Ep 229: Why Customer Support Is Everyone’s Job with Brian Childress

“Everyone—from the engineer to the CEO—should take part in supporting customers. It changes how we build everything.”

That insight from fractional CTO Brian Childress isn’t just memorable—it’s a blueprint for building better tech businesses. In this episode, Brian shares how embedding customer support into every role improves product development, team alignment, and long-term growth. Whether you’re a SaaS founder, solopreneur, or future CTO, this episode is full of sharp, actionable advice.

Brian Childress is a seasoned software architect and fractional Chief Technology Officer. With deep experience leading software engineering teams and scaling tech infrastructure, Brian helps startups and growth-stage companies make the leap from “just launched” to “ready for real users.” His superpower? Balancing deep tech know-how with customer-first strategy.

WE ALSO TALKED ABOUT

• What a fractional CTO does (and how to become one)
  
• The hardest part of shifting from employee to business owner
  
• How to prepare your SaaS platform for real-world users
  
• Why every team member should experience customer support
  
• Creating company culture without making it a “project”
  
• How AI agents can act like super interns
  
• Protecting your intellectual property while using AI tools
  
• Why understanding your team’s cultural background improves collaboration
  
• Systems and frameworks that keep solo consultancies running smoothly
  

Tune in now for a candid conversation full of practical strategies and lightbulb moments.

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RESOURCES MENTIONED

LinkedIn: Connect with Brian Childress

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Trudy Rankin is the host of the Online Business Launchpad Podcast, Director of West Island Digital and the founder of the Online Business Lift-Off program.

Affiliate Disclaimer: If you click on links on this page and then make a purchase, I may earn a commission (at no extra cost to you).  I am a proud affiliate of these resources because I use them in my own life and business.

TRANSCRIPT

Episode 229: Why Customer Support Is Everyone’s Job with Brian Childress

Trudy Rankin: [00:00:00] What we do in our day-to-day work is only a small fraction of what it takes to run your own business. That insight from Brian Childress really hits home, especially if you’ve ever tried juggling client work, bookkeeping, and tech set up all in one day. But what happens when you add managing global teams, software systems, and customer experience to the mix or the pile?

In this episode I chat with, in this episode, I chat with Brian Childress, a fractional Chief technology officer who supports growing SaaS or software as a service companies and startups by helping them scale their tech without losing sight of what matters the customer. We talk about how to transition from being an employee to running your own consultancy, what it actually means to be customer centric as a tech leader, and how to make AI work for you, not against you.

Plus Brian shares why everyone on your team from CEO to coder should be [00:01:00] involved in customer support.

Brian brings a rare blend of deep technical know-how and business strategy to the table. With years of experience scaling systems leading globally distributed teams and guiding SaaS founders through growth and chaos, his insights are gold for anyone building a tech-based business or thinking about offering services as a fractional executive or thinking about offering services as a fractional executive.

Trudy Rankin: Welcome to the Online Business Launchpad podcast. I’m Trudy Rankin and I help people who need a flexible work from home option grow the online side of their business so they can earn more stress less, and have greater freedom in how they live.

So I wanted to say thank you so much for being on the podcast today. We’re going to talk about some really interesting things. [00:02:00] And so welcome. 

Brian Childress: Thanks for having me. I’m excited to be here. 

Trudy Rankin: Yeah. So let’s go ahead and start by just talking a little bit about your background, who you are, what you do.

And then we’re going to just talk a little bit about an area that I’m quite interested in. 

Brian Childress: Okay. Yeah. So again, my name is Brian Childress, and I’m a fractional chief technology officer, and we’re starting to see the word fractional and fractional executives starting to pop up quite a bit. But for me, basically, that means that I have the opportunity to bring my expertise and many, many years

experience into various organizations that I get to work with. And my background has really been in software engineering, software architecture, and really helping companies to build and scale their software platforms. 

Trudy Rankin: And because I have a background in the information

side of businesses, the technology and the information management. I find this fascinating. And so could you maybe just describe a [00:03:00] day in a life of what a chief technology officer does?

Brian Childress: So for me, the way that I, uh, the things that kind of keep me busy day to day, I’m doing everything from, long term technology strategy, how are we going to be adopting and evolving our technology landscape to make sure we’re able to continue to support our customers.

I’m managing engineering teams. So these are groups of folks, typically for me, spread all over the globe that are helping to develop and build and support the systems that we’re building. I’m also helping with project management and more day to day type operational things. I’m meeting with customers to understand what their pain points are and how we might be able to leverage.

