An Interview with Steve Levely, CEO of Ackroo

by Jerome Knyszewski
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Steve Levely, CEO of Ackroo

Steve Levely is currently the CEO of Ackroo, which is a service provider for loyalty and rewards programs. He was named to the position in May 2014, together with other appointments to the company’s board of directors.

For over 20 years, Steve Levely has gained considerable knowledge and expertise as he delivered “successful senior leadership” to several organizations operating in the “software, telecom, and marketing services industries.”

As CEO, Steve Levely continues to promote Ackroo’s “continued focus” on creating and releasing its “innovative and cost effective” customer loyalty platform for its many customers across North America. The company has been delivering SaaS-based solutions for small to medium businesses that are looking for loyalty platforms that are affordable and customers can easily access. With this platform, the merchants and customers can quickly develop a lasting and thriving relationship that drives up the company’s profits. Also, Ackroo’s platform allows these business to remain competitive with even larger brands and major retailers.

Prior to becoming CEO, Steve Levely has been instrumental in building Ackroo’s strategies in sales and marketing. He has worked in similar roles in other organizations, such as Pitney Bowes and Maritz. At these companies, he has gained more than 15 years of experience designing and implementing successful sales and marketing strategies.

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Jerome Knyszewski: Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Steve Levely: Right out of school I began my first “real job” as a straight commission sales rep in the office equipment industry. After several years of success I made the shift into a senior sales role in the audio and data conferencing world where I worked for a mid-size company, which was followed by my first start-up in that space. I was exposed to the hardships of start-up life and so I then pivoted back into working for a large organization once again in the office equipment industry however, this time with a focus on software and service sales. It was for this company that I had my first leadership opportunity where I lead teams in Toronto then Philadelphia followed by Ottawa and then back to Toronto. In all cases I was put into struggling regions where I was tasked with further improving commercialization in these regions. I saw much success in these “break-fix” roles and was provided with plenty of personal development in areas like finance during my almost 9-year tenure with the company.

After my time there I began consulting for a sponsorship marketing firm where I realized an opportunity with loyalty marketing for the sponsorship marketing world. Simply, the idea of connecting season ticket holders with the various sponsors of the venues/teams they were season ticket holders for through a loyalty marketing model like what AIR MILES was providing. This would provide sponsorship validation for brands, an engagement channel between the venue/teams and their season ticket holders and ideally an ability to shift and lift season ticket holder spend while also further retaining them with more value add. After some commercial discussions with some venues/leagues and various brands, I presented my concept to a VC in Ottawa who at the time had some interest but weren’t ready to fully invest. I then brought my concept to a marketing agency in the Toronto area who provides loyalty marketing solutions for their clients who instead offered me a role in their organization to help expand their client portfolio. Although there wasn’t an opportunity to see my vision through, this was an opportunity to learn more about the loyalty marketing world and other aspects of what this agency provided its clients, and so I took the role. After a year with the company I left the agency and reconnected with the VC in Ottawa who connected me to contacts in their network. They had just become the executive team of a newly acquired Gift Card and loyalty processing company called MoneyBar (now Ackroo). After a few months of consulting for them I joined full-time and have been with the company ever since.

Jerome Knyszewski: What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Steve Levely: As I mentioned, the concept I had and interest in the industry is what brought me to Ackroo. With Ackroo really being a “break-fix” opportunity as well in that it started as an acquisition of MoneyBar meant it was a great opportunity for me to leverage my previous skills in an industry that I had and still do what I have a great interest in. I wasn’t the “founder” and wasn’t even on the initial senior executive team out of the gates, but I did see a great opportunity to learn while also lending my skills for growth. Within 2 years of being involved in the business I was given the opportunity to lead the business as CEO under my vision and direction and for the last 6 years we have been executing under my guidance.

Jerome Knyszewski: Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Steve Levely: There have been a few “do I give up?” moments in the journey. The very first year of the Company and my first year with the company was very challenging. I didn’t come in as a Senior Executive, I came in as a VP of Sales for one area of the business with the focus in the first year really on raising capital and re-validating the business. There was a massive struggle internally around decisions being made, what part of the business matters most, and people decisions in general. I was very close at the end of the first year of just moving onto another opportunity until the then CTO became CEO and I was asked to take on more responsibility (all sales and marketing). I was then an executive of the company worked to try and see his vision through. He gave me an opportunity to not only have a larger voice, but he treated me as a partner in the journey, teaching and coaching me through areas like the capital markets, the board of directors, finance and the business in general. This was a refreshed opportunity that re-invigorated me and really helped groom me for what was about to come.

