Ep. 26 – Ongoing Operations, Operations Manager Jonathan Derby

Our guest is COO Alliance Member Jonathan Derby, Operations Manager at Ongoing Operations.

No one knows credit union IT as much as Ongoing Operations, a financial technology company focused on cloud services and managed services to the credit union industry. With former credit union executives and highly skilled experts in that field, the commitment and expertise of this team are incontestable. One of the brilliant minds behind them is Jonathan Derby, the Operations Manager of Ongoing Operations. Adapting to a rapidly changing tech world, he reveals how to keep pace with the advancements and stay on top while keeping their on-site and remote team engaged to their vision. With his CEO working remotely, he gives away the challenges and benefits of such arrangement and why he initially turned down the offer of being the COO.


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Ongoing Operations, Operations Manager Jonathan Derby

Jonathan Derby is the COO at Ongoing Operations where he oversees the management of their computer and network security. He’s a solution-oriented leader that excels at communication, process development and building lasting team relationships. He’s been working for many years in the financial tech industry. He is highly skilled in hosted services and disaster recovery. He dedicated the last few years to create a cloud platform for credit unions that allows them to compete with large retail banks. Jonathan has dedicated to continuous learning and professional development. He’s been expanding his interest in scaling managerial services and creating incentives for employees to reach operational and sales goals. In his free time, Jonathan loves to get away to Punta Mita, his favorite town in Mexico. Jonathan is also a founding member of the COO Alliance. Jonathan, welcome to the show.

Thanks for having me, Cameron.

Why don’t you give us a little bit of your background, where you came from and how you got to where you are now.

My first job was at a credit union working with the CEO of this company. We’re in different departments. I’ve been in that space for most of my career. I also worked at Morgan Stanley in New York City. I was one of the youngest vice presidents there in technology. I was the first employee of our company back in 2006. It has changed a lot since then. I was there for several years, left for a few years and then came back. I’ve been with them for another few years. I explored some other things for a few years and came back and began working with my CEO again.

Why did you leave at that point? Why did you come back?

We started as a true startup. I was employee one. I was the only employee. When you go through those high growth cycles, the company is growing, but it’s important for the employees to keep up. I had some frustrations, which is the amount of responsibility that kept coming that was hard to keep pace with. One of my biggest challenges is I was young at that time. The company had gone from $700,000 in revenue to about $10 million in revenue in that period. Part of that is the company outgrew me. It’s important for me to take a break and work in the enterprise for a few years and get some perspective. I loved working at Morgan Stanley and working in the enterprise, but I looked at it and said, “Is this how I want to spend my entire career?” I could have been successful there. I did accumulate a lot of success in my few years there, but I said, “I was passionate about what I used to do,” and I was frustrated. My CEO and I kept in touch and there were some frustrations with my transition. When there was an opportunity to launch a new arm of that company, I got the phone call and he said, “This sounds like a great opportunity. We’d love to work together again.” Our relationship has been an uptick since that, but it was important that we took that break. Otherwise, I don’t think we’d be in touch now.

The growth that you went through when you come in as employee number one and you run a company or grow that quickly, it does start to outgrow us. I was sitting with the CEO of Infusionsoft, Clate Mask, and we were talking at a Genius Network event. He was saying that a key employee can only go through two successive doubles in a company. You can only go from $2 million to $4 million and $4 million to $8 million, but it’s hard to then go from $8 million to $16 million. To go to the outside world and come back in, what skills do you think you brought back in with you from Morgan Stanley?

The biggest one was a renewed approach to things. We had been caught up in startup mode and a lot of people on our executive team hadn’t had that much experience with the enterprise. How does the larger company solve these problems? How do you do the same thing not once or twice but 100 times consistently the same way? I grew tremendously in process development and spent a lot of time at Morgan Stanley working on, “How do we enhance this process?” When I came back, I looked at how we used to do things and I’m like, “That’s great for once or twice, but if this is going to be a product and we got to deliver it to 100 people, we have to build scale.” That’s where I focused a lot of my time. When we have a good idea, how do we build it to scale? If you can’t scale it, it’s a good idea that doesn’t go anywhere. It costs you more money than you make.

