On Creating A Sales Enablement Business

Published: May 28th, 2021
Carson Conant
Founder, Mediafly
from Chicago, IL, USA
started March 2006
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Hi, my name is Carson Conant and I’m the founder and CEO of Mediafly! Mediafly offers a suite of sales enablement and content management solutions that allow sales, marketing, and customer success to create a better content engagement experience for buyers.

Through our Evolved Selling™ portfolio, sales teams build compelling selling stories presented through visual storytelling assets, create personalized workspaces for each prospect, help buyers justify purchase decisions through value selling tools, and obtain content performance analytics to understand what works. By using Mediafly’s technology, global companies such as PepsiCo, Disney, GE Healthcare, and Sealed Air drive value and engagement for their customers.


What's your backstory and how did you come up with the idea?

My background started in media -- launching AdvantEdge Magazine in 2004 -- but my passion and drive is in technology. With the right balance of media and software engineering, along with the delusional optimism that comes with starting a new venture, I saw an opportunity to make it easier for individuals to consume digital content “on the fly.” Hence how I came up with the name of the company.

There absolutely was a lightning bolt, “ah ha,” moment when developing the idea for Mediafly. In the mid-2000s I worked for a publishing company where our primary medium was CDs, DVDs, and MP3s. Although it was way before the iPhone, mobile devices started to become Internet enabled, but the solutions, such as podcasts, were too “techie” in my opinion. They needed to be as easy as radio. So, I had the idea of creating a service that would aggregate podcasts, along with other free and paid digital content, and feed them to individuals in a smart, linear way -- like tuning into personalized radio stations.

I didn’t spend much time validating my vision. Before Mediafly, I launched a few ventures that lacked the things that I turned my attention to with Mediafly, including:

  • A product that I’m personally a passionate user/customer of;
  • A solution in a booming industry; and
  • A focus on hiring great people (I knew that I couldn’t be the smartest person in the room).

Achieving all three of these things is the reason why Mediafly is so successful today.

Take us through the process of designing your offering.

The “design” of Mediafly’s platform is the product of collaborative partnerships and customers as well as ingenuity to develop a solution that quickly delivers transformational value for enterprises. For example, Roku and Logitech were early partners that helped create our infrastructure and end-user applications. These companies told us that we needed to design an enterprise UX with the same level of engagement as consumer applications, such as Netflix and Spotify.

This “Netflix-like quality” experience is still what we strive to achieve today - it’s how sellers and buyers consume content and how Mediafly differentiates itself in the market. Along with Roku, we were fortunate to have visionary companies like Disney, NBCUniversal, PepsiCo, and RE/MAX as early adopters -- and many of them are still customers today. These companies are leaders because they think differently. They challenge us to keep up with their vision and deliver quality solutions at scale, which is exactly what we do.

Describe the process of launching the business.

Personally, I think we waited too long to launch Mediafly, which obviously impacted onboarding customers. I was so focused on building the “ideal” product, instead of launching, testing, and iterating. But what I did do during this early phase -- and this is something I’m extremely proud of -- was find the best talent. Talent well beyond our weight class at the time. These “Flyers” are why we’ve created the culture of talent and innovation that we have today at Mediafly.

Since launching Mediafly, I’ve explored nearly every method of funding except for an IPO. However, the primary source for funding Mediafly was angel investment from several investors who continue to support the company’s growth. We later brought in an institutional investment partner, Boathouse Capital, and a strategic senior lender, Sterling National Bank, which in addition to capital has brought a diverse set of experiences to the table.

One major lesson that I learned from launching Mediafly is that you need an effective marketing leader. Everyone thinks that they can learn and execute marketing strategies that work for their company, and they may be right 50% of the time. But it takes a true marketing leader to figure out which 50% is right and which 50% is wrong while pulling those ideas together to establish a brand strategy that works.

Some of the other lessons I’ve learned are:

  • Earn money as soon as possible, no matter how small. Don’t wait for the “golden” moment.
  • Don’t be afraid to pivot. Mediafly is entirely different today from the business I started. It has the same DNA but that’s about it. As a company, we’ve always strived to implement new ideas and adjusted the company accordingly.
  • Hire the best people and build a culture that keeps those people. Every ounce of success we’ve earned at Mediafly is because of the amazing “Flyers” we have.

Since launch, what has worked to attract and retain customers?

Since day one, we’ve been committed to customer success and growth. Throughout our history, we can directly correlate our highest growth periods to when we (a) quickly changed our operations to solve the problems our customers were facing (b) doubled down on our focus of demonstrating value to drive revenue.

A few years ago, we shifted aggressively toward Account-Based Marketing which has had a tremendous impact on the company. Instead of trying to reach every potential buyer, we decided to reach the buyers that fit our Ideal Customer Profile (ICP) and have a demonstrated intent to purchase sales enablement technology. This translated to spending less time evangelizing the value of sales enablement to prospects that may never purchase.

We’re a Software as a Service solution, which means we need to earn our customers’ loyalty every single day. If we don’t, they will stop using Mediafly. We dedicate significant time to our customers through initiatives like Customer Delight, and close collaboration on product enhancements. If we continue to solve big challenges for our customers, in timely and innovative ways, they will want to stay and grow with us.

How are you doing today and what does the future look like?

The long-term goal for Mediafly is to rapidly innovate in the area of engagement. Engagement of sales teams and allowing them to engage with their buyers.

You worked hard to create a great company but there’s always room to improve and become an even greater company.

We’re building breakthrough solutions that we believe will change the way companies engage their sales teams and the way that sellers engage buyers, particularly in a digital selling environment.

Through starting the business, have you learned anything particularly helpful or advantageous?

I’ve learned it is important to invest in marketing, to earn revenue early on in the business, and to hire the right people and build a culture that keeps them here.

In terms of trends outside my control, I believe there are positives and negatives in everything. For example, COVID-19 created many challenges for our business and our workforce but it also introduced opportunities. The key to navigating these trends is hiring talented people who know when to pull back and know when to capitalize on them.

What have been the most influential books, podcasts, or other resources?

The books/programs that have inspired me the most include:

The core themes from these books that have guided my leadership techniques at Mediafly are:

  • My job is to get the right people on the bus, and then find the right seat. I still spend a lot of my time finding the next “right person” for the bus, even if we don’t have the seat for them yet.
  • Don’t settle for ORs when you can look for ANDs. Companies like Sony pioneered portable electronics because they refused to believe that you could not have small AND portable. By removing this limiting belief, they invented solutions that others thought impossible.

Advice for other entrepreneurs who want to get started or are just starting?

My advice is to hire talented people and always be willing to take advice. Change is not a bad thing. You worked hard to create a great company but there’s always room to improve and become an even greater company.

Where can we go to learn more?