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.

Over the next few days I revived my network. Within hours I reached out to a retained search firm I had engaged with before. I contacted some of the recruiters I had worked with in the past. I pinged my friends and let them know I was looking. I scoured my emails and LinkedIn messages for companies that had reached out to me about opportunities in the past. I looked through newsletters (i.e. Software Lead Weekly) that advertised for job openings. I dug through sites like AngelList (A-List, Opal) and VentureLoop. I signed up on job sites like Hired and Vettery. I started going to meetups like CTO School. Then I waited.

Waiting is one of the hardest parts of interviewing. After doing a dozen things to kickstart my job search, there was nothing more I could do at the moment. I had to wait for people to get back to me. I went to the coffee shop daily and caught up on my reading. I did some hiking, biking, and lots of disc golf. Anything to keep my mind off of waiting.

Once my network started kicking in it was a roller coaster ride of interviewing and discovery. At one point I was actively interviewing with 8 companies. I had to stop looking for new opportunities while some of those played out. It really felt like a full time job, as it should. I didn’t seem to have a problem finding opportunities, or getting interviews. I wasn’t getting any offers. I was doing something wrong, but I didn’t know what.

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

100+ people interacted with

*An interview is a single day with one company regardless of how many people or hours. Meeting 12 people over 5 hours with 1 company counts as 1 interview.

On average that works out to 1 interview every 1.3 business days. That does not include interviews with recruiters or retained search firms. Another 12 interviews at least. Twice I interviewed with 4 different companies in a single day. Three times I had 5+ hour interview sessions with a single company. Mental stamina was important.

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.

I had a successful startup experience at Shutterstock. I joined the company when it was about 50 employees, and left 5 years later when it was over 600 employees. They went public during that time, reaching a $2.5 billion dollar market value. I even have some experience with Sarbanes-Oxley compliance.

My LinkedIn is always up to date, including recommendations. There are endorsements for my various skills, including bananas. I’ll get to my bananas skill later. Frameworks and libraries I’ve created are available on github. I attained the vanity metric of being in the top 3% on Stackoverflow. There is more information about me online than most technologists.

I’ve been in a leadership position for over 8 years and have earned the trust and respect of my peers and those who have reported to me. I had a professional leadership coach (Michael Teape). I’ve read numerous books and articles to learn how to be a great leader. I’ve trained many engineers in the art of leadership. I’ve done leadership presentations that have been well received.

I’ve interviewed over 250 candidates in a single year. I’m very comfortable with interviewing. This actually became a problem.

The Setup

Recruiters

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.

Most companies work with a number of recruiters. Chances are a good recruiter can get you into many companies. Find a select few recruiters you like and trust. The quality of the recruiter is more important than the quantity.

Leave instructions for recruiters on your LinkedIn profile. I instruct recruiters to mention the fruit skill I have the most endorsements for (bananas), and I guarantee a response. A friend of mine simply states to mention green M&Ms. Those that don’t follow your instructions you can just ignore. They didn’t read your profile and likely won’t do a good job representing you.

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:

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

I freely shared information about all the companies I had interviewed at. A single paragraph per company of who I met, number of interviews, how it went, my impressions. This is one of the best ways to bring them up to speed quickly on the types of companies you are looking at, the role, and your skills.

Beyond finding opportunities for me, the retained search firms provided clarity on the companies I was interviewing with. They offered insight into the culture, interview style, and level of talent at many companies. Even ones they weren’t representing. Retained search firms are in this for the long haul and want to build a relationship with you, not just place you.

Some firms didn’t have opportunities for me, but they had insight into the companies I was interviewing at. One search firm was representing a company I had already applied to online. It had been weeks without a response. The search firm contacted them and I was interviewing there the following week.

Most companies won’t give you much feedback on why they are passing on you. This can be frustrating since you don’t know how you should refine your interview answers. Retained search firms can be very valuable in this regard. They usually get more feedback so that they can refine their search. They will pass that feedback on to you. They also know the history of people the company passed on and why. They have insights that you could never get through an interview. There is some comfort knowing a company that passed on you has been trying to fill a role for a year without success.

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.

I ended up using a bar called District Social as my home base. They opened at 11:30AM and would be mostly empty until 4PM. They had free wi-fi, power, a bathroom, food and drink, and was quiet. They didn’t mind I would only have a few seltzers during the day (nobody likes an empty bar).

At the end of a long day of interviews I could have a drink, write down my notes for the day, and send any followup emails. It was a great way to decompress and reset to retain my mental stamina. I made friends with the staff, who introduced me to some other patrons. I ended up getting two interviews through people I met there.

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.

The first part of the interview focused on leadership and behavior. This was my sweet spot! In my answers I cited leadership theories and studies (team maturity models, situational/functional leadership, Maslow, Herzberg, EQ, etc.). It didn’t go well. The interviewer had never heard of the things I was mentioning. I lost him fairly quickly. It seemed like my answers were not the expected answers, right or wrong, and he didn’t know how to interpret them.

