Ep. 100 – Special 100th Episode: The Best Of Second In Command

Second in Command is now on its 100th episode! Since the podcast was launched, Cameron Herold has talked to several COOs and others in the position of the second-in-command to learn and educate others on how to increase their results, improve their business and affirm better communication with their respective CEOs. In this episode, Cameron recaps some of the highlights from over the last hundred episodes, including the following: Shopify COO Harley Finkelstein; Organifi COO Mae Steigler; TIBCO COO Matt Quinn; Grant Cardone Enterprises COO Sheri Hamilton; Vayner Media COO James Orsini; Measurabl COO Dana Arnold; Zurixx COO Andrew Way; and Leverage Head of Operations Florence Bout. Take the time to listen to these snippets of valuable information from some of the best in the COO space.


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We’re pleased to announce that we’ve reached 100 episodes. Since the launch of the show, we’ve talked to several COO and others in the position of second-in-command to learn and educate others on how to increase the results, improve their businesses and affirm better communication with their CEO. In this episode, we’ll be recapping some of the highlights from over the last 100 episodes. I hope you enjoy them. Thanks for being an avid reader and a subscriber. Please share this episode.

Harley Finkelstein, the COO of Shopify.

In 2005, I moved from Montreal to Ottawa and I started law school. Although I enjoyed my first couple of weeks of school when I got here, I didn’t know anyone here. I had no friends. I had no family in Ottawa. I had this one mentor who was teaching law. When I began to ask around where all the entrepreneurs hung out, I was pointed into a particular direction. One of the things that I’ve done throughout my life, whether it was living in Montreal or then moving to Florida, going back to Montreal, moving to Ottawa, I always found that entrepreneurs in any city were where I’d find my tribe, like-minded people who I can develop good relationships with. I moved to Ottawa. I asked where the entrepreneurs hang out. I was directed to a coffee shop in The Glebe, which is a small little area of Ottawa.

I was told that every Friday night, a group of smart entrepreneurs hung out there. Without giving it any more thought, I showed up one Friday night to that coffee shop and I met 5 or 6 entrepreneurs. It was Sam Zaid, who at the time was building Getaround. He’s moved to San Francisco to build Getaround out. It was Paul Lem who built Spartan Bioscience. It was Luc Levesque who built TravelPod, who’s now a senior leader at Facebook. It was Toby. The issue part about Toby was we are polar opposites. He’s cerebral. He’s somewhat introverted. I speak too much and I’m far more extroverted than he is, but Toby and I connected at the weekly coffee meetups. Toby at that point was transitioning out of selling snowboards online to the software company.

He wrote this piece of software to sell these snowboards because he couldn’t find any great software on the market and quickly realized that selling snowboards, maybe a good idea but selling the software behind the snowboard shop may be a great idea. In that he can help entrepreneurs from all over the world, build their own businesses. When I met him, he transitioned away from snowboard to the software. I was looking for a way to continue selling t-shirts, while concurrently going to class. In undergrad, I was able to skip class and show up for the exams. In law school, using the Socratic method, which is I’m yelling at your name randomly, and you haven’t answered the question, it didn’t work nearly as well. I needed a business that would run virtually. I ended up becoming one of Shopify’s first customers.

I built an online t-shirt shop called Smoofer with my best buddy in law school. I ran it concurrently with class and my course curriculum all throughout law school. For our business school, I did my MBA. That was about 2008 at that point. In 2008, I decided that I want to get called to the bar. I wasn’t sure that I want to be a lawyer. Law school for me was finishing school as an entrepreneur. It was like etiquette school to be an entrepreneur, which was exciting to me. It had little to do with the law itself. It had to do with the way of thinking, a way of arguing, a way of negotiating. It taught me how to read 4,000 pages to pick out the one line that mattered most.

It taught me how to be a bit more articulate in how I express myself. I loved law school, but I knew I didn’t want to practice, but I didn’t want to get called to the bar. I felt that was the last step in the process. In 2009, I moved down to Toronto and I worked for a large law firm. I articled for ten months and I hated it. It was the worst ten months of my life. Unlike entrepreneurship, it was a meritocracy. I felt that the legal profession, not too dissimilar from things like the accounting profession, a lot of it was about legacy. It mattered how long you’ve been there. It mattered who you knew.

It didn’t feel right to me. I stayed ten months and one day longer, which was exactly the amount of time I needed to get called to the Ontario Bar. I called Toby and I said, “I love Shopify. I love the product.” At that point, it was Toby, Daniel and Cody who were the three co-founders of the company. They were all brilliant engineers and designers. I’ve known them for a couple of years because I was an early merchant, early customer of Shopify. These were three of the smartest people I’d ever met. What was cool was that they had a great product. They were beginning to find product market fit, but none of them self-identified necessarily as someone who was focused on the business side of the company, they were on the technical and the product side.

I called Toby in 2009 and said, “I’d like to move to Ottawa and help you, Cody and Daniel build out Shopify. I’d like to take on the business responsibilities for the company.” That was it. My girlfriend at the time was now my wife and the mother of my child. We moved to Ottawa in early 2010. I remember asking Toby, I said, “What do you need me to do?” He said, “Whatever you can.” I remember thinking that my job was finding the things that they either didn’t want to do or didn’t know how to do. Also making sure that this amazing product that they had built, which I felt was by far the best product on the market, that we were able to properly commercialize it, sell it, market it, retain customers, build a business.

