The community, coaching, and mastermind built for your Second-in-Command.

Second First provides training, tools, and community exclusively for COOs, Integrators, and other right-hand leaders of entrepreneur-led companies — so they can lead with more clarity, move with more confidence, and never figure it out alone.

Book a Call to Save 25% off a Year of your Second First Membership!

T&Cs: Must be an Entreprenista Member

Peer Membership & 1:1 Coaching Built For Seconds-In-Command

Second First gives your Second-in-Command the structure, peer mastermind, and 1:1 coaching built for the people running your business day-to-day. Members join a private cohort of executives, attend quarterly mastermind meetings, and get confidential benchmarking and expert-led sessions on sales, marketing, and leadership. For deeper support, our 1:1 coaching uses a proven framework tailored to your business goals, whether managing rapid growth, refining leadership style, or strengthening team alignment.

Revenue Growth Member

Companies experience an average of 28% revenue growth year over year.

Improved Strategic Alignment

Members see a 25% improvement in strategic alignment with their entrepreneur within 6 months.

Less Isolation

90% of operators and Integrators report feeling less isolated in their role.

Reviews from Happy Entreprenista’s

I stepped into my role and quickly realized how steep the learning curve was. Just when I felt overwhelmed, I discovered Second First — and it truly has been a game changer.

1/3

RaeShawn Cannon

COO

There are some communities that do cater to COOs but don't have that personal touch. Megan creates an environment where people feel comfortable, and that really, really matters.

1/3

Bergen Cooper

COO

I can't tell you how many times I've referenced the materials to help prep for meetings, conversations, and new initiatives.

1/3

Connor Botes

COO

A Message from Jessica Eaves Mathews, Co-Founder

As a fellow woman entrepreneur, I understand the challenges and dreams behind your business. My goal is to give you peace of mind by protecting your brand, content, and innovations—now and as technology evolves. With 30 years of legal experience, I’m here to help you navigate trademarks, copyrights, and AI law, so you can focus on growing your unique business with confidence.

A Message from Megan Long

Founder I spent a decade as the COO and Second-in-Command of a $10 million entrepreneur-led company. Even with a Master's degree and a CPA, I spent years figuring it out on my own, isolated, without peers who truly understood the role. Through trial, error, and a lot of long hours, I built an incredible partnership with my founder and moved the business forward. Along the way I earned a few awards, including 40 Under 40, Stevie Woman of the Year, and Nashville Emerging Leader...and I still felt completely alone. When I started talking to other COOs, I learned I wasn't the only one. Everyone was struggling to understand their CEO, everyone was burnt out, and nobody had built anything for them. So I built it. Second First® exists because the Second-in-Command deserves the same investment, community, and support as the entrepreneur they work alongside.