Engineering

Why this sought-after engineer chose to work at Wisetack

Vincent Ninh

May 27, 2022
7
min read

Skilled and friendly software engineers are as coveted today as Beanie Babies were in 1998 (without the whole impending doom part, of course). How high exactly is the demand? According to their 2022 State of Software Engineers study, Hired reported that software engineers on their site received twice the amount of interview requests in 2021 than in 2020. 

This fierce competition for engineering talent is why we were so delighted when Corey O’Brien, a cloud-native genius (our words, not his — he’s too humble for that) with over twenty years of experience, decided to join our team as the Director of Engineering Infrastructure. 

But why did he choose Wisetack? Keep reading to find out. By the end, you might want to join us too. ;)

Culture is more than just a buzzword

“OuR CulTUrE IS aMAAaaAZiNg!!!”

— every job listing ever

Every company brags about culture, so it can be hard for prospects to discern how authentic this discourse is. But Corey’s culture concerns were quickly calmed after he attended Camp Wisetack — an offsite we held at the Costanoa Lodge, a rustic coastal resort located an hour south of San Francisco.

“Day 1, I got my computer set up. Then I hopped on a plane to California and was drinking bourbon on day 2,” said Corey before adding, “It was a really awesome first week because I got to connect with a lot of the people here and the heartbeat of the organization.”

"(People at Wisetack) are empathetic, motivated, excited to be here, and trying to solve an interesting problem together by collaborating in a way that’s really healthy."

This heartbeat, Corey pointed out, is a group of people who are “empathetic, motivated, excited to be here, and trying to solve an interesting problem together by collaborating in a way that’s really healthy.” 

But healthy collaboration doesn’t just happen by chance. It can only happen because of what’s at the crux of our culture: trust. We communicate openly and transparently (almost all our Slack channels are public), and measure productivity by what gets done — nothing else. This trust also means that everyone’s opinions are heard and valued. Many have brought to the table ideas well outside of their role that have been implemented.

Flexibility is the future — and the present 

In light of the pandemic (and scarcity of talent), many companies have started implementing more flexible policies. But Wisetack’s done that since day one; we view flexibility as a core philosophy, not a reaction to current events. Our approach to flexibility is a huge driver of our culture, and a key reason we were able to snatch Corey and many of the people he met at Camp Wisetack.

Wisetack is a fully remote company (and has been for most of its lifetime since its inception in 2018), and there are no plans to change that. This allows us to have a much larger talent pool to hire from, and is a big reason why we are consistently able to recruit only the cream of the crop. We also strive to be as asynchronous as possible: there are no meetings that should’ve been emails at Wisetack. In fact, there are no emails that should’ve been Slack messages at Wisetack. 

But when it comes to flexibility, perhaps the best benefit we offer is “true” flexible PTO (it’s in the name!) — guilt-free time off that we actually encourage our employees to take.

The ability to grow with a growing company

What makes software engineers tick? According to the Hired study we referenced earlier, “new challenges and continuous learning” are the key factors that attracted engineers to their career. Unsurprisingly, these two professional motivations are hugely important to Corey, and he felt like he could fulfill them — and then some — at Wisetack. In fact, he wasn’t even actively looking for a job when the Wisetack opportunity presented itself.

New challenges

Wisetack has grown exponentially in the last year and we’re not stopping anytime soon. Our engineering team is no exception. The challenge Corey is most excited about at Wisetack is finding ways to grow his team: “There are certainly a lot of things we have to solve as we grow; one of the most interesting ones to me is how to grow the team in a smart way.”

He added, “We want to make sure to hire the right people at the right time because there are a lot of things we want to do and we need the right people to do that. It is a very interesting problem to solve and one I’m already happily sinking my teeth into.”

Right now, our engineering team is hiring for three roles:

Continuous learning

Wisetack always seeks to be at the forefront of technological innovation, as our CTO Kolya Klymenko details in this article. This creates an exciting and challenging (in a good way!) environment for our engineers, and helps our engineering team foster a culture where continuous learning is a necessity. This emphasis on personal growth isn’t restricted to our engineering team either; we offer a yearly stipend for all Wisetack employees to spend on personal development. 

All engineers get to engineer

Engineers like to do engineering stuff. What a shocker, right? Unfortunately, at many places, engineers who find themselves in leadership positions don’t get to do a ton of it. Corey, for his part, doesn’t mind. The kinds of problems in a leadership role are often different, but they still require strategic planning, thoughtful analysis, and creative problem-solving efforts — and that’s ultimately what he’s passionate about.

But at Wisetack, he gets the best of both worlds. We have the mindset that everyone on our engineering team should be an engineer first and foremost, regardless of title. And so, we rely on every member of the team to have hands-on involvement in making our technology better. 

Even our CTO Kolya participates in development activities, like writing/reviewing code and helping manage our cloud infrastructure (which he will get a ton of help with now that Corey is on board). 

A product that matters

Through our culture, benefits and growth opportunities, we try to make Wisetack an amazing place to work. (Our adventure-packed offsites don’t hurt either.) But ultimately, these things don’t mean much if our employees don’t believe the product they work on has a positive impact in the world.

We believe our product helps people, allowing consumers to afford essential services while also allowing high-quality businesses to grow and be more successful.

Corey shares this belief, and this was a key decision factor for him when choosing Wisetack:  “I knew what interested me in the next phase of my career was to work with a group of like-minded people at a mission-driven startup focused on helping individual people.”

Be like Corey

Forget being like Mike. He probably doesn’t even know what cloud infrastructure is. Be like Corey instead. Here’s how to do it:

  1. Watch sudoku solvers on YouTube every night. Corey loves anything related to problem-solving, and that includes watching other people do it. Plus, unlike real life, you know the entire time that these problems will be solved by the end of the video, which is comforting.
  2. Embrace your inner geek. This includes playing all the games: tabletop games, D&D, video games, etc. Also lots of Star Wars and Doctor Who.
  3. Come work at Wisetack! You can experience Corey’s awesomeness from upclose by applying to one of our three open engineer roles, or from slightly further back (but still pretty close) by applying to one of our many other open roles.

Director of Infrastructure Engineering

Corey O'Brien