Our tools and our capabilities and the data that we have to help our customers as well. So quite a bit of different things that I get to focus on. And for me, I try to not be as focused on the technology specifically, even though that’s my deep [00:04:00] background. I really want to look at how can we use technology as a way to drive business value. So that’s really where I try and spend the most amount of time is understanding the business. And then I just happen to bring technology and where it makes sense.

Trudy Rankin: Can you just describe for our listeners just, or tell us this a little bit more about you started out, you’ve started out in sort of the software engineering, in the technology space.

How did you go from fresh out of university or whatever, you know, whatever road you took to start your career? How did you get from there to being a CTO? 

Brian Childress: Yeah, so I spent many, many years working my way up through the ranks, working with different organizations on different size challenges and solving different problems as an engineer.

And, I got the chance to work in in finance and in health care, in consumer software products as well and really for me to get to where I [00:05:00] am, I draw from the experience across all of those different roles because I had an opportunity to work with teams of different sizes, with different technologies, with different, regulations and restrictions.

And thankfully, I have all of that experience to now bring into my chief technology role. And, you know, there’s a couple of ways that someone becomes a chief technology officer or really anyone in kind of the C suite they’re either hired into it or they create that role. So I started by creating that role by creating some, some startups, with different friends and different projects. And, none of those really took off. But I was able to then start working with organizations and bringing my expertise and my leadership to their organizations. 

Trudy Rankin: So at the moment, you basically run your own business or do you work for another business as their Fractional CTO specifically who then gets you to help other [00:06:00] businesses as a CTO.

Brian Childress: So the way I’m structured, I have basically a software consultancy. So I’m a one person shop and I have multiple clients who bring me on as their chief technology officer. And for me, it’s at varying degrees of involvement. For some teams, I’m very hands-on in the day-to-day. For others, it’s more strategy and advisory.

And for others it’s coaching their team to be able to develop their own leaders internally so that hopefully one day I’m actually replacing myself with leaders that I’ve been able to grow. 

Trudy Rankin: So I’m curious, what kind of an adjustment did you have to make from going from being an employee through to being your own boss with your own sort of business?

Brian Childress: There’s a lot to learn. There absolutely is. And the things that we do in our day to day work is only a small fraction of what it takes to really be able to operate on your own, running your own business. You know, all the marketing and the legal and the accounting and [00:07:00] all of those things that we’re so grateful for somebody else taking care of when we’re in an employee situation and working for someone else, now we’re responsible for.

I think one of the things that really helped me in that transition was I developed my business. You know, I started it many years ago and just did it as a kind of a side hustle. You know, nights and weekends I would be moonlighting doing freelance software development. So that allowed me to get a lot of the systems in place that I needed for, like I say, accounting and how do we do taxes and all of those sorts of things were already in place.

I just needed to ramp up the amount of hours that I was able to commit.

Trudy Rankin: That’s a really good way of doing it because then you don’t have that sudden sort of fire hose experience of trying to be able to learn how to do all those skills all at once, which is tricky. 

I’d like to talk a little bit about one of the things that I’m particularly interested in. I know that my listeners are interested in as well. And that is that whole software as a service [00:08:00] concept where, and I know a lot of people dream about being able to come up with the ultimate unicorn type software as a service platform, like some of the ones that are around at the moment, like Canva and some of the ones like that, where you’ve create something that’s of such value to people that it just, with a lot of support and help grows and grows and grows and becomes something quite valuable.

Lots of people dream about being able to do something like that. And in terms of the types of support that’s needed to be able to take developers, you know, some sort of software as a service tool or platform or app and then be able to grow beyond that. What are the sorts of things that you would typically help people do in that kind of a situation?

Brian Childress: One of the biggest areas that I help people is kind of after they have something built is to actually make it ready for users to really use, right? We might have our first handful of users that are using the platform. [00:09:00] Maybe they’re paying, maybe they’re not. And for me, I come in and then take it to the next level.

And usually for me, that’s making the technology more stable less complex, adding in the data that we need to collect to really understand how are our customers using the platform? What benefits are they getting? What potential opportunities can we present to improve their experience? A lot of times, that’s really where I focus is what can we do for our customers?

How can we better serve them? Because we know what’s going on, what they’re doing, what they’re clicking on, where they, you know, any errors are. Let’s use that information to improve the process. And I think that’s where I see a lot of software as a service platforms start to not do so well is they seem to forget the customers, the folks that are actually paying them money each month to make sure we’re providing a great service to them.

