Ep. 55 – Maropost COO & CFO, Joseph Schirripa

Change is inevitable in all aspects of a business. When change does happen, how do you stay focused and aligned with your company vision? More importantly, how does a COO continue to build solid friendship and trust with the CEO? Let’s get the answers straight from Maropost COO & CFO, Joseph Schirripa. Maropost is a unified customer engagement platform designed to provide a single solution for all areas of business including marketing, commerce, service, clienteling, referral, and more. Prior to officially joining Maropost in 2017, Joseph consulted with the company as an investment banker for three years. Since joining Maropost, he has proven himself to be more than a standard CFO. Continually taking on projects beyond his department, the former investment banker was quickly recognized as a cross-departmental leader – while still managing to streamline the company’s financial systems for future growth. He holds both a B.Comm and MBA from the University of Toronto’s Rotman School of Management.


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Maropost COO & CFO, Joseph Schirripa

Joseph Schirripa is both the Chief Operating Officer and Chief Financial Officer of Maropost, a unified customer engagement platform designed to provide a single solution for all areas of business including marketing, commerce, service, clientele, referral and more. Prior to officially joining Maropost in 2017, he consulted with the company as an investment banker for three years. Since joining Maropost, Joseph has proven himself to be more than a standard CFO. Continually taking on projects beyond his department, the former investment banker was quickly recognized as a cross-departmental leader while still managing to streamline the company’s financial systems for future growth. He holds both a Bachelor of Commerce degree and an MBA from University of Toronto’s Rotman School of Management. Joseph, thanks for joining us.

Thank you for having me. It’s an honor.

I was talking to someone about the COO role and we were talking about a Harvard Business Review article. It was called The Misunderstood Role of the Chief Operating Officer. It’s one of those roles that in some organization, people cover very different areas like you’ve got finance reporting to you. I was talking to the CEO and that’s the last area he could ever have reported to him. How is it for you to make the transition from being the investment banking coming into the operations side of the business? How did you do that?

In investment banking, I followed and worked with technology companies in North America. I was a courier investment banker, so I’ve seen a lot of stories that never jumped in and delved into what’s behind the numbers. It’s been very exciting to do that and to be able to have the opportunity to do that. I have read that article and it’s interesting. The article goes into a good common characterization of the different types that typically companies see. What’s resonated with us is a book called Rocket Fuel by Gino Wickman and Mark C. Winters. That visionary integrator role and the difference between what needs to be put in place in order to put traction to an idea, that resonated with us. We modelled the whole business around that. Definitely lots of ways to think about it.

I was sitting with Mark and Gino at a conference called the Abundance 360, I’ve done it for years. We’re both in the program called Strategic Coach together and then we all attended Abundance 360 so we’re chatting while we are there. They did a great job.

It’s changed the way we do business here, it’s great.

You guys use traction internally then?

It’s not followed religiously. What we’ve done, and that’s one that we found is the key, is there’s no real one perfect strategy especially with this type of relationship in the company. We’ve been able to take maybe the best parts or the parts that resonate with the company and our relationship most. We use a lot of the templates for our executive team meetings from Rocket Fuel. We resonated with that type of radical candor. It’s identifying issues, discussing them, solving them and having those passionate, exhausting discussion, but we come out of them with faster decisions. One thing I’ve noticed is the investment making world is fast paced. In a fast-growing company, decisions can hold up the entire resource allocation of the company. How do we get the decisions faster and pivot sale fast, learn fast, and keep moving forward?

You mentioned the whole radical candor and fast decisions. That’s something that I think so many companies miss the point on. Just because you’re debating and arguing for something doesn’t mean you don’t like each other. It means you’re debating something you’re both passionately or many of you are passionately engaged in. That’s exactly what you’re looking for. The key is to keep the trust level high. How do you guys keep the trust level high between you and the CEO first, then also between you and the rest of the management team?

