Chuck Canton of Sourcepass On How To Use Digital Transformation To Take Your Company To The Next Level

Jason Hartman
Feb 18 · 15 min read

Leaders and employees need to understand that digital transformation never ends. You must view it as a perpetual mission to keep your business competitive. You can’t just do one major systems or platform upgrade and view it as being prepared for the digital era. That first major change is just a step in the right direction and should lay a framework for what you call “agile improvement.” What this means is that you’ve modernized your systems enough that you can make changes very quickly as you discover improvements that are necessary to lead your industry and you can do it without burdening your clients.

As part of our series about “How To Use Digital Transformation To Take Your Company To The Next Level”, I had the pleasure of interviewing Chuck Canton — Founder and CEO of Sourcepass

Chuck Canton is a seasoned and dynamic technology executive with more than a decade of experience at hyper-growth companies. Chuck brings a distinguished track-record for his successful efforts in launching and growing startups, securing growth funding, acquisitions, and sales. Over the past decade Chuck has driven $6.5 BN in enterprise value, successfully completed 20 acquisitions, and has produced a 5X average return on equity to company shareholders. Chuck is also a proven leader in successfully managing and supporting wide ranges of customers, from small to mid-sized businesses to large, multinational corporations.

Prior to founding Sourcepass, Chuck held roles as the Global Vice President of Customer Success and Operations at Vonage (NYSE: VG) and Head of Financial Services and Operations at Compass, a rapidly growing tech-enabled real estate company. Chuck was instrumental in helping Compass ($6.4 BN) and Vonage ($3.3 BN) achieve multi-billion-dollar valuations.

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?

I started my career at iCore Networks, an early-stage start up in the DC-metro area where I was one of the first employees. I was in a hybrid role: selling cloud communications services to businesses and then managing the accounts after the sale. This role was so valuable to me because I was able to work with clients through every stage of the customer life-cycle: sales and solution design (finding the need), solution implementation (the install), on-going support, and eventually the renewal. This was when I really learned how to not just interact with these businesses, but more importantly, learned how to understand their needs and how to help them run more efficiently. There was definitely a learning curve, but once I mastered this, my career really began to take off. I went from a sales rep to a sales director managing an elite market, and eventually I was running all business operations: solution engineering, service delivery, customer care, business systems, product, and account management.

In 2015, we sold the business to Vonage (Nasdaq: VG), one of the world’s leaders in cloud communications services. At Vonage, I continued to embrace a customer-obsessed approach to the business and eventually ran all post-sales processes for the entire business services division. It was my first international role, and it enabled me to learn even more about the client’s happiness, as we were in charge of Customer Success for over 100,000 companies and 5 MM end users. It was this experience that made me realize a huge gap in IT services and eventually led to the vision for Sourcepass.

Sourcepass is a business concept that we have been working on for over five years. Co-founders Bruce Simms and Roli Points and I have spent most of our careers delivering innovative technologies to businesses. Most notably, we worked together at Vonage.

The pattern we’ve noticed is that technology companies typically only focus on solving one small segment of a broader set of issues customers deal with. This causes a necessity for businesses (specifically small to mid-sized businesses) to have to rely on dozens of vendors to properly power their businesses’ required technology. As a result, they get caught up in a web of IT vendors pointing fingers at each other when something goes wrong, and they also tend to overpay as all of these services added together can be costly. This translates to a very poor customer experience that we feel no one has solved yet. We started Sourcepass last year with the goal of solving this service gap for every small business in the U.S., and then we will embark on that same mission internationally.

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

When I was working as a Direct Sales Representative at iCore, I remember my first sales appointment well. I was so excited for it after spending weeks studying iCore’s products and value proposition to clients. We were selling Unified Communications as a Service (UCaaS), so I extensively researched every aspect of what we did and why it was beneficial to our clients.

