Ep. 88 – The Importance And Impact Of Teamwork With Cybba COO, Terri Mock

No matter what industry you’re in, running your company with the correct culture and values will always be an integral factor. Terri Mock, the COO of Cybba and a veteran C-level technology executive, joins Cameron Herold in this episode to share their success in rapidly growing their company. Terri talks about different strategies on how to provide continuous growth for your team and keeping them happy to provide your service. She also goes into the inner workings of her company as she talks about the interrelationship of the different teams that run the business. Learn and understand the importance and impact of teamwork, even during a time when individuality is much celebrated.


Connect with Cameron: Website | LinkedIn

Get Cameron’s latest book: The Second in Command – Unleash the Power of Your COO

Subscribe to our YouTube channel – Second in Command Podcast on YouTube

Get Cameron’s online course – Invest In Your Leaders

Terri Mock the Chief Operating Officer of Cybba. She’s a veteran C-level technology executive, CMO, COO, CRO with achievements in delivering revenue growth, driving go to the market and scaling operations from startups to $450 million global companies. She brings domain expertise in SaaS performance marketing and digital advertising, enterprise software and eCommerce. One of the many achievements in her career is heading up strategic branding campaigns at three companies and launching four SaaS products at two companies. She has an MBA from the MIT Sloan and carries a unique ability to champion compelling business benefits of technology. Terri, welcome to the show.

It’s great to be here. Thanks, Cameron.

You were clearly one of the smart bunch. I was never qualified. I don’t think I could have gotten MIT in the correct order to put it on an application form, let alone get into that program. Congratulations, that’s certainly one of the top business programs in the world.

Thanks, but there are smart people everywhere.

Tell me about what it was that you pulled from Sloan. Obviously, it’s a prestigious program that creates a strong group that comes out of there. Any solid skills that you bring that you still leverage now?

The first thing is to be intellectually curious. In terms of anything that anyone would do, it’s always having that insatiable desire to keep learning and growing personally with an organization. That was definitely instilled. We’re always trying to solve meaningful problems. That’s what we do every day. The second thing is understanding the value of teamwork. You could be very good at one skill set. You could have a finance person who’s amazing in that or an engineer who’s good at solving problems. I do believe that the sum is better than all its parts. The value of being a team and doing more together than you would on your own type was drilled in, in terms of all the projects that you needed work.

That’s such a huge part of the MBA programs, but it’s such a disappointing part of the regular school system. In the grade school and high school system, you need to be the smartest person in the room instead of collaborating and working together as a team. It’s a huge point.

It’s collaborating together that really makes a difference.

You had people that were from all over the world and all different disciplines that were in the program as well, correct?

Yes. In fact, I was in a special cohort. They called it the Leaders for Global Operations. We pretty much survived two years of intensity together. It was a dual degree, Masters of engineering and also an MBA within the two-year timeframe. We got to know each other very well and it was a pretty intense but especial experience.

Why don’t you tell us about the brand that you’re running? Give us a little bit of background for those who haven’t heard of it.

Cybba is a digital marketing advertising tech company. We work with brands who want to get the word out in terms of driving awareness of who they are and what their value proposition is. Also, in terms of delivering the end results. Whether it’s getting you to shop online to purchase that goods or whether it’s an educational institution trying to fill up the pipeline of new applicants and students or any number of conversion points. It’s looking at the customer journey online, supporting these brands in terms of drawing in and engaging the right consumers and then driving them towards a clear value of converting or purchasing.

It’s a broad space but pretty specialized as well in the marketing niche. What’s the org chart and the leadership team look like there?

We have two amazing founders, who are serial entrepreneurs. They came into this space from different backgrounds and definitely built up a company based on seeing the opportunity in the digital space. They’re trying to have a different and unique perspective of driving that customer experience and that journey that everyone takes online and offline.

The rest of the team makeup, do you report to the two founders? Who else is working on your level?

We’re about 65 people. We grew within two years. There’s a CEO, and a president and then C-level executive, the COO. We have a vice president and also directors who are our mid-level managers who support and grow the teams. We have a happy young group of entrepreneurs that we work with. A lot of them are homegrown and we develop their skillsets. They grow with us as an organization during this time.

