Finding a Tech Leadership Job in Silicon Alley

78 days, 43 Interviews, 18 companies, 1 job

On August 18, 2016 the NYC startup I was at had a restructuring and I suddenly found myself in the market for a new job. I went from Senior Director of Engineering to Director of Job Seeking within an hour. While I wasn’t surprised there was a restructuring, the timing was unexpected, and I did not expect to be a part of it. My entire focus had been on the startup and I had let my people network grow cold. I was unprepared.

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The Numbers

78 days from start of search to accepting an offer
43 separate interviews*
18 companies with at least 1 interview
9 retained search firms
3 recruiters
2 offers
1 new job

My Qualifications

I’ve been in the technology industry for over 25 years. I’ve been a developer (front and back end), sysadmin, network admin, DBA, tech lead, director, product owner, and project manager. A full stack generalist.

The Setup


I worked at a recruiting company for part of my career. There I learned that one should not work with as many recruiters as possible. The first recruiter to submit your resume represents you at that company. That means another recruiter whose best friend is the hiring manager can’t get you in. Your resume goes on a list for review by human resources.

Retained Search

I was mistakenly applying the recruiter advice to retained search firms. Most companies only retain a single retained search firm. If you’re not working with the one retained search firm a company chose, you’ll likely never know about the opportunity. Once I realized this, I ended up working with a total of 9 retained search firms:

  • Redstone Partners
  • Riviera Partners
  • Daversa Partners
  • Kindred Partners
  • TrueSearch
  • Wheaton McCrea
  • Nace Partners
  • Collins Associates

Base of Operations

There were days where I would have both in-house and phone interviews. I lived too far to commute home. I needed a place to spend time between interviews and to do phone interviews. Coffee shops are far too noisy.

Interview Series One

My First Interview: Facebook

Facebook was one of the companies that had reached out to me about an opportunity a few months back. The day I was let go I dug up their email and responded. The recruiter phone screen went well and they wanted to proceed to the next step.

First Lesson: Mind the Gap

I was interviewing at mainly small to mid-sized startups. Many said they were looking for a strong, experienced leader. Some said they wanted someone who could train their current tech leads. The next few companies went similar to the way the Facebook interview went. I realized that most didn’t know how to interview for leadership. They knew what they wanted, they lacked the experience in how to find it.

Second Lesson: Too Much Information

I’ve acquired lots of knowledge over the years, have had many experiences, and I’ve been in almost every type of situation. When asked to describe a failure, I’ve got dozens of examples. Some of them are pretty epic. All are entertaining stories, most don’t provide anything relevant to get the job.

Reflect, Reassess and Strategize

I called a friend and asked him to mock interview me so I could get feedback on my answers. While he was impressed with my experience and knowledge, I provided too much information and came across a bit random. He confirmed I was a rambling mess of information. I needed to formulate a list of what I wanted to highlight from my experience. I needed a new interview strategy.

Time Management

Interviewing is partly about time management. The more I talked the less time they had for questions and discovery. My answers needed to be shorter and more concise. I didn’t need to explain four different strategies and experiences when a single one would suffice. If they wanted to know more they would ask. Most sessions are only an hour per interviewer, I needed to keep that in mind.

Put it in Writing

I remember reading an article that said writing helps one become more disciplined in organizing one’s thoughts and ideas. I thought this might help me in my interviews. I decided I would write my first article on leadership. That’s the role I was looking for, it seemed to be what I rambled on most about, and needed the most refinement.

Elevator Pitch

I wrote down my elevator pitch, a short and long version. It contained “hints” of topics and experiences I wanted them to ask about. I formulated slight customizations of it depending on the type of company. I would mention being in charge of fraud prevention for companies that did e-commerce. Data focused companies would hear my DBA version.

Select Experiences

I chose specific experiences that I would share. Ones that would be applicable to a range of questions. My proudest success would also be about team building. My biggest failure would be about taking ownership and learning. I thought through what happens when you type something in a browser. I wrote it all down, read it, edited, updated and read it again until it sounded right.

Interview Series Two

In the next few interviews I applied my new strategy. I listened and waited for opportunities to present my experience and leadership knowledge. My answers were now contextual and concise. I would very briefly mention additional, relevant topics I knew (i.e. I’m also a fan of functional leadership). If they asked for more details, I could delve deeper into the topic that interested them. I kept in mind that I needed to make a connection with the interviewer. It was about what they wanted to hear, not what I wanted to say.

Making Connections

To better connect with the interviewers, I researched everyone that would be interviewing me, not just the companies and their product. LinkedIn, Facebook, Twitter, Google, past companies, schools, hobbies, anything I could find. If their Facebook profile said they liked motorcycles, I would Google their name and motorcycles. One COO I interviewed with is into vintage motorcycles, owns a Triumph, and is passionate about his house in the country. One developer likes to post many, many inspirational sayings in the middle of the night. Another developer tweets how much they dislike PHP and love Node. I would mention things we had in common. My love of hiking, country living, and inspirational leadership. I would talk about Node, and play down my PHP experience.

Thinking Bigger

I realized the companies I was interviewing at were too small. They already had a senior level person in a Director or VP role. There wasn’t room for another one. They were really looking for “junior” Director, or Senior Tech Lead. I decided to target companies a little bigger.

Getting off the Roller Coaster

On Thursday, October 27, 2016 I received my first offer. I stopped accepting interviews from any new companies. I was still actively interviewing with 4 other companies. I decided my deadline to make a decision would be noon Friday November 4, 2016. That gave the 4 other companies about a week to wrap up the interview process.

On Friday November 4, 2016 I accepted an offer from SiteCompli.

Why SiteCompli?

SiteCompli had some of the best, most thorough interviews. Their interview questions matched the bullet points in their job description. They focused on discovering how effective I could be at leadership and team building. Each interview session covered a different topic. Real world scenarios were presented, some of which I suspected they were working through at the time.

  • A high value on company culture. They remember it’s the employees that make the company and the product.
  • A stable startup on a growth trajectory with big upside potential.
  • Eager to get better at leadership and team building.
  • No exit strategy. They’re in it for the long haul.
  • Sufficient compensation.
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Lego conference room table at SiteCompli

Architect of systems, people, and teams. Leadership mentor. I connect the dots of code, systems, and people.

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