I remember sitting down with the prospect: the director of IT for an association in Arlington, VA. My Sales Manager, Anthony Chapa, was with me as well. I had all this pent-up energy for this much anticipated sales call so the second we sat down, I went right into the demo of our software and its applications. I must have spoken for over 45 minutes straight without letting the client get a word in. I had so much knowledge from all the research I had done, however, the deal did not move forward. The reason for this was because I was not listening to the client to understand their unique needs and the business challenges they were trying to solve, and then speaking to what was relevant to them. Instead, I got on a soap box and just pitched without even knowing what the client needed. It’s both funny and a bit embarrassing when I look back on it.

After the appointment, I specifically remember Anthony explaining to me that you can have all the talent and knowledge in the world, but if you don’t listen to your clients and qualify them, then you’ll never move forward with your deals. “Stop. Ask questions. Listen. Understand your client. Then talk.”

He was spot on with his feedback, and I was lucky to have that guidance so early in my career because ever since, I’ve made an effort to not only listen to my clients but to truly understand their pain points and to try to see things through their eyes. From there, it’s all about drawing up solutions to their challenges that make their lives easier. If you can do this in any business, you’re going to be successful.

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?

I have been fortunate to have had a lot of great mentors over the course of my career. However, the one who has had the most influence on me is my grandfather Rocky Flaminio, who even posthumously motivates me every day as I strive to achieve even just a fraction of what he did over a successful 60-year career. My grandfather was the child of Italian immigrants and couldn’t even speak English when he entered the first grade. Even with his humble beginnings, he ended up being the valedictorian of his high school in a small town outside of Pittsburgh, Pennsylvania. He got into several top tier colleges, but instead chose to support his country by enlisting in the Marines the day after his graduation. What followed was his participation in over three theaters of war and nine accommodations medals for heroic acts during World War Two, including a Silver Star and Purple Heart.

His heroism alone during decades of military service is incredible; however, even after all of that he still had the energy to become a successful entrepreneur. He started a telecom and technology company called Tollgrade Communications that he led to an IPO on Nasdaq with a multi-billion-dollar valuation. He taught me and my siblings the importance of hard work, always maintaining your integrity, and choosing a career you truly love. I think about him every day. My wife and I named our one-year-old son, John Rocco, “Rocky,” after him.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Into The Wild by John Karauker is one of my favorite books of all time. To me, the book is all about going outside of your comfort zone and pushing yourself to do things that you never thought were possible. When you want to start a business, the timing never feels right, and as an entrepreneur you must be willing to take risks and step into unchartered territory. For me, Sourcepass initially was outside of my comfort zone but as we have embarked upon it, it couldn’t feel more natural and I’m happy with the decision my co-founders and I have made. I think we’re going to build something really special. The protagonist’s outcome in Into the Wild is obviously very unfortunate, but you can’t argue that he didn’t accomplish some amazing things along the way.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

Our purpose is to provide all-encompassing IT solutions to our clients so that they can focus on their core business and not be distracted by the need of keeping current with the ever-evolving digital era. Our vision is to be so good at this that we become the largest IT services provider in the world for small to mid-sized business (20 to 1000 employees).

Are you working on any new, exciting projects now? How do you think that might help people?

We are working with one of the largest software companies in the world to build a mobile application and customer webportal that will be the first to fully digitize the customer experience for IT services. Right now, the customer experience in the industry is a bit clunky, with long hold times, nonresponse emails, and delayed issue resolution.

What we are building at Sourcepass will solve all of that. Clients will be able to self-serve or get immediate contact with our support team for anything they need via whatever communication channel they prefer, i.e., text, phone, video, chat, or email. IT Directors and Executives will have views into their entire IT infrastructure, security health, IT assets deployed, employees onboarded and network uptime for all of their business applications.

This will help many businesses and professionals because by making technology easier for them to use, they’re able to show up to work every day and focus on their core mission.

Thank you for all that. Let’s now turn to the main focus of our discussion about Digital Transformation. For the benefit of our readers, can you help explain what exactly Digital Transformation means? On a practical level what does it look like to engage in a Digital Transformation?

Digital transformation is when a company decides to aggressively invest in their business systems in an integrated fashion across every business function and workflow.