We had the founder of a company called SweetProcess to come in and present at one of the COO Alliance events. What do you use internally as your tools to document your SOPs or document your processes? Can you give us what your baseline approach would be to come up with better processes? 

SweetProcess is something we’ve been using once we found out about it and I’ve been obsessed with it. We tried and tested out a few processes. We’ve got two to four iterations of using that. We do a lot of enterprise project management. I don’t think there’s any amazing project management tool out there. A lot of it comes down to how disciplined you are and how well you use the tool. We use a system called ConnectWise that manages all of our services and project delivery and CRM, which is built for our industry. It is the managed service provider space. In terms of documentation, we have been using for years these specific directories where we have all of our process folders and our customer folders. We use SharePoint as the backend. We are making the transition to software called IT Glue. It is a much more enterprise tool for managing documentation, managing the version control, but most importantly making sure that everyone can find your documents. A lot of times, we use document tools and you don’t think about the search functionality and you can never find what you’re looking for. If you can’t find what you’re looking for, it’s of little value to the rest of the company.

The stuff that always drove me crazy with documentation was that employees would save a copy of it to their desktop and then they would use that. It makes sense like, “I’m using it. It’s right here. It doesn’t matter.” All of a sudden, it becomes outdated or they save it somewhere else or they missed the updates. It’s always driven me crazy. That’s what you’re moving to then. Give our audience a bit of a rundown as to what Ongoing Operations does. What does your company do?

We’re a FinTech company and we focus on cloud services and managed services to the credit union industry. Helping credit unions is a big part of our vision. For those who don’t know the difference between a credit union and a bank, credit unions are owned by their members. They’re not for profit organization. They do act as financial institutions, but when they make money, they give it back to the members. It’s either lower loan rates or higher CD rates or superior member service. We help them outsource their IT needs because they usually are not on the same scale as a large commercial bank. Instead of saving billions, they’re spending millions. We want to take as much of the IT burden away from them that they can focus their time on member-facing technology and improving that experience rather than keeping the lights on or like, “How do I spin up a server in four hours?” That’s something our company does well. They usually don’t have the staff or budget to do that. We try to make their technology more efficient so they can focus on their members, which is their ultimate core mission.

I’ve always believed in the idea of focus. If you’re completely focused, you’re like a laser beam and you can cut through steel or rock. If you’re not, you’re dispersed and you can light up a room. Either way, it’s light. You have chosen to stay specific in a big niche. How did you pick that niche? Do you have clients outside of it? 

We had a lot of experience. Our CEO, Kirk, and our founder are interested and passionate about supporting the credit union cause, as am I. Our business model used to be anything for anyone as long as they’re willing to pay for it and asking for it. We started with credit unions but took on other customers outside of that vertical. Over the years, we’ve changed our habits and about 90% comes from that vertical. That’s mostly so we can bring scale and efficiency to it. The non-credit union space has different needs. We have the skill sets, we have the platform, and we do help that selectively. We said, “For us to scale our services, we have to be vertical specific.” When you look at other MSPs in the space if they go vertical specific, they can scale the company. Whereas most MSPs peak at it. They’ve got fifteen to twenty employees where we’ve got 50 and we’re still growing.

How did you and Kirk stay on the same page? Kirk is a different personality profile to you. Tell us a little bit about each of your personality profiles. Have you done any profiles on yourselves? How do you stay on the same page?

SIC 26 | Ongoing Operations

Ongoing Operations: If you become cost-competitive, people look at you as a low-cost provider. They start to disregard the value you’re adding.


About a couple of years ago, I ignored personality profiles in general. I didn’t think they’re that much value. Over the last few years, I’ve done 180 and I believe in that. I use them in my day-to-day with my employees. When you look at it, we focused on the DISC at our company. My CEO is DI. He’s dominant and I’m a DC, which are going to butt heads. We were at the COO event and we spent some time with Steven Sisler and merged our two personalities against each other. It’s amazing how much we complement each other and how much we frustrate each other and how we had to change a few habits. As a DI, his unique ability is to get something to 80% quickly. He’s a super high fast start. I am not a high fast start, but I’m the guy you want to take from 80% to 100%. We inherently complement each other. When you look at some of the personality traits, he’s inherently hardwired not to appreciate me. We highlighted a few traits where we have to meet in the middle. We have to compensate to make sure it’s a good relationship for both of us.

