Ep. 07 – Decentralizing Business Operations with Shiv Narayanan

to help manage membership, website, events and other activities. COO Shiv Narayanan dives into the impact of running an organization in a more decentralized manner while tackling the concept of natural hierarchies. Specializing in lowering customer acquisition costs, capturing and cultivating high-quality leads, and maximizing lifetime value, Shiv uncovers the three significant pillars of self-development, the ten key hiring strategies for effective growth within a company, and the key to team decision-making. Shiv also shares the changes they made to adjust and reach the target after being acquired by Personify.


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Decentralizing Business Operations with Shiv Narayanan

Shiv Narayanan is the Chief Marketing Officer at Wild Apricot over Toronto, Canada and while his title is CMO, he also functions as the company’s Second-In-Command. Wild Apricot is an all in one membership management SaaS product for small associations, clubs and nonprofits. They’ve got a huge membership base and in fact, we are utilizing their software for our COO Alliance. On top of being the Second-In-Command for Wild Apricot, he’s also a Cofounder of How to SaaS, which is a go-to podcast for growing cloud software companies teaching them marketing, sales, business development and customer service best practices and strategies. 

As if he wasn’t busy enough already, Shiv is also a strategic advisor for two companies in the tech space, Shoelace and Crossrope. Another thing that we’re going to be diving into is the Founder of Wild Apricot. Dmitry Buterin is the father of Vitalic who is the guy that created Ethereum, which is the second most popular digital currency in the world. I’m looking forward to learning about that as well and how it tied into a lot of the early stage employees at Wild Apricot, holding some of that digital currency. Shiv, welcome.

It’s great to be on, Cameron. Thanks for having me.

Tell me how you got in with Wild Apricot originally. I know the Founder of Wild Apricot. I’ll let you give us some of the fun stories and give away all the cool stuff you’ve been involved with because there’s a little bit of a fun family hyperlink there. How did you get involved with Wild Apricot and what’s the journey been for you?

In 2014, I had left my last startup. It’s a company called Mobiroo and I had slowly worked my way up the ladder. I started in an entry level position there and worked my way up to the Head of Marketing and Sales, but it was a fairly small company. I decided that it was time for a change. I was looking around Toronto to look at some of the top SaaS companies because I felt that was the space for me to go into. That’s where it came upon Wild Apricot and I connected with Dmitry who was our former CEO when we got acquired in October. Slowly from there, I came in and took over the team. I wanted to correct one of the things you mentioned which is we don’t have a second-in-command. I am the CMO of Wild Apricot and we have an interesting structure, which is we have different leaders in different areas of the organization.

That’s evolved in that time that I’ve been here. We operate in tandem to create a COO by a committee in some ways, which includes the head of product, myself and the CFO. It’s an interesting structure that we have going on and that’s evolved over time. That’s connected to the story of me joining Wild Apricot because when I joined, it was very hierarchical. Dmitry Buterin, our last CEO, all the final decisions went through him and we had the key managers in all areas of the business. One of the things that he did very well, and that’s a key part of the reason that we got acquired in October of 2017, is that he slowly started to relegate power and authority to all the leaders in the organization.

As he started doing that, he was no longer a linchpin or a bottleneck for the organization. As those leaders have come up, we’ve been able to run the business without him. In fact, in the year leading up to being acquired, he had slowly stepped away from the business because as some of your audience may know, he is the father of Vitalic Buterin, who is the creator of Ethereum. He has a lot of investments in that space, so Dmitry wanted to step away from Wild Apricot and go work in the blockchain space. Those leaders coming up in our organization helped us transition Dmitry out of the business and find a way to operate to still grow the business to the next level.

How was that? That’s only unique because he’s tied to Ethereum, but there are a lot of founders who get distracted with another business opportunity. Clearly, this is a fairly big one when his son is the founder of the second largest cryptocurrency in the world. It’s easy to get distracted in that and it’s certainly super profitable, although Wild Apricot as well is wildly successful. What was it like when you started to feel the CEO pull away from the day-to-day? How did you lead the team and how did the team get through that?

It was a process that went on for many years. Dmitry, to his credit, didn’t pull away until the right moment. There were times if he had pulled away, I think the business would have gone into a lot of trouble. The timing of when he decided to start stepping away, it was ideal because we had leaders who could step in to fill a lot of the gaps that he was taking on. Things like working on the business, growth strategy, thinking outside of day-to-day operations, that’s a lot of the work that goes into the CEO’s lap. He didn’t have to take care of that as much anymore because there were so many leaders in the organization, but that transformation took time.

