All Episodes

June 30, 2020 78 mins

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.

Mark as Played

Advertise With Us

Popular Podcasts

Fudd Around And Find Out

Fudd Around And Find Out

UConn basketball star Azzi Fudd brings her championship swag to iHeart Women’s Sports with Fudd Around and Find Out, a weekly podcast that takes fans along for the ride as Azzi spends her final year of college trying to reclaim the National Championship and prepare to be a first round WNBA draft pick. Ever wonder what it’s like to be a world-class athlete in the public spotlight while still managing schoolwork, friendships and family time? It’s time to Fudd Around and Find Out!

Crime Junkie

Crime Junkie

Does hearing about a true crime case always leave you scouring the internet for the truth behind the story? Dive into your next mystery with Crime Junkie. Every Monday, join your host Ashley Flowers as she unravels all the details of infamous and underreported true crime cases with her best friend Brit Prawat. From cold cases to missing persons and heroes in our community who seek justice, Crime Junkie is your destination for theories and stories you won’t hear anywhere else. Whether you're a seasoned true crime enthusiast or new to the genre, you'll find yourself on the edge of your seat awaiting a new episode every Monday. If you can never get enough true crime... Congratulations, you’ve found your people. Follow to join a community of Crime Junkies! Crime Junkie is presented by audiochuck Media Company.

The Breakfast Club

The Breakfast Club

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.