I was telling my Director of Operations, Rachel, and she runs huge parts of this business for me completely on her own, that I will always find the little wrong things that will drive me crazy and take for granted that I love you for the rest of the stuff that’s going great. My job is to see the little things. I’m such a high ADD. My attention deficit disorder has me seeing everything. I get wickedly distracted by the thing that jumps out at me. I don’t notice all the good stuff. I’ve got to get better and work better at the praise. Do you know what your love languages are? 

It’s the same as my wife’s. It’s quality time.

You appreciate the time you get with Kirk, which would be your one-on-one meetings or retreat time that you take away every quarter, even spending time at the COOs event together. 

I did enjoy that. My wife’s love language is quality time. Therefore, my love language is quality time. I’m probably quality time and affirmation.

Words and affirmation. You need verbal praise. I’ve started asking CEOs what their love language is and what their employees love languages are and they think I’m weird. The reality is the love languages can play over into the business area. My love languages are physical touch and words of affirmation. If somebody comes up and pats me on the back and says, “Great job.” That feeds me. Imagine if you understand your employees’ love languages as well. Steve Sisler is a world expert on DISC. His understanding of each of us and our personality profiles was shocking. 

It blew my mind. I’m pragmatic according to ADD, which is true. It says, “This is your blind spot. This is where you’re going to succeed.” It’s important to understand what those are. I wanted to argue about them and be like, “That’s spot on.”

He told me that I run at 31 miles an hour with a 30-foot vision. It’s what my vision allows me to go. Tell me about the visions. I’ve always said that the CEO has to hold the vision and the COO has to sign off on it. The COO has to come up with the plans and the CEO has to sign off on that. How do you and your CEO stay on the same page with vision? How do you and the CEO stay on the same page with the plans? 

My CEO always had a painted picture of similar but not as good as a vivid vision. He was sending out and the executive team read it and be like, “That’s nice. Thanks for doing that.” That’s about where it would start to finish. It was important to him. It’s frustrating that others were not embracing it. When I attended meetings on culture, I’m like, “This is important.” Since then, I’ve engaged with him. We’ve updated the painted picture together. We have our goals through 2020 and we’ve brought the rest of the executive team. We always talked about living it before and it was important to our CEO. We’re like, “Let’s make this our vision of the company or culture of the company and push it down to the rest of the employees.” We’ve gotten through that process a lot in the last few months. When you start making decisions based on culture, they become a lot more clear and easier to make and you can say, “This person is doing well, but we keep ending up in these situations. Their work performance is good.” It’s because they’re a high performer. They’re not a culture fit. You can’t solve that. You have to deal with it. Looking at how we look at employees’ performance and their satisfaction with the company based on culture has changed the way I look at it. It’s been a huge change for us.

The adage of hire for attitude and train for skills doesn’t get you there. You need to have both. You need to have the culture fit and the results.

We’ve brought that into our interview process. We do a culture screen before we do any interview to make it more efficient. If you’re not a culture fit, there’s no point in going to the next round. We’ve started to build that into our process. Part of it is also making sure that all of our employees believe in the vision and the culture of the company. If they don’t, they will self-select and say, “This isn’t for me.” They’ll move on and that’s fine too. We want everyone to be happy and aligned with the culture and vision.

How do you screen for culture? What do you do to screen for that? 

There are a few things we do. Our HR team leads the culture screen and we have about one of 40 questions that we look at. They choose six or eight of these questions. They are about culture and how they deal with certain situations or they’re trying to get to care about the person that they’re working with or the person they’re doing work for. Additionally, we give them a copy of our painted picture as a prerequisite and ask them to tell us about the painted picture. What do they like about it? What don’t they like about it? Can they describe an activity where they have applied that thought in the past? If they were like, “I was supposed to read that document. That’s an easy decision.” Sometimes you’ll get someone, “I like that, but that’s not my personality.” You get someone who’s like, “I love this vision, I love this culture. I want to work here.” If someone starts by saying that, we’re going to fast track them through the more technical interview process. It’s a game changer. It’s a more efficient use of the applicant’s time as well as our employees’ time to go through that process.