I would say my first year or two at Shopify was mostly being a Swiss Army knife. We raised our first round of financing in mid-2010, and we had no CFO. We had no GC. I helped raise the round. I figured out what a cap table needed to look like. Along with Toby, we went ahead and raised $7 million and that was led by Bessemer. That was my first introduction to being in a Chief Operating Officer role or a second-in-command role. My job isn’t necessarily this one thing and do only that one thing. It was figure out what are the gaps that the company that we’re going to prevent us from getting to the next step for the next level that the other three were not tackling. The first couple of years, it was mostly around building a business around Shopify, building a partnerships team, building a business development team, figuring out what sales should look like. We didn’t have a CMO at that time. We worked closely trying to build a marketing team. That was the first couple of years here. It was about being a Swiss Army knife and helping Toby however I could.

Mae Steigler the COO and Paseo Alliance member from Organifi. Those are the pretty early days for Facebook as well. Facebook had been around in the college market but came into the business world around 2010. How did you guys attract all those early eyeballs? Do you still carry some of those lessons forward today now in Organifi’s business?

Yes, it was totally different. You’re right. Back then, we had a lot of free traffic and it was a whole different experience in the business realm on Facebook. That was what grew our company before the original algorithm changed a lot. We were experiencing free traffic. We were using key terms and a lot of basics of content marketing on Facebook. It was the Wild Wild West back then. What we’ve taken forward, to answer your question, is using Facebook as a primary. It’s still our number one paid channel. We do the most on Facebook and in paid ads. It’s a slightly different way of doing things, but it’s still a primary focus and driver for our business.

Our huge focus of our customer service is handling the ads comments. We do engage highly with our customer base and are always looking to do more of that. At the COO Alliance we had a great presentation about customer voice and customer activation of feedback. It was a great reminder to look at the value of doing that and how much you can learn from engaging with your customer base. For us, a lot of those ads are essentially community-based, but they’re not customers yet, let’s say. The more we can engage and understand the obstacles to put in our product or the actual pain points that we’re solving with the product, as we see testimonials in those Facebook ads threads, the more successful we’ll be. We’re always trying to get better at that. I felt we haven’t nailed it.

Some of it is like we’re stumbling as we go because so much of this is new. We learn either through our own experiences or through a bit of R&D. One of the first early communities I’d seen on Facebook that did well was Hal Elrod who wrote The Miracle Morning. He and I co-authored The Miracle Morning for Entrepreneurs together. I interviewed his second-in-command, Tiffany. They do an unbelievable job with engagement in the community. Do you study other communities online or where did you guys gain in your skillsets to do that?

It was practice in our own and having a membership that was based on a Facebook group. It’s interesting to see. We don’t do that anymore. We don’t have our own Facebook group for our customers. We have a Facebook page for our customers. We built on our call center. We actually have an in-house call center in San Diego, which is rare and relatively unique, but this allows us to not only hear the conversations of our customers. It’s a hybrid CS and sales floor. We’re experiencing anywhere from 800 to 1,000 inbound customer calls. That’s allowing us to keep that conversation alive. We’ve transformed how we’re connecting with our customer base rather than a closed Facebook group that’s a membership like we used to at FitLife TV.

At Organifi, we’re seeing that conversation alive and well over the phones and making that a coaching conversation. We wanted to add a bit more of a tying-in that original transformation focus we had with FitLife with more than a physical product brand at Organifi. They’re incredible, but how are we unique from somebody like that? Trying to continue the in-house product education, transformation education for our own employees is huge. We do an incredible in-house leadership program that focuses our team members on their own health and transformation, giving them coaching and wellness education that they can tie into the phone conversations that the CS team is having with the customers.

In 2014, Organifi was launched. Was it mid to late 2014? Was it early 2014?

It was October.

To go from two employees to 55, plus 110 contractors, how are you funded?

We’re not. We haven’t taken on any funding. I will correct you a bit. In 2014, we probably had maybe 5 or 6 full-time employees. It was 2011 that it was Drew and I. Our current CEO Djamel Bettahar was brought on in 2014, 2013, perhaps and launched Organifi with Drew and the company. He was our first, legitimate integrator. He’s moved into the CEO role, completely accelerating the company, doing an incredible job. He has an incredible mind and stepping into the visionary role and transitioning out of an integrator role. It’s cool to see that transition.

You’re in the pure integrator role then, correct?

Yes, I am sitting in the COO seat. Djamel is in the CEO seat and Drew is in the founder role. He operates as what we call Chief Innovation Officer and works with our leadership team to innovate, essentially. Applying that strong visionary skillset that he plays expertly to.

You now got the visionary, the integrator, terms have been popularized from EOS, Traction by Gino Wickman, a great book. A lot of my clients use those systems. In the role that you’re in, in the COO role, the whole reason we even started the COO Alliance was to grow the skillset of the second-in-command. How do you stay on the same page with the CEO ongoing? What systems do you have in place? What do you guys do so that you and the CEO are always on the same page, always moving the company forward.? You said he’s a great visionary. How do you get caught up on the vision constantly and how does he get caught up on the plans that are being put in place?

SIC 100 | Second In Command Highlights

Second In Command Highlights: The more you can engage and understand the actual pain points that we’re solving with your product, the more successful you’ll be.


