Nobody Prepared You for This Job. This Room Will.
CEOs have strong peer communities. Now you do, too.
The Second First® membership gives you the structure, facilitated agenda, and peer mastermind designed specifically for the right-hand leader of an entrepreneur-led company.
Trusted by
Who Is This For
You report directly to a founder or entrepreneur
You’re not looking for another book or course, you’re looking for what’s proven
You wish you knew what the best and brightest operators were doing in their companies
You’re managing new ideas and priorities daily, with no one to help prioritize
You’re ready to stop feeling isolated figuring this out alone
You’ve hit the ceiling of what your company can teach you
The most important role in the company, and the most isolating
As Second-In-Command you’re the COO, the Integrator, the Chief of Staff, the President, the “person who runs everything.” The title varies, but the challenges don’t.
Being a Second-in-Command to an entrepreneur is a genuine superpower. You see the big picture and the details. You translate vision into action, manage up and down simultaneously, and keep the business moving forward every single day. But it can also be isolating, frustrating, and exhausting.
How do I hold my team accountable to their KPIs?
What are the best hiring practices for getting the right people in the right seats?
How do I manage my founder’s ideas without losing focus?
How do I scale while still delivering a consistent product or service?
The most successful CEOs don’t figure it out alone. They have peer groups, forums, and communities built specifically for them. Now you do too.
Second First is the professional mastermind membership created exclusively for the number-two leader in an entrepreneur-led company.
You report to an entrepreneur whose brain moves faster than the business can. You’re expected to be competent in every department without being the expert in any of them. You lead leaders and managers, translate a big-picture vision into operations, and absorb the chaos so your team doesn’t have to.
And you’re doing it alone.
There’s no degree for this. Business school trains enterprise-level theory, not the tactical needs of an entrepreneurial Second-In-Command. So you’ve been piecing it together yourself: books, podcasts, Harvard Business Review articles, conversations with AI, and lots of trial and error. It works, slowly. But every lesson you learn the hard way costs the business time and costs you confidence.
There’s a faster way. Inside the Second First membership, you’ll get structured mastermind support, expert-led trainings, practical tools you take straight back into the business, and a peer group of people who hold your exact seat. Everything here is built for the specific demands of being Second-In-Command.
Mastermind: a small, intentional group of people who meet regularly to help each other reach their goals. Members share challenges, offer feedback, and hold one another accountable.
As a member, you will…
Lead Leaders
Build the next layer of leaders, and the scorecards to hold them accountable.
Your cohort works through how to develop managers who can run their departments without you, and how to build scorecards that show who’s on track before the quarterly numbers do. Members bring their own scorecards to the table, so you leave with a version another Second-in-Command has already tested.
Drive Enterprise Value
See the numbers clearly, and fix where work breaks down between your teams.
Benchmark your financials against operators in non-competing industries and learn how other Seconds-in-Command give their founders real financial visibility. Then tackle the handoffs that quietly cost the business money, like the gap between what sales promises and what operations delivers.
Become Indispensable
Become an indispensable asset to your entrepreneur by getting meaningful time with your founder back on the calendar.
Only 1 in 3 members say they have dedicated, big-picture one-on-one time with their entrepreneur. Most get tactical check-ins that are the first thing canceled. Your cohort shares how they protect that time and what they bring to it, so your one-on-ones are spent setting direction, not putting out fires.
Invest in Yourself
Build a plan for how you’ll lead, not just what the business needs next.
Every member writes and presents a personal plan to be a more effective executive: where your time goes, what you should stop doing, and what you need from your entrepreneur. Your cohort holds you to it every quarter.
Our Mastermind Format
Second First cohorts follow a proven, facilitated mastermind agenda designed specifically for Seconds-in-Command. Every quarterly meeting has structure, dedicated topics, and accountability built in.
You don’t need more open-ended conversation or commiseration.
You need solutions and great ideas you can implement on Monday morning.
📊
Benchmarking
Confidential benchmarking of key operational metrics against peers in non-competing industries. You see where you stand, and where the opportunities are.
📝
Report Projects
Members prepare on 1–2 specific topics before each meeting, creating structured peer accountability and producing real insights you can bring back to your business.