It started in the winter of 2015 where we had our annual meetings. There was this book, it’s called Reinventing Organizations by Frederic Laloux. I highly recommend it to your audience, especially if they care about culture. It’s a framework on how to run an organization in a more decentralized way. You may be familiar with how Zappos has been implementing holacracy and Tony Hsieh has been putting that into place and they’ve had their ups and downs and that’s been documented. What Tony Hsieh has shared as well as holacracy is a type of an organization that’s mentioned in reinventing organizations, which is a teal paradigm.

A good comparable to think about it is as cities double in size, they increase efficiency. For example, there are more people going to work, more people doing more activities, more jobs, productivity increases and more things are getting done. When a company doubles in size, efficiency decreases. The reason for that is there are far more bottlenecks. Let’s say person X in the customer support team wants a computer. That goes to their middle manager who goes to the chief customer officer who goes to the CEO/CFO, then the decision comes down the ranks. For a decision as simple as buying a computer, there’s a lengthy decision-making cycle of two weeks. That’s way too long if the decision is too small. The idea of this paradigm is to put the power of decision-making into the hands of the people as much as possible to remove those bottlenecks and that cycle that goes up and takes up a lot of time to come back down.

That’s what we’ve been implementing ever since then. We’ve had a lot of false starts, similar to the way Tony Hsieh has documented the way they made mistakes at Zappos, but where we are at now is we have a lot of natural hierarchies and those natural hierarchies lend to leaders to emerge. Those leaders have the authority to make big decisions. As they step up more and more, it gives the people that were previously filling those roles space to take the organization into the next level. That moves up the chain all the way up to where Dmitry’s seat is. That was a seat that we no longer needed to fill because of the people that were right below him in the former hierarchical structure have stepped up so that we no longer need that.

Did Dmitry start Wild Apricot?

He did.

Does he still own equity in the company or did he sell?

He sold all of his equity.

Once that happened, what was that transition like and how did that culture change? How did you adapt and get the team to adapt to the new culture of being owned by other owners? Who acquired you?

We were acquired by a company named Personify. It was an interesting process. Throughout the acquisition process, we had been transparent with all the employees and stakeholders involved. That process started in about December of 2016, then we were finally acquired in October of 2017. I did a full podcast episode of this on my podcast where I documented all the different stages of the journey, but in that time, we did multiple pitches and talked to multiple different parties who were interested in us. A couple of things that we were looking for was one, somebody who aligned with our mission. They understood our market. They want to do the same things for our customer base. Also, they aligned with us on culture so that we didn’t have this conflict of somebody coming in and saying, “Now you’ve got to go back to the two-headed dinosaur of a CEO/COO model and you’re reporting up and there are hierarchies back again.”

We wanted somebody who would respect that and Personify has done a great job. Their CEO, Eric completely understands our culture and that has helped the transition a bunch for us. The other part of it was over that transition, we’ve had to educate all the different stakeholders involved. We were educating our employees on how operations will change in the new world where we are owned by another company, and also there are other complicated factors like we’re owned by a private equity firm. There are reporting structures and dynamics that didn’t exist in the past, educating our employees on that, building communication and education for Personify and their executive team to let them know how we operate. They’re increasing their understanding of our strategy, how our culture operates just so that nobody feels this panic mode, knee jerk reaction to come in and try to fix everything. As you build that understanding, that also breeds trust when you try to make plans, strategies, forecast, financials, all those things that are a pivotal part of operating a business.

There are so many different components to it as well. If you look at all those aspects of the company that you’re involved in, what would your unique ability be if you had maybe two or three things that you can do and you can do for free? What would the core parts of the business that you just love and get energized from?

For me, it’s a growth strategy. It’s thinking about what the next growth lever is. I would say that’s the only one that I try to focus on. Over time, as I’ve relegated my own authority and given more and more power to the people that used to report to me if you will, that’s been the area where I’ve focused the most. Where are the next two, three focus areas where if we put all of our energy into in terms of marketing, product support, engineering, everything put together, that’ll take our business, our growth to the next level? That’s what I’ve been focusing on, and that was a big part of the acquisition. You have to explain where the growth plans are because at the end of the day, they’re buying an asset. If they’re buying that asset, they’re not just giving money to let it sit still. They want to want that asset to appreciate and potentially even flip that asset in the future, especially if it’s a private equity firm. They have investors who have money that they put into buying Wild Apricot. They want to realize that return at some point. Growth strategy is the place where I put all of my time.

Jim Collins used to call it the flywheel effect. If you had that one area of your business that you were completely pushing on, it would start to go faster and faster almost with its own momentum.