SIC 88 | Teamwork

Teamwork: If you can take a new grad and give them the right skillsets, disciplines, and core abilities, they’re going to be really good as they continue to learn and grow.


The mid and senior-level team. I’m curious because one of the things you talked about earlier was the insatiable curiosity for growth and continuing to grow yourself. What are you focusing on with your direct reports and with the mid-level team or senior team? How are you helping to grow them and what are you focusing their growth on?

There’s so much to do in a startup. You can be torn apart in 5,000 different directions all at once it’s in terms of what is urgent. All of us, myself included, we need to focus on what’s truly important, not only what’s urgent. That’s the balance that we all need to learn and focus on, day-in and day-out. Instead of always fighting fires, trying to figure out what the root causes of some of these problems and issues are. You try and resolve them ahead of time. There are times where you can’t do that and you need to put out that fire and do a debrief afterwards. A lot of it is focusing clearly on one or 2 or 3 strategic things you need to do and driving hard and pushing them and charging towards that goal. That’s a concept that we work on in terms of amplification. Everyone can buy into that same concept about vision and where we’re heading and that is all amplified throughout the organization.

How do you get everyone to buy into that common vision or how do you get a common vision into your company?

For us, as we have grown, it’s a vision that needs to be adapted and changed. We’re thinking about branding, once again, in terms of where we want to hit for the next 2, 3, 4 years. It’s a constant process of seeing what the value is in the marketplace, where the market is going, what the needs are and then adapting towards those needs. Putting in place on the development roadmap or the customer service that they need, in order to take you there. It’s a combination of the technology behind what we offer, and the talent and the team that provides the services to support that.

Take us back in your career a little bit. You’ve graduated from the Sloan School of Business. You’re going into some of your first professional roles. Walk us through what a couple of those were and what some of your big learning points were that made you the COO that you are now.

I was fortunate that even as a student, I’ve worked at my professor’s startup at MIT and I was amongst the first 30 employees in his company called Aspen Technology. It is an engineering software company. It’s currently a leader in the process industry. It fit well with my undergrad degree. He was my professor. As a young student and a new grad coming out of school, it was a great experience because there was tremendous growth during that time and I was also growing professionally. To see the company grow from a startup to a $250 million company, pre-IPO. That was a great experience for me. I remember when everyone was gathered in a conference room and our CEO got up and said, “We’re going to be a $500 million company.” We all looked at him saying like, “What is he talking about?” It was that vision of how we can do something special that he drove home that resonated with all of us.

That’s what gets people excited because more people aren’t going to be that excited to join a company based on what it looks like now. They’re going to join you based on what you’re building and what they can contribute towards that, right?

Yeah. It’s a vision of where you want to head but then you could see that we were making concrete steps to get there. For example, I was working on consulting projects that we knew we were using state of the art new technology. We were hiring like the best people doing a PhD coming out of the best programs and teachers in a doctoral thesis would be implemented into the software we were developing. We were publishing papers and it’s a very technical product. We had the best technical people. It’s a close-knit community within that space and we were clearly seen as leaders as we were developing and growing that company.

Think back to when you’re starting Cybba. When you guys were growing it over the years, you had to go from 0 to 65 quite quickly. What is it you’re doing to attract and recruit these senior people into such a small startup company? What have you done to be able to do that successfully?

A lot of our managers are homegrown. We do look for leaders from outside but what we found to be most effective were to keep, retain, and grow talents from within. In terms of our director of sales and director of account management, they all started as account managers or EDRs. To progressively give them a challenge and to see them take on new challenges, that’s been rewarding. For them to pass it on to others on their teams, that’s been working for us. We found that to be the best trajectory for us. It was set in the example that if you come in, we care about you.

In fact, we have a program where we would hire someone for the position, a lot of them straight out of school. Honestly, when you’re straight out of school in the first job, you don’t really know what you want, but we put them in a role that they apply for. We evaluate after six months or a year. They have complete flexibility to move within the organization. We’ve had delay analysts become account managers and technical people becoming analysts. It’s something that we allow people to explore and figure out where their home and passion are and we let them make that transition. It’s worked out for us.

It sounds like you’re identifying the people that are able to take on the core projects and new responsibilities and excel at them. Is that how you’re identifying the next leaders?

