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Lessons Learned from Failure: How I Didn't Become the CTO of a Promising Startup

Posted on December 19, 2014

This post is the first in a series about failure. Most people post about their successes - their new job, successful acquistion of their startup, or how they made $XX,XXX in 1 week after launching their product. It makes sense - show and promote the best of yourself. I definitely do.

I’d like to focus on failure though. Not just general failure, but my personal failure, and the lessons that I learned. Why? Well, I’m sharing my failure in the hopes that..

This post is the story of how I went from thinking that I was being considered, to not being considered, to definitely in the running to become the Chief Technology Officer (CTO) of one of the hottest startups in Atlanta and the lessons I learned along the way. I’m sharing not only my interview experience, but also the compensation package (salary and equity) that was discussed. That way you’ll have an idea of the market if you are interested in engineering leadership positions for startups in Atlanta.

Finally, the names of the company and individuals have been changed since they don’t really matter.

The Story

Let’s get started. Like most opportunities, this opportunity was a result of a word-of-mouth referral.

A good friend of mine went to lunch with, Bob, the CEO of Pied Piper…

One of the hottest startups in Atlanta. Bob mentioned that he was looking for engineering talent, specifically a CTO, to join his company, and my friend told Bob that he should meet with me. My friend introduced Bob to me via email, and we agreed to meet the following week. When it came to his company, Pied Piper, I didn’t know much. However, I’ve heard and seen a lot about Bob since he was very active and popular in the startup scene.

Over the past 3 years, I had been diligently working to improve my technical, project management and product management skills while leading the technical development for startup clients at Big Nerd Ranch and my own startup, Body Boss Fitness. In essence, my dream job is to lead engineering as a CTO for a promising startup. So I was definitely intrigued to hear what Bob had to say.

We met for coffee…

And I quickly got the sense that I could have a very candid conversation with Bob. We discussed his background, the story behind Pied Piper, and even the reason for the departure of the previous lead engineer. He told me that they just closed a round of funding, and they were looking to bring on 2 people - a CTO and another engineer. The fact that he was looking to fill 2 positions was news to me, so I asked the obvious next question, “For what role am I being considered?” Bob responded that he was already in discussions with someone else for the CTO role. I was being considered the engineer that would work alongside the CTO. Needless to say, I was disappointed. Also, I felt stupid and naive for thinking that I was in the same league as any potential CTO.

I was still sulking when the following game-changing email showed up in my inbox a few hours later:

After our meeting, I had somehow propelled myself into contention to be the CTO of Pied Piper. Needless to say, I was both excited and terrified - I needed to get some advice about how best to approach this potential opportunity.

Before the 2nd interview…

I reached out to a friend who happened to be a CTO at a startup that shared office space with Bob and his company. We met for coffee and talked about my goals and whether they align with goals and culture of Bob and his company. My CTO friend assured me that the salary of $100k+ and equity of 4-6% being offered was market value for a startup of their size and funding.

The 2nd interview consisted of a short meeting with Bob, and then I ended up meeting with 2 of the brightest technical minds in the Atlanta startup scene. They lead the technical team of a very successful startup, and their company is also a customer of Bob’s company. I shared the story of my career so far - from Georgia Tech into consulting and then software engineering. They shared how after almost 2 years of trial end error, they fortuitously stumbled on a winning product after one of their intern-built tools went viral. We ended our talk by brainstorming how Pied Piper could turn their product into a must-have solution for their customers. It was awesome to talk product with them, and I thought the interview went well.

A couple weeks later…

The following email showed up in my inbox:

I wanted to write and let you know that we decided to go with [the other candidate]. At the end of the day, [the other candidate’s] interest and interviews with our current customers really demonstrated his passion towards building Pied Piper into a $100mm business.

It was a hard decision because you’re extremely talented.

I look forward to keeping in touch!

I had made a series of missteps that would ultimately lead to me not getting the job. These mistakes are encapsulated perfectly in a single statement from Bob’s email:

At the end of the day, [the other candidate’s] interest and interviews with our current customers really demonstrated his passion towards building Pied Piper into a $100mm business.

The Lessons Learned

After analyzing that statement, I identified my major mistakes and formulated 3 actions that I should have taken to establish myself as the best fit for the job:

  1. Come Prepared with Ideas on How to Improve the Product
  2. Follow-up with the Decision Influencers and the Decision Maker
  3. Exude Passion

Come Prepared with Ideas on How to Improve the Product

[The other candidate’s] interviews with our current customers…really demonstrated his passion towards building…a $100mm business

My interview with 2 of Pied Piper’s customers didn’t go as well as I initially thought, especially when we discussed Pied Piper in its as-is state and its potential to-be state. This brainstorming session focused on how Pied Piper could find the stickiness that would transform their product from a nice-to-have to a must-have for their customers. To be honest, I was totally caught off-guard and unprepared for this discussion. So much so, that I contributed just a single idea - Pied Piper should add gamification in order to increase engagement. It was a terrible idea - gamification was a fad that died years ago. It was no surprise that my idea quickly got shot down. No doubt about it, my performance during the brainstorming session was underwhelming.

