In this episode, we talk to Jim O’Neill. Jim is the cofounder and chief technology officer of SaaSWorks. His company is focused on helping subscription and software-as-a-service companies improve their net revenue retention by providing data-driven expert assisted insights and recommendations.

Prior to SaaSWorks, Jim was a founding team member of HubSpot, where he held the CTO, CIO, and chief people officer positions over different times of the company’s growth. He also helped scale the company from pre-revenue through $400 million and over 1,500 employees worldwide.

In 2015, Jim was named Boston CIO of the Year and was a member of the Massachusetts Governor’s Council on Innovation. In our conversation, we cover a wide range of topics, including the formation story and early days of HubSpot, how maintaining good work relationships through the years has benefited Jim many times over, and how trust can help break down silos and help early stage startups succeed.

We get into the idea that SaaS businesses are more like e-commerce companies than enterprise software companies. We spend time discussing how data helps you understand your business and how it can be key to your success. We also cover Jim’s thoughts on the future of product-led growth and the benefit of the freemium model, how it can help decrease customer acquisition costs (CAC), and how freemium and product-led growth leads to better customer relationships.

We also get into Jim’s angel investing strategy and the Boston startup ecosystem, his advice to recent grads and current job seekers, and a whole host of other great topics. Please enjoy my conversation with Jim. And if you have questions that you’d like to hear covered in future episodes or recommendations for future guests, please email me at shawnjenkinsblog@gmail.com. Thanks and enjoy.

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