🎉
Hot Seat
One member’s biggest goals and toughest challenges get the cohort’s full attention. The group serves as a compassionate board of directors: direct, experienced, and honest.
👥
Roundtable
Crowd-sourced discussion around what’s top of mind across the group. The challenges you thought were unique turn out to be universal (and solvable).
With Proven Results:
Based on member benchmarking data, 2025.
↑ 28%
average revenue growth
year-over-year
↑ 25%
improvement in strategic alignment with their entrepreneur
90%
of members report feeling
less alone in their role
Testimonials
“Having a community of peers matters because they know what it’s like. Even if they don’t know your exact situation, you don’t have to take the time to explain the details because the details don’t matter — They know what it’s like to be in your shoes.”
Reagan Thomas, VP & Integrator
If you’re a COO feeling a bit lost or just looking for that next level of growth, I can’t recommend this enough. Megan’s mentorship is invaluable, and genuinely excited about what comes next!
RAESHAWN CANNON, COO
FORT WORTH, TX
I have learned so much in a short amount of time – the experience and the value I’m going to bring to the rest of my business and the rest of my people is incredible.
KORY THOMPSON, MANAGER
CINCINNATI, OH
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.
BERGEN COOPER, COO
BROOKLYN, NY
One of the big differences with Megan’s Second First is that she asks a lot of deep questions of each of us. That’s allowed us to have deeper conversations than just superficial “How’s your business doing?”
FORREST DERR, COO & INTEGRATOR
FAIRHOPE, AL
“I was a little nervous coming in, a little imposter syndrome as most people have, and [Megan] has made me feel so comfortable.
She has really taken my role seriously, and has put me in a room with amazing people with incredible jobs.
She’s made me feel really at home, and smart and capable. I think that’s what anyone would want in someone helping you take your next step in life.
I really appreciate being here, and I appreciate Megan.”
Belinda Ligotino, Operations Manager
Included in your Second First Membership:
✔️ A private cohort of up to ten Key Executives from non-competing industries
✔️ Four half-day virtual mastermind meetings a year
✔️ NEW: Monthly open peer-to-peer roundtables (requested by members!)
✔️ Expert-led virtual sessions on sales, marketing, leadership, and operations
✔️A library of downloadable tools and templates
✔️A private cohort space on Circle for year-round connection
✔️Access to the national Second First® community
Your entrepreneur has a peer group.
Now you do, too.
Most members’ companies cover Second First as professional development. Investing in a Second-in-Command is one of the highest ROIs a CEO will receive, because every system you bring back multiplies their impact.
“How do I ask my CEO to pay for this?”
We wrote an email template for you to use:
Subject: Professional development request: Second First membership
Hi [Name],
I’d like to join Second First, a peer mastermind built specifically for COOs and Integrators in entrepreneur-led companies. Each quarter I’d meet with a private cohort of up to 10 operators from non-competing industries to benchmark our numbers against theirs and work through real operating challenges, then bring what works straight back to us.
The investment is $425/month for a 12-month membership. The time commitment is one half-day meeting per quarter plus 1 to 3 hours of prep.
I’d like the company to cover this as professional development. Can we talk about it this week?
[Your name]
Founder Megan Long also wrote a letter directly to your entrepreneur. You can download it here: A Letter to the CEO, from Megan Long
SECOND FIRST® MEMBERSHIP
$425
/MONTH
12-month membership, billed monthly.
➡️ Usually company-paid
Most members expense their membership as professional development or training.
➡️ Partner rate
Entreprenista League members and select Entrepreneurs’ Organization chapters receive a discounted rate.
Created by someone who was the Second-In-Command.
Megan Long spent a decade as the COO and Second-in-Command of a $10 million entrepreneur-led company. Even with an MBA and CPA, she spent years figuring it out on her own — isolated, without peers who truly understood the role.
Through trial, error, and a lot of long hours, she built an incredible partnership with her founder and moved the business forward. Along the way she earned a few awards — 40 Under 40, Stevie Woman of the Year, Nashville Emerging Leader. And she still felt completely alone.
Talking to other COOs, she learned she wasn’t the only one. Everyone was struggling to understand their CEO. Everyone was burnt out. Nobody had built anything for them.
So she did. Second First® exists because the Second-in-Command deserves the same investment, community, and support as the entrepreneur they work alongside.