It’s something we’re always developing, and I love continuing to update and develop our own meeting rhythm and how we run our operations. We started with Traction, the framework of our company. Gino Wickman’s right. The Traction book, incredible format for meeting pulse. We essentially do a daily standup, a daily huddle at 9:00 AM every day, the entire manager team and above. We go through our primary objective for the day or our number one thing. Have you read the book, The ONE Thing? It’s a great book. Our team read that a couple of years back. We’ve always done, “Here’s my number one priority, the one thing, gets everyone on the same page.” I want to connect, because we do have a bit of a remote team as well.

It’s 9:00 AM daily huddle. Everyone does their one thing that lasts about five minutes tops, even less. We go over our company dashboards. We run through all of our metrics, it’s all visualized data. It’s a screen-share. We typically will do quick company announcements. If there’s a birthday, we’ll sing happy birthday. It always sounds horrible because we have remote team members on Zoom, so it’s a nightmare and it’s hysterical and we love it. Any frontline announcements, new hires and whatnot on there. It close out with a quote. That’s every day. Weekly I meet with my CEO, Djamel. We do an hour and I break down the operations side of the business. He also meets with our CMO Amy Beaver once a week. She breaks down the marketing side of the business.

We break it up in half and we run through my one-on-ones with my key direct reports and I’ll have them fill out a weekly one-on-one assessment, I meet with them for an hour a week. We run through the dashboards and get an update on what’s working, what’s not, any obstacles, missing systems, you name it. It is built on the traction format. We have company rocks and gigantic KPI board in the office that everyone updates once a week. Color-code those for on-track, not on-track and below projection. I think DJ, Drew and myself are extremely visual people. We need that visual indicator where we are and how we’re doing. We have a 3×3 TV wall that has all of our company dashboards on it that we go over on the daily huddle. That’s live all the time.

Our call center, which is in the main floor has their TV dashboards for their daily sales and call wait times and whatnot. We keep those front and center. Otherwise, it’s hard to keep that transparency on what’s moving the company and certainly feeling being less in the business. It’s a challenge to keep the transparency and keep the communication alive. It’s always something we’re working on. We also do, we call it like the hedgehog meeting, which is a once a week, hour-long meeting with the C-level team. We have extra time. We also do the Level 10 meeting format once a week from the directors. We have a pretty solid meeting rhythm, subscribed to your book, Meetings Suck, and we try not to have that many and focus on the most important ones, keeping them as short as possible. We do run a 90-minute Level 10 meeting, which gives us more time to go over where we are weekly with each department. The 90-day calendar we run through IDS, which is Issues, Discussion, and Solutions, and finish up with who does what by when.

Matt Quinn, the COO of TIBCO. I’ve coached CEOs and teams now in 28 countries so I’ve had some exposure to it, but most people don’t see what you’ve been able to see in terms of being embedded these different companies and truly seeing the culture and not the language difference, like in London where turnover means revenue and in the US it means losing employees. What are the differences in terms of leadership and style, and the way companies approach business between Australia, London, Houston, Texas, and California? What have you seen?

It is still the language. There are both professional and personal language choices that you make in each one of those places that still to this day, bring a smile to my lips. One is in the UK and in Australia, to tick something off is to cross something out. I still remember being in a meeting and say, “Take that one off. We’ve finished that used case.” The person’s like, “Why are you angry at the piece of paper?” I’m like, “What do you mean?” The other was, in every other part of the planet, a sweater is a jumper, especially in Australia and the UK. I was living in Houston. It’s freezing cold in the office buildings because of air conditioning even though it was boiling hot outside. I’m going to go find a jumper. The guy that I was working with thought that that was the funniest thing he’d ever heard that this young Australian kid was going to put on a jumper.

I had one where we had some friends over from Australia and they were starting to work with our company, 1-800-GOT-JUNK?. Our Australian guy from Sydney was in Vancouver and we were walking down the street and we came across a store called The Roots and he started laughing. He goes, “You’re kidding. You have a store called The Roots.” I’m like, “Why?” That means like, “The fuck?” The logo on the roots is a beaver. He was dying, laughing. This is too much. What about the leadership styles? Do they manage businesses differently? Do they think differently or is it pretty much the same?

It is different in all three places. I spend a lot of time in Germany as well with people like Deutsche Bank and others. One of the biggest lessons I learned was you can’t stereotype a country and their business practices because while things are different, you can’t make those types of gross assumptions, because ultimately people are all individuals. A good example of that is Europe. We’re still no Brexit. I’m going to count the UK as part of the EU. I look at my time in all those countries and I could see how I learn different ways of doing business. In Australia, for a lot of bigger purchases of technology, everyone’s quite concerned and making sure that they’re making the right choice. There’s a lot of work that goes on up front to make sure that the choice is the correct one.

In Europe, there’s a lot more focus on standardization and following business process and business rules. They tend to like software that is much more standards centric. The US on the whole always felt to me being able to make more aggressive decisions earlier on. It’s the fail fast mentality to look for advantages, but obviously to press at home once something has been successful. I’m endlessly fascinated by this. I used to spend a lot of time with banks and you’d go around and you’d speak to the same banks and even outposts of the same banks in different countries and have different ways of doing business even though they’re all part of that macro organization. Companies that embrace that difference are the ones that are the most successful.

