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Steve Levely Ackroo: “Cash is king and hard to come by”

Cash is king and hard to come by. It’s critical to have a laser focus on the cash short term and constantly be thinking about how you will solve for it long term as the unexpected will happen. As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of […]

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Cash is king and hard to come by. It’s critical to have a laser focus on the cash short term and constantly be thinking about how you will solve for it long term as the unexpected will happen.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewingSteve Levely.

As Chief Executive Officer of Ackroo, Steve leads the company’s corporate strategy. Steve transitioned into this role after previously serving as the company’s EVP of Sales & Marketing.

Prior to joining Ackroo, Steve worked for Maritz Canada helping lead their strategic business development division. In this role, he supported their Sales Channel Enablement, Engagement Marketing and Consumer Loyalty go-to market strategies. Prior to Maritz, he spent over 8 years at Pitney Bowes, where he held various senior management positions in both the United States and Canada. An expert in commercialization and operational efficiency, Steve brings over 20 years of successful senior leadership and business development experience from various organizations within the software, telecom, and marketing services industries.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

After several years of working for small and large businesses in various leadership roles I was eager to become an entrepreneur myself and lead my own business. I came up with a loyalty marketing concept that I pitched to a VC who in the end introduced me to a group of people who just got into the space themselves and were looking for someone like myself to help them commercialize their new business. At first I was hesitant because I wanted to be the founder to create and build something from scratch, but while reflecting on my past careers it was always more about improving a business than it was about creating one from scratch, so I joined on. I also saw it as a great opportunity to learn from their successes and failures firsthand and that in time I could leverage those learnings into my own success as a leader. Within 2 years of joining them I achieved my initial goal of leading the business myself as the board and outgoing CEO asked me to step up and become CEO myself. Thanks to some initial reflection and some patience, I was able to achieve what I wanted with much more knowledge and experience than I would have had otherwise.

Can you tell us a story about the hard times that you faced when you first started your journey?

As mentioned earlier, I was not the initial “founder” of Ackroo. I joined as a senior leader in the business. I also wasn’t even an executive of the business during the first year. I was a VP of sales for the company, so I wasn’t exposed to many of the details, nor was I able to drive many of the decisions. After the first year, the company had burned through the bulk of the capital raised and so I was planning to exit the business. It was at that time that the then CTO contacted me asking me to hang on. Within a month, he moved into the CEO role and he promoted me to Executive VP of Sales and Marketing. This gave me that step forward and voice I was looking for which a year later led to me being much more prepared and ready to become CEO of the Company.

Once I became CEO things became very challenging. As I took over, we were completely out of cash and burning close to 500k dollars per quarter. I was forced to make a number of difficult decisions around staffing, focus, dilution to shareholders and more to allow the business to survive. I literally had to call various shareholders to bootstrap payrolls for a couple months as I worked through changes needed to get us back on track. Very difficult times.

Where did you get the drive to continue even though things were so hard?

The drive for me came from progress. For every challenge we faced there was also progress that was being made. The progress personally and collectively really fueled my desire to keep marching forward. We could go a week or two of struggle and then suddenly a massive win would give us the confidence and hunger to keep moving forward. Those small and large wins along the way have been key.

So, how are things going today? How did grit and resilience lead to your eventual success?

We have come a very long way. We become a profitable business 2 years ago which was critical for us. We wanted to be self-sustaining as soon as possible where we would use investor support to scale, not need investor support to survive. We had to face many difficult and rushed decisions along the way and although many were far from perfect, every decision always led us one step closer. We really focused on fast decisions vs. perfect decisions. In the end, I believe the speed to make decisions and the nimbleness we all have demonstrated personally and collectively brought us to where we are. The main “ability” the staff at Ackroo has had to have is “adaptability,” and it is that trait that has helped us get to where we are today and what will continue to push us forward in the future.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

In the first year of the company, my initial focus was on building “coalition programs” for the Company. So think mini airmiles programs for groups of merchants and similar to my original loyalty marketing concept which was for season ticket holders. At the time, the Company had one coalition client in CAA and so the thought was to leverage that program and build many more like it. I quickly went out to my network and found a sailing group out of Port Credit Yacht Club that was open to trying new things to further promote their racing circuit and drive in more sponsors. I was excited to think my initial vision could come to life through Ackroo and that we would all see great success along the way. In very short order we hit tons of roadblocks. We had our “program” created, had merchants/sponsors signed up, and even a big launch of the program at one of the groups large races that summer (a big splash). The problem however was that our technology didn’t work operationally well with any of the merchants. The software didn’t integrate directly into their point of sale environments. It was stand alone and so it was clunky for them to use it. We then discussed with the merchants “how” they would want to use the tech to engage the client base and the many reward schemes they asked for and communication tools they needed. The technology didn’t have either. What we also learned is what the clients really wanted was their own programs where their business was the brand, not the group. Think again, Airmiles vs. brands that work with them. They wanted their clients loyal to them, not loyal to the program, and they also had a need for simply gift card automation as many were still using paper certificates at the time. We had the big launch, merchants signed up etc. but didn’t deploy to a single merchant. Not a single transaction processed on the program so a major bust. This however gave us lots of lessons learned though. The main lessons being that although our concept was helping the sailing group and may help with sponsorship validation etc., it only works if:

