Ep. 115 – Stringcan Interactive Chief Operating Officer, Sarah Shepard

If the CEO is the one in the company who carries the vision, it is the COO who develops the processes and structures to make that vision a reality. Stringcan Interactive COO, Sarah Shepard sees that line separating her responsibilities from those of the CEO very clearly, allowing both of them to be the best in their respective roles. This professional relationship is part of the reason why the company continues to lead in the digital marketing for wellness space. Sitting down with Cameron Herold for a conversation, Sarah shares how this interaction plays out in real life. She also talks about some of the current obstacles in the digital landscape, keeping employee engagement, finding the right subcontractors and tips in selecting a marketing agency.


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StringCan Interactive is a digital marketing agency that accelerates the growth of businesses dedicated to wellness and wellbeing. StringCan Interactive creates brilliantly focused digital strategies with world-class implementation. Services include persona development, marketing roadmaps, content marketing, media planning and buying, and more. Sarah designs and improves the processes and structures that enable StringCan to deliver industry-leading solutions for their clients in the most fiscally disciplined manner. She’s also a cultural curator at StringCan where ensures that the team can always be their best self at work and at home. For fun, Sarah enjoys her time teaching yoga, convincing others that green smoothies aren’t scary, enjoying a wedded life, and binge-watching Altered Carbon, which I have to check out. Sarah, welcome to the show.

Thanks for having me, Cameron. I’m super excited.

What is Altered Carbon about?

It’s like a sci-fi, futuristic, robotic, ninja type show.

It is like the Singularity? Is it like when computers and humans are all merged?

Yes. It’s fascinating to see where people’s minds go if that is ever a possibility in the world and what that might look like. It’s believable and scary.

I will check it out. I’m nearing the start of a new season of something so I’ll check that one out. Tell us a little bit about StringCan. What do you guys do exactly so we all understand?

Digital marketing is a pretty interesting realm. People have all kinds of things that come to mind when they think about digital marketing whether that’s websites, PPC, Google Ads, or whatever that may be. We help businesses get found online to be super simplistic about it. Our clients come to us and they’re looking for help. It comes from a place of either they’re not getting found, not focused or they’re lost. They can be brand new businesses or even existing businesses that have lost their way online. There’s so much out there. It’s unreal to keep up with. It’s pretty hard so you find yourself needing someone that’s an expert in helping you navigate this ever-changing world, which is part of what I love about digital marketing.

Do you have specific niches that you’re deep into or experts into or are you all things digital?

Do you mean on the service side?


Our bread and butter is something that we excel at and we find our clients value. It helps them in the future, which a lot of agencies either don’t do or don’t invest the time and money that we do in its strategy. It’s a tough thing to quantify your ROI on strategy, but we have a robust process. Whether the client sticks with us on a recurring basis or not, they end up using the strategy for the long term. It helps them understand their clients better than they ever have. It’s a part of our process is secret shopping, which we love. It’s pretty fun.

Where do you get your clients?

A lot of them are referral based. I don’t know if you have ever met Jay Feitlinger. He’s awesome in this space. He talks to people in a way that they understand why this is important because it’s important to us to help our clients. A lot of businesses find success and they’re like, “Have you heard about StringCan?” We end up meeting with them and they find us to be relatable, friendly and we get the job done.

Not to say the other agencies don’t do that, but there’s something about helping those especially family-owned businesses or entrepreneurial types. They get it because Jay is an entrepreneur through and through. He gets where they are so they speak his language and he speaks theirs. It’s a great relationship from the start. Often, it’s like, “Have you heard of so and so?” We’ve got a lot of referral business, which is a great thing.

Is that your niche? Are the mom and pops, smaller businesses, are smaller entrepreneurial companies your target clients?

It’s an SMB so we have a couple of larger clients so it’s about the persona for us. There’s the person who’s trying to get out there. They’re trying with their 1 or 2 person marketing team and they’re at their wit’s end, which is most entrepreneurs. They’re trying to do everything including running their marketing department, and they’re finding themselves failing miserably, or totally overwhelmed. We like helping those kinds of clients and there are other clients that are a little bit more sophisticated who push us. They’ll ask for services, or will provide a strategy for new and exciting things and they’re willing to try it, which is awesome.

