Corporate to Startup – Tips for Making the Jump

I moderated a panel a few days ago called “The Corporate Escape” in which four panelists and I discussed how we made the transition from traditional corporate jobs at Fortune 500 companies to small tech startups.

A lot of knowledge was dropped for the attendees from the Suits to Silicon Alley meetup group and I wanted to share some of what we discussed here along with my own personal tips since I’m frequently asked about this.

If you’re thinking about making the switch to “tech” or the “startup life,” read below. This isn’t exhaustive but a quick list of some of the best learnings since I forayed into the startup world several years ago.


  • Industry – Get Specific. People who work at startups hate hearing that a candidate  “just really wants to join a startup.” Get specific about why you want to join that sub-industry and show you know their products and competitors inside and out. I initially got rejected a lot when telling people “I really want to work in tech” or “I really want to work at a startup.” I had to narrow down my fields of interest to be able to carefully craft a compelling motivational story. I read as much tech news as I could and found I was most interested in mobile advertising (advances in NFC, RFID, etc) and tech education.
  • Roles – Be patient and give seemingly non-sexy roles a chance. Everyone wants to go to a startup and do “strategy” and say its impossible to get a decent role that isn’t engineering or product management. You need to look harder! Operations, Sales, and HR are great places to start out in small startups.
    • Ops I started out in operations and was given great advice to do so by my first boss (Vincent Ponzo). I was considering other roles at larger tech companies where I would get to do strategy (lots of modeling) and he told me “If you want to, you’ll always understand and be able to execute strategy by working on the ground, in an operational role. You won’t always understand the ins and outs of a business working in a strategy role.”
    • Sales Many in the startup industry will tell you there are only 2 vital roles at any company – engineering and sales. If you can’t build your product, you don’t have one. If you can’t sell your product, you don’t have a company. Sales is a difficult and well paying role in many tech organizations and on the rise in popularity. (talent auction site) recently added it as their first non-technical role they recruit for.
    • HR Human Resources is one of the most underrated areas of an organization and one of the most vital to a fast growing company. You get a birds eye view of everything going on and get to help shape direction of key company initiatives.
  • Size of Startup – Deciding the right size startup to join is hard. Join a 3 to 5 person team and take on a lot of risk? Join a 500 person behemoth and miss out on some of the exciting growth? While ultimately this is a call you should make based on your own personal risk appetite and belief in the product that company is selling, I have seen that there is the most room for growth balanced with the right amount of security if you join a startup right before or around their Series A. Don’t take my word for it, check out Stanford professor Andy Rachleff’s advice

Get Started….

  • Be Helpful while Networking – I went on dozens of coffees as I got to know people in the NYC startup scene. Initially I felt that I was wasting everyone’s time as I asked them general questions about how to get into their fields. Finally I had enough of feeling like a potato sack and started making coffees useful for both sides of the table. I did this by turning coffees into product feedback and strategy sessions. I would read up on the person’s company and review their website in detail – looking for anything that wasn’t intuitive, anything broken, any feature I would have wanted and didn’t see. I also studied their competitors to see if they had the features I wanted and to glean more product ideas. Then in coffees, I would become their user and discuss feedback and potential features. Startup employees love talking about how an outsider views their company and product. The coffees instantly became valuable for both of us and I became more remembered.
  • Analyze the Culture – Morgan, a developer on the panel, said it best – if you’re a new developer and interviewing with a startup, look for clues that the startup culture is thriving and that they value their employees, especially technical talent. In a technical role, you’ll want to look for and ask a few things – 1) physical comforts & large monitors – for designers and developers to do their work well, they have to stare at screens much of day. If the company doesn’t have large monitors and comfortable chairs, run away. 2) Ask about how they prioritize their project backlog and what drives decisions – product needs, business needs, or a combination of both? If the technical teams seem overly frustrated and references not having any input on the business direction, run away. 3) Nice to have – if the startup is large enough, look for company perks – free food, no vacation limits, comfy couches – these things all spell the company is all about motivating its employees to do their best.
  • Learn Product Management – Product Management is a sought-after, catch-22 job that many corporate types pine after. Or, as panelist Leo from Deal Roadshow explained, something he expects every employee at his small company to embody. I couldn’t agree more. At a small startup, product management (validating, designing, and executing on a product strategy that creates the perfect product for your audiences) is something that (similar to strategy) shouldn’t only be something a few people consider part of their roles – it’s everyone’s job to constantly ask if we’re building the right product for this audience base.
  • Get Recruited – Found a company you’re interested in? Before you apply, take a look at the LinkedIn profiles of people who currently work there. Optimize your LinkedIn to use language and terms similar to what current employees use in their titles and to describe their roles. Their recruiters will find you faster than you can believe and your resume will go to the top of the list when setting up interviews.
  • Prove your Value – Jamal O’Garro sent me this tip: “When trying to make the transition from the corporate world to the startup world it is very important to demonstrate how you can add value to a team. Startups are very small companies and hiring the right or wrong person can have a huge impact on a company. For this reason founders are very careful about deciding who to bring into their companies. The best way to prove your worth is to volunteer your time by working on small projects. If you can consistently add value then you’ve already got one foot in the door and may receive a job offer sooner than you think.”


Thanks to the awesome panelists for your participation and all the ideas you contributed to this recap!


Leo Efstahiou, Founder of Deal Roadshow

Jamal O’Garro, Co-founder of Code Crew

Morgan Polotan, Software Engineer at Tapad

Carolyn Ganon, Software Engineer at Bedrocket Media Ventures

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