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Celebrating our 4th Anniversary

Written by 5&5 Team | 13th May 2024

In this special anniversary Q&A piece, we sat down with our founders Johnathan and Tiffany to discuss their motivations behind building this company, the foundational ethos that pulses through their daily endeavors, and their aspirations for the future. We’re thrilled to share this 4 year anniversary with all in the industry – partners, clients & team members included. Join us in celebrating this journey and learning from our visionary leaders who’ve instilled a people-first culture and navigated us through four years of growth and achievement!

Q: 75+ employees… 170+ brands… 45+ partners, and counting… Looking back, is the journey that led to this point in time what you thought it would be when initially forming 5&5?


Johnathan: Honestly, no. We’ve always told this story to our teams internally, as well as some of our partners, but 5&5 wasn’t created off of some enormous vision to become the leaders in the IT managed services space that we are today. When we had started 5&5, at the height of COVID, we had both been laid off from our jobs because the agency we were working for was concerned about the impact COVID would have and so they let the entire team go. With hiring frozen at essentially every business, we weren’t left with many options and decided we’d take a chance on ourselves. Starting with a team of two, working up to 16 hours a day, sometimes 6-7 days a week. We’ve been incredibly lucky to see this organization grow to what it is today. We’ve grown far larger and we’ve reached milestones that I never thought were possible. When we first started, I thought it would be incredible to have a team of 6 people, because that was the size of my former agency. Now to be a thriving, international organization and seeing our team hit personal and professional milestones is what I’m most grateful for. Just knowing we were able to build an organization that allows our team to reach the dreams and goals they have is what keeps me motivated.

Tiffany: We grew substantially more than what we had expected when we first started 5&5 back in 2020. Our goal at that time was to ensure that we would be able to find something that we both enjoyed doing from a career perspective, find the right amount of resources to help us out and be able to maintain the business long term. Little did we know that we tapped into a niche industry and growth roughly 2x’d each year.

Q: Reflecting on the past four years, what’s one piece of advice your company would give to its younger, startup self?


Johnathan: “You’ll never regret doing the right thing, so just focus on doing that.” In the times where we’ve made a mistake as an organization in supporting our team correctly, or when we’ve made a mistake in a support request from a client, there’s always this innate human response to want to downplay the issue, scapegoat someone else or deny any wrongdoing. Despite how hard it is or how anxiety-inducing it is, we’ve always insisted on being honest and transparent. We’ve always taken full accountability for our mistakes, we’ve always apologized and we’ve always built processes in place to be better. Pretending to be perfect is not only dishonest, but it stunts our ability to grow as people and as an organization. In the rare instances where it’s happened, our brands have always surprised us with their responses. They are always more grateful for our honesty, which has allowed us to build even stronger relationships and partnerships. In those moments where I struggled the most, I’d remind myself to always focus on doing the right thing because no one can fault you for doing that. I’m thankful to my past self for always making that choice, even when it was difficult, but the present me can now say, definitively, that doing what was right was always the best decision.

Tiffany: My quote is a tweaked version of Johnathan’s, “You won’t regret trusting your gut feeling.” For me, there were many instances where I felt like something was going to happen or a situation that we could’ve dealt with a certain way, but because of XYZ, we chose either the safer route or the “this is how it should be done”. And every time I noticed my gut feeling was right, but I didn’t listen to it or try harder to advocate for it, it felt like a heavy pit in my stomach.

Q: What are your thoughts on workplace culture as a people-first organization that operates fully remotely?


Johnathan: For us, developing a strong workplace culture is non-negotiable and being people first is beyond important to everything that we do as an organization. I’ve had a lot of leaders in different companies ask me what our secret sauce is and I always say it’s our people. We are able to do what we do in powering digital for the brands we work with because of our people. Building an organization that allows them autonomy in their work, that allows them growth, personally and professionally, that gives them work/life balance, and led by leaders who have built everything we do (from the ground up) is a powerful influence in delivering the quality of work that we do. Most, if not all of us, have come from toxic working environments, where we were numbers on a spreadsheet and had to juggle office politics. 5&5 was built to be everything we wanted a company to be but never got to experience in our previous roles working in corporate. It’s very simple: if we take care of our people, our people will take care of our customers.

Tiffany: Workspace culture is SUPER important to us. Remote workplaces, or remote work culture, only became more popular post-COVID. Going from in-person to virtual isn’t easy to adapt to if you’ve never had prior experience. It can be very lonely, unfamiliar, uncertain, and different. But as leaders, if we can bring culture, familiarity, certainty, and communication to our team members, we can be stronger and more supportive than any typical organization. We want to make sure that our people are taken care of, are heard and continuously working on how to better their professional and personal goals.

Q: What internal achievements or milestones are you most proud of?


Tiffany:  I’m most proud of the amount of structure and processes that we’ve built as a team from literally nothing. It’s always easy to build something, but building it effectively, troubleshooting the negatives, and continuously optimizing is not. I’m especially proud of this development because this is a key component of what makes us successful and it differentiates us from other companies, both internally and externally.

Johnathan: There are so many it’s hard to list them all, so I’ll just provide a couple. For one, I’d say watching our leadership team grow from sole contributors to department leaders. When we first started to build defined departments, we had to figure out a lot on the fly. I’d never run my own business before and most of our team had never scaled a business, so there was a lot to learn. Seeing the dedication and commitment from our leadership team to make 5&5 what it is today is a huge accomplishment. Another milestone moment would be taking our entire team to Disney World last year. Disney World is expensive for a family, let alone an entire organization. To see our People Operations Team work hand in hand to pull off such an incredible retreat was an amazing experience to be a part of. I never got to visit Disney World when I was growing up, so to see our team and their families be able to enjoy it as a thank you for all of their hard work was really an unforgettable moment.

Q: What aspirations are associated with the upcoming 5th anniversary of 5&5 in 2025?


Tiffany: I would like to grow the Creative team and introduce a new department to our organization to expand on existing and new services that’ll allow 5&5 to tap into a few innovative sectors. More details to come closer to 2025!

Johnathan: We have a lot of really exciting services and new offerings that we’re looking forward to announcing to the greater ecosystem, but as we take steps towards our 5th year anniversary, my focus is on continuing what has made us successful from Day 1: unwavering commitment to our team and our clients to deliver the best support internally and externally. Innovation is important, but it should never overstep or overshadow what made us good to begin with. The minute that we decide to stop focusing on why brands work with us today, when we start to focus on making more money versus adding more value, and when we stop being the people-first community we are, then we’ve made the wrong choice. Growth is good, but our growth has always been calculated. We grow when we can maintain our ethos. If that isn’t possible, then we don’t. We would rather make less money than make more if it meant compromising who we were as an organization. Versus aspiring to grow larger, I aspire to continue to do more of and maintain what makes us who we are today. Growth will naturally follow when you do the right thing.

Cheers to 4 Years!

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