We’re continuing to provide features that they’re looking to use to, for them, [00:10:00] help grow their business or improve their lives or whatever it may be. 

Trudy Rankin: I know one of the things, because I work with a number of people who have started a business and they’re still small and still growing.

And one of the most important things for them when they do purchase access to tools, software tools, is the customer support that comes with it. How does that work when you’ve got all this money going into the development of a tool? Just explain a little bit about the process that you use to work with your customers in terms of helping them understand that customer support is absolutely critical and vital if they want their customers to stick with them.

Brian Childress: Yeah, one of the interesting rules that I try and put in place for, you know, with my customers is actually everyone gets to play a role in customer service and customer support. And so everyone from every engineer to the CEO, we all get to take part in supporting customers, answering their chats.

What is it [00:11:00] like to onboard them onto the platform? Because when we really see it in the day to day, it’s a completely different view of what it takes to support customers and what their needs and their challenges are because now, you know, from the finance department to the engineering department, we have a different perspective.

We’re really thinking much more customer centric and that changes our view on things. 

Trudy Rankin: Yeah, I think that’s a really, really useful way of looking at it. And how challenging is it for people working with people who are typically potentially not necessarily outwardly customer focused?

They might have internal customers, but not necessarily outside customers. I’m thinking finance and people who might be more inwardly focused. Do you tend to get resistance at all from people in terms of focusing more on customer support. 

Brian Childress: Oh, absolutely. You know, there’s everything from folks saying, well, that’s not really my job or I’m too [00:12:00] busy, I don’t have the time.

It has to be very much a cultural thing, and it has to be driven, in my opinion, from the top. We have to say, no, this is something that we all do. No one is above supporting our customers and making sure that they’re having a great experience. And if they’re not, let’s figure out how to make it better for them.

It has to be just core to the way that the business operates. 

Trudy Rankin: That’s kind of interesting, because you’re touching a little bit on something that’s actually really, really critical to just about every organization, and that’s culture and how you develop culture. If you’re working with startups or businesses that have, they’re not quite past the startup stage, but they’re in into the growth stage.

How do you go about helping them develop a culture of, we’ll talk about customer support, but there’s the overall cultural view. Do you help them actually develop a culture that’s going to be good? 

Brian Childress: I do. I and I hesitate because I try not to make it an explicit thing, but it’s part of what… [00:13:00] in working with me and the way that we start to partner together, we change the culture over time. It’s everything from how do we show up to meetings? When do we show up to meetings and really? Trying to guide the leaders that I’m working with the stakeholders, the teams and demonstrating this is how we operate. This is how we work. This is how we share documentation and information and just really modeling what it looks like that we’re trying to get from our teams and our colleagues and from there, the culture will slowly evolve, but it really requires everyone to take a conscious effort and focus on it.

On getting us there, but we can’t say, Hey, this week, we’re going to focus on changing our culture. It has to be just a very organic thing, I find. 

Trudy Rankin: Yes. Yes. And then just sort of a follow on question because you said you mentioned that you team members kind of all over the globe, or you’ve got People who help [00:14:00] support your clients who are all over the globe.

How do you manage situations where culture that culture of that particular place where your team member lives might be different to the culture of where your client lives? 

Brian Childress: It’s a very important thing for us to consider, I think, and it’s something that I find we often end up forgetting.

For me here in the United States, we work constantly. We’re expecting everyone to be readily available. I work with folks in Europe and other parts of the world and just the work culture and the way we think about things is completely different. The holidays that we celebrate are different.

And so I like to start by being really curious about that person where they live, what their interests are and, while they’re telling me I’m doing some quick research so I can get up to speed. So I want to make sure that I really respect what they’re doing, their cultures, their lifestyle The environment that they’re operating in.

Unfortunately, a lot of folks that I’ve [00:15:00] worked with in recent years have been very, very close to war zones. And, that changes the dynamic and the things that they’re considering. When there’s bombing happening just 50 miles to the south of us, talking about spreadsheets and those sorts of things.

It’s a different conversation. So I have to be very, very respectful of that and, all of that, I think, comes back to the culture that we develop.

Trudy Rankin: It’s an interesting time in the world, and I think that just about says a lot. And there’s a couple of things I’m curious about, but Firstly, for your business and for the people that you support, the clients that you support, have you been able to find all the tools that you need to be able to support them well?

Or have you had to develop some for yourself?