The term painted picture was the old term that we now call the vivid vision. People used to think that a painted picture involved diagrams or vision boards. We now call it a vivid vision, which is that four or five-page written description of what your company looks and feels like in the future. If you want details on it, it’s written up in the book Double Double. It’s chapter one in Double Double. It’s also been covered in the book, The Miracle Morning for Entrepreneurs. There’s a book called the Vivid Vision, which outlines the whole process of writing one for your company or your personal life. I love that you’re using it at the beginning of the interview process to screen out candidates as well to push people away if they’re the wrong fit and to attract the ones that are the right fit. Do you share copies of your vivid vision with your customers and suppliers at all?

A few customers have asked for it. It’s their management or leadership team. We’ve been happy to share it. We have not published it publicly, but there’s no reason not to. It’s a great vision and something we believe in so why not share it with everyone?

SIC 26 | Ongoing Operations

Ongoing Operations: People believe in value. If they’re seeing the value, the pricing won’t be an issue.


I would encourage you to start sharing it with 100% of your customers, 100% of your employees, 100% of your potential employees. Share it with your banker, your lawyer, your accountant. Share it with all the circles of influence on the company. What ends up happening is they start getting excited about what you’re building. They want to be a part of it. They’ve never seen stuff like this. They’ll bring it into their businesses. When you started having an impact on the rest of their business, you’ve locked them up as a client forever too. We were talking a little bit about pricing and our rates. You were making some decisions or thinking about yours. Are there any thoughts you want to share on those?

We’ve been looking at some of our pricing strategies over the last decade. The reality is our cost has continued to rise because at the space we work in, you’re trying to cost competitive. If you become cost competitive, people look at you in a low-cost provider. They start to disregard the value you’re adding. I had a quick session with Cameron. My CEO and I said, “Our profit is not where we want it to be.” That creates other issues in the company. The simple question was asked, “When was the last time you raised your prices?” We said about several years ago. Since then, our costs have gone up. Our labor acquisition costs have gone up. It has for our customers. They’re facing the same challenges we are, but we’re supposed to be the experts. We took that back and had philosophical conversations. Do we want to be Walmart? No, we want to have a premium service where the value is there. If we’re creating value for our customers, they’re going to be able to work with these new prices. We are raising prices across the board and working through that. It was great advice and we looked at how the industry has changed, how the costs in the industry have change. We’ve stayed relatively flat. We’re making some modifications there for sure.

You rarely hear a buzz. You rarely hear raving fans talking about a brand that is low price. They don’t create that raving fan environment or they don’t create the raving employee environment. When you think about the best places to work, they’re a higher price. When you hear about great fan experiences or great employee or customer experiences, they’re usually higher price. The Ritz-Carlton is not the Holiday Inn. Nobody runs around talking about how wonderful the Holiday Inn is. I can’t even think of any lower priced brands. Even Disney is a high price. It’s not cheap to go to that place, but they provide an amazing experience. 

We’ve been selling on value over the price. People believe in value. They see the value. If we stick to that technique, the pricing won’t be an issue. If we’re successful, they’re successful. We do a lot of mutual alignment there with our customers.

You talk about the vision and people being all on the same page for vision. What do you think the keys are for executing your vision? The management team and all your employees, how do you start getting them on the same page? How do you start executing your vision?

We had to guide our executives to embrace it, which is something we tackled and says, “This is our CEO’s vision. Does this align with you? Do you love this? Do you hate it? Would you change anything?” We were in good alignment and we’ve taken it to the next level. We’re making sure that employees that hadn’t seen it in the year that any important meeting. I start by reviewing the vision and how are we doing against our vision. More importantly, when we look at our goals, we looked at the goals of our company. The goals were template business goals not aligned with the vision. Moving forward, we’ve aligned our goal cascade to come down with our vision that our employees are always thinking about it. If someone wants to challenge you or disagree with you, they’re going to be a lot more successful if they tie it back to. We’re not honoring our vision or disregarding this part of the vision by making this decision. We’ve taken it from being this thing in the sky that our CEO loved to pushing this throughout the company. It’s something that we’ll talk about at meetings and it’s tied to your performance and your goals for the year, which is the biggest change and how I push it out.