Megan personally interviews every applicant and facilitates the mastermind meetings herself.
Frequently Asked Questions
Who should join the Second First membership?
This community was created for leaders and executives in entrepreneurial businesses. Regardless of your title, if you report directly to the CEO/founder/entrepreneur, this membership is for you.
Common titles of our members are Chief Operating Officer, Director of Operations, Vice President, or Integrator. We also welcome fractional executives. Most of our members come from businesses averaging $1 million to $30 million in revenue, but some are well below and well above those averages. We do not have a revenue or employee threshold.
Can my company pay for my membership?
Yes, most members have their membership paid for by their company as a professional membership or investment in learning & development. Investing in a Second-In-Command is one of the highest ROIs a CEO will receive.
How much of a time commitment can I expect?
We get it. In your role you’re busy with little free space on your calendar. Here’s exactly how much time you’ll be required to spend as a Second First member:
Quarterly, your mastermind cohort will meet virtually for a half-day. In the weeks leading up to this meeting, we will send a benchmarking questionnaire and report projects to complete and submit. Report projects are a list of 5-7 questions or prompts for you to answer on a specific topic. This meeting prework takes about 1-3 hours to complete.
Outside of the quarterly meetings, everything is optional. We encourage you to use the community and chat with other members to make your role easier, and speed up your decision-making. Any expert trainings or events are recorded and can be viewed on your own time in our video library.
What if it’s not a good fit after I join?
That’s exactly what the interview is for. Before anyone joins, Megan Long spends 30 minutes making sure the cohort is the right fit for you and that you’re the right fit for the people already in it. Bring every question you have to that call!
What if my cohort isn’t the right fit?
We place every new member in the cohort we believe will be most valuable to them, based on their role, their company, and what they’re working on. It’s a careful process, but not a perfect one. If your cohort isn’t the right fit after your first meeting, just let us know and we’ll work with you to find a better fit in another cohort.
My company runs on EOS®. Is this appropriate for Integrators™?
Absolutely! About 60% of Second First members use EOS® in their business. All of the tools and trainings are made to complement whatever business operating system your business runs on.
Is what I share confidential?
Yes. Everything discussed in your cohort stays in your cohort. Every member agrees to keep cohort conversations in the strictest confidence, permanently, whether or not they remain a member. Guests and the Second First team are held to the same standard.
Your numbers are protected too. Cohorts are built from non-competing industries, so you’re never sharing benchmarking data with a competitor. In all written materials, including benchmarking reports and meeting summaries, we use company aliases instead of company names.
What is the investment to join, and what is included?
All memberships are 12-month commitments at $425/month. Included in your monthly dues are:
- Access to the entire Second First community & directory of Seconds-In-Command across the country.
- Private Core Cohorts with all the information (benchmarking, Report Projects, Hot Seats, etc.) from each mastermind meeting. Stay in touch with this group year-round in a confidential, private setting.
- Downloadable Tools – a library of every single one we have in our framework.
- Live, expert-led sessions (or catch the replay in our library of past sessions) covering a wide variety of topics like sales, marketing, documentation, automation, leadership, and personal development. Sign up for what interests you, skip what doesn’t.
- Discounts & perks from our partners (think complimentary consultations with industry experts and consultants, free accounting/tax review, discounted software, and more!)
- Heavily discounted registration for future retreats and in-person events.
*If you are an EO or Entreprenista member, you will receive a discounted rate.
How does the application process work?
The first step is to submit an application by completing the application above. Once you submit your application, you will be redirected to a calendar link to book your virtual interview with founder Megan Long. Please allow 30 minutes for this interview, and expect a laid-back conversation to ask questions and determine if Second First is a mutual fit.
We review and approve members on a rolling basis. Once approved, your welcome email will contain all details involving your onboarding and the membership platform, Circle.
Apply To Second First
Membership is by application. We review every one personally so the room stays the right size and the right fit for the people already in it.
Complete the membership application below.
Hit submit and you'll be redirected to a calendar to book your virtual interview with founder Megan Long.
Your interview takes about 30 minutes. It's how we make sure every member reflects the quality, professionalism, and collaborative spirit our network is known for — and gives you a chance to ask questions of your own.
Second First Membership Agreement: https://secondfirst.com/membership-agreement