Advice on Managing Your Career

I recently accepted a role as Chief Technology Officer for a firm here in Raleigh. It’s a career goal ten years in the making. Of course I’m very excited about joining this particular firm, but I want to focus on the career growth aspect of this story for now.

Why CTO?

Ten years ago as a developer at iContact I first got to see the role of CTO up close. Ralph Kasuba did a great job of displaying transparency, honesty, integrity, and a commitment to his responsibilities. The entire leadership team there was phenomenal. Mary Thorn, Bob Galen, Andrew Parker (now VP of Engineering at Pendo.io), and several others created a culture unlike anywhere I’ve worked before or since. Several iContact alumni have remarked that we’ll likely spend the rest of our careers trying to recreate what we experienced at iContact.

It’s hard to succinctly capture what made it so great.

• A true, deep sense of ownership over our work
• Very high talent bar: to this day those teams were the most consistently highly skilled people I’ve ever worked with
• Psychological safety: we passionately disagreed sometimes, but once the team made a decision everyone got behind it to make it work
• A clear understanding of our customers and users and what success for our work meant to the business
• Healthy competition between scrum teams; all of us wanted to impress each other at sprint demos and the talent level made that a very high bar indeed

I saw that if the CTO wasn’t doing their job well, then that culture would never exist. Without that culture, iContact wouldn’t have been able to compete. I wanted to do that job. Partly because I wanted prestige and respect (misguided) and partly because I had this feeling that it was a role that would make the most use of my potential (much more accurate).

It was also the first time in my career I started to understand how unprepared I was. As a prideful young man, that was not an easy reality to face.

I became very thoughtful and intentional about self awareness, self improvement, and job and role changes. What people say is true: Nobody is going to manage your career for you. I developed two main criteria to decide if an opportunity was right for me:

1. Will I learn things that will make me a better CTO?
2. How will this role improve my story when talking to the next employer after this one?

My two cents: Look at your colleagues and the roles they fill. What inspires you? Make sure you look outside your business unit at other teams and functions. Be curious - buy people coffee and ask them about what they do and how it’s valuable. Figure out what drives you and work purposefully towards it. There is no role out of reach, but you will have to be patient.

Mentors and Mentoring

There’s no way I would be in a position to take on this next challenge were it not for my mentors. A mentor inspires you to form a picture of what “great” looks like and helps you think through ways to achieve it. They call out gaps in your skillset and point you to ways to fill them. I’ve been very privileged to have people like Doug Kubel, Doug Kaufman, O’Hara Macken, and Jonathan Meyer provide that type of mentoring. Most of all, the man who has been there mentoring me my entire career: my Dad. He’s been a true inspiration and invaluable source of wisdom. Thanks, Dad.

My two cents: Find mentors. It doesn’t have to be a formal thing. I didn’t ask those folks above if they would be my mentor. Instead, I bought them scotch and respected their time. I also made sure they knew their investment in me was making a difference and that they weren’t wasting their experiences. Mentorship is a two way street - if you don’t respond and demonstrate growth they may disengage and that’s to be expected. If a mentor suggests a book, for example, make sure you read it and talk to them about what you got out of it.

Never let a little thing like qualifications get in your way

HP published a great study on why people don’t apply for jobs. Most of the time it’s because people don’t think they’re qualified, and either don’t want to waste their time or experience rejection. However, think about the times in your career when you’ve been the most motivated and when you’ve done your most valuable work. For me, it’s been the times when I was most out of my element.

This is one of the reasons I hate resumes. They are crappy hiring tools. When I’m bringing someone on board I care much more about where they are going than where they have been. When you can align someone’s passion and ability with what you need, you’ll have a powerful team member who will do great things for your firm. Remember, hire for attitude, aptitude, and then technical ability.

I’ve never been a CTO before. Why would these people hire me? It’s because my passion and goals line up perfectly with what they need, and my story clearly shows I thrive in challenging, ambiguous situations. Because I need a chapter in my story that tells exactly the story they need in order to grow their business.

The delta between your last role and the one you are shooting for has to be covered by your ability to tell that story. If you’re a job seeker shooting for a big jump in responsibility, you’re going to have to be able to tell that story really well. The greater the responsibility, the tougher the audience is going to be because the stakes are higher.

My two cents: Practice telling your story. Hone it, simplify it. I can break my twenty year career down into two acts: technical contributor becomes leader, and large scale change agent becomes executive. Practice telling people about your career goals and how this job you want aligns with that story. Good employers will care a lot more about that than your resume.