I had a client that I coached for a number of years and at the time they probably had about 250 employees. They had a marketing budget of about $1 million a year and they had an $80,000 Director of Marketing spending it. I was like, “I don’t think they know what they’re doing and the CEO doesn’t have the time to coach them, nor does the CEO know what they’re doing to spend $1 million budget.” You need to get $50,000 a year of coaching, $4,000 to $5,000 a month of coaching and direction for your director of marketing. Get an outside CMO to tell them what to work on so they can then execute on it and maybe spend $950,000 on marketing instead of $1 million. They went even heavier than that. They went for about $150,000 in strategy and plan work with companies like you, let the director of marketing implement an $850,000 budget, and knocked the cover off the ball. Do you guys do that as well where you’re coaching teams? Are you coming in as the consultant and working with them or is it a bit of both?

It’s a bit of both. We work well with other agencies so if someone has an existing agency, and let’s say they’re specializing in maintaining their website, and they want to do ads, but perhaps this other agency doesn’t. Some of them are pretty niche where they don’t diversify. We’re easy to work with and we enjoy working with other agencies because we want to make it easy on the client. Once they’re managing more than one agency, you don’t want them to scratch your head and go, “I don’t understand what’s happening here.” That’s something we’re proud of and there are others that need the help. We could do everything for them so instead of doing everything let’s focus on what’s going to move the needle and make your life easier because the last thing we want to do is make a CMO’s life harder. There’s a lot to do.

How did you get involved with StringCan?

I moved back to Arizona a few years ago and I was staying with my parents. My dad was recovering from cancer surgery so it was a good time to be back and help out my family. I saw this job posting for StringCan. At the time, it was a part-time executive assistant to the CEO. I read through the job description and I had come out of building code legislation so this sounded exciting to me. I have never been in digital marketing before. I didn’t even have a Facebook account at that time, which we still joke about now. How did I get hired without a Facebook account? It ended up being the perfect fit. Jay and I clicked off the bat and it was a great partnership from the start.

For a lot of COOs, one of the most valuable things for me getting to this place was being his assistant and understanding what makes him tick and what he needs help on, and learning from the back end. What did you say? You said, “If you don’t have an assistant, you are an assistant.” I laughed. That was a great statement. I was like, “There it is. He doesn’t realize at that moment, but that’s exactly what happened.” He needed that to move forward and to be the best CEO and visionary that he could be.

It’s a huge partnership. I was telling someone that the first thing a CEO or an entrepreneur needs to do is hire an executive assistant before they hire the second in command. The second question should come afterward. How many people are in the organization now?

We’ve got about 10 to 12 staff. We’ve got several independent contractors and partners that we use across the country. We are growing. We hired someone around Valentine’s Day so she’s had a wild ride.

Welcome to the company. See you never. See you maybe.

SIC 115 | Stringcan Interactive COO

Stringcan Interactive COO: You cannot sit still in a digital agency. If you don’t enjoy that part of the role, then it’s not a good place for you.


She’s been out of the office working remotely more than she’s been with us, in person.

Are you guys an office-based company or do you have some people remote as well?

We are office-based. We do offer flexible working environments for everyone. Which we’re now transitioning to our back to work plan. It’s one of my big focuses. We’ll see how that goes with whatever’s happening. It’s day-to-day for right now. For the most part, we work in the office because we enjoy the environment with each other. It’s like a family. It’s a fun group to be around and we work in Old Town Scottsdale so there are definitely worst places to work.

My old house was in Arcadia. I’ve got a new place near Old Town. It’s a perfect area. Talk to me about what it was that attracted you to come into StringCan. What was it about Jay, the CEO that you liked and how have you guys worked to build that relationship as the CEO and COO?