We’ve definitely seen that. You wrote that book Double Double, which I’ve read. There’s another mentor of mine, his name is Jay Abraham and he wrote this great book called Getting Everything You Can Out of All You’ve Got. I’m from that school of thought, which is every business has a certain number of levers. You’d have to know the right configuration and each business is different but when you pull the right levers, there’s a lot of value to be captured from what’s already there inside the business. I’ll give you an example. Wild Apricot processes about $300 million in payments annually through our platform because we have all these membership organizations that charge their members for regular membership dues or events or donations. We don’t take a cut of that.

One of the projects is we launched our own payment processor in partnership with another payment provider. We get a cut of every single transaction. That’s a project that took us a year to put into play because it’s not as simple as we’re going to launch a payment processor. First, you need to get alignment from all the key stakeholders. You need to go negotiate the contract and evaluate your different options, then you’ve got to put it into the product roadmap, deal with bugs. You’ve got to do the go-to-market planning, prepare support, prepare the billing. There are so many different areas and it’s taken us a year to put that into place. We have a forecast based off of that strategy.

When you’re sitting looking at all this stuff, how do you prioritize your time? How many employees do you guys have inside Wild Apricot?

We’re at about 100 to 110. It varies.

How many were there when he joined?

About 65 to 70.

It’s still a reasonably good size, but you still doubled. How do you prioritize your time?

Most of my time goes into either those big growth levers and those big initiative projects that we’re talking about, that would be number one. Number two would be anybody who is dealing with growth areas. I spend a lot of time supporting them with coaching, advice, education, whatever I can to help them achieve whatever they’re trying to achieve. That’s an interesting topic we should touch on is how we manage forecast and accountability with people like that. Number three I would say is a lot of stakeholder management. Probably the most omitted and most pivotal part of any growth leader’s role is managing expectations across all the stakeholders. For us, it’s even bigger than ever before. Before I used to just talk to Dmitry and our leadership team, but now it’s our leadership team, plus the new CEO of Personify, plus we’re talking about the private equity firm. There are more nuances than ever before. There are a lot of meetings, one-on-ones. Those would be the three places where most of my time goes.

SIC 07 | Decentralized Business

Decentralized Business: As cities double in size, they increase efficiency; but when a company doubles in size, efficiency decreases.


It’s funny because I always say that the leader’s number one job is to grow people. It’s interesting that you said it’s around stakeholder management. Tell me what you mean by stakeholder management and how you focus on that.

A good example I like to use to explain to people is I’m a big fan of hockey and in the hockey world, there are a lot of GMs who get fired every year and just like any sport. General managers are getting fired left, right and center as a team doesn’t perform. Something interesting has happened. The New York Rangers, they released a letter to their fans saying, “We’re going to start sucking for a while. We’re going to trade some of our good players.” After that, they traded two of their best players. When they did that, nothing went wrong. The fan base understood and there was this sense of transparency. Managing up is as important as managing down.

That’s something that has taken me a very long time to learn and I make an extra effort to do that. I think that that’s something people miss is your job is to make sure everybody understands what the expectations are, what the growth rate is. Even if you miss your target, why did you miss your target? What are the nuances that went into that missing that target? What are the changes you’re going to make to adjust and reach your targets? There are so many different conversations that need to happen. You can avoid that. In the pursuit of chasing the target, you might ignore the communication piece, but the communication piece is part of your job description.

You’ve got your insights on this stuff. Where did you gain your skills along the way?

It’s a lot of mistakes made along the way and I have no problems sharing this. There’ve been many times. In the middle of 2016, we were having a tough time on our marketing side. The thing about Wild Apricot is it’s an exceptional business. Our fundamentals, our strategy is so sound that the business continues to grow. It’s grown significantly, 20% plus, over the years. What happened in 2016 is as we were figuring out this cultural dimension, there were some parts of our marketing and sales area that weren’t going well. I’ve had moments where I’ve thought, “Maybe I’m not going to be here in a couple of years.” As you have moments like that where you think you’re on the verge of being fired or you make a big mistake or you make a mis-hire, you have to let go of somebody who you thought was going to help you solve a major problem, all of those big decisions and moments come up. To be honest, the only way to learn things is making those mistakes and then you recover and learn. “Here’s what I did wrong in this situation, here’s how I can implement it differently.”

You’ve also talked about a couple of things. You talked about the fact that you’re a part of a mastermind group where you work with the Entrepreneurs’ Organization. I started a group called the COO Alliance, which is the only network of its kind in the world for the Second in Command. You’ve also mentioned even having read my first book Double Double, so you’re clearly into self-learning. Did somebody tell you to read Double Double or did you just grab that on your own?