You’ve had a lot of exposure over your career, working in these big multinationals, the big Fortune 5 or the enterprise level companies, also selling into those companies. What do you think we can learn from working and selling into those big organizations? What are the cheat sheets of getting in those doors and selling to them? Are they different?

If you did something that worked a few years ago, it won’t work now. These companies are moving so rapidly and evolving so rapidly that relying on your knowledge from few years ago is tough. All companies are going through a period of reinvention whether it be a bank that wants to become a software company, the taxi company that’s decided to deliver meals. Everyone is looking for those transformational elements and it is changing the culture of these larger corporations incredibly rapidly. While at the same time, the ones that are successful in those transformations still have almost a core mission. It’s something that they believe in that while their businesses may change, the tactics and the technology may change.

There is something about who they are that has become increasingly important to their minutes. It used to be the brand, but it’s not the external brand as much as it is their internal brand about how they want to be perceived by vendors, by customers and by their own employees. Someone much smarter than me had read something to me. It went something like, “People join a company because of the mission. They want to achieve something. The ones who stay, stay because of the values.” I think that large corporations have worked that out. That people might come because it’s an exciting project. If you can get them to stay because of the core values that you represent, that’s pretty important, especially with the paucity of talent that you have available now.

Sheri Hamilton, the COO for Grant Cardone Enterprises. Give us the helicopter tour of the Cardone Enterprises that you’re running now, then the 107-ish employees. What functional areas of the business report to you and are there any areas that still report into Grant?

Every single area of the company reports into me. We’re starting to see that these division branch out into coming into be is their own companies almost. That is the challenge, but we have Grant as the public speaker, the keynote speaker that travels the world. We have Grant as the unbelievable multifamily investor. That venture is going so incredibly well right now. It’s growing so much that it’s something that we are going to have. It could be its complete own entity with another operations manager. We have ten employees over there. We’ve got another thirteen employees in the ad agency that we started. We have our eCommerce group. We’ve got the Online University group. Grant is an author, writing books, that’s a whole other division. Let alone Grant as the host of the Cardone Zone, the G&E Show, the Young Hustlers Show, the real estate show and our whole division that is Grant Cardone TV, on top of that with the whole live event. The live event thing has taken on a life of its own.

He’s a classic underachiever.

It does take a special person and group to support him.

What is it like to be in the shadows of the brand? This is very common of every second-in-command. One of our jobs is to make the CEO iconic and it is often walk in the shadows. What’s it like for you to walk in the shadows when you know you’re doing so much of it and often you walk as an unknown?

If you are in a position where you desire the spotlight, you must have that acknowledgement, it’s probably the wrong role for you. You should probably be out there doing something else that would get that for you. I never needed that and the satisfaction that I get comes from every single day when I have an employee that’s doing better because of something that we’ve talked about or the statistics rise or something else is happening. We pull off a huge event. It’s our first time doing an event and we’ve pulled off 9,000 people at the Mandalay Bay Events Center. Those kinds of things bring me the gratification that I need. If I were the type of person that needed that attention or acknowledgement, I’m afraid it wouldn’t last long because it’s not that role.

He’s a quick start. Grant is an idea, plan later. How do you play cleanup to that? How do you say no when you feel you need to say no? How do you give him the permission to start all the things he wants to and then you get to figure out the how later?

It’s probably because I know what he’s trying to do, and I’m 1000% on board with what he’s trying to accomplish. I love the mission of what he wants to do. That’s why it’s my privilege to support him and making sure that gets executed. He calls himself The Hurricane. It’s no mystery to him. He comes in and he causes all sorts of problems and messes. What we do is we try to put processes in place beforehand. Every time we have something happened, we go, “This is a mess.” I meet with the team and say, “Guys, what can we put in place that allows for this in the future, that it’s not such a logistical nightmare in the background?”

We learn as we go how to prepare to allow him to be as free as he wants to be. That’s where the skill comes in because you have to think outside the box for sure, the usual ways don’t work. It’s true every single day, we’re trying to figure out how do we do something different, better, faster without all of the red tape that we would normally see in something. When it comes down to, “We cannot do that. That would harm our brand. That’s something that is going to be detrimental to the customer. It’s not a good customer experience,” I talk to him and say, “Chief, what we’re finding is we’re finding this and we’re hearing that.” He’ll say, “Who’s telling you that?”

When I go to him with those, I always have some examples. I said, “Watch this. When you go here and you do this, or when you hear this and you go there, you reach a dead end,” or whatever the example might be. He’ll say, “I don’t want that.” It’s simple because he’s such a great person and the purposes are so aligned. I’m not trying to do something other than what he’s doing. As long as I communicate to him, challenges that we’re having and executing, his plan, his dream, his mission. He’ll be like, “We can’t have any stops or any blocks on that.” It works out fine.

James Orsini, the COO of VaynerMedia for Gary Vee. James, when you came in as COO, they typically talk about the first 90 days, first 100 days of somebody coming in as a Senior Executive. What was your first 90 days like coming into the organization? What did you focus on? What would you have changed? If you were able to go back now, would you have done anything differently in the first 90?

SIC 100 | Second In Command Highlights

Second In Command Highlights: Different companies have different ways of doing business. Companies that embrace that difference are the ones that are the most successful.