Jay is incredible. He’s the most amazing boss I’ve ever had. He’s the most amazing mentor ever. He’s super generous with his time and his resources. He never gets frustrated by questions. He’s growth-oriented with the person. He’s not selfish at all. He’s the most generous person and he loves Christmas so it’s always funny around that time of year. He goes hog wild so being the fiscally responsible person than I am, I’ve got my work cut out for me around the holidays.

How do you divide and conquer roles and responsibilities between the two of you? What reports to you and what reports to him?

We’ve been continuously revising and transitioning our processes, especially when it comes to people and accountabilities. About eight months after I started, I went to him and I said, “I love it here at StringCan and I want to be COO someday.” He was like, “Okay, part-time assistant. It sounds good. Go ahead and make a five-year plan for it.” I said, “Okay.” I made the plan and he continuously checked in with me on it. “How are you doing? What do we need to do? Do you need resources and tools?” Whatever it is. On my own, I went out and hired a business coach. I’ve been growing, learning, and trying to figure out everything that I can about this business. Have you heard of the Entrepreneurial Operating System, EOS?

I know Gino Wickman who wrote the book. I know EOS well. I know one of the top implementers in the world is based in Scottsdale, as well as we’re good friends Michael Lee Roth.

Michael’s protege, Scott, is our implementer. Shout out to Scott Elser for sure. We took the Visionary and Integrator test and it was funny. I was high 80% on the integrator and Jay was high 80% on both.

That’s where I fall as well, high on the COO and CEO side.

What’s funny is what do you like to do out of those things? They had re-sent the Crystallizer Assessment, so we redid it. He goes, “I think about this in terms of servicing our clients. The parts where I score high in the integrator are what I like to do on the client-side,” but it’s not what he loves to do on the business side. For me, it was taking things off of Jay’s plate and asking for forgiveness versus permission. I was careful about it. There were things where I thought, “I know he’s not doing this because he doesn’t love to do it and I want to do this. I’m hungry to do it.” I had enough confidence if you want to call it that and just took it on. He started giving me more seeing how it was working.

It was a natural split, which I don’t know how common that is for the visionary and integrator split to happen, where I’m operating the operations and the business and he’s running the vision. In 2019, we fully transitioned where I am the full-on integrator and I’m managing the leadership team when it comes to solving problems. I’m managing the P&L and working toward accountability on all of those aggressive goals that we’ve got going. Jay is focused on helping them strategize and see their vision for their department, people and clients. We’re still both having one-on-ones with them, but they’re focused and they’re different topics.

You’re finding your path. I love that you have found EOS and you’re putting it into the organization, too. We’ve got probably about a third of our members of the COO Alliance would use EOS. I’d say probably another third use Scaling Up, and then the other third are bumbling their way trying to find some systems to put in. They don’t use one overall. They’re taking best practices from lots, but I love EOS. When you get to 50 to 70 employees, it starts to break down a little bit. You need a little bit more mature, bigger systems, but it’s fantastic for small to medium businesses for sure.

It was life-changing for us. We self-implemented for about a year. We had a good system. We were doing annual planning meetings for two days, did presentations, and O&O, obstacle and opportunities sheets. We’re organized on an obsessive level, and especially, goal-oriented. It was starting to become about 40 hours of work each day. It was like, “There’s got to be a better way. This is a lot of work for a two-day meeting.”

It’s also nice to bring in that outside expert. When I was growing up, I would have thought my parents were idiots and I probably would have thought your parents were amazing. You thought your mom was a jerk but my mom would have been great. You don’t listen to your own parents but you’ll listen to your aunts and uncles. There’s something about that outside facilitator. If you bring in the one that fits your culture, they can work well and it allows the leadership team to take a backseat and participate versus having to have your brain on running and facilitating as well?

