Growing a Multi-Million Dollar 24/7 Live Chat Service—w/ Jon Tucker of HelpFlow


“There’s definitely chaos as far as getting it right.”

That’s what Jon Tucker, CEO of HelpFlow told me about his multi-million dollar productized business when I talked to him recently.

In this growth story, Jon teaches us some critical nuts-and-bolts advice to building and scaling a successful productized service for eCommerce. 

HelpFlow is a business that provides 24/7 live chat support to eCommerce stores to help reduce checkout cart abandonments.

And when Jon first started his business, his goal was to get to a million dollars. 

With 6 years in business, he’s already scaled from making $97 in his first sale, to becoming a multi-million dollar company that serves over a hundred eCommerce stores.

With a solid team of 120 people, Jon’s business is on track to keep skyrocketing and helping other businesses drive more conversions and sales. 

So if you’re an agency looking for some inspiration, or the owner of a business with ambitions to keep growing, I think you’ll extract some gold nuggets from this interview.

Let’s dive in to learn what Jon did to build and scale and how you can do the same for your business.

In a rush? Want to download this interview as a PDF so you can easily take action on it later? Click here to download this article as a PDF guide.

Key Points:

  • [01:15] Jon talks about how he started as an SEO agency with a $97 first sale, had HelpFlow as a long-term vision, and scaled it to a multi-million dollar business.
  • [02:47] How he took zero outside investment to scale his bootstrapped business and how it was profitable since day 1.
  • [03:40] He taps into the importance of scaling with a good team of people and quality work.
  • [04:20] He talks briefly about how he started doing web design and driving traffic for small businesses and why he started narrowing in on just SEO.
  • [05:00] He reveals how a simple comment from someone about Google made him realize that his first business could be hard to scale in the long term.
  • [05:30] John mentions the reasons why big agencies needed his SEO service but how there wasn’t really an opportunity to scale other marketing services to those agencies.
  • [06:40] He opens up about how stressful it is to build a business where you can’t do annual planning or 3-year plans, and where you don’t really know what’s going to end up changing.
  • [07:00] He shares his thoughts on Google and the reason why he thinks other businesses succeed in the SEO industry.
  • [10:00] He goes in-depth on the main things that he would do differently in his business—starting by making the price point higher.
  • [10:25] He talks about the importance of pricing close to the value of your products or service. And he says that when you’re very clear on the value your product or service provides, it’s much easier pricing closer to that value.
  • [11:55] He explains his strategy and the psychology behind not showing their pricing on HelpFlow’s website.
  • [15:37] He talks about how he removed himself from the work early on and how he made sure first that his business was actually working and running.
  • [16:10] Jon explains how he built his business model calculating how many chats per hour and per agent could be handled by his team, and how that would equate out to a client of his service.
  • [18:20] Jon recommends one of the Entrepreneurial Operating System’s (EOS) frameworks—traction—because you can implement all of it in your business.
  • [19:25] As a system-focused person, Jon says the biggest things that are really important to get right is the numbers of the business and the actual system on how you deliver.

Top 5 Critical Takeaways:

  • [03:29] Not every company scales thanks to ads. Jon mentions how his business grows as he keeps the quality “really really high” and how they don’t deploy a hundred thousand dollars a week in ads in order to scale.
  • [16:00] In order to grow, you need other people to help you do so. John talks about his organization and how you need to have a team who is well-trained and staffed so you can take on any number of clients and scale.
  • [07:20] Changing your business model can be daunting—especially for agencies. John tells us how he rowed the boat into a different direction and saw clear patterns that pushed him to start offering live chat support.
  • [21:00] Jon mentions that you need other people to own certain parts of the business so you can own what you’re truly best at.
  • [26:50] His goal was to get to a million dollars. But as he got close and surpassed that number, a lot of the growth slowed down.

Resources Mentioned:

  • WP Curve
  • “Entrepreneurial Operating System” book

Keep AutoGrowin’, stay focused.

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