It was interesting because Gary said, “When you come in, James, I want you to breathe. I want you to observe the culture. I want you to understand how it is that we operate here at Vayner before making a decision or advising protocols and things like that. Get a feel for how we operate.” The terminology was “breathe.” That was great for me in understanding the culture that he built. What’s unique is he’s not an ad guy and he never set out to build an advertising firm. It happens. That’s both a blessing and a curse because the blessing is, he doesn’t come encumbered with 150-year industry baggage, but then that also comes with the loose structure of, “Here is the way things are done when you’re dealing with a Fortune 100 client base.” What is so special about what it is that he’s created and help it live in an ecosystem that permeates structure and guard rails? It’s the race horse that we want to make a run on the plane of Texas rather than virtually fenced-in in somebody’s yard.

Are you focused on the system side of the business right now, or the people? Is it strategy? Where do you tend to?

I go wherever Gary needs me to go. I’ve played so many chief roles in my past, CFO, COO, CEO, CIO. I’ve been a Chief Administrative Officer. I’ve seen a lot of different things. I know how departments interact. Do I help advise on systems? I do. Do I help advise on structure and process? I am and I can. Do I help him find the right key individuals and hires that build out his leadership team? I have. Can I help him with infrastructure, office operations? I was actively involved early on in the opening of the office in Chattanooga, in the Aboriginal upstate in London. I helped him with his first big acquisition of PureWow, which has now created the digital publishing division under the Gallery. I have a role in his facilities build out structures, whether it was here in Hudson yards or our 40,000 plus square-foot studio in Long Island City. I go where he needs me to go.

Tell me bit about the acquisition. What did you guys learn doing your first acquisition?

I’ve been part of companies that have had big and explosive growth, but that was mainly through acquisition. I’ve been part of a company that has grown organically like Gary’s. There was a time when he wanted to get into the publishing side of things, and it was going to be hard and long to grow it from scratch. Relationship with Ryan Harwood, who was the CEO of the Gallery. We helped them structure a deal that was a combination of equity and debt, through our partners at RSE and went through the process due diligence acquisition and the integration.

How do you identify the wrong people, either the cultural cancers or the people that are underperforming and remove them from the organization?

If they’re not selfless. When they become selfish, we quickly realized that they may not be the right fit for us. When they step outside. When they’re doing things that are best for them and not what’s best for the logo, we step outside. We have a few key indicators that tell us, and if they’re not your basic performance of tasks. We give everybody a chance to succeed. it sounded like, “You’re one mistake and you’re out the door.” We over-index. I think another thing that’s great is that we will find you a role outside of these hallways if we mutually decide that it’s time to part ways. We’ve placed numerous employees at other companies, which have now come back to be our clients, because we did the right thing on the way out.

I read about that whole idea in a book called The Dream Manager and how they try to move people off. Are there a couple of core areas that you might be as an organization trying to grow your mid-level team in terms of their management or leadership skills?

We go back and forth on the mid-level, trying to determine, are they the most valuable commodity in the building or are they the least valuable commodity of the building? Gary over-indexes heavily on junior talent, the hustle of junior talent, that’s important for us. The question is, do you move to a fewer better model on the senior side and then get this young, hungry, hustling talent beneath them? We’re exploring that. Over the past few years, we’ve been taking the time to bring in some professional development, whether it’s presentation skills, training, storytelling, initiatives to help develop that at level beyond that. We have to realize here is one year at Vayner is like seven years in the industry. We’re careful with how much we spend in a structured professional development, because the way we service our client changes every six months.

It completely changes. Give me an area then that you guys have struggled at as an organization and what you’ve done to turn that around in an area that you spotted that you had to champion or lead.

We’re still questioning our project management role, not the capability we know it’s needed in the building. What we’re questioning is where does it belong? Does project management at Vayner belong in a separate department as it had existed for long? Does it belong rolling up into the production division as it now resides? Does it belong as part of account management and account services as we are debating? Remember where this company came, it was micro content, a lot of pieces thrown out into the internet, small bits of creative, with community management or people seeing how others were engaging with it and doubling down when they see where somebody engages. It’s fewer better pieces of creative content with media dollars behind it. It’s a different way of operating. Therefore, the visions that were right and built in a certain way need to change because the way we’re servicing our clients changes.

Dana Arnold, the COO of Measurabl. Tell us about your background then. What things did you see in Measurabl that attracted you to come in as their Chief Operating Officer? What do you think they saw in you to bring you on-board? It’s a critical role.

Around the time when I was exploring joining Measurabl, Measurabl is about 20 people, still founder-led everything. The CEO, Matt Ellis, who founded the company back in 2013, this is around 2017 when I joined the company, he was still doing everything from running payroll to strategically leading founder-led sales, to managing customer success, to leading the product team, you name it. He was the only business operator within the organization. We were primarily software developers, a few customer success, two sales guys, one marketing person. It was crucial state of the business. He had closed a second seed round to fund the next growth stage of the business. When I started chatting with Matt, it was clear that he needed a lot of administrative help in growing and scaling the business.

What attracted Measurabl to me in the beginning, I was working for our quasi-competitor, Goby out of Chicago. I saw his approach to solving similar challenges in the commercial real estate market around utilizing technology to enable scale and growth in this space. When I had the opportunity to explore some new career options, I thought, “Wow, I want to work for that guy, Matt. I think he’s solving these things in new and innovative ways that typically sustainability is led by consultants or tech-enabled consultants that use a lot of people to solve challenges that technology can solve.” That attracted me to Measurabl and to Matt personally. I reached out to him and said, “I like what you’re doing. Can we somehow work together? Whatever you need, I’ll do it.”