The second part was architecture and white board programming. They asked me to architect Facebook Messenger at their current scale (1 billion active monthly users). For the next 45 minutes I drew boxes, lines, arrows and data flows on the white board wall. There were questions, clarifications and requests for additional functionality throughout. Then there was an awkward silence when they just stared at what I drew. “Good, you got all the boxes we have.”

Facebook ended up passing. I did well on the architecture, poor on the leadership/behavior. This was just the opposite of what I had expected going into the interview. In hindsight I wasn’t listening with intent during the interview. I should have focused more on what they wanted to hear, not what I wanted to say. I needed to impress them on their terms, not mine.

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.

The questions the interviewers usually asked were about architecture and coding. A small fraction of the interview questions were about the leadership bullet points in the job description. Most didn’t know how to interview for leadership and resorted to a technical interview.

Typical job posting bullet points:
- Have proven and recent experience building and leading a team.
- Champion and enforce engineering best practices.
- Develop and mentor engineering and leadership talent.
- Help build consensus between teams.
- Contribute to strategic and tactical product planning.

Leadership is a lot about wisdom gained from experience. Many of the interviewers had a little over 10 years of total experience. At most a few years with leadership responsibilities, usually without training. Without experience, the leadership theories and philosophies I presented lacked context and were thus largely meaningless. I was presenting my knowledge of leadership, not my wisdom. I was focusing too much on what I knew rather than how I applied what I knew. There was an experience gap I needed to cross in order to communicate my value.

I also needed to close a coding skill gap I didn’t realize I had. While I have over 20 years of coding experience, I’ve been almost all management/leadership for the past few years. I’ve been inspiring people, architecting teams and optimizing communication. I realized I had lost my coding muscle memory. I could no longer do it by instinct, I had to think about it. Plus, I was never good at writing code on a white board.

I’ve conducted hundreds of interviews over the past few years. Interviewing has become instinctual for me, though from the other side. I realized I had a tendency to slip into interviewer mode and lead the interview. Especially with an inexperienced interviewer. The interview experience gap was causing me to flip things. I was learning about them, they weren’t learning about me. I needed to guide the interview, not lead 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.

I’ve been doing this for so long I’m full of tangental information. I would be asked to describe what happens when a user types a URL in a browser, in as much detail as I can. I would start explaining USB, OS interrupts, the 7 layer OSI network stack, and TCP/IP. It would be a few minutes before I got to DNS and HTTP verbs, which is what they were really looking for. In my defense, they did ask “in as much detail as I can”.

I realized after a few interviews that I was probably a rambling mess of information and experiences. How could they possibly figure out the value I could provide? I needed to figure out which of my experiences and knowledge would be the most applicable and have the most impact.

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.

My first draft was extensive, convoluted, and disorganized. Over a dozen iterations later I managed to narrow the scope and have something pretty coherent. A month later I published my first article. My ideas and knowledge on leadership were now much more organized.

During the whole job search my Stackoverflow vanity achievement was mentioned once. The article I wrote was mentioned by 7 interviewers.

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.

The interviews would now be much more Q&A, rather than Q&AAAA.

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.

I was definitely connecting much better with the interviewers in subsequent interviews. I still wasn’t getting any offers, but for a different reason. I was deemed overqualified. Clearly I was telling a better story, perhaps too good. They were looking for someone to manage a team of 4–6 people. I had been managing 4–6 teams. It didn’t seem to matter that at my last job I started out managing zero teams of zero people.

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.

I discovered that the larger startups I began interviewing at weren’t much different. They had more people and more revenue, but had been around about the same amount of time. They really didn’t have much more experience than the smaller companies. They actually had more in depth coding exercises. One company had me stub out an investment system with automatic rebalancing. Another company asked me to code review my white board code.

The interview process was definitely slower. They said they would typically take 4–6 weeks. As a manager I had always strived to get the interview process down to 2 weeks, 1 week if necessary. So this timeline was somewhat frustrating for me. I had no leverage, so I couldn’t shorten the timeline.

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.

Many articles on interviewing say that the most important thing you can do in a job search is to get an offer. It doesn’t have to be a great one, or one you would accept. It’s a bargaining chip to get companies to act. I was inexperienced in how to use an offer as a bargaining chip. I consulted with one of my recruiters (Kainne Hansbury) who advised me how to inform the other companies there was an offer and a deadline.

The remaining companies were now working to organize full day interviews with the appropriate people within a week. One company said they couldn’t interview me until that Thursday, the day before my deadline. I informed them that they would have to be able to make an offer that same day. They struggled to do it but agreed.

Ultimately 1 company couldn’t move quick enough, 2 interviewed and said I wasn’t a fit, and the fourth was ready to make an offer. My job search was over.

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.

They met all my top criteria for the type of company I wanted to work for. Most companies, and all recruiters, will ask what you are looking for at some point during the interview process. This is my list in priority order:

• Building a product that would pass the ‘mom test’. Something I would be proud to tell my mom about.
• 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.

SiteCompli has been on Crain’s Best Places to Work in NYC three years running. They work with Life Labs to provide training on teamwork and leadership for the staff. They also happened to be the only company I discovered through a former co-worker and friend. Finally, they have a conference room table made of Legos!

Lego conference room table at SiteCompli