492 | Jason Jaynes - Divine Leadership Secrets Every COO Turned CEO Must Know Now

Second in Command: The Chief Behind the Chief

Second in Command with Cameron Herold

Entrepreneurship, Business, Management, Careers

4.5 • 1.6K Ratings

🗓️ 15 July 2025

⏱️ 38 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

What does it really take to lead a mission-driven company from the inside out? In today's episode of the Second in Command podcast, Cameron is joined by Jason Jaynes, former CO and now CEO of eCatholic, creator of digital tools and services tailored to Catholic parishes, schools, and dioceses.

In this insightful conversation, you'll be taken behind the curtain of a rapidly evolving organization as its leadership navigates succession, growth, and transformation. Jason reflects on the decision-making process involved in identifying and promoting the right internal talent, exploring how mentorship, trust, and long-term planning played key roles in building a strong leadership team. Get a glimpse into how one leader balanced humility with decisiveness in preparing both himself and his team for the future.

The discussion also explores the personal growth journey of the guest as he transitions from a behind-the-scenes operator to the public face of the company. He opens up about the challenges of stepping into the spotlight, embracing new responsibilities, and learning the nuances of strategic sales and marketing leadership in a niche space. The discussion explores the courage to seek help, partner with outside experts, and shift perspectives in order to lead effectively.

This episode offers a candid, inspiring look at how thoughtful leadership can shape not only a company’s trajectory but also its culture and impact. Curious about how eCatholic helps faith-based organizations thrive online? Visit eCatholic.com to explore their suite of digital tools.

If you've enjoyed this episode of the Second in Command podcast, be sure to leave a review and subscribe today!

Enjoy!

In This Episode You'll Learn:

An overview of eCatholic, a company founded to provide digital tools for the Catholic Church, as well as their focus on helping churches reach their communities online.

Jason's previous role as COO, focusing on systems, processes, and scaling the company in the first two years.

The transition from COO to CEO, focusing on becoming, in his words, "three miles wide and one inch deep."

The process of identifying and grooming Karen (Lackey) for the COO / VP of operations role, including her previous roles and responsibilities.

The importance of hiring experts in areas where one lacks expertise, such as sales and marketing.

And much more...

Guest Bio:

Jason Jaynes is the CEO of eCatholic, a company that provides a suite of digital tools and services tailored specifically for Catholic parishes, schools, and dioceses. With over 27 years of experience in the software and technology industry, Jason has held a wide range of leadership roles, including Co-founder, COO, CTO, VP of Product, VP of Business Marketing, and Senior Systems Engineer. His diverse background reflects a deep expertise in both technical innovation and strategic business development. Jason holds a Bachelor of Science in Computer Science from Texas A&M University and earned his MBA from the University of Texas, equipping him with the skills to lead mission-driven digital transformation within faith-based organizations.

Resources:

Connect with Jason: Website | LinkedIn

Connect with Cameron:

Transcript

Click on a timestamp to play from that location

0:00.0	One of the things that I think is unique that stood out to me is the signal to noise ratio
0:05.3	outside the Catholic market is really high.
0:08.0	You know, when you think about, especially and we'll just broadly define it as the Protestant
0:13.0	space with Baptist, Methodist, Lutheran, any religion, you know, besides being Muslim or Jewish
0:20.1	that did something on the umbrella of Catholicism,
0:23.1	they operate in a lot of ways like small businesses do.
0:32.8	Welcome to the Second and Command podcast, produced by the C.O. Alliance and brought to you by its founder, Cameron Harold. In the Second in Command podcast, we talk to top COOs who share the insights, strategies, and tactics that made them the chief behind the chief. And now, here's your host, Cameron Herald.
1:03.1	Our guest today is E-Catholics, former C-O, and their current CEO, Jason James.
1:08.7	E-Catholic has also got their new C-O-O-O-O-Liance member, which I'm excited about.
1:11.4	Jason is an experienced software engineer with 27 years of practice across multiple functions, including management, product management,
1:16.8	software engineering, marketing, support and sales, multiple disciplines including cloud computing,
1:21.8	IoT, mobile security, social media, online advertising and SaaS. He's currently the CEO of E-Catholic and he's going to
1:28.5	talk to us about his progression, joining as the COO, moving through that over a period of five years
1:34.1	and then moving into the CEO role and also then bringing on his successor and making sure
1:39.8	that she's set up for success as the new COO. So it's an exciting episode. It's one of the rare
1:44.1	times we've ever had a CEO on the podcast and you can understand why. We'll see you on she's set up for success as the new C.O. So it's an exciting episode. It's one of the rare times
1:44.4	we've ever had a CEO on the podcast and you can understand why. We'll see you on the inside
1:48.9	and this is one you can watch on our Second and Command podcast YouTube channel as well.
1:57.7	So Jason, welcome to the Second and Command podcast.
2:02.8	Thanks, Cameron. Really happy to be here.
2:08.3	Yeah. So you are a rare breed, and that's why I've actually invited you onto the podcast today.
2:13.3	As we just heard in the introduction, you're actually the CEO now of a company called E-Catholic.
	...

Transcript will be available on the free plan in 27 days. Upgrade to see the full transcript now.

Previous episode

Disclaimer: The podcast and artwork embedded on this page are from Second in Command with Cameron Herold, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Second in Command with Cameron Herold and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.