Jabes

      I think that’s a very fair point; the opening paragraph is definitely hyperbolic to the extreme.

  • tsupasat

    ExtraHop is a great Seattle startup looking to hire the type of engineers and technical folks described in this post. Check out our jobs page: http://www.extrahop.com/company/jobs/

    I’ve been at ExtraHop for two years and love working here. We have a diverse and talented team, and it’s a great place to DO THINGS.

  • Kevin Merritt

    Good post, Boris.

    If you’re a software engineer, program manager or product manager at one of the various big tech companies, note that there’s an event on October 21st specifically for you to meet some of the fast-growing startups. Socrata, SmartSheet, PayScale, Avalara and EnergySavvy will all be there. Here’s a link: http://www.getarealjobfair.com/. I’ll be there and would be happy to tell you more about Socrata.

  • beentheredonethat

    This post has been named a finalist in this year’s Seattle Passive-Aggressive awards.

    It’s also mostly true.

    • Boris Jabes

      It was really meant as a set of tips for people that are looking around! I admit there’s a bit of hyperbole in there.

  • guest

    Most pathetic article. It looks like this author was fired from MS and venting his frustration albeit in a thinly disguised fashion. Why did you specifically write about MS, this could apply to Google, Apple, Face book or any other company.

    • Jane

      I took the liberty of looking up Boris Jabes on LinkedIn and it turns out he worked at Microsoft for about 6 years, he must have forgotten to include this in his article. It is strange that this type of article has made it onto the site as for many years MS has contributed over 100,000 jobs to the global economy, they must be doing something right? Yes there are a few issues at the moment, but I wouldn’t write them off just yet. Selecting an employer is very much up to personal preference and should not be viewed from a bias perspective.

      • Heather

        “Here are a few tips I’ve gleaned from my own experience and that of my friends on how to leave Microsoft and join the startup scene.”

        Seems pretty clear to me that he worked at Microsoft.

  • Stan

    Is this line correct?

    > Having side projects shows that you can’t help making things, even when you’re not paid to.

    I would change CAN’T with CAN :)

  • Stefan Batres

    As someone who left MS after 15 years to join a startup, I agree with a lot of what is here. The compensation bit is critical: You are not leaving MS to make more money, you should be leaving because you want to – and there are many reasons you might want to leave, not all related to negative happenings at MS.

  • KevinHee

    The only thing this article taught me is never to work for a company named Meldium.