My relationship with Ross, the CEO, is one of friendship and mutual respect. Clearly defining our roles and what each set forth on and is accountable for is important. When you have that commitment to telling the truth no matter how much it could be painful in the short term and that we’re all on the same collectives, rock it together, that reassurance helps a lot. What resonated most with our leadership team is the transparency. One thing we do well here is the CEO and I, our discussions are our discussions. Things that happen between us are sheltered there and they stay there. We disseminate and communicate in an aligned fashion to the company. That’s very important. Having different conversations, solidarity and consistency help build that trust. It’s something that continuously needs to happen over time and it’s nurtured.

That’s a huge one that you uncovered and I think that so many people, maybe we haven’t touched, talked about it enough yet. That’s why I believe CEO, COO role is so critical. It almost has to be two parents raising a family. You can’t separate the two parents from each other. They can argue, debate and discuss but in front of the children, they have to remain that unified force. Let’s say that you and Ross are passionately disagreeing on something. Are you doing it with the rest of the team around or do you often try to have those discussions and debates privately?

Never with the other team around. We’ll be in a leadership team meeting for example, and a topic will come up that maybe the CEO and I haven’t seen eye-to-eye on just yet or we haven’t gotten to the bottom of what our past forward is on that specific issue. We’ll defer it. The teams should never see us misaligned. We hold through that and we have definitely deep passionate discussions afterwards. We seem to have always, over the course of our relationship and I’ve known Ross for much longer, a good structure of coming to agreement. Even if it’s agree to disagree. I like Jeff Bezos’ term, “Disagree and commit where we sometimes want to defer but be behind that decision fully.” Not have revisit it later on and do the whole, “I told you so.” It’s discipline. It’s hard because human nature is to maybe not have that type of reaction. It’s definitely time-consuming and consumes your thoughts. It’s having that discipline.

You mentioned something about when you got involved as the COO and you started to see the business behind the numbers. What did you start to see that you never saw as an investment banker? What do you think investment bankers are missing that when you got in there, you saw something different?

Coming through the investment banking ranks, you can tell what’s a good management team. There’s an investment piece and you understand good market, good financials, strong revenue growth, path to profitability, when you think about a tech company at some point or depending on what phase of their life cycle they’re in, good management team and so on. It’s that management team and the team that you build. I almost got immersed into it and felt that what’s behind the numbers is people. When I came into Maropost, we were growing so fast and decisions were made to bring people on that just were filling hole.

It’s like, “You know how to do this? You’ve done it before? I need you in marketing.” “You sound great, let’s put you in this role.” Everyone had the aptitude but maybe not the right fit for our company. I’ve been able to notice how when you put a group of collective people together with a shared value set and the ability to learn, to have the aptitude. There are a lot of great things that can happen and so one of my first focus was bringing in and getting sharp on our hiring. That doesn’t mean we want hiring better people. It meant we were focusing on who fits well and who had the Maropost DNA in them.

SIC 55 | Focus To Achieve Change

Focus To Achieve Change: Never let the entire team see the CEO and COO misaligned.


That was where I was hoping you were going to go, was into the people side. When you sit and look at the numbers or the spreadsheet or business plan, it’s easy to sit there and expect certain things to happen. If you pull these two levers, X plus Y equal Z, not necessarily when there are people involved. That is the complexity of the business too. Tell us very quickly about Maropost. What is Maropost for any readers who don’t know what you guys do?

When we say who we are, I always default to talking about who we were and how we’ve evolved. Maropost began as an email service provider and over time, we’ve evolved. When I joined, we’re focused on cross channel marketing automation and building out. Not just email but social, mobile and other types of communication channels that marketers typically would use. We’ve evolved into a customer engagement platform for B2C companies and being able to simplify customer engagement. We’re doing that in marketing and commerce. The natural evolution from the cross-channel marketing automation tool and to adding the other customer engagement channel, which is transaction and the ability to have a platform that can manage and give that 360-degree view of a customer, all in one platform. Companies like Salesforce, Oracle, Adobe have been acquiring their way to that 360-degree view and it’s our true belief that building that platform from the ground up is going to be our approach to that market.