Yes, that’s definitely one of our approaches. We’re at a point where we’re looking to bring in a few leaders from outside with other additional experiences that can add to the culture, the level of expertise that we have. It’s a blending and mixing of knowing how to get in an opportunity within the people that have been loyal and have grown within the organization and then bringing in the right mix of people that’s also 110% committed to the same goals. Having them slot right in giving them the same opportunity. That’s a challenge that we’re working with in making sure that we’re recruiting with an identification process by bringing in the right people.

You’re going through that process of identifying the key leaders and moving them into their new roles. What are you doing to grow their skills? What skills are you working with them on in the early stages of them going into these new roles?

We have a pretty refined onboarding process. We didn’t initially, but we put quite a bit of work into it where we’re building playbooks for the sales team, so they know what to expect. Usually, it starts with a BDR straight out of school and there’s an awful lot of mentoring and coaching that happens. Because if you can take a new grad and give them the right skillsets, disciplines and core abilities, he’s going to be good as he continues to learn and grow. Our Director of Sales spoke about how he’s going to put even more effort into coaching and making sure his team is well equipped. He’s there to answer the question and support them in their growth. That’s why they want to stay. They know that we care about them and want them to have an opportunity to grow and we’re part of their success.

It seems like that’s something that Gen Y more than any other cohort is looking for right now as well as growth in their roles. It’s a company that cares about their growth. Is that what you’re finding?

That’s for sure. They want different experiences, so the opportunity to move from one part of the company to another when they find themselves. That’ something they appreciate too. The fact that you care about them as a person. That you’re attracting them and coaching them along and that you give them freedom of exploration to find their passion. That makes all the difference.

SIC 88 | Teamwork

Teamwork: The digital space is so dynamic. There’s new products, new ways, and approaches that are being built every day.


You mentioned the playbooks that you’re putting in place for all the different roles or responsibilities that they have. What software tools are you using to develop those playbooks that they then work from?

We’re early on in terms of automating them or putting them in the system. It’s a document or binder that we have, where we put in all the key aspects. For example, for BDR, what are the key segments? What our value proposition is? What verticals are we in? How to prospect? What’s the personas of the people we’re after? It’s giving them in one place, all the tools that they need to get going. We’ve been building it up as we’ve gone along so that it’s not like we are reinventing the wheel each time. As we get better at it, we’ll systematize a lot more. What we found is this not just finding a fancy platform to put it in, but having that coach right next to them. Walking through and like, “Here’s the playbook,” explaining it. On a day to day, week to week basis, following up with them. Asking them, “Are you following through? Do you have any questions? I’m jumping on your call.” We actually record the sales calls that they have and then we go back and review them what was good, what was bad and how could you improve for the next time. That’s the kind of coaching that combined with the playbook, gives them a heads up.

I agree that there’s no point in dropping it into the perfect software until you have the right system that you’re actually following or the right process in place first and training around it. After that, you can migrate it into something like Process Street, SweetProcess or something else. Walk us back to the two cofounders. You’ve got two cofounders and they’re both still involved in the company. How do you get those two on the same page? How do you sync up with both of them?

I’m responsible for the operations part of the business, which entails marketing, design and tech services, analytics and operations. Our president, who’s one of the cofounders, he’s in charge of the commercial side, which is the sales and account management. We did this at the beginning of the year because it allowed us to focus on operations or commercial. That’s helped us to know our two roles. Working with both of them, they’re business partners and they’ve been business partners for a while. They certainly have a cadence of a constant back and forth and it’s also presenting to them with some data and facts. Like what is working? What are some suggestions on what we can do better? Talking together in terms of what our ongoing strategy should be. It’s providing the support and the facts and data to say. This is where we should head. Maybe it’s my background, but I tend to be much more analytical in my approach.

You think about the plan, and they’re thinking about the vision and then you just get both of those in sync, correct?


How about getting the leadership team working together? What meeting rhythms do you have in place for the leadership team?