The second “do I give up?” moment was a year after the second CEO took over. The company had run completely out of cash and struggled to raise funds. We literally had 90 days of runway left and had some hard decisions to make. Do we exit? Do we sell? How much staff do we lay-off? These were incredibly difficult times. The then CEO decided it was best that he exit as CEO and join our board instead, while I was then asked to step up and fill his shoes. It was certainly a scary time with so many unknowns infront of us and my first opportunity to be a CEO of a company. With fear also brought excitement and an opportunity for me to leverage the learnings I have had my whole career and the most recent guidance I had received from the 2 previous CEOs of Ackroo.

Since taking over there have been lots of moments of frustration, questioning decisions made around people and the business, but never a “do I give up?” moment. I have taken a “burn your boats” approach to Ackroo now where giving up isn’t an option. I expect success now and although the road certainly isn’t straight and is filled with lots of challenges, I am certain we will achieve great things here and an outcome for ourselves and our investors that everyone will be proud of.

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

Steve Levely: Things are continuing to trend in the right direction. Our success has been less about grit and fighting through the struggles and more about making swift decisions internally and externally to always make sure we are pushing forward. We have focused on fast decisions vs. perfect decisions in order to keep us moving forward as speed is important. We have used as much information as we have and a bit of gut feeling and have continued to make constant tweaks and adjustments to the business along the way. Some small and some big, but constant adjustments to keep us moving forward.

Jerome Knyszewski: Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

Steve Levely: In the first year at the Company, my initial focus was on building “coalition programs.” So think mini AIR MILES programs for groups of merchants and similar to my original concept of loyalty marketing for season ticket holders etc. 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 is that our technology didn’t work well operationally 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, but the technology didn’t have either. What we also learned is that the clients really wanted their own programs where their business was the brand not the group (think again AIR MILES vs. brands that work with them — they want their clients loyal to them not loyal to the program) and that many 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, but we didn’t deploy to a single merchant. Not a single transaction processed on the program, so a major bust. This however gave us a lot of lessons learned though. The main lessons being that although our concept was helping the sailing group and may help with sponsorship validation, 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 as we instantly began to pivot the business away from coalitions to direct company gift card and rewards programs, advancing the tech through point of sale partners etc. What matters to the customer is all that matters, so listening to customers more and pivoting quick is the path to success.

Jerome Knyszewski: Can you share a few examples of tools or software that you think can dramatically empower emerging eCommerce brands to be more effective and more successful?

Steve Levely: Naturally solutions like ours at Ackroo can be of great help. Whether it be digital gift carding, digital marketing, online rewards, online payment etc., a platform like ours can certainly help attract customers, engage them, shift and lift their spending behaviors and through our payment options, save them money. There are also many great e-commerce stores out there like Shopify, Magento and others that do a great job of providing that instant infrastructure for new businesses looking to scale, so I would source a core software platform that will not only drive your core business online but that integrates to many marketing and payment solutions like Ackroo has so that you have lots of options and opportunity to leverage these platforms for success.

Jerome Knyszewski: As you know, “conversion” means to convert a visit into a sale. In your experience what are the best strategies an eCommerce business should use to increase conversion rates?

Steve Levely: Conversion is key. In my opinion, you either need to clearly be solving the need at a price and/or speed the customer cannot say no to, or you need to make the decision easy to “try” and decide after.

Jerome Knyszewski: Of course, the main way to increase conversion rates is to create a trusted and beloved brand. Can you share a few ways that an eCommerce business can earn a reputation as a trusted and beloved brand?

Steve Levely: Having brand advocates is important. Customers that will praise the quality, speed, effectiveness etc., of your product or service. So first make sure that you are delivering in these areas and then make sure you are sharing their advocacy of your product and service and find a way to thank them for that advocacy.

Jerome Knyszewski: Ok super. Here is the main question of our interview. Based on your experience and success, what are the five most important things one should know in order to create a very successful e-commerce business? Please share a story or an example for each.

Steve Levely: In no particular order:

  1. Know your cash. Understand the capital you have and plan to always need more than you expect (kind of like a home reno) and have a plan for how to get it.

  2. Expect to make mistakes. Whether they are people mistakes, business mistakes or even timing, you will make mistakes. Don’t let mistakes hurt you. Allow them to teach you.

  3. Inspect what you expect. The details matter and so take the time to really inspect what you expect in order to make the right decisions. Don’t over trust your instinct or your team, inspect and understand.

  4. Speed matters. Both speed to make a decision and the speed to execute on it. The digital world is moving so fast, if you can’t move quick you will be left behind.

  5. Be honest with yourself. Know your personal limits and your personal strengths. Make sure the majority of your time (and your teams for that matter) is spent doing the things you do really well and leverage others to fill the gaps.

Bonus one would be make sure you are taking the time to work on your business not just in your business. This is also critical.

Jerome Knyszewski: How can our readers further follow you online?

Steve Levely: You can find me on:





Jerome Knyszewski: This was very inspiring. Thank you so much for the time you spent with this!

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