Moving forward: how Directors of Product and Engineering, CPOs, CTOs, and CIOs decide on career changes

It might seem that career changes for IT professionals are easier. After all, these become sought-after professionals very early on. However, when it comes to higher levels of the organizational chart, decisions on switching positions become much more critical to professionals and companies. 

We interviewed Aunt Bertha‘s Senior Director of Engineering, Tommy Morgan, to understand what drives moves. A seasoned practitioner of 20+ years, Tommy has risen through the ranks of startups to corporations and shares what impacted his previous career changes – and will continue to do so for the foreseeable future.

Career changes for IT professionals: how do you know you’ve outgrown your role?

The main reason for someone to take on new career opportunities (be it a new position or a whole different company) is timing. Personal and company goals change and evolve. The great match of four years ago might not be as relevant now as before. And that’s ok. Healthy turnover is important to keep companies and professionals competitive.

Recollecting on when he left rental marketplace startup Homeaway for Datatrak (a publicly-traded HealthTech), Tommy explains that it sometimes has nothing to do with the business, product, or team. 

“I went through rapid growth and had plateaued”, he said. Individual career goals matter. “I went from individual contributor to manager. However, in a company of that size, the upward process is slower.” 

In this sense, trading companies meant more opportunities to learn and experiment.

Not surprising, given career changes for IT professionals are usually brought on by the same motivation as that of any other profession:

• It’s no longer challenging. There is little to learn and you find that you can do your job with little effort.
• You’ve got bigger career goals. Not necessarily a larger paycheck, but something exciting to work on.
• The fit isn’t right anymore. Organizations and products change over time, and maybe your ideas are simply no longer in sync with the way the company now operates.

Although it is your job to be positive and bring a learning attitude, and employers will invest in motivation and engagement, it might be time for a career change.

Asking for a promotion vs. Moving to a new company

Product and Engineering teams share the same goal: add value to the company by building and delivering the best possible experiences for customers and users. If you’re still engaged and feel like you can contribute, but in another way, go ahead and negotiate. 

You can – and should – discuss new attributions and compensation to match. But if you don’t feel challenged and learning, you’re probably ready for the next step. So let’s explore how you can move on from your current role.

There are rational points to a decision of what kind of company you want to gravitate towards. Tommy explains what made him pick his current employer: 

“We’re venture-funded, so there’s that aspect. We’re also bound by HITRUST compliance.”, – challenging and new aspects to get excited about. 

There are also emotional factors to take into consideration. The mission your work to support gives your day-to-day sense of purpose. For companies, a solid cultural match and shared goals usually mean better retention rates – so this is definitely something for HR, leaders, and professionals themselves to keep an eye on.

“I can go to other places such as Facebook and Google and make more money.  But here I have a mission to help people, and that’s important to me”, he exemplifies. This makes a lot of difference if you’re dedicating so much time and energy to a cause. The explanation is straightforward:

“Seeing what I can do to identify people by tracking users and using it to benefit companies instead of users wears me down. I’m squarely aligned with Aunt Bertha’s mission to connect all people in need and the programs that can help them (with dignity and ease), instead.”

Career changes for IT professionals of any rank – but especially leaders, that need to inspire their teams – should be a matter of both mind and heart. So if asking for a promotion can no longer do it for you, here’s how to move to a new company.

Tips on finding new positions

Of course, there are higher-level jobs available on job boards. However, Directors of Product and Engineering, CPOs, CTOs, and CIOs usually benefit from better suited professional match-making.

In Texas, as in many other states, there are boutique recruiters and placement firms available to support IT professionals on their way – with all due discretion. The relation to some of these began years before, those times in the position of a hiring manager.  

“The thing about really small companies is that they will give you a personalized touch” – and thoughtful processes usually pay off. Tommy only spoke to two companies before making his decision and final choice. 

Then what made him turn down the other offer? “They needed a frontline manager, and the job was of very limited scope. The money would have been better, but boring!”.

How to pick your next job?

Talk to the relevant people: CTOs, CPOs, and other leaders of Product and Engineering teams. 

“I interviewed the VP of Product and Engineering again and again. I wanted to know we had a shared philosophy on software development, DevOps culture, interested in quality and automation… and that we would move fast.”

Doing your due diligence is a must. “I asked for references, looked at Crunchbase, investors, and the profiles of the leadership team”, he elaborates. Everything has to align up, especially given leadership roles are longer-term than operational or tactical jobs within digital product teams. 

What does a rewarding job look like?

Tommy is grateful to have opted for a more “socially-driven, noble cause” (his words). The success of the change became clearer once other hires began to match the shared goals and mission as well. “We’re building a team I’m proud of“, he signs off. 

Looking to improve your leadership of digital product teams? Have a read of our article: Go Distributed: how tech leadership should build, manage, and scale.

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Scheila Farias Silveira

International Marketing Leader, specialized in tech. Proud to have built marketing and business generation structures for some of the fastest-growing SaaS companies on both sides of the Atlantic (UK, DACH, Iberia, LatAm, and NorthAm). Big fan of motherhood, world music, marketing, and backpacking. A little bit nerdy too!