Interview with Carson Conant, Founder and CEO, Mediafly

Carson Conant

“Marketing leaders who can make decisions based on clear data, can move faster and focus on the right things because they know what works and what doesn’t.”


Tell us about your role at Mediafly and how you got here.

I am the Founder and CEO of Mediafly, a Chicago-based provider of sales enablement technology. My objective when I founded Mediafly was to assemble an incredible team of leaders that excel in their unique areas and are passionate about their work. I focus most of my time collaborating with them on the vision for Mediafly and ensuring they have the teams and resources they need to make Mediafly successful. It’s challenging, humbling, and thrilling to work with such talented individuals.

What inspired you to found a B2B sales enablement platform?

Most enterprise solutions are designed for administrators but a burden for end users. Mediafly was uniquely positioned to provide an enterprise content management platform and mobile application that addressed the needs of management while also being user-friendly enough for sales reps to want to use the technology. Our first sales enablement customers included industry-leaders like Goldman Sachs, PepsiCo, and NBCUniversal — each of whom brought a different set of needs and product vision which laid the foundation for the platform we are today.

What’s the most interesting part of leading a sales-focused company in a tech-heavy ecosystem?

Mediafly gets to work with the most progressive companies, enabling them to transform the way they sell. We become a core part of their sales strategy, enabling their sales and marketing teams to come together and win against their competition. Most companies are stuck in a “show up and throw up” sales model where they present from static, linear presentations. Seeing companies embrace a technology platform like Mediafly to enable interactive and data-driven sales stories is inspiring.

Given the changing dynamic of marketing analytics and customer insights, how do you stay on top of your game?

The enterprise sales and marketing space is constantly evolving and we had to architect Mediafly to keep pace. Our Extensions platform enables us to leverage partners to rapidly build new custom and turn-key sales tools that can be deployed within a customer’s Mediafly environment. This allows us to explore new and progressive ideas in partnership with customers. We get to learn with our customers and bring the common elements back to the core platform. This model decreases the time to value and allows us to enable companies that have unique objectives.

How has the tech industry evolved since the time you started your career?

When I founded Mediafly, the iPhone and iPad had not yet been invented. As these new devices hit the market, Mediafly was ideally positioned to leverage mobile to help companies sell in a new way. We had a front row seat as companies wrestled with concerns around BYOD, security, cost, and more. I believe that within each concern is an inherent opportunity if you can tap into it. For instance, companies wrestle with the cost of buying iPads vs. touchscreen laptops. They each have their strengths so there is no right answer. We’ve been able to create applications for both laptops and iPads that leverage their individual strengths so that as companies pick their direction we are ready.

The recent move to the cloud was a similarly interesting challenge for companies and presented an opportunity for Mediafly to offer new security capabilities that allowed them to confidently make this move. In many cases, the Mediafly application was the first place a company put sensitive content outside of their own servers.

Now, the desire for Machine Learning and Artificial Intelligence as it relates to analytics and recommendations is a new trend that companies want to leverage but often don’t know where to start. By making ML/AI part of the core Mediafly solution, we get to work closely with companies to answer “holy grail”-type questions, such as “what sales stories drive the most business?”. When Marketing and Sales departments can definitively point to quantifiable success of content and sales stories instead of debating based on anecdotes, it is a game changer.

Can marketing and sales teams survive without data?

They can probably survive, but if they are in a competitive industry, they certainly can’t win without data and knowing what to do with it. Companies need to be collecting key data, they need to know what questions they want answered and they need the right solution in place to use that data to get answers.

In the sales enablement space, companies that have the ability to use customer-specific data insights in their sales stories, can sell based on facts rather than assumptions. Marketing leaders who can make decisions based on clear data can move faster and focus on the right things because they know what works and what doesn’t. A progressive new sales motion is risky for a company to roll out because it can get lost in translation or fail to resonate with buyers, but when backed by data that shows which sales stories perform in terms of revenue, marketers can remove the guesswork and know definitively if new messaging outperforms the status quo.