Absolutely. One of the biggest a-ha for us was, “Facilitating this meeting is a lot.” I’m having a hard time contributing, honestly, and trying to keep track of all the notes, and the same with Jay. It was a big decision for us to hire Scott. It was like, “This is a deep commitment. Are we ready to do this?” Every meeting is unreal how much value we are getting from this process and from Scott reeling us in, and he gets us. I’ve interviewed a couple of implementers before we hired Scott and I’m glad we went with him. He’s incredible.

I used to run a bunch of strategic planning sessions near LGO. Anybody who’s not from Scottsdale, Arizona won’t know what we’re talking about. Over near LGO, there’s a place called the Royal Arcadia Hacienda. It’s a 10-bedroom, 5-kitchen, old mansion where two presidents and Liz Taylor have stayed. It’s dated. It’s almost like decorated from when they were here last, but it’s this beautiful spread with palm trees and a pool. I take in ten people. They all stay in their own bedrooms. We run the two-day sessions in the living room and dining room there. It’s a cool place to completely immerse.

That’s a great idea. I might have to borrow that for annual planning.

Drop me an email. It’s not that expensive either. The guy who owns it is a Canadian. It’s a great space for running facilitated retreats. What are you struggling with in terms of the digital space? There’s a bit of a roll-up happening in the digital industry. There’s specialization. Digital has changed so much. From ten years ago or so, you could never find an expert and now, it seems like we’re tripping over them. What are you seeing changing in the industry? What are the obstacles that you’re encountering growing the company?

Part of it is finding when to pivot and when to pause. We call this shiny object syndrome where it’s like, “This thing is cool.” Let’s call it some ad platform. One, getting the experience on the ad platform. For example, blogs. It’s tough sometimes to talk to the value of organic traffic. When somebody is not clicking on something and making a purchase, clients seem to struggle a little bit with how does that fit into my overall strategy? Let’s call it an old-fashioned type of marketing and it’s SEO.

SEO is a complicated and intricate system. It’s so much more than that. Part of it is people know enough to be dangerous, but you want to help focus them. Getting their trust and then guiding them toward what makes the most sense for their business and their customers, and continuously having to refine that messaging. What worked six months ago is not going to work now. That’s partly because the algorithm changes. We’ve got to keep adjusting. Part of the struggle is you cannot sit still in a digital agency, cannot sit on your laurels, and just rest. It’s not part of the deal.

If you don’t enjoy that part of the role, then it’s not a good place for you. If you love constantly having to pivot, provide different opportunities to your clients, and then educate them, which is important to us, we want them to know what’s going on and what’s new, that’s a little bit of a struggle. For the most part, we enjoy the challenge. Jay, in particular, thrives on being thrown into the fire of some new opportunity. We are all gung ho about figuring it out.

It counters the board and the entrepreneurs. We need the new new thing. Even if we don’t need the new new thing, we think we need the new new thing. It’s crazy. It feeds our ADD. I have 17 of the 18 signs of attention deficit disorder. My ex said that if I was paying attention when they did all the testing, it would have been 18 for 18. She’s probably right. One of the things that I’ve always been curious about is it’s tough to keep Gen Y in a company for more than 2 to 3 years. Gen Y in the digital agency space are all wanting to go off, freelance, and start their own companies or start freelancing. How do you keep them? How do you keep them engaged, happy and working within an organization when they feel like they can go off and start their own company? In often cases, they’re wrong.

It’s funny, Jay is transparent in a thoughtful way. People say that they’re transparent but maybe that’s more TMI than transparency. We’re transparent with the way we run the organization and parts of our financials. We always have our revenue goals on the board. It’s in a formula so nobody can decipher it on the fly. Once people understand how much time, effort, work, blood, sweat, and tears goes into running a company, they’re like, “Jay, Sarah, and the team take on a lot of that burden for me. I have a lot more to understand if I want to run my own business.”

I started a small yoga business and it didn’t take off. I was busy with other things at the time and took on too much. Jay was helpful in getting me to understand where I needed to go and what to do next, and it was a little overwhelming at the time. I thought, “I’m not the visionary type.” For me, that solidified I like doing the implementing, integrating, and helping him see his vision because it’s not my unique ability. Even for myself, having that entrepreneurial spirit, I was like, “Reality is, it’s not what I love.” People have a little bit of rose-colored glasses when they want to do the entrepreneurial thing.