It started some interesting conversations in those early moments. I’ve understanding the approach of utilizing technology to solve global challenges around climate change in a way. Buildings over 40% of energy. We spend over 90% of our time indoors and commercial real estate is the fifth largest asset class. The opportunity for huge impactful change around how we handle and prevent climate change is in this core-set of challenges. It requires a global solution to help solve these challenges and these problems. Consultants and Excel are not going to solve these problems in and of themselves. Utilizing a technology so consultants can solve the impactful change that they need to and removing the data management and the data architecture and some of those insights, centralizing that into a centralized software platform. You can SaaS that. When you have a software platform, you can turn it into a subscription model that scales and grows with customers over time.

You guys are a SaaS model than subscription-based business?


Matt’s the CEO and you’re COO. How did you divide and conquer in terms of your roles and responsibilities and how has that evolved over your two plus years with the company?

It definitely has evolved. Day one, it was one of those mission critical moments where Matt was like, “I need to focus on strategic stuff and I need to get a lot of these administrative things off my plate.” That was day one of our “what are the tactical things that needs to get done?” so he can focus on a lot of the strategic things within the business. It was one of those moments too, where I had not been in a chief operating officer role. I had experienced in running a twenty person and data team that had a fairly large budget. I was responsible for all the hiring and managing of the budget and spending of the cash to deliver on the services. In talking with Matt, I was like, “Whatever you need in the business, I’m here. I will do it. Whatever it takes to work with you, I’m here.”

When talking with him, we didn’t ever discuss necessarily the role or the title or anything of that. I remember getting the job offer from him and reading, being like, “Chief operating officer? What?” Having that moment of like, “What does this mean?” I remember going and googling, “What does a chief operating officer do?” It was that moment of learning that this role is so dynamic and different depending on the industry, depending on the business’s needs, depending on the people involved. I’m coming into Measurabl from a much of a subject matter background expertise of working in the commercial real estate space, working with sustainability in the built environment, from graduating college with a degree in Architecture where I thought I was designing and building buildings. Now, I’m building software to help make buildings better.

It was those moments of trying to figure out how can I be successful coming into this role in supporting a young growth organization in those early days. The main tactics in those early days were taking over a lot of the administrative functions of the business that needed to get done. You need to run payroll. Not sexy things but there are things that need to get done. How that role has transformed over time, looking at what the next stage of the company was that we needed to fund for that next stage. That first good six months into the role was working on our Series A funding round so that we could move and accelerate the business forward.

That was a fun project of learning that whole world of venture capital and raising money. That was a new, fun experience for me. Gone through the whole process twice. The Series A was designed to raise cash, to build in a leadership team. At that point in time in the business, it was Matt, myself and Lance who’s our CTO. He handled all of the software, the development work, managing the development team, which was our largest team at that time. We didn’t have a head of sales, no head of marketing, no head of customer success. Those were some of the crucial roles that we needed to bring in as well as some additional administrative members of the team to help accelerate growth, including our now CFO, Nicole, and our head of HR, Jessica. Those were some of the key things that transformed my role into getting back into the strategic side of operations of the business.

You’ve been in since the early days. You had to then work on your skills as well. As the company has evolved you had to evolve as a leader. What have you been working on to grow your skillset?

SIC 100 | Second In Command Highlights

Second In Command Highlights: Visions that were right and built in a certain way need to change because the way we’re servicing our clients changes.


It’s something that I’ve been thinking quite a bit about. The balance between tactical things that need to get done in the business and what are those strategic things that I can do to support the growth of the business. I’ve got a team of people that are supporting the administrative functions of the business, looking at how from a business operation standpoint are we strategically enabling growth within the organization? It’s easy in this role to get bogged down by the tactical things that come up on a day-to-day basis. Coaching myself to be diligent around. Is this a strategic priority in the business? Will this enable growth with our people, with our product, with our customers, with our investors? If it doesn’t fit into that model, maybe it’s something we shouldn’t be doing. Even though it might be something people might expect that someone in HR or someone in business operations would be doing these things, guiding ourselves from our strategic perspective and aligning with business growth opportunities.

Andrew Way, COO of Zurixx. Tell us about Zurixx so we understand what Zurixx is. I want to go backwards in time to where you got your experience of becoming a COO.

Everyone thinks that their company is weird and unique, and most people aren’t wrong. They’re not generally weird and unique in the ways that they think they are. You probably wouldn’t want anyone to get the amount of businesses that you have deep insight into. There’s an 80% overlay in a lot of these things, despite the industry. Zurixx is a pretty unique business. I say that because there’s not a lot of other businesses that have constructed their sales funnels and to some degree their marketing funnels like we have. To use that word that I was referring to, Utah liquor laws, we’re arcane in that we do a lot of stuff in person. Zurixx itself has little or no brand value if you will and that’s by design. Our education brands that we put out on the front foot, those are all headed by celebrity partners. Part of what makes us unique is that all of our product lines and individual brands are headed by a celebrity partner. The degree to which these people are celebrities is subjective, and everyone has their own opinion.