You mentioned some of the tools related to customer engagements, so you see a lot of the data and understand customers from a pretty wide breadth of different companies that are your clients. What do you think that companies are missing on the customer engagement side?

Sometimes it’s not building those many different touch points. Communication in general has started as one-to-one conversations. There was a time where communication and engagement were one message to many. Where we are now is being able to have one-to-one conversation, that personalized experience at scale. Understanding the customer a little bit better and enabling someone to be able to have those multiple different communication points and conversations with customers across different channels is super important. Companies now need to reach multiple different channels and it’s evolving at such a rapid pace that being able to be current on what’s resonating and what’s not is important. Getting that data back on where our conversations and our touch points working well and being able to act on that, it’s hard to do. There’s tax text that are bloated and you’ve got multiple information across different solution to run your business. Trying to have that all in one spot to get one view is difficult to do, but it’s a problem that we’re trying to crack. I think we’re doing a great job with it.

Do you think we’re going to lose the one-to-one connection with our customers when we start putting in place things with automation and artificial intelligence to have those parts of this system automated more? Are we going to lose that connection or do you think that AI can deliver as well as a human can?

It depends on how you use it. That’s probably a good consideration. However, what AI and machine learning should be able to do is help you better engage and have more meaningful conversations with your customers. People are craving for that personalization and human touch. If you can use technology to enable those conversations better, that’s where success will most likely come from. It’s not trying to replace the human touch and the human personalized conversations. It’s more so using technology to enable more conversation, more meaningful ones as well.

You talked a little bit about your role with Ross. Walk us through how you get on the same page with him, what his vision is for the company. How do you keep him on the same page with you, your vision or your plans to make the vision come true? How do you stay on the same page?

It’s definitely a well-documented process. Once a week, we’d have our one-on-one that’s pretty structured, that focuses around what are our top three priorities this week, each of us, and what were they last week. We hold each other accountable to staying focused. That’s one thing that our weekly one-on-ones help to do, is keep each other focused because there’s so much noise. There are so many things we can be doing and it’s in rigorously focus on the top three priorities in any point in time, which helps us do the things that move the needle. Our one-on-ones facilitate that. We have consistent touch points. We’re on WhatsApp. Our internal messaging system we use for our company is Teams. We’re always in touch, but we like this and have a video chat or in person, once a week. We have monthly check-ins which are usually offsite, similar to the Rocket Fuel style.

Offsite meeting is where we catch up personal life as well. We’re very much friends and involved in each other’s personal lives. Maintaining that relationship on a personal level is something we do monthly. At that time, we talk a little bit more high level on the vision and how we are sharpening what exactly that is and how we can continuously align priorities to focus on that vision. We have regular quarterly check-ins that usually are ahead of the board meeting that we align there. There is multiple different touch point that we have in the calendar and they don’t move. There’s nothing that can get in the way of those meetings. We schedule around them and we think of them as hard, firm parts of our calendars. That’s the structure, and along with a lot of casual conversation via instant messaging along the way.

You clearly got the systems in place for it. How many direct reports do you have?

We are that type of Rocket Fuel style. All of the functional groups report to me from that integrator perspective. I have nine direct reports. That’s the product side and the technology side. We have an office in India that houses our support team and software development out of Chandigarh in India. Great finance, customer success and support, sales and marketing and HR are all under my purview. The way we see Ross as the CEO is the visionary leader. A loose structure such that we both have accountability to those areas, but our approach is more from a vision and integrator style.

Tell me about some of the people issues you’ve encountered that you have had to struggle with internally and what you may have learned from those.