I love that you tie to their goals. I also love that you’re talking about it at all of your meetings too. That’s critical because you get people thinking about the future about operating or executing on now. I was speaking at a big conference of CEOs in Montreal and I was talking to them about how the company needs to have four core goals for the year and the quarter. The first most primary goal should be your employee Net Promoter Score. Your secondary goal would be your customer Net Promoter Score. Your third would be profit and your fourth would be revenue. Most companies mess that up and they think of a revenue goal first, profit goal second and the customer third, etc. I’ve always believed that if your employees are super happy, they’re going to take care of everything. If your customers are super happy, that’s where the profit revenue comes from. Do you have any philosophies around that at all and how you take care of your employees?

You brought up the employee Net Promoter Score with us, which is something that we are going to build in. We do an annual survey with our employees around their satisfaction. We go through that a lot of detail to make sure we’re not violating our values. Rolling out the employee Net Promoter Score is going to be our next step. That is the right order of the employee than the customer then the profit.

It will pay huge dividends when you start having those discussions, when they start to feel that you are obsessed about their engagement as well. Talking about the employee experience, are your employees all in one location or are they remote? What percent would be remote? 

We’re about 70% remote and about 30% of our employees are in the opposites. When I talk with my COO peers, we’re the number one differentiator and it creates unique challenges when you have a remote workforce. It makes it much more challenging. You’ve got to make a much more conscious thought if you want to build culture remotely than if you’re in the same workplace.

What challenges are you dealing with there? How are you working through them?

It starts at the hiring. Not every person is built to work from home. Certain personality types are going to not collaborate, who are prone to depression or mood swings. If you don’t have the work ethic or the discipline to work from home, it’ll be evident quickly. We screen for that on the front end. We’ve got all these employees that work remotely. We get face-to-face the entire company once a year. We’re aiming for two times. We’ll be doing two events. We’ll get the entire company together. We get the management and the executive team together a lot. We’re also trying to meet with other employees, flying them into certain cities where we can all meet. That face-to-face is important. On the virtual side, we do monthly meetings. We have people turn on their video and get the entire company together.

We leverage a ton of video conferencing. The downside is, we have more meetings than we need to because we’re trying to increase interaction and collaboration among the entire company. That’s something we are always balancing because the more they see each other, either on video or in person, collaboration goes up and better ideas come up. We also tried to do some things together as an entire company. Every Monday afternoon we have documentation call. Everyone in the company that joins said, “This is what we want to accomplish.” The teams break up and they update the rest of the company at the end of the meeting. It creates some good documentation. More importantly, it gets the entire company together once a week.

One of my clients were playing their retreats and I was curious. They were running it in Tucson, Arizona. I’m like, “How did you pick Tucson?” He said, “We always pick secondary cities and secondary markets because we can get higher value hotels or Airbnbs. We can get more great places for a lower cost.” Instead of going to San Francisco as their event location, they go with Tucson and they end up with a wicked Four Seasons resort or a Ritz-Carlton or killer Airbnbs, but they’re doing it for half the price. Where do you run yours? 

The last years have been out of Hagerstown, Maryland, which is where our corporate headquarters is and that’s a convenience of the space. We’re going to do one there and another one potentially in Phoenix where our other location is. It is interesting getting out of there. Our challenge is since we are the IT hosting background. If we want to include everyone, it has to be at one of our offices because we still have to cover shifts and make sure we’re taking care of our customers.

SIC 26 | Ongoing Operations

Ongoing Operations: The threat of getting out of alignment when you work virtually is much higher because you’re not seeing that person.


Is it true that you turned down the original COO role, that you didn’t want it? 

We discussed this. I’ve been in the position about a year and the conversations started. It was like, “If you want to move into the COO role, you have to accomplish XYZ.” We let that conversation go on for about a year. The CEO was waiting on me the whole time to say, “Yes, I’m ready to tackle this.” We started the conversations about a year in advance and he put some goals in front of me that I needed to tackle to get the role. We did that and it was good that I didn’t take the role a year prior. We worked through that process for about a year and then he said, “Yeah, you’re ready. Let’s do this.”

Tell me about what it’s like working with a remote CEO because you and he are not in the same city. 

