Podcast Title: Second in Command: The Chief Behind the Chief with Cameron Herold
Episode: 492 | Jason James - Divine Leadership Secrets Every COO Turned CEO Must Know Now
Release Date: July 15, 2025

Introduction

In Episode 492 of the “Second in Command” podcast, hosted by Cameron Herold and produced by the COO Alliance, listeners are introduced to Jason James—the former COO and current CEO of eCatholic. With an extensive background spanning 27 years in software engineering and multiple operational roles, Jason shares his journey from COO to CEO, the challenges he faced during this transition, and the leadership secrets vital for COOs aspiring to ascend to CEO roles.

Company Overview

eCatholic was founded in 2005 by Josh Simmons, aiming to equip the Catholic Church with digital tools to enhance community engagement. Starting with website development in the mid-2000s, eCatholic has expanded its offerings to include live streaming, communication tools like email and text messaging, tithing solutions, and church management software (akin to CRM systems for churches). Celebrating its 20th anniversary in 2025, the company has significantly grown, extending its digital solutions to dioceses, parishes, schools, and ministries.

“We want to give them the tools that they can leverage to allow people to find them online, to learn about them online, and then to be invited in to become participants and to stay participants of that community.”
— Jason James [03:53]

Jason's Role and Transition

Jason joined eCatholic in 2019 as the 19th employee, stepping into a company poised for expansion but lacking in operational processes. Over five years, he helped double the company’s size, customer base, and product offerings, while nearly tripling revenue. Initially functioning as COO, Jason focused on laying foundational systems, investing in infrastructure, and executing growth strategies.

Transition to CEO:
In 2024, recognizing Josh Simmons' intention to transition out of the day-to-day operations, Jason was promoted to President and subsequently to CEO in January 2025. This shift required him to move from an in-depth operational role to a broader strategic leadership position.

“There’s nothing different about having that title on your shoulders, but when you wake up and you have that title on your shoulders, you just carry a different weight around with you.”
— Jason James [22:25]

Challenges and Learnings

Implementing Change:
Transitioning from a startup environment to a growing company presented challenges, particularly in introducing new processes and systems. Jason emphasized the difficulty of managing up to the founder while also leading a team accustomed to a family-like atmosphere.

“If you want something done and there's nobody to do it, you're on point to go figure out how to get it done.”
— Jason James [12:17]

Overcoming Resistance:
One significant hurdle was letting go of a long-tenured lead engineer, which was necessary for the company's growth despite being emotionally challenging due to the existing trust and reliance the team had on him.

Strategic Focus:
Jason highlighted the importance of prioritizing critical issues from extensive reports, focusing on areas that could jeopardize the company's survival if left unaddressed, such as security and system reliability.

“I knew that for the better of the company, it was going to be required.”
— Jason James [14:20]

Leadership and Team Building

Vision vs. Operations:
Initially, Jason grappled with balancing his visionary entrepreneurial spirit with his operational responsibilities as COO. Recognizing that his role wasn't to be the primary visionary, he collaborated closely with Josh to align operational execution with the company's vision.

Succession Planning:
As he transitioned to CEO, Jason focused on empowering Karen Lackey, the new COO and a long-serving member of eCatholic, to take over operational duties. This move was part of a broader strategy to delegate effectively and allow himself to concentrate on strategic growth.

“We have to bring people in the door. We think differently.”
— Jason James [34:12]

Personal Growth:
Jason has been actively working on enhancing his external communication skills, such as participating in podcasts and public speaking, areas that were not his natural strengths.

Future Directions and Advice

Expanding Market Reach:
eCatholic under Jason's leadership has been exploring non-Catholic markets through a separate brand, Gabrielsoft.com, aiming to cater to other religious organizations with customized digital tools.

Leadership Philosophy:
Jason advocates for empathetic leadership, fostering a work environment built on trust and collaboration. He emphasizes the importance of learning from mistakes and encouraging a growth mindset within the team.

“I want people to believe and see the world the same way that I do. But I want to do that coming from a position of love and not from a position of being this hard, driven manager.”
— Jason James [36:11]

Advice to Aspiring Leaders:
Reflecting on his journey, Jason advises younger professionals to embrace mistakes as learning opportunities and to develop a balance between managerial duties and visionary leadership.

“I don’t be so afraid to make mistakes. I am who I am today because of that mistake and a lot of other mistakes I made along the way.”
— Jason James [35:22]

Conclusion

Jason James' evolution from COO to CEO of eCatholic offers invaluable insights into effective leadership, strategic delegation, and the importance of aligning operational excellence with a compelling vision. His experiences underscore the significance of adaptability, continuous learning, and empathetic leadership in driving organizational growth and success.

Notable Quotes:

• “If you want something done and there's nobody to do it, you're on point to go figure out how to get it done.” — Jason James [12:17]

• “I want people to believe and see the world the same way that I do. But I want to do that coming from a position of love and not from a position of being this hard, driven manager.” — Jason James [36:11]

• “I don’t be so afraid to make mistakes. I am who I am today because of that mistake and a lot of other mistakes I made along the way.” — Jason James [35:22]

For more insights and leadership strategies from top COOs, visit COO Alliance or subscribe to the Second in Command podcast on your preferred streaming platform.