Just self-research and I talk about this a lot with a lot of people. I see three major pillars of self-development. The first is self-study and that is finding any kind of book, YouTube video, TED talk, audiobook, podcasts, anything that you can get your hands on to get good at that thing. The second pillar is peers and that’s where tools like COO Alliance, my EO group. I also hold a mastermind on my own for growth leaders at other software companies or key marketers around Toronto. They help because you go in and you share your experience and they bring their experience and you can learn from each other, “I’m having problem with this employee. Do you have any experiences that can help me here?” or, “I’m having a problem with the sales processes. Does anybody have an idea?”

The last piece is mentors and coaches and having a person who’s ahead from me for a long time. “That was Dmitry. I know Cameron.” There are a lot of CEOs that you coach yourself. Those people will understand that you need somebody who’s done it before to be able to coach you through whatever problem it is that you’re facing. The last piece is a pillar as much as I would say it’s essential to getting the most out of these three pillars. It’s a sandbox or a place where you can take everything you learn and test, experiment and understand your version of the truth. What works for me and Wild Apricot with all the learnings that I have doesn’t necessarily work for another software company. I have to learn as much as possible, come back, test it, then reject anything that doesn’t work except things that do work, change things, adjust things, then also building as many reference points as possible.

You mentioned in the intro that I’m a strategic advisor for a couple of companies. That’s part of the reason that I do that. It adds a lot to my plate in terms of the time value of money. The return is not as much as the experience of having that many reference points. It’s been four years that I’ve been doing this, I have 20 or 30 companies that have gone deep into their business, looked at their financials and help them. Whenever I look at SaaS company, I know, “This is the problem that you’re facing. Here’s how to address this.” Maybe it’s sales, maybe it’s customer success, maybe it’s demand generation. You just know based on the number of reference points you have.

You’ve got your 110 employees. How many are centralized out of your home office in Toronto and how many are decentralized working remote?

We have two offices. Toronto is our head office and we have 30 people there. That’s all the customer-facing functions and our leadership team, then Moscow is where our entire development and engineering team is. That’s 80 people.

Do you have no one who’s working remotely? Are they all in those two offices?

Yes, that’s right.

How do you work with a team in Moscow? Is it six time zone differences?

It’s about six hours. I would say the biggest challenge with that is the language barrier. It’s not as big of a problem as you would think because we have English classes there. People have made a big effort to learn English and that’s gotten a lot better. There are a lot of key players and leaders there who don’t have that problem at all. The second part is more about the distance. If there are a lot of customer-facing activities here, that distance makes it hard to say, “I just learned this thing from a customer. Here’s a problem that I’m facing.” That disconnect is something that we’re constantly working on. One thing we’ve done is we’ve taken ten people from here over to Moscow, brought twenty people from there over here to build those personal connections so that when you run into problems, you have ways of working together.

You said something that I thought was cool. You said that a lot of people over there have taken the initiative to learn English. I was at one of our COO Alliance events and we were talking about training employees and how the leader’s job is to grow people. Somebody in the group said something profound to me and it was that, “Why are we so focused all the time on growing people? Why don’t we hire people who grow themselves?” It’s hiring people like yourself that are self-driven learners that are hungry to get better and are working on self-improvement in business and personal. Is that something you guys use in part of your interview process at all? Do you look for that as a core trait?

100%. I mentioned that time in 2016 where we had somewhat a tough time and myself personally. One of the big reasons was we made some mistakes in hiring. When you coach players who aren’t the exact right fit for certain roles, that becomes a far bigger problem. Hiring to me, one of my biggest learnings has been that is where it all starts. Forget the post-hiring processes like people onboarding and retention. It starts with hiring and I’ve put a lot of effort into thinking about every time we’ve had a problem with an employee that we’ve had to part ways with conflict and issues that seeing unresolvable, there seem to be some issues that are in place. I’ve made a list of about fifteen or sixteen things that I look for in candidates when I interview them and it has nothing to do with technical skills. It’s entirely about attitudes.

For example, number one, are they self-aware? Are they self-reflective? Do they constantly evaluate better ways of doing things? Number two, are they committed to deep work and mastery? You may have heard of Cal Newport’s Deep Workbook. Number three, do they fully commit to doing everything that they want to achieve? Do they put in the time? Do they hustle? Number four, do they actively invest in their own growth like self-study, peer groups, mentors? Number five, are they a stoic? I think this is one of the most important ones of them all because one of the biggest problems you have during conflicts is people feel like a victim, with a victim mentality. I try to screen that during the interview process. Anytime somebody comes to me and says, “This didn’t work out at my last job because my manager was the problem.”