Brian Childress: I think I’ve had to develop more frameworks and systems. I, I haven’t developed any, software tools necessarily even though I have all the capabilities to do that. I have [00:16:00] been able to really do a lot with what’s out there and readily available, even the things that are free I’m able to do quite a bit with.

For me, I’ve had to really develop the systems and the frameworks to be able to effectively manage multiple clients and multiple projects so that I am able to deliver. 

Trudy Rankin: Do you have a particular project management tool that you use? 

Brian Childress: I don’t because each one of my clients has a different project management tool that they use, so if, if they don’t have something I might recommend like a linear for managing projects or a Trello or something along those lines, really it just, it, it depends on the level of complexity of what we’re trying to manage.

Trudy Rankin: Yeah. In terms of the next question, if you were to imagine a situation where you’re onboarding a new client, and you’re just starting that process of working with them to help them obviously grow their business through the support that you provide, what would be the first three to five things that you would get them to focus [00:17:00] on very strongly so that they could just basically get up and run?

Brian Childress: I think it’s most important when we first get started to set expectations and make sure that everyone is crystal clear on what the expectations are for me coming in. A lot of times when I’m coming in, it’s, there’s an expectation for me to fix. The thing that’s been broken and really challenging the business for months.

And I’m the silver bullet that’s going to come in and fix everything in a week. And you know, sometimes that’s true, sometimes not. And so really setting that expectation, I think is important. Also really understanding the business. I think from the CEO, I’m going to get one perspective and from the folks that may be kind of down in the trenches, I’m going to get a completely different perspective.

And so one of the ways I try and kind of get a holistic view of what’s going on to know what can we attack. First is really sitting with everyone and just seeing what they do day to day. How did they work? What are the tools they [00:18:00] use? What inefficiencies do they have? What are the gripes that they have while we’re transitioning conversation topics?

Maybe they complain about something. And if I hear a theme among different people, maybe that’s something I can key off of. And that becomes a focus area as well. But a lot of it’s just really understanding the business for me, because then I know what I can really help and guide.

Trudy Rankin: Yeah. Yeah, definitely.

So my next question is a topic that is probably top of mind for a lot of people. And that’s artificial intelligence, AI, and the impact, the effect that it’s having on lots and lots of different businesses.

From your perspective, what kind of an impact is it having on your clients right now?

Brian Childress: It’s having a really big impact and in different ways for different clients. Because a lot of what I focus on is very technology focused. There’s kind of two questions that I get asked most often from the companies that I’m working [00:19:00] with, how can we better leverage AI just across the entire ecosystem?

How can we, beat our competitors to market? How can we improve our workflows, our efficiencies with AI? And then the second question is, how can we protect our business from AI, how can we AI proof the business? And those are two very. Interesting questions that I get a lot. And I think, you know, when we compare it to anything else in history, we’re going to see such a seismic shift in the power and the impact that something like artificial intelligence is going to bring.

We can’t even fathom it yet, which is wild. You know, I’m trying to stay at the bleeding edge of the conversations that are going on and we just, we don’t know what impact it’s going to have on the business and on on jobs and those sorts of things, but it’s going to have a very big impact. We just don’t know how big yet.

Trudy Rankin: So in terms of your own business, you’re saying you’re trying to stay on the bleeding edge. But [00:20:00] there are already, there are some known ways that AI tools can help with business efficiency and productivity. Can you just describe a few ways or one or two ways that you’ve been able to use those tools on your own business?

Brian Childress: Yeah, so some of the ways that I love to use these tools is I’ve been recording my meetings with different stakeholders and individuals for quite a while. And so I’m taking those meeting recordings, the transcript, the video, compiling all that into various AI tools to do everything from content generation to developing frameworks that I can use to bring into new client engagements.

I’m using that to remind me what the heck we talked about last time we met. You know, just the things that were always either got misplaced, forgotten, or weren’t top of mind. Now they’re top of mind. I’m developing my own agents to do just a lot of [00:21:00] the tasks that I would either have to do myself or pay somebody to do managing my email, managing my calendar.

All of those things become much more efficient and effective, which then allows me to stay focused on the thing that I do best.

Trudy Rankin: Can you just talk a little bit more about that whole concept of an AI agent? If you could just maybe just define it for our listeners first of all, and then I’ll follow up with a question.

Brian Childress: Okay. Yeah, so this is something I, for me, even with years of software experience, I have to break things down into their very simplest level. And really taking it to first principles to understand. And so for an AI agent, it’s really a digital employee. It’s a digital colleague that we’re able to communicate with assign tasks to get information from.