Do smaller enterprises manage data better than larger enterprises*?

I believe the use of data is independent of the size of a company. The solutions used to capture data are readily available to both small and large organizations. However, this data is useless without the ability to understand the data and act on that understanding.

I have worked with very large companies that have a clear idea of what they want to measure and the ability to act fast based on new insights. I have also worked with large companies that do not take the necessary steps to ensure they are capturing important data. In the end, the desire and respect that the company has for data drives its value.

What’s the idea behind your Evolved Selling solution?

Mediafly’s Evolved Selling philosophy is the encapsulation of the common sales strategies that we have seen effectively used by successful companies to increase market share and revenue through sales transformation. It comes down to 4 steps:

  • Dynamic – Offer sales teams the ability to access and assemble various content types on the fly throughout your presentation. This not only increases sales efficiency but also ensures reps are equipped to easily pivot conversations to address what the buyer wants to talk about.
  • Interactive – Incorporate tools like ROI and TCO calculators, product configurators, and more into your presentation to capture input from buyers, and use the information to guide discussions for more educational and consultative sales interactions.
  • Informed – Enable sellers to automatically pull data from various sources and present it in real-time to create a more relevant and engaging buyer experience that addresses challenges unique to the buyer’s business or industry.
  • Integrated – Integrate Mediafly with other core business systems like CRM to enable easy meeting tracking and follow-up, measure sales performance, and determine which content drives revenue. Use the information to optimize existing content and processes and to inform future strategy.

What is the ‘State of CRM and Lead-generation tools” in 2018?

CRM has essentially become a hub – a central location where data from all other marketing and sales tools, including marketing automation, AdWords, and more, is stored. With organizations utilizing more disparate systems than ever for data collection and data-driven targeting, it’s imperative to have all of these systems successfully integrated back to the CRM to truly harness the power of the data collected. Siloed data isn’t useful to anyone, because it doesn’t provide the full picture. What most businesses today don’t realize is that by also integrating a robust sales enablement platform like Mediafly with CRM, they can measure things like what content drives revenue for reps in the field and use the information alongside lead generation and marketing automation data to optimize collateral and inform future campaigns.


At Mediafly, we’re using Pardot for marketing automation, Salesforce CRM, and, a personalized selling platform, in addition to our own Mediafly sales enablement solution for Evolved Selling.

Could you tell us about an outstanding digital campaign/ Customer Success story at Mediafly?

It is hard to isolate one story; we pride ourselves on our high-touch approach to customer success, which is why our customers often expand their usage of Mediafly by 5-10x after our first engagement. Our customer Givaudan, the world’s largest flavor and fragrance company, is a great example of this. The company initially implemented Mediafly for use by their North American-based sales reps before expanding use of the solution into all three of their other business regions in a second phase, global rollout. In phase three, the company will look to see how other departments across the organization can leverage Mediafly.


Once we have achieved Artificial General Intelligence, whereby a machine can perform any intellectual task that a human being can, the world will change fundamentally for everyone, but we aren’t there yet. When business leaders talk about AI today, they usually mean Machine Learning, in which computers can learn to recognize specific patterns in data or behavior and use those patterns to draw conclusions about future events or actions.  For instance, a Tesla car can learn to self-drive and Google Photos can learn which faces belong to which people. But unlike Science Fiction, they don’t have personalities and aren’t trying to take over the world…yet.

Thanks to the Machine Learning frameworks available now, companies like Mediafly can create learning models to perform highly sophisticated tasks that were nearly impossible a few years ago. One example of Machine Learning delivering real-world benefits to the Sales Enablement space is the identification and classification of sales meetings. ML can be “taught” to identify when a sales rep has completed a sales presentation (vs. preparation or training), which customer the presentation was for, and what sales topics or themes were presented. Marketing can then take the information collected and gain valuable insights into which sales stories generate the most revenue in various sales scenarios by propelling deals forward.