My number one question back to that is, “I hear you. Your manager probably was stupid, but what could you have done differently? Can you list something for me that you could have done differently?” If that person can give me a tangible answer, that shows me that that person doesn’t think they had any power in this situation, which is nonsense because we always have somewhat of a choice in every situation. I want people who can see every obstacle as an opportunity. Number six, do they have true grit? That’s about being resourceful. There’s a book about this as well and a TED Talk by Angela Duckworth which is to get something done, there’s always going to be that dip that Seth Godin talks about. You’re going to start something and then you are going to hit a roadblock. People who finish things are the ones that are truly gritty.

Number seven, do they value the team over the individual? It’s clearly important. Number eight, do they have an A-plus attitude? Are they always positive even when things are tough? Number nine, did they have a high EQ? Did they have a high dose of empathy? I think this is very important because when things get tough, it’s very easy to blame and it’s very difficult to put yourself in the other person’s shoes, so empathy is critically important. Number ten, do they take on extreme ownership for everything they do? There’s a book by Jocko Willink on this topic who also has a great podcast and it’s about taking self-accountability for anything that happens and there’s a bunch more. I can go on forever, but these are the types of characteristics. I think A players have more soft skills than B players. It’s not about technical. I can teach technical.

You just nailed it right there that the A players have more soft skills than the technical skills of B’s. I don’t know if you’ve read any of Simon Sinek’s materials, Start with Why. Simon and I had been friends since 2003. He flew out to Vancouver to meet me because he read about me in Fortune Magazine. We’ve known each other for a long time before other of us got known. He’s extraordinarily well-known, clearly. He talks about the golden circles of the why, how and what and the why being that core that companies need to exist. 

I took that model and overlaid it over top of training and said that we need to make sure that all of our employees are trained on why we exist: our core values, our core purpose, the history, the lore, our vivid vision of the company, the real why we exist and why we get up in the morning. The second circle is how we do what we do. That’s all the soft skills of situational leadership: time management, coaching, delegation, conflict management, problem-solving, all of the core leadership skills. I think we miss on that, then the outer ring is what we do. I think too many companies are focused on training people on what without training and certifying everyone on the why and the how. I think it sounds like one of your core tenants that you focused on as a leader and certainly Wild Apricot but mostly it’s the area of the how you do what you do.

That’s where the cultural piece also comes in. Steve Jobs has this great quote where he talks about if you want to hire great people and have them stay working with you, you have to let them make a lot of decisions and you have to be run by ideas, not by hierarchy. When you think about why we do what we do, we have a very clear mission. Half of it is about our customers and how we’re going to serve them better to help them run better nonprofits and organizations to make an impact on the world. The other half is about our employees. It’s about giving them a place where they can reach self-actualization and be the best version of themselves. That’s a powerful way that unites our company. It brings everybody into work pumped up to do what they do. That to me is more important than more of a flowery why statement.

I talk about my vivid vision and I talk about it in the book Double Double. Do you guys have a vivid vision or what I used to call the painted picture in Wild Apricot?

We have something that we call the company book and it outlines every aspect of our business, including culture, strategy, where we’re going, implementation level work. It’s everything.

Do you share that with your customers and your suppliers as well?

We share parts of it that are relevant to them, but not everything because obviously there’s some internal stuff in there.

Just for fun and especially that your CEO moved on, take a look. My book that came out, it’s called the Vivid Vision. Take a look at it because I took the concept of chapter one from Double Double and expanded on it so that companies can truly understand how to replace mission statements with this four or five-page written document describing their company in the future. It might be cool for you guys in the next phase of your growth. Another thing I want to ask you about is meetings. One of my books called Meetings Suck. People are buying it for every employee at every company because they realized that meetings don’t suck. We suck at running them. My guess is that you guys are pretty good at running meetings. Tell me what you’ve learned and how you’re running it successfully in high impact meetings?

First, on the Vivid Vision book, that’s on my list to buy and read. I’ve seen it all over the place, so I will read it for sure. On the Meetings Suck thing, I’ve also read that and we are strong believers and not wasting anybody’s time with meetings. That’s part of the decentralization. One of the biggest ways people deal with solving problems in a super hierarchical organization is, “Let everybody get into a meeting.” That’s the solution to every problem that people face. I think one of the ways we tackle this is by something that we call the advice process.

What’s that?