Digital transformation starts as a cultural shift for businesses when they realize the criticality of embracing technology to enhance their customers’ experience. The companies who successfully transform are the ones who have buy-in from all employees to perpetually innovate the way they conduct business and measure their success with one factor: building customer loyalty. Customer loyalty goes beyond customer experience. When digital transformation is done right, your customers and employees truly start to love your business and are the ultimate advocates for your brand, because you make their lives meaningfully easier.

Which companies can most benefit from a Digital Transformation?

The candid answer to this is: everyone. Digital transformation is no longer a choice but rather a requirement for all businesses that want to remain viable through the next decade. You can see examples all over the place of businesses who are driving technology innovation vs. just watching from the sidelines. Think Amazon vs. Border’s Books. Uber vs. traditional yellow taxis. Netflix vs. Blockbuster.

We’d love to hear about your experiences helping others with Digital Transformation. In your experience, how has Digital Transformation helped improve operations, processes and customer experiences? We’d love to hear some stories if possible.

We have experience driving digital transformation within businesses we’ve worked for, as well as assisting clients from previous organizations we worked with. One case that’s a great testament to why all businesses should embrace digital transformation comes from the work I did for my previous company, Compass. Compass is the fastest growing real estate company in the world with a current valuation of $6.4 BN.

Their business is built on helping real estate agents stay competitive and relative in the face of aggressive competition stemming from digitally native industry disruptors like Zillow and Redfin. Similar to stockbrokers in the 90’s losing business to online trading platforms like E*-TRADE, real estate agents are at risk of losing business to technology platforms that are seeking to automate the entire real estate transaction process without the need for a real estate agent.

At Compass, the mission was to provide these entrepreneurs and small businesses the technology they need to efficiently run their daily lives, but more importantly, make sure they are equipped to support very demanding clients who have many competitive options to facilitate buying, selling, and renting homes.

We approached this by offering the agents a Customer Relationship Management (CRM) software that automated many of their daily activities: i.e., pricing homes, sending out contracts, or placing ads on Facebook. By doing this, agents saved time with administrative tasks and could spend more time with their clients demonstrating why having a real estate consultant is the best way to transact. It ultimately equated to a 30% increase in sales productivity for Compass agents, and their clients viewed real estate agents as truly essential after working with them. It’s great we helped solve this dilemma for real estate agents, but there are so many other sectors that need the same support on a broader scale, hence the reason we started Sourcepass.

Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?

Every company faces challenges with digital transformation in terms of cost, effort, and resources. However, the ones who wait the longest and fall the most behind have significantly more difficulty with their digital journey. For digitally native companies it’s easier because their platforms are designed with open APIs (Application Programming Interfaces) and they can easily integrate with new software or easily make enhancements to the current platforms. The companies who have systems that are outdated by a decade or have very manual processes have a huge disadvantage because the scope of the transformation is larger and therefore more disruptive to their business. These companies also tend to have employees who are not the most technologically inclined. They end up struggling with overhauling systems, training employees, driving cultural changes, making new hires, or identifying partners to support their infrastructure. The biggest challenge they face is the inability to insulate the impact on their clients who feel the pain of this transformation as well.

The best way for a company to resolve these challenges is to force their way through it. If a company delays the transformation, it will only get more difficult and will eventually come to a point where it’s practically impossible to successfully complete. When you reach that point, your business is at risk of obsolescence.

To mitigate this, we recommend businesses start with small wins. Do a few platform upgrades and process changes to show your team and your clients the benefits they bring. Once you’ve accomplished a few of these, you then begin the bigger, more foundational changes.

Ok. Thank you. Here is the primary question of our discussion. Based on your experience and success, what are “Five Ways a Company Can Use Digital Transformation To Take It To The Next Level”? Please share a story or an example for each.