We’re talking D-list or A-list here?

To us, they’re all A-List. That’s unique. The way that we sell is that we market fairly traditionally. These days we’re digital for the most part. We also still send direct mail. We’re still making that work. We still use radio and making that work. We still use billboards and that works. As you might imagine, that means we have a pretty heavy attribution engine and business intelligence group here, so we know those things work. We’ve put on live events all over the country, and they’re the things that you’ve seen. Come to this free event to learn more about real estate investing, or to learn more about entrepreneurship, or to learn how to take your business to the next level.

I’m on the business side where we’re represented. We work with two guys from Shark Tank, one named Robert Herjavec. One named Daymond John, and we’ve been working with Daymond and his team for a few years now. We also work with a guy that some people may have heard of named Grant Cardone. On the real estate side, we work with slightly less famous people from the TMZ standpoint. We worked with people who are on HGTV, primarily targeting Christina from the original Flip or Flop show and Hilary Farr from Love It or List It. That’s the only thing as a quick aside, that my mother understands about what I do. She knows that I work with Hilary Farr and she tells all her friends. It’s her social equity.

We work with those folks and people come out to see their teams, nothing more than a personal time. The tip of our sales funnel is our free live events where people come out to learn about wealth building. We refer to this internally as disruptive education. We feel like we are out there meeting people’s needs right where they are in the most efficient manner possible. People can then choose to participate with us and buy more products up the product line after the free period for the free event. That education can take many forms. There’s one-on-one coaching, group mentoring, lots of bootcamps and fast starts and more and more education. The highest value customers spent six figures with us.

Are you running all of those sections of the sales funnel or the front end getting them to the event?

Personally, in terms of revenue operations. I am running most of it. Our structure here is cooperative. There’s four of us, there’s three founding partners and here’s me. We tend to team up on things honestly. There are some things that I have primary accountability for, that’s how I prefer it. I find the teaming up sometimes inefficient. It’s been part of the culture and it seemed to work. For instance, let’s take marketing. I have 100% accountability for marketing where I’m in much more of a support role with our high-end tele sales groups on the backend. I’m involved in all these things. I have 100% accountability for our brand management group, and that’s a fairly hefty group here because that’s the group that interacts with our celebrities. We have some people who are rightly concerned about their reputations. We’ve spent an enormous amount of money and other resources on making sure that we enhance their reputation. In terms of client services and PR and corporate communications and stuff, that’s all mine as well. It’s sales where we tend to team up.

You do all the sales for these companies as well, not getting them to the events. You do the sales.

We do everything soup to nuts. We do everything from marketing, we do all the fulfillment on the education. There are a couple of places where we have a fulfillment partner. That’s a third-party contractor where they’ll come and do specific pieces of education that would be inefficient for us to hold in-house, but I’d say 85% of the educational fulfillment is done inside the building.

Let’s back up a bit. Walk us through where you got your skillsets as a COO. We’ll talk about how you got involved with Zurixx as well.

In terms of where my skill sets have come from, I have had the benefit of dumb luck and great timing. How those two things manifested themselves over the years have been in fundamental primary experiences that I didn’t seek out that happened. Also, relationships with people that I did seek out. The first instance of dumb luck was responding to an ad in April of 1998 for customer service rep openings at Amazon.com. At that point in Amazon’s evolution, there are a couple of things that the people don’t remember. One was always sold those books. Everything was in Seattle. Our distribution center was down by the Kingdom. There is no Kingdom anymore. All that stuff’s gone. Being a Communications and Cultural Anthropology Major, I had returned from traveling in Southeast Asia.

I believe at that point I was operating a deficit. I didn’t have any money. I’d spend it all in Asia. I’m trying talk to then buy drinks for Australian women. I needed a job when my parents told me I had two weeks. I was working to live at the house and eat and do laundry and do all the normal things I would do. For two weeks, I had to be on my own. I’ve been intrigued by Amazon because I had used Amazon from an internet cafe in Thailand to send my mother and sister I think birthday gifts, or maybe Mother’s Day gifts while I was gone. I was fascinated that I could do that from an internet cafe across the world. T They would wrap the present and put a note on it for me and send it directly to my family.

Florence Bout, the Head of Operations for Leverage. Tell us about the vision that you have for Leverage. Where are you taking the company now over the next few years? How do you get aligned with Nick’s vision? Most entrepreneurs have this vision swirling around in their head of where they want to take the company. How do you get on the same page with him? How do you get him on the same page with your operational print plan to make it happen?

Where are we going to take Leverage? We start our wait and we’ve launched our new dashboard. We’re still massively improving it. We’re still transitioning all the client’s office and onto the new system as in off the old system and onto the new system. We’ve got a timeframe of wanting to do that so we don’t have to need paying two systems. The first vision would be to do that. Becoming a SaaS product with the services, because we want to have a great platform, which facilitates the service. We have a version two coming out later in the year that will support the services much faster. That would be the next year vision. Everything comes back to the development and what will support both of those.

You mentioned a lot of communication. Talk to me about the communication protocol or how you and Nick work with each other. Are there regular meetings? Do you work over Slack or Asana? Do you do a lot of face-to-face or over Zoom? Are you in the same office as him or are you remote as well?