SIC 07 | Decentralized Business

Reinventing Organizations

When you have decentralized authority, people always ask me, “If anybody can make any decision, how do you guys make sure the right decisions are being made?” We started this whole process because we saw two videos from Spotify on how they run their engineering culture and I highly recommend your audience looks that up as well. They talked about how they run a massive engineering team to produce this world-class product. They talk about this concept of, “Agile at scale requires trust at scale.” If you’re going to build something massive, you need to have a lot of trust in your teams. When you give trust to people, then part of that is accountability. When you give people total trust, they’re accountable based on the freedom that they have. The other part is that you almost have to trust them to loop you in at the right time. A lot of seconds-in-command come on your podcast, they have implicit trust from the CEO that the CEO will be looped in when there’s an operational decision that requires a CEO.

Why can’t that concept descale to all other people? That’s where the advice process comes in. You have people on the team. Let’s say I have to make a decision. We’re running a webinar and it has a speaker and I’ve got to figure out what the topic is. If I have to have a meeting and talk to our head of content, Donald, and say, “Donald, what’s the webinar topic? Let’s talk about it together.” I’m leading the initiative. Instead, if Donald thinks about the topic, talks to this speaker who’s coming on the webinar, puts the presentation options together, then he loops me via advice because I have a few things. I have expertise in the area, I have context, I have an understanding of our strategy. Based on all those things, he goes, “Shiv is an advisor I need to talk to before I can finalize this decision.” I trust Donald to loop me in at that right time. That might just be a five minutes sync-up versus it being a one-hour meeting where we’re spending talking about webinars going in circles. That advice process shortcuts the number of meetings we end up having and they ended up being smaller meetings.

You’re just talking about who the subject matter experts are and letting the stakeholders know what’s being involved and how the decision’s being made, whether it’s being made by a group or consensus or one person, but at least people, if they’re being involved in the process, are being told in advance.

The idea is that if you do that, inevitably all the right stakeholders will be looped in anyways. One of the biggest problems in meetings is there are people in the room that have no reason to be in the room. Whereas when you give that power to the person who is making the decision and say, “Loop in only the people that you think are important here.” Let’s say there is a critical omission. Let’s say he forgot to include me and it gets to a point where a mistake was made. We can have a conversation and say, “Can you please loop me in next time?” Most of the time with most decisions, you don’t burn down the business. It usually seems far worse than it is. It is also giving people the freedom to make mistakes. Mistakes need to be part of the culture. Accepting them, embracing them because that’s how people in the organization grow. As people grow, that’s how you can build a company that can scale to $100 million or $1 billion. There’s no way me or if Jenny who leads our product or Shawn who’s our CFO, there’s no way just the three of us can be the leaders of the business if we go to $100 million. It’s impossible. We need multiple leaders.

We do need multiple leaders. It’s interesting how you guys have worked through the whole decentral organization. I want to ask a couple of questions about that. You touched on something that you breezed over quickly and it was, “We shouldn’t be inviting people to meetings unless we give them a voice.” I don’t remember what it was exactly you said but that was the way I interpret it. How do you decide as a company who to invite to meetings and then how do you not invite people who shouldn’t be there because their time is better spent working on other projects? How do you not invite them without hurting their feelings? This is a huge lesson for people to think about.

I think we’ve gone through that evolution. That’s a word we’d love around Wild Apricot is everything is an evolution. There’s no drastic change. We’re evolving just like anything else. There was a period when people had some feelings hurt, then over time including myself, there was a time when I was involved in every decision related to marketing and growth all the time. We start leveling up and the people on your team started leveling up. They don’t necessarily need you in the room anymore. There were times when my feelings were hurt. Do I need to be in there? Am I making a mistake by not being in there? There were times when maybe they made a mistake that could have been avoided if I was in the room. As that evolution has been going on, you can see the value of it. You can see how people have stepped up, how much more freedom I now have to be able to think about other areas of the business, those big topics that we were talking about, which I didn’t have before because I was so in the operations of the business.

One topic I do want to touch on is accountability to that because when you have so much freedom, you can go in the wrong direction. That’s why you need accountability. Accountability is a core part of those fundamentals. I’ll give an example. Let’s say we’re talking about webinars again. The way forecasting usually works in other companies, at least as I understand it is there are a few select groups of people that do the forecasting. In our company, instead of me creating the forecasts of how many new accounts we’re going to land, how much growth we’re going to have, it’s a question that I put back to every person on the team. I’ll go to Donald who heads up our webinars and say, “How many webinar registrants are we going to get? How many of those webinar registrants will go to trial? How many of those people will get to paid status?” I’ll ask the same thing to our paid media manager. “How much are we going to spend on Google ads, Facebook ads, Bing ads, Capterra? How many trials would that bring? How many upgrades will that bring us?”

