Top 5 Tips to Transition from Enterprise to Startup


Most people know I left my BIG corporate job at Cisco to go out on my own. I am a HUGE advocate of stepping out of your comfort zone. But leaving a steady corporate job for the unknown is hard. NO DOUBT.

So for those that are considering taking the leap…not necessarily just going out on your own, but going to a smaller operation, I thought these tips might help prepare you for the leap. And it is a leap—a leap of faith—that I don’t think you will regret!

Top 5 Tips to Transition from a BIG Enterprise to a Startup or Smaller Company
  1. Be willing to take less money – Call me Captain Obvious, but that is a big one. You have to be willing to leave a big “known” salary. That doesn’t mean you will make less, it just means you aren’t guaranteed that monthly paycheck. When I left the big corporate world, I actually made more money. I was scrappy for sure, but for the first 6 months I sweated it. You should try to save up for what I call a Freedom Fund. You should have enough in the bank to sustain you for at least 6 months, but the more you can save the better. Put together a “lowfi” spreadsheet of your monthly bills and then save accordingly. Oh and get ready to change your diet, e.g. more eggs and peanut butter sandwiches, less lobster and steak.
  2. Forget the Title – Titles don’t matter as much in a smaller business. I often joke I am president and janitor. In all seriousness, when you take a position in a smaller business (e.g. NOT a Billion dollar business), you have to do things that others used to do for you in a big enterprise. For example, when I worked on web projects for Cisco, we always had an analyst spit out reports and insights. When I went out of my own, I learned how to pull my own Google Analytics and interpret them. You have to be willing to be OK with less complete data to make decisions and willing to learn new skills and add new responsibilities.
  3. Embrace your own decision-making – In a large enterprise, everyone has opinions and often you aren’t the final decision-maker. (On a side note that is usually the biggest reason why people want to leave the comforts of the Enterprise.) When you work in a smaller organization you are responsible for the big decisions and that can be scary. At first, I found this to be paralyzing…after all the complaining I did about not being able to make a decision at my fancy corporate job, when it was time for   me to make the decision (and live with the outcome) I was super nervous and found my confidence not so bold. Lean in…nothing is permanent AND there is never perfect data, so make the best decision you can and work like hell to course correct if it doesn’t pan out like you expected.
  4. Be willing to try new technology – When I was at Cisco, all I knew were the systems, software and technology they used. Most enterprise companies have sanctioned software which often makes sense because of their investments and security requirements.  When you are in a lean business, you learn to use every free trial, evaluate technology differently based on ease of use and price point. I tell all my big company friends that when I left my big technology job, I learned more about technology. I didn’t have the 20 page requirements document to limit my choices. I didn’t have legacy systems to consider. I didn’t have technology policies I had to adhere too. I have done more, faster and cheaper with open source and monthly SAAS products now than I ever did with million dollar systems I used before.
  5. Be Humble – I never saw myself as arrogant. Confident, yes, but never arrogant.  But when it came time to work with clients with less budget and different processes, I had a moment (internally mind you, my mama taught me well) thinking why on earth are they doing it this way…we used to do this…and that… What I learned is that when you don’t have an average sell of $100K or your margin isn’t 80% you have to make different choices. You have to create processes that work for your company at the size you are and cash flow you have. Granted I used my big corporate experience to help my clients, but often times I learned more from them on different ways to achieve the same goal. You must be adaptable and humble to make it outside the BIG C….

These tips will come in handy when you take that leap so that you cannot only survive outside the big enterprise but thrive.  If you are considering making a leap…contact me…I will help you quit your job and open your mind to new ways of working and new ways of taking control of your career.

If you have other tips, please share them in the comments section!

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