And I think right now what we’re seeing in the industry is that digital colleague is a very smart intern. They have a lot of the capabilities, but they don’t necessarily have the level of [00:22:00] expertise to do certain things, but the tasks they’re able to accomplish are very much at that like very smart intern type level.

And, I like to also remind my clients that today is the worst that AI will ever be. It’s only continuing to progress every single day. 

Trudy Rankin: So if somebody was going to or was thinking about developing this intern type colleague, your intern level colleague and they’re thinking about doing that,

what would be the sorts of things they would need to think about in order to develop something that was useful in terms of an A. I. Agent?

Brian Childress: Yeah, it’s a great question. I think in order to develop a very useful A. I. Agent, we need to start with what are the tasks that I’m trying to automate and what are the things that I need to have in place to automate that?

So what’s the knowledge base? What are the steps that I would normally take if I were the human performing that action? You know, the standard operating procedures, the access to data that I would need to to be able to [00:23:00] grant to make sure that somebody could perform those actions. What decisions do I want that agent to potentially make?

And do I want to be the final say in, you know, if I have an AI agent crafting email responses for me, do I would just want to let that agent send out emails or do I maybe want to wait and I actually review it, maybe tweak what’s created so that AI agent has saved me 70 or 80 percent of the work and I’m just doing the final final touches to humanize it before it gets sent out.

I think those are a lot of the things to really consider. And for organizations I’m finding we’re actually developing those standard operating procedures. We’re actually cleaning up our data sources to make our agents more efficient. And if we had it for our human employees, maybe things would be a little different.

Trudy Rankin: That’s always the key, isn’t it? It’s always garbage in garbage out, whether you’ve got humans working with stuff that’s not so great, or whether you’ve got agents working with data that’s not so great. So [00:24:00] one more quick question before we wrap this up. And that is, is that one of the things that worries a lot of people is that if they’re using agents, or when I say agents, let me just back up a little bit.

If they’re using AI tools, like ChatGPT, Claude, all the different ones that are there, there’s this sense that they’re actually feeding into this massive pool of knowledge, and some of their confidential business information might escape out into the, you know, the world, unintentionally through using AI tools.

What would be one of the things or some of the things that people might need to do in order to make sure that that doesn’t happen with AI tools? 

Brian Childress: It’s a very real possibility and there are a lot of organizations that have either experienced that or are very concerned about it. We’re gonna really see better support for running models, these tools, these agents locally on our, our computers.

So it actually never leaves our computer or our corporate network. And I think we’re going to see quite a bit [00:25:00] more of that. A lot of it comes down to education, as well within our employees. Hey, what information do we supply to some of these tools? Those are kind of the big areas that I think we focus.

Unfortunately I think it’s going to happen quite a bit before we start to figure out what’s the level that we should be, protecting our IP. 

Trudy Rankin: Yeah. So at the moment, be aware, be careful, make sure you understand.

That makes it kind of interesting when it comes to using AI and experimenting.

Brian Childress: Yeah. If I could add I don’t want, I wouldn’t want somebody to be limiting themselves with using these tools and starting to understand and play with them for fear that, you know, their intellectual property may escape. I think it’s really important for us to still learn these tools, really use them, try and like force them into our day to day workflow so that they become just, very much a part of the way that we live and we [00:26:00] work, because, like it or not, that’s really where I think we’re headed is it’s going to be very much just part of our world.

Trudy Rankin: Yeah, definitely. Most definitely. Brian, it’s been really interesting talking with you. I really appreciated you sharing some of your insights around those things. And if people were interested in reaching out to you or finding out more about you, where would they go?

Brian Childress: The best place to find me is on LinkedIn.

 Brian-Childress, I’m readily posting on there. So I encourage folks to reach out, send me a message and I’m happy to connect. 

Trudy Rankin: Fantastic. Well, I’ll put that up in the show notes. So once again, thank you very much. 

Brian Childress: Thank you.

Trudy Rankin: I hope you found Brian’s behind the scenes look at being a fractional chief technology officer, chief Technology Officer.

As interesting as I did, especially his approach to building customer-centric cultures and using AI agents like smart interns. There’s so much here to chew on if you’re thinking about scaling your business or even just launching your first product. If [00:27:00] you enjoyed this episode, make sure you hit subscribe and leave a review.

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You can sign up at Online Business Liftoff dot com slash newsletter. That’s Online Business Liftoff dot com slash newsletter. Thanks for hanging out with me today, and until next time, keep things simple. Keep showing up and remember, technology is powerful, but it’s your heart and your leadership that drives real success.