  1. Leaders and employees need to understand that digital transformation never ends. You must view it as a perpetual mission to keep your business competitive. You can’t just do one major systems or platform upgrade and view it as being prepared for the digital era. That first major change is just a step in the right direction and should lay a framework for what you call “agile improvement.” What this means is that you’ve modernized your systems enough that you can make changes very quickly as you discover improvements that are necessary to lead your industry and you can do it without burdening your clients.
  2. Digital Transformation, especially for a company that has outdated technology, will initially be disruptive to the employees and the customers. Your goal needs to be that no matter how chaotic things can get internally, you will minimize the impact to your clients. To the extent this is not achievable, which is common, then you need to transparently communicate to your clients what you are doing, why you are doing it, and why they will benefit from the investment. You’ll find that customers will be patient or more forgiving for issues the transformation causes them if they know that the end state will make their experience with your organization better than ever.
  3. “Build for your customer not the company.” This is a quote from my former CEO at Compass, Robert Reffkin. He wouldn’t approve a single investment in the technology at Compass unless you showed how it would improve the lives of our customers. A lot of companies make the mistake of basing their transformational agenda on how it impacts their employees: i.e., does it make their jobs easier, does it make them more efficient, does it increase morale? Those objectives are important and need to be factored in, however, if none of your initiatives improve your customers’ experience, then you did nothing to move your organization forward. Therefore, you must measure the success of your digital transformation journey based on the impact it has on your customers.
  4. It’s okay to break some things along the way, as long as you break them in an attempt to move the company forward. To successfully navigate through the digital era, you need your entire company to have a culture that embraces digital innovation. There are several ways to do this, but the first and most important is that you must make sure your employees are encouraged and not afraid to change the status quo. With this will come some challenges, and even business processes being temporarily broken. Employees need to know that this is okay, as long as it was initiated by a desire to improve the customer’s experience and they see the enhancement all the way through. You can’t have team members that are afraid to embrace change due to worries about being reprimanded, or in the worst case, fired.
  5. Take a bottom up and not a top-down approach. You can’t have a team of senior executives, who don’t spend time with your frontline employees, make the decisions for digital overhauls, unless they are intimately aware of what it’s like for your customers to interact with your team. The best way to learn this is to spend time with your customers, and we’ve established that. However, it’s also important that you spend time with the frontline employees who interact with your clients daily. This could mean a CEO trailing a customer care agent for a week, or a CFO going out to customer sites with a project manager, or a CIO going out on sales calls. You will find that most of your opportunities for improvement are best realized on the front lines. A leader who is disconnected from their customer-facing employees results in being disconnected from their customers, and that is a recipe for failure.

In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?

First, it should be embedded in every company’s core principles and every leader in the organization should reference it daily. Secondly, you must find meaningful ways to measure innovation. Employee reviews, promotions and raises should be based on how your employees innovate for the customers.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Get closer than ever to your customers. So close that you tell them what they need well before they realize it themselves.”

-Steve Jobs

I came across this Steve Jobs quote while putting together a presentation for the annual sales kick-off at Vonage in 2017. I wanted to demonstrate how truly understanding and advocating for your customers translates to career growth and business success. I can’t think of an entrepreneur who built a career based off of customer obsession better than Steve Jobs. He knew his consumers so well that, even today, almost a decade after his death, his vision for customer-focused technology is still relevant and being carried out by Apple.

Although a simple concept, it’s not always the obvious answer for leaders who have lost perspective on their company’s priorities. Oftentimes looking to the customers and customer-facing employees can be the solution. In the spirit of Steve Jobs, I strive to regularly implement what I call a “customer engagement blitz,” where I clear my schedule for several days and only participate in customer-facing activities. I join random sales calls, I shadow Tier 1 Support Reps and take customer calls with them, I go out to project kick-off meetings, search for customer escalations that I can personally address, and I place random calls to customers to check in and hear their feedback on how we can improve.

Every time I do this “customer engagement blitz,” my acuity is restored, my priorities solidify, and I feel more equipped than ever to move the company forward.

How can our readers further follow your work?

We just launched our digital presence. We will be documenting our entire entrepreneurial journey so our followers can learn from our successes and our challenges.

Here is our website:

You can follow me on Instagram and LinkedIn:

Instagram: @chuckcanton

LinkedIn: Chuck Canton

We also just launched our sourcepass sites on:



Instagram: @Sourcepass

Thank you so much for sharing these important insights. We wish you continued success and good health!

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