SIC 115 | Stringcan Interactive COO

Stringcan Interactive COO: Marketing is all about patience and letting things do their job. It’s not going to solve everything overnight.


Jay is supportive of anyone’s goals and dreams. He’ll tell them how to get started and what to do. We’ve never held anyone back for that reason. We’ve had people grow, flourish, leave and stay. Being flexible in pivoting that not just with your clients, but with your team. We are never the same type of team with the same goals and reward systems. Everything is constantly changing to adapt and adjust to what people need and want.

It’s smart. You’re approaching it the right way. Can you talk about how you find the right subcontractors? You said you’ve got some subcontractors that you work with or is it freelancers? What is it outside of the normal employees? I’ve often found that companies work hard at interviewing, recruiting and selecting employees, which is the theme of one of our COO Alliance events is the recruiting and interviewing side. They don’t tend to do it when they’re hiring subcontractors or freelancers. They tend to go, “I’ll take that referral and hire them.” Do you have a process for bringing those people in, finding them, or interviewing them before you say, “Yes, start?”

We do. It’s funny, the last contractor that we found, we were having an issue and we found an article online that was describing this process. It was an unusual, glitchy thing that had happened. We reached out and this person helped us out. They communicated with us directly as the author of this article and we ended up hiring them for future projects. It’s been incredible. The way we’ve gone about finding people has been unique.

A bunch of our freelancers has been with us for several years. We’ve had good luck with our process. It’s a blend between the recruiting process and also the sales process. Having the independent contractor understand how you go about in your sales process, what we need from them, and how we like to organize. We’re flexible so we utilize all types of platforms to what suits them as well. If it’s Slack, then it’s Slack. If it was tracked up longer, but if it’s a different software platform, we’re easy to work with.

For us, it’s being clear with what’s expected and what we need from them. Using them and then giving them feedback in real-time. A lot of people deal with a freelancer. They either fail miserably or they don’t live up to expectations, and then they let it go versus trying to nurture that relationship and investing a little bit into it. It’s important for us to keep nurturing those relationships, creating a good set of expectations, and then reciprocal friendship back and forth.

How about the company’s hiring and marketing agency? What do you think companies do wrong when they’re selecting a marketing agency?

It’s tough because it depends on where the client is emotionally at the time. When you’re broken down on the side of the road, you will take any ride that comes along. You just need to get home. It’s getting clients to think strategically about their future. What is it that you want long term? Interviewing your agency as though they were going to become a part of your team or a partner and being clear too, what are they doing for you? How are they helping you make your life easier? Do they understand what you need to succeed in your role?

If it’s a CMO with aspirations of being a CEO, how can we help you get there? If it’s someone who needs some great, on-time, fast deliverables that are excellent, let’s do it. They’re either being told. When they’re not doing well, “I need help with X, Y, and Z.” Let’s help you think a little bit more strategically about that long term on how to help your department do better, not just get this thing done for your boss.

You keep pushing back up the strategy, too. I like that. How about your firm? Do you in StringCan spend money on marketing and advertising?


There was an article that was done years ago. I don’t remember who put it out. They interviewed the top ten ad agencies in the US and they said, “What percent of revenue do you spend?” It was 2%. They’re like, “How can we tell everyone to spend 8% to 10% when you’re only spending 2%?” It’s like the Cobbler shoes. What does your firm spend your money or your efforts on?

We do all kinds of different things. We love being our own guinea pigs and we are our own client. When we do projects, for example, we redesigned our entire website, we tracked it as though it was a client project. There were client weekly meetings. There were reports done so we test everything out on ourselves. We are our own worst critics for sure. It has to pass a stringent test to get through the StringCan team. Testing out all kinds of services, whatever is new, we’re going to do it first to make sure that one, we built a relationship if it’s a new vendor. Two, did it work or what did we learn from that? We don’t want our clients to be the guinea pigs for anything new. We spend money on advertising traditional. We do content of all types, lead magnets, SEO blogs. We join a lot of local groups. Jay is a member of the PBJ Trust. Part of it is getting yourself out there and networking.