How do you inspire your people to work with technology?

At Mediafly, we eat our own dog food. Every member of our team is expected to act as an ambassador of what is possible with sales enablement by using Mediafly. This often involves using the latest devices and technologies. While we know not all cutting-edge technologies are ready for prime time, we’ve created a culture where we engage with new technologies early and often.  Many solutions are ahead of their time for our industry — Google Glass, Cryptocurrency. By embracing these technologies early, we are ready when the market is. We’re technologists at our core, so we love this stuff!

One word that best describes how you work.

Supportive. As CEO, my job is to is to hire exceptionally brilliant people and provide them with the support they need to do great things.

What apps/software/tools can’t you live without?

I can’t live without remote conferencing solutions (e.g. Webex, GotoMeeting, Zoom), even though they are a constant frustration for anyone in sales or who has to do mission-critical remote presentations. There is no shortage of startups in this space *trying* to build something that makes web conferencing as simple as making a phone call or sending an email. I look forward to the day someone succeeds, but in the meantime, I’ll be over here watching “A Conference Call in Real Life” on YouTube for comedic relief.

What’s your smartest work related shortcut or productivity hack?

I write emails in a small window. Emails are typically written on a computer but read on a phone, so if you shrink your composer window down, you’ll have a better perspective of how long your emails will appear to the recipient. You’ll find yourself writing shorter, more succinct emails that have a higher probability of someone reading or responding to them.


I’m currently reading Life 3.0 about AI. Read it after reading Sapiens for a better understanding of where we came from and where AI is going to take us. I’m a geek at my core — I love engineering and technology magazines.  A few books have fundamentally changed the way I built Mediafly, including Jack: Straight from the Gut by Jack Welch and Built to Last: Successful Habits from Visionary Companies by Jim Collins and Jerry I. Porras.

What’s the best advice you’ve ever received?

“People are like tea bags. You don’t know what they are made of until you put them in hot water.” This quote has various derivations, one of which is accredited to Eleanor Roosevelt.

Anyone can claim to be honorable, respectful, and ethical when things are good. It’s when times are unbearably tough (hot) that you really find out who a person is. In business and life, you want to surround yourself with people who can remain classy and honest in even the toughest circumstances. I’m proud to say that I’ve been impressed to witness the behavior and actions of my family, friends, and colleagues under pressure.


I have a unique ability to find insanely talented and fun people and convince them to join me in my entrepreneurial endeavor.  I personally selected most of the 50 founding members of our team, and in some cases, spent years wooing them to join the Mediafly family. I excel at getting people here and keeping them here, as evidenced by Mediafly’s placement on the 2018 Crain’s Best Places to Work in Chicago list where we earned the #1 spot in the Small Business category.

Thank you, Carson! That was fun and hope to see you back on MarTech Series soon.

Carson founded Mediafly in 2006 and has led the growth of its enterprise solutions that is being used by some of the world’s largest and most admired companies. Under his leadership, Mediafly has been ranked four consecutive times in Inc. Magazine’s “5000 Fastest Growing Companies” annual edition. When Carson is not traveling to be with customers, prospects, and shareholders, he spends time with his beautiful wife and two rambunctious children in Chicago.

The Evolved Selling™ Solution. Mediafly was founded on the principle that people hate being sold to because it rarely addresses their needs. By using our technology, the world’s top companies are able to shape the sales presentations in real-time, rather than boring their customers with generic pitch decks built the night before. Sales teams using Mediafly are more effective in each meeting because they engage their customers with insights that are directly relevant to them. We call this Evolved Selling. Evolved Sellers become more flexible, dynamic, and interactive, resulting in increased sales and stronger customer relationships. Mediafly works with Global 2000 companies, such as MillerCoors, GE Healthcare, Charles Schwab, and Sony.