One thing is we’re a very transparent organization, so three times a week at the end of the day, we call it the company meeting. We all come together for 15 minutes to 30 minutes to talk through the highlights of the day. We count the new accounts that have launched. Things to get excited about. The events that people have gone to. We have required reading so we could discuss a little bit about that. It’s a way for all of us to be aligned in terms of key things that are happening and keep everyone in good communication. You might think that’s an awful lot of time, but it’s a real commitment for all of us to be in sync and to hear across the board, what’s happening in the organization.

Going back into some of your earlier roles and the senior roles that you’ve done, what skills do you think that you have, that makes you a strong COO?

In the SMB space, I have worked for the big size companies, but I would say the characteristic is resiliency. There are highs and there are lows, but I don’t get too high and I don’t get too low. The reason is that there are lots of things to celebrate and we do celebrate it. There are a lot of times where you can just be down where you’re at or how you could be growing more or doing better as a company. Keeping focused and staying the course and being resilient through those highs and lows. Actually, in the end, you’ll get there like you’re still focused on what’s important and where you want to hit. That’s the aspect of it.

It’s critical. Your resiliency, problem solving, and analytical skills are all solid. How about some of the challenges you faced over the years in your role as COO? What challenges have you had to overcome?

As we were forming, we needed to reach out to our clients into a new technology platform that would give us a heads up for future development. We had a certain timeframe of making that transition. However, because of the competitive situation and so forth, that timeframe was short-lived into something that you could also almost say was impossible to do. I think when you give a team a challenge like, “We need you to stand up and get this done,” and you put that goal before them, that’s when you can tell whether that team is resilient enough to get through it.

We were able to get close to 600 customers into this new platform within a span of 1/6 of the time that we were expecting. Going through that experience, we were up at night, every weekend. In the end, we were seeing the light and we’re pretty much amazed like, “We did do this,” and we did it together because it wasn’t just one person getting it done, but they charged in and owned up to it. Our motto is like, “Whatever it takes, we’re going to get this done because it’s what’s important for the company or it’s important for our clients.” That boundless the trust that we built because of that and that’s going to enable us to do much more greater things.

It sounds like you’ve got the company grounded around core values and behaviors. Is that stuff that you bring into your interview process, as well as that some of the things you’re looking for when you’re recruiting and hiring?

It is true that we need to find the right people for your culture and is bought into who you are and where you’re going. We found this out more and more, as we’ve done more recruiting and growing our team. I would say that’s a key criterion. They have to have the competencies to do their job, but beyond that, it truly is their fit into the company. We want them to make this their home, have friends here and feel like they’re being valued and adding to what we’re doing. All that is important to retain that talent.

Is here a physical space? Are you all running out of one physical office space? Are you running out of multiple offices or do you have remote people as well?

Our headquarters are in Boston, we have an office in Phoenix, in Toronto and Brazil. The heart of the company is in Boston, but we never forget our remote offices, too. I’m in charge of the Phoenix office as an example. That’s a great team that we have out there and we have a good relationship with them. They’ve done great work for us. Each office has a similar culture that there’s some uniqueness to each one, but overall, we have a great culture.

SIC 88 | Teamwork

Teamwork: Developing a culture where people want to be together and work together can smoothen the path if you’re trying to solve client issue.


It’s great. I run some events in Phoenix called the COO Alliance. We have a network only for second in commands and we have three events per year there. The Phoenix business farm is amazing right now and the technology sector in Phoenix has been growing. It must be a good recruiting market for you?

Yeah. We’re hiring so we want to grow that.

How did the Brazil office all of a sudden evolve? Was that when you found a couple of key people or was it a market you were moving into?

Yeah, it was finding a couple of key people. Network is everything as you know and then finding the key people to get that office going was key. As in everything, people make the difference, whether you’re going to be successful.

It’s a huge component. We’re also starting to face a bit of an opportunity/necessity to start hiring people remotely. It’s hard to find people who want to work for a specific company within a specific skill set and happened to live within 25 minutes so they can have a life. Being remote is part of that. In terms of your future growth, you said that you’re always trying to stay curious and stay driven in learning. What are you focusing on for your skillset right now for learning?