What’s the PBJ Trust?

It’s the Phoenix Business Journal.

I was like, “Peanut butter and jelly time. That’s awesome. I love this.”

We do have a lot of acronyms in this business.

The PBJ Trust is smoking pot in the morning and hanging in the afternoon. I’m a part of a group called Baby Bathwater and it sounded similar all of a sudden. That’s so sad that it’s the Phoenix Business Journal.

Baby Bathwater, you have to tell.

You should go. It’s a good event that is focused on digital marketing, business development. It’s 150 hand-selected individuals at the CEO or COO level. It’s held at a place called Eden, Utah. It’s where Powder Mountain is. It’s the group that runs Summit Series and Summit at Sea. They have three days of learning. Everyone stays in chalets together. There are six attendees per chalet. You wake up in the morning and you’re hanging out and you’re in t-shirt and shorts and chatting with each other and having coffee before you go off to the events. The events are all held at different levels of the mountain during the days. You hang out and they open up the hot tubs at noon. Someone does spark up a joint at 4:00 and they have a Bloody Mary bar at 10:00. They’re usually on mushrooms or molly in the evening. It’s 150 CEOs chilling, but getting deep on all things related to business and marketing. It’s a solid group.

That sounds like an excellent visionary retreat.

I’ve got a number of members of our COO Alliance, the Second in Commands that have gone to Baby Bathwater and they like it because they do get pretty tactical there. Because the theme tends to be all things related to digital marketing, there are people there that are geeking out in their space more than an entrepreneur event might be. How about your growth? How have you had to scale? You came in as an EA and now you’re running as a second in command. How have you had to grow your skills?

Doing what needs to get done. I come from an entrepreneurial household. My dad ran his own business my whole life. Digging deep and getting crap done, that’s it. If you see something that needs to get done, do it. You are never too high or too low to take out the trash. Pitch in where it’s needed and figure it out. When I transitioned to full-time, I took on the content department. I have great reading and writing and editing skills. It was a natural fit for me, but then it was, “What else can I take on? How else can I develop the team? How else can I grow?” Thinking about how I can help others forced me to look at the flaws that I had and where I was possibly failing them and to work on those things.

My dad passed away. I was rolling high. I was feeling like I crushed it. I was educating myself on a constant basis on anything, you name it, self-care, marketing, leadership. It was a couple of months after he passed where I thought, “I need to dig deeper and I need help.” I hired Jane from Patterson Sports Ventures and she was my business coach. She’s been an incredible help to me. Going outside of myself and then I also worked with a mentor for my finance skills. Honing those and getting to know the CFO of another agency, Sandy, she helped me out a ton. Meeting other people and getting myself out there.

I was never the one to go volunteer for an event. If you’d asked me years ago, “Sarah, would you ever be on a podcast?” I would laugh at you. “I’m not going talk to people, that’s crazy. I’m not going to go to an event and introduce myself.” Getting uncomfortable was helpful to make myself grow. They say that a lot about COOs, they don’t aspire to be CEOs. I find that to be true for myself. I love being second in command and helping Jay do whatever he needs to get done. I thrive with getting down into the nitty-gritty and doing this stuff.

The CEO wants to talk about interviewing for fifteen minutes and you want to talk about it for a day and maybe go into a second full day. We’ve got members of our COO Alliance from five countries. I don’t think I can think of any of them that would ever want to be an entrepreneur. They want to work and build a great entrepreneurial organization, but they have no desire to be in that role. I can’t think of many CEOs who are good at the COO as well. They have to be strong operationally and most aren’t, nor do they need to be. Where are companies making mistakes on marketing? In a small and medium-sized space, where are most of them making mistakes marketing-wise?

