September 29, 2020

Software Hiring Trial By Fire, With Steve Caldwell

By Kevin Huynh

Steve Caldwell is an ambitious engineer – something that’s been apparent at every step of his career.

Though he got his start with the Army Corps of Engineers doing help desk work, he always had been interested in building a website, and he parlayed that help desk role into a position doing web app development, where he began managing his first employees.

From there, he went on to start a development consultancy, then founded his own software company, Strap, a wearables analytics company that grew out of Steve’s own desire to track his activity on his Pebble watch.

Today, Steve is the VP of Data, Infrastructure, and Security at Springbuk, where he leads a fast-growing team that’s been hiring like crazy over the past year.

Steve has become a widely-respected software leader, able to grow and manage highly effective development teams. But what often gets left out of that conversation is the frequency with which those lessons are learned through trial and error.
In our conversation, Steve opens up about the lessons he’s learned about effective hiring and management – including those he learned the hard way. We talked about the hidden expenses of hiring, and ways that your startup can hire more effectively when you’re growing quickly.

Listen to the Full Episode Here

Here are a few of the key lessons we picked up from Steve:

Hiring is Time Consuming (Read: “Expensive”)

Oftentimes, when we ask “how much would it cost to hire another developer,” we’re thinking about costs like salary, benefits, and a recruiter’s fee.

But that calculation fails to take one key factor into account: the opportunity cost of the time you’ll actually spend hiring.

“We didn’t calculate how much time we would spend recruiting and hiring,” Steve said in our interview, “which has ripple effects throughout the whole business.”

When you’re looking to expand your team, therefore, avoid this common mistake by scaling down your product roadmap accordingly.

Sorting By Aptitude Cuts Time and Cost

On paper, the first hire that Steve ever made was flawless: a 4.0 student, straight out of school with a double major. They interviewed perfectly, and Steve was impressed.

Unfortunately, they didn’t have the technical aptitude to be successful. Six weeks later, Steve was asking his boss to let them go. This was a foundational experience for Steve, and now he uses Woven to prioritize applicants by their ability to actually do the job so he can avoid making the same mistake again.

Prioritize Culture Early, Save Time Later

We all talk about finding the right cultural fit when we’re hiring, but not everyone is willing to turn away a qualified candidate after a phone screen if they’re not right for the company.

Steve refuses to make that mistake. Instead, he places a heavy importance on cultural components of the interview, and asks relevant work environment  questions early in the interview process.

Ultimately, finding the right fit is hard and time consuming – but committing to the task is necessary. Most important to that commitment, Steve says, is effective communication within your organization about the sacrifices your team will have to make in order to hire the right candidate.

“Understand the amount of time you will have to spend with candidates to ensure the culture piece that you have worked so hard to build isn’t poisoned.”



This show is brought to you by Woven. At Woven, we help software teams screen engineering candidates so they can spend less time on bad interviews, uncover hidden gems, and back their hiring decisions with evidence. If you want to learn more about how Woven could help you scale your software team, you can check us out here.

Our team is excited to help you build your perfect software team, and we are always looking for your feedback about how to make the show better. If you have anyone you think we should interview, tweet us at @woven_teams and our team will reach out.

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