How to find a job at a tech startup and decide if you want to take it

Take a creative approach to getting your resume in front of hiring managers at startups and be ready to ask tough financial questions.

businessman pressing job search button on virtual screens

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IT professionals who don’t live in traditional tech hot spots have more job opportunities now that remote work has become the norm. 

If you are interested in working for a startup focused on machine learning, quantum computing, or 5G technology, you’ll need to be creative in your job search. Chris Dessi, vice president of the Americas and Australia for Productsup, has four tips for IT pros who want to make a jump to the world of tech startups. First, you have to know how to find the opportunity and market yourself. The  next challenge is to figure out whether the  job is a good fit.

Dessi said that when he wanted to move up from director of sales to a vice president role, he had a hard time getting headhunters to support this move. He had recently started a blog and decided to use a recent post in his job search. He sent the post to the hiring manager to start a conversation and ended up getting the VP job.

“I leveraged this backdoor mechanism to get myself in front of startups for the rest of my career,” he said.

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His next move was to copy the tactic of a woman who used the domain name “Twittershouldhireme.com” to establish some social media credibility with his own new site, “Facebookshouldhireme.com.” Fortune magazine interviewed Dessi about creative ways to get a job in tech, paving the way for his next career move. 

Productsup is a SaaS platform for integrating, optimizing, and distributing product content on social media sites and other marketing channels.  Dessi is currently leading the expansion of Berlin-based Productsup into the American and Australian markets.

Track what VCs are chasing

In addition to looking for creative ways to get the attention of startup hiring managers, Dessi suggests paying attention to the companies and technologies that venture capitalists are investing in. 

 “Go to VC firms, see where they are looking to hire, and figure it out from there,” he said.

Here are links to the job boards on some of the top venture capital funds focused on tech:

These job boards round up open positions at the startups that the VCs are funding. Some of the boards, including the ones at GGVC and Index Ventures, allow you to search for remote positions.

Find a social platform and participate

If writing is not one of your strong points, turn to social media to find opportunities to interact with tech leaders.

“All of these VCs are active in these communities, and many of them have a social profile so they can learn about new startups,” he said. “If you’re an experienced IT executive, you should have an opinion, so offer it.”

Pick a tech topic that you are interested in and check out the conversation on that topic on Twitter on a weekly basis. Find a group on LinkedIn that interests you and join the conversation by commenting on posts and sharing your own posts. 

Quora and Stack Overflow are other good places to learn about a particular topic and join a tech community. Create an account and post regularly. This track record of activity will show your engagement with the community and that you’re willing to learn and engage.

Finally, if a company you want to work for has a blog, read the posts on a regular basis and comment on the posts. This will put you in the flow of conversation at the company and provide some natural questions and comments in future interviews.  

Be prepared to ask difficult questions 

Once you’ve got the interview, the next step is to get ready to ask direct questions about the company’s finances. Offer to sign a nondisclosure agreement to protect any sensitive information.  

Dessi recommends asking these questions of a startup CEO during the interview process:

  • What is your year-over-year revenue?
  • What is your burn rate?
  • Where are you raising money from?
  • What is your philosophy on raising money?

“That will give you a robust painting of the startup and help you understand where they’re going,” he said. “If they don’t want to sign an NDA and share that info with you, run.”

A job seeker should ask plenty of questions but also present what he or she has to offer to the company.

Dessi said that an experienced IT professional brings business acumen, patience, and a global perspective to young entrepreneurs who have a great idea but not much business experience.

“Someone who has been at IBM for 25 years can use his nuanced scar tissue to help a group of newbies avoid a few mistakes,” he said.

Dessi said the smartest thing that he did to keep his job options open was to continue to write posts for his blog and share his opinion on tech trends.

Networking advice for introverts

Dessi is a sales professional and almost by definition an extrovert. For people who do not have selling in their DNA, he has a blog post with networking advice for introverts. Before you contact tech leaders or VCs about a job, try these tactics to prepare:

  • Build context in advance: Read the company’s website, check out the CEO’s social media accounts, and read news about the company.
  • Have questions ready: Ask about the company’s technology or current projects and come up with big-picture questions as well about management philosophy.
  • Follow up: Send an email thanking the person for his or her time and connect on LinkedIn. Also, think about how to use what you learned during the interview to reconnect again soon.

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