During the COVID time, turning it off or not adjusting their messaging. It’s hard because who am I marketing to? Where am I spending this money? Cash is tight. We get it. The last thing you want to do is lose the momentum that you’ve worked hard for because a lot of this stuff is delayed. Google doesn’t happen overnight. When you put an ad live, it is not magic. It’s not a panacea. It’s not going to solve everything overnight. It takes time. The issue with marketing is patience and letting things do their job. Either turning off marketing entirely, which we have some pretty savvy, smart clients that ended up adjusting their messaging or changing their direction or focusing on something else, maybe a project that they’d wanted to get to but didn’t have time to. That was pretty helpful for them. The ones that are either unable to or were told from a different department or a leader that, “We need to shut everything off.” That’s tough.

SIC 115 | Stringcan Interactive COO

Stringcan Interactive COO: Being the teacher is one of the best ways to get people to understand processes.


Unless you’re operationally shut down, to shut down your marketing is irresponsible because you can get it for free. I’ve got a client who spends $5 million a year in marketing. He was buying billboards, bus benches, radio, TV spots, and digital. He’s got between 30% to 80% more impressions for the same ad spend that he was spending before. He goes, “I’m going to be in business for the next ten years. This is all about building brand and building flow. Why wouldn’t I keep spending it?”

He’s spending the same. Meanwhile, all of his competitors have either cut or gone to 50%. He’s getting 4 to 5 times the amount of marketing and impressions that his competitors are. He’s destroying them. It makes a whole bunch of sense. Unless you’re a company that you shut down and you can’t operate. It makes sense to maybe turn it off a little bit. The other one is probably strategy. They don’t spend enough time thinking about where they’re headed with their marketing and they’re all over the place sporadically spraying messages.

Part of the strategy is where the opportunity is. There are a million opportunities. It’s like the game of golf. There’s no perfect when it comes to marketing.

It’s no perfect, for me, when I play.

I’m getting into it and that’s the best advice my husband is giving me so far.

I was a member at Arizona Country Club. I almost got kicked off the course one day. They nicknamed me Pinball because I hit the same house three times with one shot. It ricocheted.

That’s my worst fear.

I was playing with the Young Presidents Organization’s president of the organization and another couple of members from YPO and they looked at me and they nicknamed me Pinball. I was almost in tears, I’m like, “Get me off the course.”

“I’m done with this game.”

How about onboarding of people, what do you do in terms of bringing good people into the organization? You hired somebody and then you had to quickly switch to being remote. How did you onboard her and how do you onboard people into the organization?

Our onboarding process gets better and better and a little longer and longer. When I started, I had a decent onboarding process. There was some commitment there. It’s tough when you’re busy and you’re trying to go and then you got to pause and bring someone on. That’s a little bit where we were. We were in the middle of transitioning departments. Me, being the integrator full-time and then bringing on Michelle, I worked hard on refining the process. What’s valuable? What’s useless? What’s out of date? Getting her comfortable with the company and the culture and then getting her comfortable with the services and understanding how her brain worked.

We use the Predictable Success model. A couple of people are familiar with it. He has an assessment called the Leadership Assessment. We have all people take that. It’s like the second step of our recruiting process. I wanted a processor brain in the organization. We don’t have one in the organization. I’m a synergist-operator and everyone else is visionary. I needed someone else to help balance out those four types. It was hard. She was the only one that tested and I’ve never fully committed to the results before. I’ve taken them on, “This is what we have.” I wanted that processor brain. I organized the onboarding process to work with her brain and how she would interpret information, which is easy to do when you’re onboarding one person at a time. I can’t imagine if you’re doing multiple people at a time.

You’d figure it out. As you scale, you start to iterate and figure it out. What’s interesting is hearing how you process this information of the individual and their mind and how you onboard them based on that. There’s not an entrepreneur on the planet that would either A, think about doing that or B, based on the time on it, they’ll be like, “I like them. Bring them in.”

“Sit her on her desk, turn on her computer and she’ll figure it out.”

That’s where the photocopier used to be.

