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My Next Big Thing

I got laid off from my previous employer at the end of January this year. This is a post about how I used modern tech to find a job in a very strange time. I’m writing this in the hopes it will help some of my friends find their next job.

I didn’t see it coming at all. One minute I think I’m having a one-on-one with my manager on the phone and the next minute the HR person is giving me details about my upcoming separation. I had an out of body experience and I found it very difficult to focus on what was being said. I still say it was like a scene from “Up in the air”, where George Clooney’s latest colleague promotes ‘corporate downsizing’ by video conference.

I was lucky in that two days after my initial notice, I had a meeting with my financial planner. We were originally going to talk to him about something else – and I don’t even remember what that was anymore – and he gave me two major pieces of advice:

The Advice

  1. Review your financial position and figure out what you need to do to protect yourself and your family. In a time like this, you might not be thinking very clearly. And with the pandemic raging with your retirement, you want someone with a clear head. If you don’t have a financial guy, then get a recommendation from a friend.
  2. Use LinkedIn ruthlessly and shamelessly to connect to recruiters, hiring managers, and anyone else you might need. I’m going to spend most of my time talking about this one and how I made it work for me.

You’re now faced with some interesting choices. Do you want to now start that second career and follow your dream? Maybe now is the time. The primary reason for step 1 above is so you can get a sense of what your options really are and how you might do something really different if that’s what you want to do. You need to take stock of what you really like to do, what you believe you are really good at, and why you are good at it.

My thinking at this point was, “Gee, the kids have left the house and we’re empty nesters. I wonder if I could finally do that startup thing I’ve wondered about”. And that largely drove my job search. It is axiomatic that the closer you stay to your previous skillset, the more salary you can likely get. But startups don’t pay all that much so you have to decide on what kind of working environment you want. For me, I wanted a late-stage, pre-IPO startup, in part because where I live is really expensive and late-stage would have a higher salary.

I also wanted a company with values like mine and was recognized as a good, if not great, place to work. I was planning to continue as a competitive intelligence person, working on sales enablement and product marketing. I was doing that at my previous employer and I liked it. I was good at it as well. I had a great boss who I considered a friend of mine. All in all, my previous gig was a really good one. So having determined what I wanted to do – continuing to be a competitive intelligence person – and the types of company I wanted to get to (late-stage pre-IPO; but for you, it could just as easily be ‘Healthcare’ or ‘Public Sector’), now I can focus on identifying the companies to target. I was determined to mount a sales campaign and I was the product.


Do you see now why the first step is important? If you can’t focus your energy on the future, you will struggle with this important activity. I get that for some people, living paycheck to paycheck, this can be difficult. We were living paycheck to paycheck as well. If it wasn’t for the financial advice I got, I would have become obsessed with the idea of getting any job and restoring cash flow. And I would have just f*cked the whole thing up. You can’t interview well if you are obsessed with immediate survival. You have to be able to momentarily free your mind enough to compartmentalize on the task at hand – getting the right job.


So now you have job search criteria. The kind of job and the kind of company. You hit the job boards and start looking for job postings that might be close to the job you’re looking for. Get a list of companies and job postings. I suggest writing down the job posting number if you can; you will want to be clear on which job posting you apply to and which resume or cover letter you use. You will have to research the companies using Glassdoor and LinkedIn. Also, ask friends and colleagues about them. Start networking early. Take people out to coffee. Ask a lot of research questions.


When I was young, getting laid off was generally seen as a badge of shame. That isn’t true anymore. Businesses downsize all the time. Many people you meet have been or know someone has been laid off. Recruiters will tell you to avoid saying, “I was laid off off” or, “I was downsized”. These phrases can sometimes shut down the conversation because the other person doesn’t know what to say. Should they be empathetic; should they change the topic; it can be awkward. Rather, change the way you look at the problem and rephrase it as, “Well, after 21 years at my previous employer, I’m now free to pursue other opportunities, like a start-up”.

Two things about this phrasing. First, it will sound awkward at first. You should practice this in the mirror. Practice on your significant other. It will come more naturally to you. It allows you to keep the conversation going and allow you to steer the conversation in the direction you want to go. Second, and I think this is really important, it will change the way you look at this situation. It really is a new opportunity and it could be a really positive force of change for you.


At this juncture, I had made a list of candidate companies and jobs for competitive intelligence or something close to that:

  1. Databricks – my number one choice. Late-stage pre-IPO, cool tech, well regarded, Glassdoor rating is pretty high (4.8 out of 5). This was a competitive intelligence, sales enablement posting.
  2. Salesforce – not an IPO at all, but a lot of my former colleagues from Documentum went there and love it. I must know 30-50 people there that I worked with. This was a competitive intelligence, sales enablement posting.
  3. Snowflake – another late-stage pre-IPO company, growing like a weed. Enormous growth, managed by Frank Slootman, who used to lead Data Domain. Data Domain was the division I joined shortly after it was acquired by EMC. However, subsequent interviews with people working there indicated that it might be a bit of a “s–t show”. This was a competitive intelligence, sales enablement posting.
  4. Docusign – another recently post-IPO company, pretty cool place to work. Not a start-up though. The recruiter to whom I was able to connect was an absolute jewel. I really enjoyed talking to him; he gave thoughtful feedback and guidance. I told you, you have to network and ask a lot of questions. Not a CI job – this was product management – but pretty close to CI and I’ve done this before.
  5. Simpson StrongTie – this company makes construction supplies but friends really like the company and it’s in my hometown. This was an e-commerce management position. But in my hometown, I mean, c’mon!

At this juncture, I haven’t included one other company: RingCentral. I applied to them early on and the job interview process took a while to get going. Once I broke through to the recruiter, it took off like a shot. I did get a job offer from them; I turned it down because I thought that Databricks would come to fruition. RingCentral is a great company and anyone who works for that team will have a hell of a ride.

Well, I have a list. It’s not rigidly locked to my ideals – timing is everything and you have to see what’s out there – but I haven’t had to sacrifice too much. Still pretty close to my job posting criteria. Now on to the big step: how to develop the contacts. How to get to the recruiters or hiring managers?


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