We have to make the time. We have group meetings every week, but just us one-on-one. It’s a halfway change. The best thing we’ve done is once a quarter, we meet up or I usually fly to his house in Southern Oregon and we spend a solid day-and-a-half to two days talking strategy. What are the challenges? What are the obstacles, barriers we’re both working through? Take a full uninterrupted day-and-a-half to two days and align where we are and where we’re going. That’s the best thing we’ve done. I’ve suggested that to a few other COOs that are not in the same city as their CEO. We both have to detach and make that an effort. Invest in our relationship but keep us aligned. The threat of getting out of alignment when you work virtually is much higher because you’re not seeing that person. You can avoid them for weeks or months if you want to. We always have to be communicating because we’re going to be in person 60 days from now or 90 days from now.

You’ve also touched on something that’s even critical if you’re working in the same office, which is getting offsite for a day every quarter to get completely aligned. You can often get off track even though you’re working right beside each other. Sometimes the business gets busy and we go through the motions and we don’t have the bigger discussions or confronting the bigger issues or talk through some of the people stuff or strategy. It’s important to do that regardless of where you are, but for sure when you’re remote. 

The biggest strategic changes come with one to two weeks following one of those. We align and there are no questions about the next steps and we start executing. It’s powerful. You could look at work performance throughout the company lining up to when we have those off sites.

Every COO is in a completely different wheelhouse. They have different functional areas that fall underneath them. In some cases, IT reports to the CEO and in my case at 1-800-GOT-JUNK?, it didn’t. IT reported to Brian the CEO. What areas of the business report to you? Which ones report to Kirk?

Reporting to me is about 30 of our 50 employees and that’s our entire support organization as well as our implementation organization. Our CEO oversees sales and accounting. The CTO, which reports to our CEO, that’s the R&D and the platform development of a team. About five people are developing our new products and solutions and responsible for the architecture of our entire platform.

His unique ability is getting things to 80%. He’s a high quick start. If he’s able to get things to 80% and pass them off to you, how do you take those handoffs? How does he pass things to you that you’re up to speed? High quick starts entrepreneurs do a lot of the work in our head and then we pass it off to somebody in a twelve-second delegation. How do you get the rest of the story before you accept the handoff and run with it?

I intentionally slow it down. He’ll take an idea and launch it 80%. We had our meeting in Scottsdale and I had eighteen ideas that he felt he’d already got to 80%. I said, “Let’s slow this down a little bit. Let’s prioritize. What does success look like here? Can we focus on three or four of them?” I ask a lot of questions and make sure I understand not how it got there, but where he wants to be going and can fill in the dots. I do force a lot of prioritization exercises. I don’t care about a thought process that he took to get there. I want to understand where he wanted it to go. Instead of arguing about the process he took to get there, but how do I help him? He’s at letter X or Y, how do I get him to Z? That’s how I approach it.

We talked a little bit about the tool called the decision filter where you get what the ideal outcome looks like, what the ROI is and how much time and money and people inputs we want to put into the project. If he’s now handed back to you eighteen ideas that he’s ready to run with, for you it’s like, “How do we prioritize that? We can’t do all eighteen this year, let alone this quarter.” Let’s say we narrowed it down to ten. In what order? Some of them are going to be a higher impact on the business or will some of them create momentum? How do you start to filter those projects out and put prioritization into them?

We use the decision filter. I don’t think he realized that’s the tool I’ve been using until we did one together in Scottsdale. We went through a few ideas, but it’s shifted our way of how we prioritize. We first look at what’s the reward and what’s the actual potential downside. We organize everything by what’s the high reward and we look at what are the resources it takes to do it. We go off the criteria that are exactly in the decision filter. We focus on what does it take to do it and we get a relative value out of those things. We have been using that constantly to slow down and make sure, “Are we going to get what we want out of this idea?” A lot of times, you have an idea and you start putting it on paper. It was a great idea until you put it on paper. We go through the exact decision filter that you taught us when I joined the COO Alliance.

Once you start flushing it all out and looking at it on paper, sometimes that idea becomes, “Maybe it wasn’t great after all. Maybe it’s a big hairy one.” Maybe it’s a great idea, but it involves 1,000 hours or a whole bunch of people that we don’t necessarily want to throw the bandwidth at. You have specifically chosen US-based contractors and US-based freelancers versus international. Why is that? Walk us through your thought process on that.