It’s all been around hiring the right people. There’s always going to be struggles in each individual. You have to be dynamic in how you get the best out of each of your employees. What we’ve noticed is when we hire the wrong leader, it wasn’t that they didn’t have the aptitude. It was not the right fit for us. They hire those in a similar fashion and getting that leadership hire right has helped us avoid a lot of the people issues that we’ve had in the past. We believe and we spend a lot of time and effort on recruiting, especially at the leadership level. We have a world-class team and it’s only getting bigger and better. We’re starting to see that Maropost has become a destination, so we’re excited. It’s hiring right that’s been helping us avoid any major people issues.

SIC 55 | Focus To Achieve Change

Focus To Achieve Change: Set meetings to discuss the top priorities, catch up on personal matters, discuss company vision, align priorities with that vision, and to further align with each other.


You guys are in a tough market now where you’re to compete against Shopify and other technology companies. How are you competing against them and are you exclusively hiring from internal marketplace or are you also hiring in other remote cities as well?

I’ll go back where those start, with hiring. We have an office in Toronto and in Chicago. We see the Chicago office as our go-to market office. We’ve got a deep sales and marketing presence there. We have some sales and marketing employees in Toronto, but the majority of the employees are finance and administration. Our customer success team is housed in Toronto. We’ve got a product and development team here as well. Those are the two markets where we’re hiring. India is our other office. We have three right now. India is customer support and some software development.

The competitive landscape is very noisy and in MarTech, for example, there are 7,000 different companies and that’s what we’re starting to notice. We’re starting to notice that it’s a confusing landscape. Customers are dealing with a very difficult issue. When we sit down with CMOs, there are so many ways that they can communicate their message and engage their customers. They’re getting hit by multiple different companies claiming to solve their problem, but it’s all about ROI. We feel that way and we’re trying to simplify customer engagement to the point where, our space being so noisy, we want to make it easier. Customers deserve that. We’re not focused on our competitors. We’re focused on delivering solutions that companies and CMOs are going to help them deliver ROI while also simplifying their team structures and their go-to market strategies.

Talk to me a little bit about the IT and engineering groups. It always felt to me that a company that has their engineering group completely aligned and were building only the things that are most necessary, building them lien. Then the second half is the group where the engineering and IT groups are building stuff they want to build and they’re overcomplicating everybody’s world. How do you get IT and engineering to be listening to customers and building only what’s needed?

I’m going to make it sound easier than it is but it’s very difficult. Number one, your internal communication and feedback loops has to be tight. I’ll start it also at keeping focus. Simplify is not just a word for us, it’s something we live by. It’s splashed up on the wall. How did you simplify your day today? How did you simplify your customer’s experience with us? Communications, anything, all the way down to, “Did I send someone a calendar invite with the link in the location.” Simplifying everything and making everything easier than it has to be is something we relentlessly focused on. How we do that on the product side is getting granular on the scoping effort.

To begin with, number one, we’ve gone down the path of scope creep and teams wanting to having grand ambitions. Then you end up sometimes with nothing. You’d scope it so broadly and it sounds great but putting the rubber to road is a lot more difficult than you thought. We think about the initial scoping effort as making it simple and focusing on what is going to deliver a simple solution and a simple result for our customers. We have sales, customer success, marketing, monthly roadmap meeting that we discuss this stuff in detail so that we’re staying hyper focused on delivering the best functionality that is craved. That includes our current customers and perspective customers and we try and keep our finger on the pulse.

I’ve always been worried that IT can be the tail wagging the dog and it’s how you avoid that. They’re wickedly smart people but the rest of the business often doesn’t understand them.

What we do is we have a rotation. Our customer success team has regular calls with our customers. We’re checking in, and anytime there’s product feedback, what we do is we have the engineering team, our development team, we have one or several at a time join the call, listen, take notes and deliver back a communication to their team. Every single month, there’s a continuous education of having the IT team, the engineering team listening to customers and providing context to some of the items that they’re thinking through. That helps them have the ability to make decisions on how they do architect things or how they do creative solution.