They’re doing backward forecasting on all that spend and then giving me a number. With all the different functions combined like SEO content, paid, other growth ideas like that payment processor concept that I mentioned, combined that into one single forecast and that’s what’s presented. Everybody on that team is accountable to the number that they helped to create. I have a mechanism to hold people accountable as well to say, “These aren’t my numbers. These are your numbers.” We’ve gone back and forth and to crafting this together, but we had a core agreement. We had an agreement on what those numbers would be. That that gives us a foundation for having a conversation instead of me trying to manage with control, it’s managing with trust and accountability.

I can’t imagine you guys have a lot of turnovers.

We don’t. People don’t leave Wild Apricot.

You’re in a very competitive job market in the IT space. For our very first podcast, we interviewed Harley Finkelstein from Shopify. He’s the Second-In-Command there. How are you competing against a brand like Shopify in the Toronto marketplace?

I think there are a few things. One is our culture. It’s a huge differentiator. Shopify is a great company and a lot of people that worked and Harley’s a great guy and smart. Shopify is definitely one of those companies. For us, we are separated by culture. I can tell you the number of times I meet candidates who are interviewing with us who say that the last company that they were working for, it was completely unclear as to what the strategy was. Their role was completely restricted. They were told to sit in a corner and write a blog post and that’s it. They had no idea what the numbers were. The financials were not transparent. It’s a different environment. People love coming to work with us. If you think about a common metric for a product, which is NPS, Net Promoter Score, that tells you how likely some of your customers refer your product to somebody else. Companies are like that because employees refer other employees. The retention of an employee is just as important as hiring somebody. With Wild Apricot, we’d barely have had any turnover. I can probably count within ten fingers the number of people that have left us.

I had a client that I coached for years out of New York City and they only ever had one employee in nine years quit or be poached by another company. They had a huge wine rack in their New York office. It was filled with Bordeaux and Burgundy wines, expensive ones. Anytime an employee attempted to be poached by a search firm or another company, all they had to do is say, “I got poached by this company. I told them that I’m not leaving.” They could walk over to the wine rack and grab a bottle of wine and it was like a badge of honor. It’s like, “I almost got poached twice. I get two bottles of Bordeaux.” They used to joke out of it. No one was ever quitting. It’s almost like they were running job ads for themselves just to get recruited so they can fill up their own wine cellar.

If I can add one thought to that. With employee retention, the reason it’s a big topic is companies lose a lot of productivity when employees leave because the cycle to hire somebody else, potentially that person may not work out as well as the person that you had in the past. It leads to a macro impact if you look at it across the board of product, support, marketing, sales. By keeping people building a healthy business is far more likely than if you have a lot of turnovers. That’s another differentiator for us amongst all the SaaS companies in Toronto. I would say we’re in the top five just based off of that. Our financial health is way higher than a lot of those companies simply because we have employees who have institutional memory, who know the ins and outs of our market, who know what our customers want. That leads to even more health in the long-term as they stayed longer with us.

You guys are an extraordinarily well-run company. Why are we not hearing more about your company as the best place to work in Canada yet and one of the best run companies in Canada? Are you not entering the awards or am I just daft and not seeing you up here?

We don’t enter a single award. Not yet. We started the show off with Dmitry, so it’s an important one to mention is the way Dmitry runs his life is always inward, always focused on internal mastery. When you talk about CEOs, companies are often manifestations of their CEO and that’s how Wild Apricot has been built. That’s one of my personal missions as well is to get the word out for Wild Apricot by doing things like this where we’re in super hiring mode. I want people around Toronto and everywhere else to know how great of a place we are to work and how great of a business we are as a SaaS company. The other thing is we haven’t raised any money because Dmitry sold his last company to Microsoft and it was completely bootstrapped by him. When you raise money then you get the Hoopla or you go to Y Combinator, then you get the press coverage and all that. We haven’t had any of that. We’ve just been chugging along, running a great business.

I want you guys to scream and shout from the rooftops a little bit because you are doing a fantastic job. I know a lot of the best companies to work for, certainly in Canada and as well as in the US. I coach a lot of them and have coached award winners in about six countries. I’m just impressed that you guys are as well run as you’re coming off. I encourage you to get your company entered into every contest you can because that third-party credibility, that social proof is huge. Sharing your vivid vision and the process of what you’re getting and garnering will be huge for you guys as you continue to grow. I want to shift gears and just ask one more question. I’m not trying to cut your knees out from underneath you, but I think you said that you learned from your failures. Let everybody learn from one of your failures. What was one big failure that you had along the way and the big lesson that came out of it?

