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By Eleanor Bennett


5 min read

For our latest specialist interview in our series speaking to technology leaders from around the world, we’ve welcomed Bill Kunneke, Chief Technology Officer at Leasecake.

Bill has over twenty years of experience as an IT professional and a proven technical leader who delivers large and often transformative IT projects while communicating complex technical solutions to key stakeholders and executing strategic IT functions.

He spends much of his time at Leasecake focused on security trying to understand who is trying to hack and what are they getting to hack. More broadly he works to verify the Leasecake platform is secure.

__Tell us about the business you represent, how did the idea come about to found your enterprise? __

Leasecake is a software-as-a-service platform for commercial tenants, brokers, and landlords. They use it to track cash flow, lease expirations and renewals, critical clauses in lease agreements, and other time-sensitive, mission-critical responsibilities.

Our founders searched for intuitive, easy-to-use location-management software back in 2017, but everything they found was bloated, over-featured, and built for huge enterprise operations. There was nothing for the average business owner. So we decided to build it.

Our vision is for everyone who rents or owns commercial real estate to have Leasecake on their computer and mobile device.

What notable IT challenges have you overcome?

Better securing the environment. Just over a year ago, we were a one-person development shop. And with sparse resources, you're careful about picking and choosing what to do at that stage. So we did the typical types of things a SaaS software company would do. But as we ramped up our team over the past year, it was time to formalize our security protocols.

With a team of three developers, we first performed an OWASP ASV self-assessment. It took some time but revealed opportunities for improvement. We remediated, reviewed the work, and moved on with additional comfort in our security.

After finishing the self-assessment, we then hired an outside security firm to run penetration testing. The firm only found a few minor issues, nothing high risk. Once again — we remediated. Those two actions gave us peace of mind and laid a framework for regular due diligence.

How has your business adapted during the Covid-19 pandemic?

It was easy from a technical perspective. We already used Slack for internal communications and had connections into our commit-and-build process to provide visibility into development work. In addition, we had previously used offshore development resources off and on, so the team was familiar with connecting and communicating remotely. Tools such as Tuple and GitHub were also already integrated before the pandemic.

I think the bigger re-tooling was from a biz dev and sales perspective. They previously relied on a lot of travel and face-to-face interaction, which was no longer possible. Virtual conferences, Google Meet (followed by a transition to Zoom), along with the traditional phone and email landscape, provided a path to this new world.

Being the CTO, what does your day to day responsibilities look like?

This may sound cliche, but there isn’t anything consistent about my routine. I love and thrive on the fact that no matter what I think I'm working on for the day, my plans almost always shift before it’s half over. I’m in a lot of meetings, both internal and external, on a combination of technical, operational, and general business subjects.

Generally speaking, I divide much of my time between technical and operational concerns. On the technical side, it’s reviewing Jira tickets for completed work or tasks in the queue. There is rarely a day that I’m not writing some JQL to either gain a sense of progress or a forecast of where we will be.

From an operational standpoint, I spend time every week setting up or monitoring operational and support metrics. I stay close to operations because, as our front line, they have a lot to offer in terms of customer feedback. If I can leverage a technical solution to a customer challenge, the payoff is worth the effort.

What advice would you give aspiring CTOs and entrepreneurs?

Don't aspire to be a CTO!

But, all kidding aside, I think some things did help.

Pay less attention to titles and more to the opportunity. At the second startup I joined, the title was quite a step down from where I had been — but the opportunity was fantastic. It was a solution engineer role that involved meeting with customers and working with engineers to implement a platform and integrate disparate systems. I learned a lot in that role and got a lot of exposure to negotiating with business and technical resources.

As either a CTO or entrepreneur, you should be willing to do whatever it takes for the company to succeed. Don’t worry about job descriptions. Just get things done. We lost a customer success manager early in my CTO role here, and I quickly filled in while searching for a replacement. Someone needed to handle that job, and I learned a lot from it. That’s a win-win.

What new challenges are CTOs facing today?

The rate of change in available tech stack options gets faster every year. Keeping up with those changes is challenging, especially in a smaller shop where the CTO wears many hats. New threat actors emerge constantly. Without sounding paranoid, you have to sleep with one eye open. When it comes to recruiting, things look very different in a post-COVID world. Geographic boundaries have largely disappeared.

What do you see as the hottest trends within your industry today?

I’ll start by coming at this from the opposite side. A lot of people assume brick-and-mortar retail is trending into a death spiral. But that’s not accurate. Sure, plenty of restaurants and retail brands had a tough time during COVID-19. But others thrived.

As our CEO, Taj Adhav, says, “The strong are getting stronger, and those that are struggling don’t want to be left behind.” We’ll also see continued growth in the medical space. More people are embracing wellness and preventive care — and they want convenient access to those services in locations that fit into their daily routine.

What can we hope to see from your business in the future?

Without giving away too much of our roadmap, I can tell you we will continue narrowing the gap between commercial tenants, landlords, and brokers. They’re part of the same ecosystem, and we work every day to make life easier for all three groups.

If you enjoyed this article then why not check out our guide to the ELK Stack or our post on software deployment tools?

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