It’s something we are exploring heavily. We are in a highly regulated space. Credit unions throw up to the NCUA, which is the same as the FDIC. The regulations for using offshore resources are much more stringent. We’ve seen in our industry it is starting to happen, especially for a lot of procedural driven work. It’s something we’re looking at. The vetting and controls that have to be in place for us are much more advanced. Although it is a huge efficiency gain and cost savings, which might cost another company $10,000 would cost us $20,000. You have to have this control framework, due diligence and vetting process that goes into it, which also includes visiting the location of where that stuff.

How do you stay entrepreneurial in such a regulated environment?

SIC 26 | Ongoing Operations

Ongoing Operations: Your employees are your best asset. If you are hiring people that are better than yourself, you got to work with them and don’t limit them to your way of thinking.


It’s less about credit unions and the whole banking industry. If you look at technology as a whole, you’ll see the financial services, banking industry usually be a few to several years behind it. Entrepreneurial for us is changing the way credit unions think. The blessing is we get to look at technology, what was successful, what panned out, what is super applicable to our vertical. The good news for them is they rarely try a solution that fails. By the time the industry is even accepting the concept of the solution, it’s already been vetted out. We’re able to get the best solutions and take them to market relatively quickly because it is vetted technology. You’re entrepreneurial for the space that we’re in and we try to push our customers quickly to get to those best standards. It’s overcoming objections because financial institutions holistically don’t like change. Change equals risk. You have to convince them to take risks and look at what adopting this platform can do to your members. They want to give the best services to their membership. Taking that angle, they say, “Look what I can do. If I get to go with this online banking or mobile platform, I can do this much more for my members.” It’s always approached from that, but you have to convince them to make the change, which to them is to take the risk.

We used to use the adage to sell them and don’t tell them. That sounds like that’s what you’re doing as well. You sell them in that direction and then move them there slowly. Leave us with one final parting thought on leadership. Is there anything that you’ve learned over the years that has helped you succeed in your role as a COO that maybe you wish you’d learned earlier on or one that you’d like to share with anybody?

The biggest things for me is knowing your weak spots and understanding the people around you. Those are the biggest changes I’ve made in the last few years. As a leader, I wanted people to do things my way with little care of thought as to how other people perceive that or how that affected their personalities. I’ve invested a lot of time in understanding the people around me, how they operate and how the best way to work with them is. I’ve gone from my way is the only way or the highway to more of an individualized leadership or management where it’s like, “I know this is your personality type and this is a plan that’s going to make you successful that gets us to alignment.” Instead of saying, “There’s one way to do things.” That’s not the case. That’s the change that I’ve been focused on the last couple of years. It’s paying dividends for me and something I take seriously. Your employees are your best asset. If you are hiring people that are better than yourself, you got to work with them and don’t limit them to your way of thinking.

The reality is if you are hiring people better than yourself off and they have better ideas, enforcing it to do it the way we want to do it isn’t going to grow us. It also gets more empowerment for them or also more excitement into their roles when they’re involved in the process and their ideas are getting put in place as well. Jonathan Derby, the COO for Ongoing Operations. Thanks very much for sharing with us. I appreciate the time. I’m looking forward to seeing you at one of our upcoming COO Alliance events as well. I appreciate it. Take care.

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About Jonathan Derby

SIC 26 | Ongoing OperationsA key member of the executive team, Jonathan is a solution-oriented leader with excellent communication skills that excels at managing large-scale projects, collaborating with cross-functional teams, driving process development, deploying technology to create successful solutions, and building lasting client/team relationships.

Jonathan has nearly 15 years of experience in technical project and program management within the Credit Union industry. In Jonathan’s previous role he worked as a Vice President at Morgan Stanley in NYC where he led the Corporate Equity Solutions Technology unit through the transition onto the Morgan Stanley platform. Jonathan’s career started with NIH Federal Credit Union as a Systems Analyst, where he acted as a Conversion Team lead, responsible for the migration of the Credit Union’s core financial platform.

Jonathan graduated from Clemson University with a BA in Finance. Jonathan and his wife have two boys that keep his life busy.


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