If I had traveled to the future, and read this blog post, I would have performed this brainstorming exercise beforehand, formulated a list of the top 3 ideas, and come to the interview prepared to intelligently discuss them. For example, let’s imagine that Pied Piper offers a SaaS product that enables personal trainers to track the workout performance of their clients. I could have presented the following ideas:

  1. Personal training “coaching” add-on - service that provides ongoing and actionable advice to help personal trainers improve sales, retention and engagement.
  2. Referrals feature - Easily enable existing clients to refer friends with a referral code that allows both existing and new clients to receive a discount on their workout sessions.
  3. Engagement automation feature - Weekly reminder emails sent to existing clients that enable them to book their workout session for the coming week.

It’s not that any of the above ideas are revolutionary or would end up being the killer feature for Pied Piper. What’s important is that I demonstrate the ability to formulate and communicate ideas that could potentially transform Pied Piper.

Follow-up with the Influencers and the Decision Maker

[The other candidate’s] interest…really demonstrated his passion towards building…a $100mm business

After the 2nd interview, I went dark. For whatever reason, I didn’t send follow-up thank you emails to Bob or any of my interviewers. Bonehead move. I know. I know.

I definitely should have sent a short message to the 2 persons that conducted my technical interview. Bob trusted them to vet me. They would directly influence his decision to hire me or not. Yet, I didn’t send them anything. It could have been as concise as the following:

Thank you for taking the time to meet with me to discuss my background. I enjoyed our discussion, especially your insight on X topic. I look forward to seeing you around.

The message to the final decision maker would have demonstrated my interest in the role and an outcome where I could help the CEO reach his goals for the business. Something like:

Hi Bob,

Thanks for meeting with me today. I enjoyed my discussion with X and Y - it’s clear that they are 2 of the brightest technical minds in the industry. It has been great getting to know you and the team at Pied Piper. If given the opportunity, I’m confident that I would play an integral role in helping Pied Piper become a $100mm business. If you have any further questions for me, please don’t hesitate to reach out to me. I look forward to hearing from you.

Exude Passion

Finally, I made the mistake of being a little too reserved / relaxed throughout the interview process. Bob’s passion is Pied Piper. His goal is to grow a $100mm business. I didn’t demonstrate a similar amount of passion for being an integral piece that would enable him to reach that goal. Passion is an intangible that is hard to simulate. I’m passionate about building awesome products, and I should have better channeled that passion to build a better Pied Piper.

There Is Always a Silver Lining

Along with the lessons learned that could have gotten me the job, the entire experience was a net positive for me for a number of reasons:

All in all, I wouldn’t have traded this experience in failure for anything.

Have you failed to get that dream job or achieve a goal? How did you deal with it? What lessons did you learn?

About

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Hi, I'm Don Pottinger.

I love building things with computers. At 10 years old, I wrote my first program using BASIC. I built my first computer when I was 12 years old. I studied Electrical and Computer Engineering at Georgia Tech. Now, I'm a full-stack software developer and entrepreneur passionate about building rich web and mobile apps. My weapons of choice are Ruby, Javascript, and Objective-C.

I live in Atlanta with my amazing wife and son. For fun, I play too much soccer and follow my favorite soccer clubs, FC Barcelona and Arsenal F.C.

My CV so far

  • Chief Technology Officer at Kevy (2014 - Present)
  • Co-founder and Head of Technical Development of Body Boss Fitness (2010 - Present)
  • Co-founder and Head of Technical Development of Kickdrop (2014)
  • Resident Nerd, Full-stack Developer and Backend Team Manager at Big Nerd Ranch (2012 - 2014)
  • IT and Management Consultant for Accenture and Slalom Consulting (2008 - 2012)
  • Graduate of Georgia Tech with BS in Electrical and Computer Engineering (2008)

My Recent Projects

Facts About Me

  • I was born in Jamaica and raised in the United States.
  • I speak English, Spanish and Jamaican Patois.
  • I love to travel. So far, I've visited Peru, Argentina, Spain, Switzerland, Germany, Greece, France, Italy, Canada, Jamaica, Hawaii, Mexico and England.