[0:30] Tell me about your current role.

I’m CTO for CPAP.com, a medical equipment company. We sell more CPAP machines than anyone else in the world and are branching out into Sleeping.com in the next 18 months because it’s a huge industry.

[02:06] What does your role entail?

As a smaller company, I get to wear a lot of hats. One day I might be working on site content, and the next working with developers on architecture. There’s recruiting, budget, scaling, and redundancy.

[03:28] What are some of the challenges you face and what platform are you based on?

AWS, and our legacy stuff is on PHP, MySQL, and WordPress. Some of our systems were built by our CEO when he was in college. It’s tightly coupled, so we are looking to replace some APIs. It’s hard to replace a piece, so we are looking to make it more modular. We just built out Magento for ecommerce.

[05:36] What does your team look like?

It’s a small team of 25. We have 3 agile teams that are QA developers, product donors, and UX. One team works on pre-sale product pages, one for the cart, and one for the back office and shipping. Then, we have an infrastructure group.

[07:49] From a finance and selling perspective, how does that work?

We are looking at affiliate links and potentially selling products through the site. Sleeping.com was originally an experiment to see how we would fare in Google rankings if we branched out. One thing we learned is that we are being dinged on our natural SEO search because we need to provide more educational content.

[10:39] What’s it like having a technologist for a CEO?

He’s entrusted the technology to me and moved on to focus more on the CEO role, but he still loves to geek out.

[12:09] Tell me about your history in software.

When I was about 12, my dad bought a Commodore machine for his business. As the company grew it needed to be more automated, so my dad learned how to program a simple code to handle orders. That got me interested, so I learned and rewrote our programming and joined a user group community based around Clipper. Then, a member asked me to join his company.

[15:00] What are some of the most interesting projects you’ve been a part of?

I wrote the programming for a machine that talked to kids for a Bank UTD. It was a touchscreen machine that would help them set up a bank account, and they could see what money they had and how long it would take them to save up for a toy. At the same bank, we developed a retinal eye scan that got a lot of coverage as it was the first bank to do it.

[18:55] What are some new things that you are exploring right now?

We are looking at KOLO and AWS sharing a facility and storage. Also, containerizing our code in Docker and looking at it to help with data transfer ease. Security is always a concern, so we’ve outsourced ours to eCentire who have provided fractional CSO service.

[22:40] What other roles have you seen change and become more important?

Fractional work has become much more important. I don’t know if it’s due to COVID or not. I got my job at CPAP.com doing fractional work, and I like to take advantage of outside services. Instead of sending teams on several months of learning, I’d rather get someone in that already knows and can guide my team.

[26:15] What have you learned using fractional work? How do you know how to get good people?

Taking advantage of connections and recommendations; word of mouth.

[27:15] What would you like to accomplish in your role?

I enjoy learning from the different places that I go. I’ve learned about ecommerce at previous jobs and now I have been learning about medical equipment sales and security. It’s been great working at a small company as it grows and finding the sweet spot on the leadership team.

[30:30] What’s next with technology? What’s a game changer?

I think AI is going to be so involved in everything we do. It’s going to revolutionize data collection and analysis.

[48:00] What work is getting out of hand? What needs solutions?

Some of the VI that we do. Data scientists are expensive. You need to have the ROI on that data or what’s the point.

[52:10] As a CTO, how do you improve your skills?

I love PluralSite.