Thoughts on freelancing, careers and hiring from 2 software leaders

The best way to learn how to build a resilient career in tech is talk to those who’ve done it.

There are a few paths available in software. One option is to freelance, working on a temporary basis with firms. Another is to seek a full-time job with a company, and join a team. The choice is one that has particular resonance in this moment. The pandemic brought a spike in freelancing in 2020 as remote work and an economic shock took hold. This year brought The Great Resignation, with an unprecedented wave of workers are quitting their jobs and exploring new paths, with plenty of mid-career tech workers among them.

To learn about what the folks who are hiring seek in each of these types of roles, we talked to a pair of experienced engineers. Dan Dutrow is the director of software engineering at data firewall platform maker Qualytics. and Daniel Schiavone is the test lead handling quality control at government-focused tech and design firm CivicActions. Together, they have over 30 years of experience as software developers in the industry. They’ve led and hired full dev teams, been contractors and freelancers, and they know the ins and outs of what makes a happy client and an attractive hire in tech.

Dutrow has had a steady rise through the ranks, beginning his journey in tech at the U.S. Naval Research Lab before spending over ten years at Johns Hopkins Applied Physics Lab. Then, he went to the private sector as an analytics team lead at Zavda Technologies. In the last several years, he was director of engineering at Fells Point healthcare analytics firm Protenus before moving to his current position at bwtech@UMBC-based Qualytics.

Through leadership roles, he has plenty of experience hiring full-time roles. In that case, it’s important to find a technologist who would fit with a team, and explore their approach to the work. This sets up an ongoing relationship.

“Whenever I am hiring for a specific position, I look for alignment with the candidate’s natural skills and interests,” said Dutrow. “Some of the most intriguing candidates I have interviewed will post their portfolio online (through a personal website or GitHub) and show off whatever they can in the course of an interview. This sets me up well to ask deepening questions about their work in context of real problems. This gives me confidence that they will be successful once they join our team.”

Schiavone in his time has worked as a senior dev for System Source, a legacy tech company in Maryland, and as a tech consultant for Slate Magazine. He also ran Snake Hill, a Baltimore web agency that specialized in Drupal.

In some cases, tech firms opt to work with freelance developers on a contract basis. In that case, it’s important to get all of the professional steps right, even if it feels like one is working for themselves.

“From the hiring side, the number one thing was someone that’s going to show up,” said Schiavone about freelancers. “You’d be surprised how often that doesn’t work out. After that it’s communication and if they’re engaged.”

The biggest issues in Schiavone’s experience with building teams and finishing projects are nontechnical. The answers to what makes dev teams successful with freelancers are pretty straightforward: communication with the client of what you can and can’t do and being engaged and clear about availability are the secret sauce that lead to a long and fruitful career in tech. On the other side of the coin for those hiring freelancers, it means being clear about expectations.

“As a person that’s hiring a freelancer, be really clear on expectations and what you’re looking for,” said Schiavone. He emphasized being clear on how and when you’re communicating.

“As a freelancer, just be real honest about your time and availability,” he said.