Disrupting the Direct Mail Marketing Industry

4 Minutes Read

Episode 169

Are you holding on tight to your vision of what your business can do? You may think your attempts are effortless and miss your chance to succeed. If you are ready to find out if direct mail marketing is a thing of the past or if past practices are circling back around, you’re in luck!

Dennis Kelly is CEO of Postalytics, a fast-growing direct mail automation software company. Postalytics helps marketers do more in less time with streamlined production, integration into the marketing tech stack, and real-time direct mail campaign analytics. Postalytics is Dennis’ 6th startup. He has been involved in starting and growing early-stage technology ventures for over 30 years.

Here are three reasons why you should listen to the complete episode: 

  • Learn from Dennis Kelly’s journey in starting six businesses.
  • Get insight into how direct mail marketing is integrating with modern CRMs.
  • Discover which industries are using direct mail marketing to increase their reach.

Episode Highlights 

Dennis’ background and journey

    • Dennis started in the tech sector as a young guy out of college.
    • He worked for a couple of years in Manhattan for Prudential insurance.
    • He tried to make money in any way he could.
    • His parents encouraged him to knock on doors, scrap it, and find ways to put money in his pocket.

Taking control of his destiny 

    • Dennis jumped into a startup with his friend and his friend’s brother.
    • It was a disaster for a couple of years, but they hung in there and were eventually saved by the PC revolution.
    • Their startup was a nice success around one of the first online calendar systems.

Dennis’ problematic beginning

    • Dennis and his partners built a solution that worked for a very small percentage of the market we’re trying to sell.
    • It threatened their prospects to get them to change their behavior and adopt a new way of doing their jobs.
    • They encountered financial struggles and spent a year with little to no income.
    • They had to rebuild the company as a software company and weren’t selling hardware anymore.

Sticking it out and not quitting to go back to corporate

    • Dennis believes if you believe you can do something, you just can’t quit, and you have to keep grinding.
    • It would be deflating for him to quit on something that he knew was going to happen.
    • They kept going because they knew the nursing homes had to adopt computers at some point.

A breakdown of the companies Dennis built

    • The first startup Dennis was a part of was the healthcare software that assisted with accounting and patient record keeping.
    • The second was the online calendaring system.
    • The third was a company down in the data center dealing with some issues we discovered connecting these different content providers at home.
    • The fourth one was mobile application development, right on those early handheld computers that corporations could deploy for remote workers to capture data and do business processes.
    • His fifth was still wireless, where he built a chain of Verizon Wireless retailers to take advantage of the changeover from flip phones to smartphones.
    • The sixth one is what Postalytics started as and has now morphed into what they are doing today.

The emotions and pain points of creating a startup 

    • According to Dennis, a startup is an emotional roller coaster.
    • He says you don’t over-celebrate too long and can’t cry too long either.
    • You get these sprints involved in startups and then realize that if all you’re doing is constantly sprinting, you can’t run this marathon.

Dennis’ role in the direct mail world

    • Direct mail is not at its peak in terms of the total mail sent in the US around 2008.
    • The direct mail industry in the US is about $40 billion annually.
    • The mainstream is forgetting about the ancient workflow with this marketing channel, but it’s still a great big business. 
    • Postalytics has been growing between 50 and 100%, on an annual basis, for the last five years.

What Postalytics has provided for businesses

    • When they pivoted to Postalytics, they targeted what they think is a fairly narrow, ideal customer profile.
    • Ideally, they worked with marketers with small and mid-sized businesses with 20 to 200 employees.
    • They decided to radically simplify the production process of direct mail as a starting point because what they heard as they talked to digital marketers was they wanted to incorporate direct mail.

Dennis’ plan for the future

    • Dennis never approaches a business with a particular outcome.
    • He projects this business to have a good ten or 15-year run ahead of it because tremendous innovation, consolidation, and worldwide growth are available.
    • If you focus on building value through customers, products, and employees, you’ll have a lot of options along the way to finance, exit, or partially exit.
    • Dennis tries to put businesses in a position to have a lot of options and then make good decisions from there.

What Dennis would like to be remembered for

    • Dennis wants to be remembered as a good husband and father.

3 Powerful Quotes

4:00 – “Working in the corporate world was great, but I felt I needed to control my destiny more.”  

19:19 – “You get these sprints involved in a startup, and you get heads down and go 100 miles an hour. Then eventually, you realize this is a marathon, and if all you’re doing is constantly sprinting, you can’t run this marathon.”  

22:17 – “Do not let investors tell you what your business is. They have to buy your vision of your business; if you can’t find the fit, move on. There are a million investors, and there are no shortcuts.”  


About Dennis Kelly

Dennis Kelly is the CEO of Postalytics, a fast-growing software company that automates direct mail marketing, measures the results, and connects it to CRM/Marketing Automation.

Postalytics evolved out of Boingnet, a software tool used by direct mail service providers and agencies to provide landing pages and email campaigns that complement personalized direct mail.

Dennis was co-owner of Wireless City – a chain of 37 Verizon Wireless stores based in Florida, Massachusetts and Georgia. The company was acquired by Go Wireless in October 2011. Prior to Wireless City, he was CEO at Adesso Systems, an enterprise mobility software company. 

Previously, he was CEO and Co-Founder of Adjoin Solutions, Inc., an early market leader in the Web Services Management market. Adjoin was acquired by Computer Associates in July, 2003. Before founding Adjoin, he was VP of Web Services at Palm (PALM) leading the Palm.net wireless business, the MyPalm web and mobile portals, and other Palm web properties. 

He was also COO & Co-Founder of AnyDay.com (sold to Palm), headed sales for Achieve Healthcare, the largest provider of enterprise software and services to the post-acute healthcare industry and COO at Genesis Business Systems (sold to Achieve). Dennis holds a BA in economics from Colgate University.


Connect with Dennis Kelly




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Thanks for listening,


Picture of Darrell Evans

Darrell Evans

Darrell Evans is a serial entrepreneur, investor, and Co-founder/CEO of Yokel Local Digital Marketing Agency. He and his teams have helped businesses generate over $300M+ in revenue online. Every month, he leads virtual workshops teaching actionable strategies and tips from his experience helping companies market, grow and scale. To attend an upcoming workshop, click here => https://www.darrellevans.net/free-training.