We are focused on having that customer centric feedback loop. Without the broken telephone of the customer success manager passing on a message to maybe the leader of the engineering team and then that gets then passed on to the team and maybe a weekly meeting. We want to go right to the source of that. We minimize any of those communication friction areas.

You talked earlier about top threes. You were saying that everybody had their top three. Walk us through that process.

We have our company goals. This is a long process that we went through, but we find it to be super critical. We have our top five company goals for the year and those goals, they’re not smart goals. They’re visionary goals and what we do is we set targets that align with those goals quarter by quarter for the course of the year. In our HR software, we use BambooHR and they have this cool ability to tie your personal goals to the broad company goals. We set our goals and targets upfront. Each and every one of our direct reports have their goals set that directly tie to one of the top five company goals. That trickles all the way down to our individual contributors. Each of their goals ties to their manager’s goals which then tie all the way back up to our broad company goals. It keeps people aligned on, “How do I spend my week? Is this activity aligned with what my goals are for the quarter and through the year?” It helps them prioritize.

What I mean by top three is each week, we’d encourage a one-on-one check-in with all the direct reports that each manager has. What they do is they look at the priorities, talk about them and literally have the goals of the quarter right beside, at any point in time. We look at them and say, “This one’s not aligning to your goals. Let’s change what your priority should be this week.” We keep that rigorous focus. I’ve noticed how easy it is to be busy and working hard, but not using that number one needle-moving activity at any point in time can be the difference between faster success and slower success. It’s definitely been the needle movement for us.

You are following all the best practices. You’ve been either sitting in and reading a lot of my books or I’ve been teaching you or somehow, we’ve been reading the same information. The flow of how you are doing things is so similar to how we were running the business at 1-800-GOT-JUNK?.

I read your books like Meetings Suck. That’s my next focus, it’s meetings. It’s on my list.

SIC 55 | Focus To Achieve Change

Focus To Achieve Change: Doing the number one needle-moving activity at any point in time can be the difference between a faster success and slower success.


That’s an easy one. Have every single employee at your company read Meetings Suck. Get them for every employee in India, Chicago, Toronto and have every employee read it. It’s written on how to not only run meetings, but how to attend them and participate and show up at them. One of my whole tendencies has always been that the leader’s job is to grow people. The more that we grow our people, the faster our organization grows. Do you have any systems or any beliefs around growing people at all?

It starts from the top. I interact with every single employee that way, but I have most touch points with my direct reports. This starts up with Ross, the CEO, as well. That’s how he treats me. Maropost is a destination and an opportunity and a tool for each and every one of our employees to achieve their goals. Their personal goals, career goals, we want to be a conduit for that and help them with that. Most of our conversations when we have our check ins on a quarterly basis for example is, “Are we still taking your personal career boxes of what you want? If not, is there another area in the company that you could be valuable? That you’re interested in? Is it time for us to part ways?” We had to part ways with people. One of our key employees moved on because it wasn’t aligned with her opportunities or her goals in the short-term. It was very amicable and we’re helping her find something else that better aligns with her goals. When people feel that we care not only about what they do every day, but if they’re inspired and are achieving and going in their career path and goals, then they take care of us.

You have what Jim Collins talked about, getting the right people on their right seats. You’re asking them and proactively trying to make sure they’re in their right seats. Even by asking them, “How are we doing? Are we fulfilling what you need for part of your career?” you’re understanding how to handcuff your A players. If you take care of what they’re looking for, they’re going to stay. It’s that old adage in a relationship. You think the grass is greener on the other side of the fence, go water your own grass. If you’d taken care of your employees, they’re going to go through brick walls for you. Where do you struggle? Where have you struggled as a leader?