I grew up in India and I lived there for ten years of my life and it was a very competitive academic system. In the summers, I would play outside for about a couple of hours and the rest of the day was studying. The narrative there and the school system is always the higher the marks that you get in school, the more of a genius that you are. Over time, one of the things that I have had programmed into myself is that genius is about being smart. I’ve had to flip that at Wild Apricot. Initially, I did think that is that if I could just be smarter, learn one more thing, implement one more growth strategy, that’ll take the company to the next level. The flip that it’s come from me from the skill transformation, from the decentralization, from finding ways to lead people without power as much as possible, is that genius isn’t about being smart. It’s about leading people and it’s about working with people. The sooner people realize that I think that’s the fastest way to make a big impact. If you want to do small business, a solopreneur, eCommerce store, you can do that alone but if you want to make a big impact, run $100 million company plus, it’s all about the people.

It is all about people. Jim Collins talks about getting the right people on the bus, the wrong people off the bus and everybody in the right seats. It truly is an impact when you get the people component down and culture. I always say that you have to build that’s a little more than a business and a little bit less than a religion. It has to be in that zone of a cult. I’ll give you a balance. Instead of telling us something you screwed up on, if you could stand on the rooftops and brag and say, “Look at us at Wild Apricot or look what I’m bringing on the table.” What would you be saying is one of the unique ability skills that you could maybe impart on our audience?

I wouldn’t focus on myself but more just overall on Wild Apricot. The amount of effort that we focused inward has produced an amazing business. That’s what I would encourage other people to do as well is dialoguing with customers as much as possible. Increasing the amount of empathy you have for your customers, falling in love with them, understanding what it is that they want and need from your business. It’s doing the same for your employees. A framework that we use internally is called nonviolent communication. The idea is that nobody in the world is evil. Everybody has needs that they’re trying to meet. As long as you can help them meet those needs, everybody can get along and be fine, things like big wars have been solved with that framework, so it’s something that we believe in. I think that is what shows in our business results. Business results are the outcome of the amount of work that we put into all the different areas that are involved people.

You guys are doing a good job. Where’s your office in Toronto, roughly?

It’s right by Union Station.

You’re right downtown, so you guys are super close to another one of my clients. Do you know a company out of there?

What do they do?

Digital Marketing.

You’re talking about Powered by Search. I know Dev Basu very well. He’s a good guy. We’re in front of the university but Dev and I had a lot of conversation. He’s been on my podcast. I’m going to be publishing that episode.

He does a great job and also Matthew Bertulli. I don’t know if you know Matthew is a couple of floors above Dev and runs a spectacular company in Toronto as well.

I don’t know him, but I would love an introduction.

SIC 07 | Decentralized Business

Start with Why: How Great Leaders Inspire Everyone to Take Action

Do you ever go out to a company or a restaurant in Toronto called Baro?

Yes, it’s a great place.

That’s the guy who was my last day at 1-800-GOT-JUNK? was his first day. He’s one of the co-owners there, Michel Falcon, but he’s a global expert on customer engagement.

That’s a good place to eat too.

Thank you so much for joining us. If I can help you in any way with any of your business, let me know, but I appreciate all the wisdom and the time that you shared with everybody.

It’s my pleasure. I appreciate you taking the time to do this. It’s hard to talk about culture usually with people. I know that you get it and you’re always emphasizing the COO Alliance. I appreciate you doing this.

You’re welcome. The big thing about culture, I’m trying to get people to understand is it’s not about the free perks and the giveaways. It’s about alignment with the vision, people, culture, and communications. The media is reporting. They’re missing the point. I’m glad you got it.

I appreciate it. Thanks.

Take care. Thanks for being on the show.

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About Shiv Narayanan

Shiv has led multiple global product launches (NA, EMEA, APAC, LATAM) with a diverse portfolio of products, verticals, business models and clients in mobile, SaaS, retail, eCommerce and mCommerce.

Specializing in lowering customer acquisition costs, capturing and cultivating high-quality leads and maximizing lifetime value by increasing transaction size, frequency, and velocity, Shiv is constantly studying the underlying reasons behind why companies are able to scale exponentially and are passionate about creating a preeminent position within the marketplace as the foundation for long-term success.

Wild Apricot is industry-leading web-based software for small associations and non-profits to help manage membership, website, events and other activities. In fact, Cameron Herold‘s team uses Wild Apricot to help manage COO Alliance!


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