Definitely, I want to keep on top of all the things that are happening in the industry. The digital space is so dynamic. There are new products, new ways and approaches that are being built every day. There are new platforms that we evaluate and add to our tech stack. Keeping on top of the latest into technology, and then consumer trends. Their experiences are quite different because of the advent of mobile. That’s changed a lot of what we do towards your servicing brands. There’s also a lot going on in terms of making things local and personalized to each person. The technology is followed in terms of geofencing. If you look at how we work with brands to reach consumers, all those consumer trends as they impact how we service them, and how we reach to them on behalf of brands.

Stay on top of technology is definitely one aspect of it. Another aspect is continuing to know how to motivate, provide direction leadership to teams. How to continue to mentor and grow people within the organization. Setting up the type of environment as we go and try to be more scalable. We do need more processes and what processes that would be balanced between owners that have more tasks to do, versus something valuable. Every company goes to a stage where you can’t just wing it, but you don’t want layers and layers of paperwork or hierarchy. Having a very good balance between that is something we were looking at.

For your skills now for what you’re seeing, you got the trends in the digital space, new platforms to be on top of and the new trends with the consumer. How about on the soft skills side? The specific things that you’re working on for yourself in terms of managing, leading and growing people? What are you working on?

It’s definitely understanding the Millennials and the Gen Ys that are entering the marketplace. They’re different. The way they look at careers is a little bit different. I actually think they’re more well-balanced, which is nice. They seem to care more about social good. Having a work experience that meets their needs is actually quite important in terms of retention and giving them a sense of value. We have a culture committee and we have parties. It’s doing those small things that get us together as a body.

I definitely have been seeing a lot of those changes happening as well. Are you seeing anything with the Baby Boomer workforce? Do you have many of the 55 to 70-year-olds working with you or are you pretty much a Gen Y, Gen X culture?

We’re never close to anyone because of that, but our makeup is much more Gen X and Gen Y currently in our company.

It feels like that the only way we’re going to get the whole Gen Y to get adapted into the workplace is to get them to start to work with Gen X and with the Baby Boomers. It’s a little bit of collaborating and teaching them teamwork, but how are you finding that working? They come in with great ideas. They drive and have great balance. Are they able to collaborate with teams?

Yeah. One of the key things about culture is we actually like each other. We honestly do like each other. I have people on various teams going on vacation together and one time, I asked them, “Don’t you see each other enough? Why do you even go on vacation together?” They just liked each other and they wanted to. Developing a culture where people want to be together and work together, it smooths the path if you’re trying to solve client issues. Knowing that you can work with someone on different teams from different perspectives and yet you still like them and they might have different perspectives. It takes away as the pointing fingers approach, but more like, “Let’s work together and solve the issue. I know that we’re all in it together and I actually like you.”

It’s the key because that attracts other people into the group and it gets rid of people that don’t like that, which is you don’t want them anyway. Terri, if you were to go back to your 22 or 24-year-old self, you’re graduating from Sloan, what word of advice would you give yourself back then that you know to be true today, but you didn’t know when you were just starting out in your career?

When I was heading back to business school, I asked my direct manager like, “What do you pick up the business school? What’s one thing?” He said, “Their strategy, which are high-level things that you need to think about at a high level that sets the direction of what you’re doing. There are also tactics, like, ‘How do you get it done and how do you actually provide and drive results to figure out how to balance doing things on a strategic level and do things on a tactical level in order to execute.’” In any given week, there are times where I might be too focused on one or the other and then I have to reset at the end of each week. Before I start the next week, “What is the balance between strategy and tactics that are needed, overall for myself or the company, for our clients?” It’s a constant evaluation process that I can improve. We can all improve on, but that’s definitely something that you keep working on.

I love the balance that you bring into your roles. Terri Mock, the COO for Cybba. Thanks very much for sharing with us. I appreciate it.

Thank you.

Important Links:

About Terri Mock

SIC 88 | TeamworkTerri is a veteran C-level technology executive (CMO, COO, CRO) with achievements in delivering revenue growth, driving go-to-market, and scaling operations from startups to $450 million global companies. 

Terri brings domain expertise in SaaS, performance marketing, digital advertising, enterprise software, and eCommerce. One of the many achievements in her career is heading up strategic branding campaigns at 3 companies and launching 4 SaaS products at 2 companies.

Terri has an MBA from MIT Sloan and carries a unique ability to champion compelling business benefits of technology.


Please Fill The Form Below To Apply: