Navigating the Challenges of Scaling

Navigating the Challenges of Scaling

The Duct Tape Marketing Podcast with John Jantsch

In this episode of the Duct Tape Marketing Podcast, I interviewed Jason, the CEO of ActiveCampaign, a leading platform for intelligent marketing automation.

A lifelong entrepreneur, Jason has been named to Crain’s Chicago Business 40 Under 40 list and was named EY’s Entrepreneur of the Year Midwest. He is a member of the Young Presidents’ Organization (YPO) and The Economic Club of Chicago. Jason also serves on the board of the Future Founders Foundation, a Chicago-based organization that empowers the next generation of business leaders and entrepreneurs. He is also a regular contributor to Fast Company and Forbes.

Having founded ActiveCampaign as a means to fund his education, Jason pursued a degree in fine arts until shifting his focus entirely to growing the company. He is a self-taught software engineer and technologist. Our conversation dives deep into the challenges that businesses face when scaling up, offering valuable insights and strategies for navigating this crucial phase of growth.

Key Takeaways

Jason emphasizes the importance of maintaining customer focus, embracing change, learning from failure, building a strong team, and staying true to your values when scaling a business. By prioritizing direct interaction with customers, fostering a culture of innovation, viewing setbacks as learning opportunities, investing in employee development, and upholding integrity and ethical conduct, businesses can navigate the challenges of growth and achieve sustainable success.

Questions I ask Jason Vandeboom:

[01:02] Is there a reason why ActiveCampaign was decided to focus specifically on small to mid-sized businesses?

[02:33] Have you been able to keep that self-taught view in the value system and culture of your company?

[03:52] How has your personal life changed since running such a demanding business?

[05:10] When it comes to failures do you have any business advice for people starting out?

[07:37] Do you have a management philosophy as a first-time manager of people and teams ?

[09:10] How do you make decisions about how to innovate?

[12:10] What are you hoping to communicate in positioning yourself as the marketing automation CRM of small teams powering big businesses?

[13:40] What role does AI play in your road map as a leader?

[14:52] Is it an oversimplification to say it’s just better lead scoring?

[15:54] Describe the Leap Year special event ActiveCampaign is organizing?

[17:57] What’s your secret to never getting bored with what you do as a CEO?

[20:16] What’s on your bucket list in the next 5-10 years, outside of work?




More About Jason Vandeboom:


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This episode of The Duct Tape Marketing Podcast is brought to you by ActiveCampaign

Try ActiveCampaign free for 14 days with our special offer. Sign up for a 15% discount on annual plans until Mar 31,2024. Exclusive to new customers—upgrade and grow your business with ActiveCampaign today!


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ActiveCampaign, Jason Vandeboom