It’s completely remote. It was funny seeing them for the first time. I only saw them for the first time after year of working together. It’s like you have all this additional information suddenly when you meet in person. We spent much time on conference calls before that but that was the first second. We’re heavy in Slack then we do use Asana for project management, Zoom as well. That’s more setting up the goals, the week-to-week tasks between the calls. We have a weekly call to check-in on all the weekly tasks and be like, “What were the targets for this week on next side or my side? Where did we get to with that? If not completed, why?”

Ad hoc project calls. Half of my day-to-day would be from what I call the maintenance of making sure that everyone has the right information, the right knowledge system processes to do their job effectively and efficiently. The other half of the project, there’ll be more of a structured project. For example, this transition from the old platform to the new platform. That would be a project that we treat separately, but all day long in Slack.

Your CEO is focused on systems, processes, automation and the software side of the business?


How do you support that drive, but also rein him back in bit to avoid the perfection trap so that you can launch now with that whole minimum viable product idea?

It’s more the other way around. I’m like, “I don’t know. Is it ready?” He’d be like, “Let’s get an 80%. Let’s work on this 80/20 rule,” which is what I learned from him because he was like, “The dashboard let’s launch it.” I’m like, “I don’t know what about this? What about that?” He’s like, “No, I think it’s good enough. It’s MVP. It’s 80% and we’ve got the developers. We’re going to work on it and we’ll get the feedback.”

SIC 100 | Second In Command Highlights

Second In Command Highlights: The COO role is so dynamic and different depending on the industry, the business’s needs and the people involved.


That’s huge growth for him then because when I spoke with him, he wasn’t quite there yet. He was still driving for everything to be perfect. That was something we talked about.

It’s in that regard. In the high-level vision, there are other times that he does become perfectionist. It’s about saying, “Nick, I’ve got this, it’s fine.”

When Leverage is working with customers, tell us a bit more about Leverage so we understand how the model works and what work you might do for clients.

We’re on demand. They come to us. Let’s say we’re on a podcast. They say, “I want to start up a podcast.” We’re like, “We can definitely help you with that.” We’ve got our marketing team within the marketing team is the media team. For example, Mike, he’s our head of media. It would come to ENMAX income, they would come to him. He’d start saying, “Let’s look at all the systems and the tools, where do you want to host it? Where have you recording it? Do you want a summary? Do you want show notes? What are the images?” We organize that whole aspect. We’d make sure that we got the design or the template images needed, that we had the whole process for what you wanted written up once you wanted a transcript or not.

We would figure out where we wanted to publish that podcast whether if it’s going to iTunes, to SoundCloud, things like that then using this transcript and the summary to go to medium and write a blog based on it, whether it’s going to the website and of course the social media aspect around that. We do from start to finish depending on the client needs. That’s an example of podcasts, but we could talk any other process more on the business operation side, marketing strategy, things like that.

What’s your typical client? Who do you look for as a client? How would you describe them to us?

Usually, entrepreneurs of the small businesses and they’re probably looking to scale. They probably have a small team behind them. We would complement their in-house team. We do work with startups that are sole entrepreneurs as well, because those are the people that need us, since they’re a one man show or one woman show. Our client avatar would be the small businesses that are starting to look to scale.

Give us an example of an operational project that you’ve worked on with companies.

The two last projects I did. One was with a legal team and one was a boutique hedge fund. With the legal team, using a tool called Process Street and it’s documenting all their processes. This is again, going to the client avatar and setting them up for success and setting them up for growth. We wanted to make sure that they can hire more people. They would all be following the same cheat sheet, the same process. If someone went on vacation, that transition could happen seamlessly. That was more in terms of business operations, documenting the processes, spending a lot of time talking through what happens at this stage, what happens at that stage, who’s responsible, when is it you buy, what is the deliverable and documenting that whole process.

That was for the legal team. For the boutique hedge fund, there was a lot more behind the scenes. They’re back-office. They have a 20 to 30-person team. What happens in the hiring process? What happens when they want to go to conferences? The last request actually I’ve got a call scheduled with them is as simple as organizing team travel. There were many conferences and people requesting time to go travel and the budget management of that. We wanted to streamline that, have a funnel. See funnel and develop that funnel a lot with automation so that all the right people were being informed and all the information was going to the right place for something as simple as a travel request.

You spend a lot of time working with the client, understanding their business or their processes. I guess what you were saying with the legal team and helping to organize it in Process Street. You’re doing what maybe some of their operations people can’t do or don’t have the unique ability for. Does that start setting them up for scale?

Maybe that they don’t have the in-house operations person available or they’re not knowledgeable. Part of this would be training because if we are going to set them up for scale, they need to be able to do the day-to-day management once we’ve done the bulk of it. It’d be usually training up their in-house person so they could do the small tweaks later on. I use a personal example, but I don’t want to limit that to me. We have a whole team that does that as well.

When you’re working with a client, how do you get the vision of what they want on a project? You’re working with them remotely, aren’t you? You’re not on site with many of your clients.

All remote, which is wonderful. It’s a lot of calls. I always start and that’s the same for the business operations and the marketing strategy people is let’s get on a call and listening, listening to their needs and catering to their needs because it all has to support what they want. I can’t impress too much my opinion on things. I have my opinion and I can make suggestions, but at the end of the day, the process has to work for them. They have to buy into it because they have to use it at the end of the day. If they don’t have that buy-in, then they won’t use it. That would be a shame.

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