  1. You can make the product easy to use
  2. You are solving an important problem for the business

We didn’t talk to our customers enough to understand what the ideal operational/technical product needs to be, nor did we understand their main pain points to see if we could solve them. In the end, the time and money spent here turned out to be extremely valuable though as we instantly began to pivot the business away from coalitions to direct company gift cards and rewards programs, advancing the tech through point of sale partners, etc. What matters to the customer is all that matters and so listening to customers more and pivoting quick is the path to success.

What do you think makes your company stand out? Can you share a story?

I think we have shown operational excellence for quite some time. We have not only managed our business through difficult times (cash flow etc.). We have now acquired 9 different companies over the last 6 years, where operational efficiency is critical to integrate and better operate. We have been “better operators” for quite some time and now we are working hard to also be the “better technologists” in the space by taking a unified and simplified approach to our industry.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Everyone needs to feel success if they expect to endure. You can’t simply set a goal and work at it for years to finally feel success. You need to have small successes along the way in order to keep that internal fire alive. So my advice is to make sure you are not just chasing your long term goals, but make sure you have short term goals that you can and do achieve. That you win early and often and have lots of moments of success. I was taught years ago how important it is to help your new salesperson get their first sale, so they can taste success so they know what it feels like and keep wanting more of it. The same goes for running a business. You need to feel that quick win and keep feeling it if you expect to achieve that BIG success.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Team is everything. You are only as strong as the people around you and I have been blessed over the years to be surrounded by many smart and successful people. It’s a part of why I obsess over the hiring at Ackroo and want to be a part of that process as much as I can.

I don’t want to call out one particular person in my business career, however what I can say is that I have fortunately had many people who have helped me over the years who had no direct reward for doing so. Yes I have had great leaders and colleagues over the years, but it has actually been those that have taken the time to give me feedback and advice who didn’t directly benefit from it that has had the most impact. Ex-colleagues that have moved on and have stayed in touch to talk about their successes and failures. Friends and family that have had plenty of current and past experiences to share and ideas to give. I have learned just as much from my network “outside” of my business than “in” the businesses I have been a part of and I think that has really helped me along the way.

How have you used your success to bring goodness to the world?

Our success at Ackroo isn’t just helping to feed my family, it’s feeding and supporting the other 30 + families we have. As much as I am proud of our ability to support our growing Ackroo family, we have decided it’s important that we also find ways to help other families in our area as well. Over the last few years, we have started getting involved with a large local charity in the Hamilton, Ontario area by supporting events that they have in an effort to give back and to help our local community. It’s a small thing so far, but as we continue to grow we expect our support of various organizations will grow as well.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each. In no particular order:

  1. Cash is king and hard to come by. It’s critical to have a laser focus on the cash short term and constantly be thinking about how you will solve for it long term as the unexpected will happen.
  2. The CEO role is the loneliest job in the company. Those hard decisions and the fear of failure will weigh heavy on you. Expect to feel alone at times but also realize you will get through it.
  3. Play to your strengths. All of us have skills that are stronger than others that helped us get here. As much as it’s tempting to focus on where you want to develop, you have to spend much more time on what you are best at.
  4. Get the people right and don’t be afraid to let go. The hire slow fire fast methodology is key. The wrong staffing (whether it be hiring or keeping) can set you back materially. The hiring decision needs to be slow and methodical, however like the rest of the business the firing decision needs to be fast. Speed to let go is critical. It doesn’t help anyone to hang onto staff who aren’t growing themselves or growing the company at a level you need. Decide and move on.
  5. Have passions outside of your company. For both balance and to avoid burn-out you need to have other passions outside of driving your company’s success. The company cannot be your only passion.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

There are a few movements that come to mind however one that stands out for me is really about the demand for more SUCCESSFUL business people in politics. The government is the largest employer in the country with many citizens as their employees and ALL citizens as their customers. I strongly believe if the government was led by successful business leaders that had to show their success in the private world first and get the respect of all citizens for how they achieved success before being able to go into politics our country would be a much different place. Not just economically but in all facets of our lives.

How can our readers follow you on social media?

You can follow the company and myself on LinkedIn, Twitter and Instagram.

Personal LinkedIn: www.linkedin.com/in/steve-levely-4a665b/

Company LinkedIn: www.linkedin.com/company/ackroo

Web: www.ackroo.com

Facebook: www.facebook.com/doyouAckroo/

Twitter: www.twitter.com/ackroo

This was very inspiring. Thank you so much for joining us!

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