I don’t know where it is now.

I love personality profiles because you learn a lot about individuals. Everyone in our COO Alliance, we have them do a Kolbe profile on themselves that talks about how you start projects. We also have them do a Kolbe profile on the entrepreneur. They learn how to communicate and work well together. Any personality profile you do teaches you more about the other individuals and how to work together and collaborate together and how to learn about yourself so you can communicate that way, too. You don’t want to change the person so much as leverage them and collaborate better.

Using the assessments, understanding it’s not about you, and having everyone else work their way around you and what your brain looks like. For me, that was big because everyone else has a similar thought process. They’re all visionaries on that model. I wanted her to feel successful and not feel like, “I don’t understand what’s going on in his organization.” Checking in with her constantly. I spent every minute I possibly could the first week with her. We always start people on Wednesdays so that they don’t feel overwhelmed by the process. They have plenty of time to process what’s happened.

In the first couple of days, I make sure that they have a computer with everything set up, their name, their printer. All they have to do is log in and I teach them how to use the software, which is Jira. We use it for our project management system. It’s continuously practicing and honing. You sit there with me and I will show you. The next week, you show me. Being the teacher is one of the best ways to get people to understand processes, “How can you make this better?” It’s constantly, “What do you want to do differently?” She’s given us some amazing feedback in her 30, 60. We haven’t even had her 90 day yet, but she’s given us some great feedback and feels comfortable letting us know what’s to improve about the process and what’s going well.

You guys are operating nicely at the stage. You’re going to scale well. I coached a digital marketing agency in New York called The Lead SEM and they had about 30 employees when I started coaching. I made about 300 when we stopped. They’re similar to you guys. They were putting the operational best practices in the early stage where it sometimes felt painful to be putting them in place, it’s growing 30, 60, 90 with people but it’s powerful what comes out of that. It’s strong. Final question, if you were to go back to your 21, 22-year-old self and you wanted to give yourself some advice on your career, what leadership or business advice would you give yourself that you know to be true now, but you probably didn’t know when you were 21 or 22?

One of the most valuable things I do is focus. Part of the COO mentality is that there are a million things commanding your attention and you want to tackle all of them. I bought myself a full focus planner. This is my third quarter and it’s been one of the most valuable tools in my arsenal. If I’d have had that in my early twenties, it would help me feel accomplished. It’s not twenty things on a task list. It’s big focus items that are driving the needle. Celebrating those wins. Here are actual tangible things that I did to move the needle. I feel good about that and reveling in the success that you have versus focusing on the things that you didn’t do well or you wish you would have done better. I’m notorious for beating myself up. I’m trying to focus on the things that I do well. I did a Michael Hyatt training. One of his first things is take some time to celebrate those wins. Feel good about the things that you’ve done well.

If you’re driving a car and you’re driving to try to get to the horizon, if you’re only going to be happy when you get to the horizon, you’ll never be happy. You’ve always got to look in the rearview mirror and see how far you’ve come and take satisfaction in what you’ve covered and still keep driving. I always want to keep improving. I always want to keep growing. You got to praise yourself for all this stuff and praise the company. Sarah Shepard, the second in command for StringCan Interactive, thank you so much for sharing with us. I appreciate the time.

Thanks, Cameron. It was a pleasure.

I appreciate it.

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About Sarah Shepard 

SIC 115 | Stringcan Interactive COOStringCan Interactive is a digital marketing agency that accelerates the growth of businesses dedicated to wellness and wellbeing. StringCan Interactive creates brilliantly focused digital strategies with world-class implementation. Services include persona development, marketing roadmaps, content marketing, media planning and buying, and more.  

Sarah designs and improves the processes and structures that enable StringCan to deliver industry-leading solutions for their clients in the most fiscally disciplined manner.  She is also the cultural curator at StringCan where she ensures that the team can always be their best self at work and home.

For fun Sarah spends her time teaching yoga, convincing others that green smoothies aren’t scary, enjoying newlywed life, and binge-watching Altered Carbon.


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