Crowdsourcing My Job Search: An Update

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It was a month ago that I publicly announced I had quit my job and would be essentially “crowdsourcing” the search for my next job. I figured this would be a good time to provide an update and to share some of my experience.


First of all, I’ve probably watched more of the 2016 US Presidential Primaries than any sane person should. After a month of following this pan-ultimate American reality TV show and seeing all the shenanigans, particularly in the Republican race, I’ve decided that what we need are some real outsiders in the race.


When I have not been obsessing over the Presidential race, I’ve been spending my time job hunting. This has included fielding inquiries from various companies and reaching out to folks I know in my social network. From the start, I’ve had two criteria that I’ve followed when doing any initial evaluation of opportunities:

  • A role that focused primarily on Technical Evangelism/Advocacy/Marketing with the opportunity to work with various tech communities.
  • A company that has a history and a culture of including remote employees effectively in their organization.

Over time and after conversations with several companies and with friends, I added a third criterion:

  • A roles that focused primarily on cloud computing and cloud native applications.

So that ruled out ~50% of the inquiries I received, both from early stage startups and more established companies that did not have a clear Idea of why they would need a technical evangelist, had few remote employees, and/or were not focused on technologies like scale-out infrastructure or container management. They were all good companies but ones I knew would not be good fits because of the above criteria.

Thankfully, I have also been in discussions with potential employers who may be a good fit for me as a technical evangelist working remotely from New York City. In some cases, I’ve even been able to write my own job description.

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To help me properly assess these opportunities, I decided to include community input into my search process as well. To accomplish this, I created and regularly updated a Google doc where I ranked all active opportunities and “crowdsourced” comments and questions from a group of trusted friends in the tech industry. Their input has been invaluable to me and I am extremely grateful for their wisdom and help. They have helped me to rank opportunities, decline inquiries that would not have been a good fit, and given me a better idea of what criteria I should value.

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My hope is as the process moves on, I will be able to build a consensus or at least some strong leanings from this group towards one or more opportunities. That is, of course assuming that I am fortunate enough to receive one or more job offers. The input from this group, I am betting, will help me to make the right decision not only about what potential offer to accept but which ones to decline.

My experience to date has taught me some valuable career lessons:

  • Don’t be afraid to reach out to your social network for help. You may worry about being a nuisance but actually most folks in your network are probably eager to help and you may be able to fill a need that they have in their respective companies.
  • Know what are some of your non-negotiables are when you start the process so you can focus on the opportunities that make sense to pursue.
  • Don’t just apply to companies with known openings. Opportunities may not have been made public yet or you may have the right skills and experience so that a company would create a role for you.
  • Have a good idea of what type of job you want but be prepared to modify some of your criteria if they are negotiable or to add new criteria as appropriate.
  • Engage your community, not only to look for opportunities, but to advise you on what to pursue and what to avoid. Find a group of friends who can advise you along the way.

I am hopeful this job crowdsourcing experience will soon lead to the next great adventure. Meanwhile, I am very thankful for my family’s support and encouragement. And I’ve just recently given them another reason to hope that our job search process will soon come to and end.

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Of course, if I decide to crowdsource that decision too, may family may have to get used to my new look.

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  1. I love the “new look” – Also, huge thanks for “Open sourcing” your social-career-journey. You might be able to start referring to the inputs of your trusted colleagues as “pull requests” – Q: Would you recommend this type of leap to others, and/or is there a way you think that people can leverage (i.e. “fork”) some of these learnings without having to leave their current roles?

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