All of this has been a struggle. It’s so exciting and it’s been such a great ride. I can’t wait for the next two, five, ten years with it. In investment banking, there’s a diminishing marginal return to each minute of work done. To get to 80% if it takes an hour, to get to 100% probably takes you another six, and that was a trade offset in investment banking. You have unlimited time and you’re at a university or as you go through your career, it’s that competitive landscape and you’re in the services business so that’s okay. That’s understood. It took me a year to deeply understand that. I understood it at the surface level, but I didn’t feel it and people noticed that. I had to work on getting it to 80%. The velocity of work is more powerful than less work but maybe a little bit more polished. There are certain things where you can’t let anything at less than 100% go out the door. That has been the biggest challenge for me and I think I’m still learning in overcoming it, but it’s something I focus on a lot.

What were your grades like in school?

High enough.

SIC 55 | Focus To Achieve Change

Focus To Achieve Change: Remember that changes take time, hard work, and conviction. If you stay on course and continue, great things will happen.


I think you’re having to unlearn what the school system lied to us all about and they all told us that perfect was what we are supposed to go after. The reality is no one’s ever looked at our transcripts since the day we graduated. It never mattered. We could’ve gotten by with a solid B- and had more fun, join more clubs, been more involved, met more people, dated more. I don’t think I could’ve played anymore drinking games than I did, but the reality is I think we were lied to. In the business world, we’ve heard about this whole concept of minimum buyable product. In some ways, it has to be a minimum buyable everything, but not completely out the door. We have to pass it to another person who can then tweak it and make it a little bit better, but it’s that momentum that creates momentum right?

Iterative work and velocity of work is impactful and it compounds.

To sit and talk as noble on your yard and keep making it bigger is one way but to start rolling it, it grows on its own. The momentum, we got to start rolling the damn snowball. We get stuck in business. I find it frustrating watching these companies that gets stuck instead of moving it forward. I’ll give you a perfect example. My book called Free PR came out and we worked hard on it. I have a co-author, Adrian, who I used to coach. He’s built a company called DNA11. We co-authored this great book, worked hard on it, worked with a great editing team and I’m proud that when my books go out the door, there aren’t spelling mistakes or grammar or problems with it. Somehow, one of the editors took a comment that we’re talking about Alice Cooper. He said that Alice Cooper was the front band for the band Kiss. I’m like, “What?” I talked to Alice Cooper personally in a restaurant so I sent a friend of ours a note. I said, “Bill, you may want to let Alice know that we said he was the front band for Kiss.” I’ll get it changed for version two.

The way you were saying that, it’s true. I was watching that in front of us. That paralysis of lack of velocity because there’s even sometimes a fear that you don’t want to do anything because if it’s not perfect, you might get feedback on it. It’s viewed as negative versus sailing fast and moving faster and we had to pick up the velocity of work. It’s an excellent point.

You probably got a big opportunity to take that back and deep into your company as well. That whole idea of perfectionism, it’s got too big of a grip on too many of us. Give us one parting tip, something that you wish you’d known earlier on in your business career that you’ve learned, that you now know. What’s a good lesson that you can give us that’s something you wish you’d known earlier?

When I was coming in to Maropost, I thought that all of my initiative that I had in mind to improve how the company was running, the things that I could do. I might have thought they were happening a little faster than they should’ve and change is hard, change takes time. You have to focus on the processes and the process goals that will lead to those ultimate results focused and achieve end results. You can get frustrated when you don’t see immediate results for change. It’s hard and there are people involved so it takes a lot of work and conviction, but if you stay the course and continue, great things can happen. Expectations are important. Think about them when you set them ahead because if you set them too tight, they can sometimes be demotivating. That’s one thing that I learned in my time at Maropost so far.

I heard a good quote from a mentor years ago and he said, “It takes a long time to get to the night before you become the overnight success.” You got to keep working at it. Joseph Schirripa, the COO and CFO from Maropost, thanks very much for joining us. I appreciate having you.

Thanks for having me.

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