Charlie on a fence

THE CONNECTED

MEMBERSHIPS

Success can be lonely. The Connected Members are more than just group coaching. It’s an exclusive, invite-only suite of executives, VPs, directors, managers, and coaches at the top of their game.

Joining a coaching group isn't just a career move — it's a life-changing commitment. It can transform not only your professional trajectory but also how you show up every day, in every aspect of your life. That’s the value of having the right team.

Member Options

Core

    • Live strategy sessions once a month

    • Deep-dive workshops to refine your approach and execution

    • Full access to the video vault for on-demand learning

    • Private Slack group for real-time insights and connection

    • Built-in peer collaboration for shared momentum

Pro

    • All-in bundle - access to every CORE feature

    • 30 minute 1:1 - Accountability

    • The Connected Monthly Video Courses - structured lesson/exercise to implement right here, right now

MVP

    • 1:1 coaching for tailored strategy and execution

    • Full access to every course, every resource

    • A customized roadmap designed around your unique goals

    • Dialed-in client strategy to help you stand out and win

THE WORK

  • Engage in one interactive session with YOUR team every month (75 - 90 minutes).

  • Speaker Series: Enjoy a monthly spotlight featuring business leaders, professional athletes, or a dynamic combination of both.

  • One Roundtable Coaching Call: Join office hours for a post-game debrief. Dive into any topics with members from outside of your group during this 1-hour lunch and learn session.

  • Access The Connect network anytime, anywhere throughout the season.

  • Worksheets & Modules: Practical resources designed for immediate application. Dive deep into skill module coaching with personalized 1-on-1 sessions.

  • Enjoy exclusive perks like early event access, and discounted 1:1 skill modules.

Need flexibility or support from your company?

The Connected offers customizable solutions to collaborate with your company, covering costs or providing discounts based on your specific needs.

  • Gain clarity and direction with insights from peers who understand your unique skill set and mindset.

  • Build meaningful connections with leaders across industries. Our groups are crafted with purpose and specificity.

  • Apply and adapt your knowledge with the help of other leaders to elevate and sustain your team’s performance.

  • Leverage the collective wisdom of the group to stay disciplined and focused on your goals.

Our cohorts are designed for live, member-driven discussions. You are the content. That means every session is unique, timely, and practical. You can expect to:

WHAT ARE THE BENEFITS?

Charlie sitting on stool

join the Connected

COMMIT & APPLY

1.

Ready to take the leap? Submit your application, and we'll conduct a brief interview to understand your background, goals, and who you are. We'll also get to know what you do, so we can tailor the groups to fit you perfectly.

Once you're confirmed, it's time to meet your team. You'll join a roster with 4-6 other leaders who share your goals, mission, role, and stage of life. Think of this as your new locker room.

PUT THE JERSEY ON

2.

Our team meetings are structured to foster a collaborative environment where you’ll be pushed, challenged, and celebrated. Sessions will derive impact and insights from the collective experience and wisdom of the group.

YOU SHOW UP MONTHLY

3.

COACHING faq’s

  • After submission and acceptance, you'll be introduced to your new team that consists of 6-8 leaders/peers with a similar vision, mission and focus based on roles, and current life season. You'll get a confirmed start-date and be added to a group thread via Whatsapp.

  • Meetings are held monthly for 60 - 75 minutes once a month.

    We suggest attendance as frequently as possible with limited flexibility. As with any team, you want teammates you can count on when you need them to be there.

    For this reason, we require a 6 month minimum to ensure trust, challenge and the appropriate amount of push.

  • Your Connected Cohort will consist of leaders in similar seasons (of life), roles and targets. Industries may vary but the nature of your work will be familiar.

    Expect different perspectives, backgrounds, wins (and losses) to give you a sounding board that's tailored, timely and actually helpful.

    An example cohort may be...

    • VP Enterprise Saas Software

    • SVP Strategic Sales

    • VP of Sales at mid-size start-up

    • Senior Account Executive at a Fortune 100

    or

    • MLB Pitching Coordinator

    • MilB Field Coordinator

    • NCAA Div 1 Assistant Coach

    • MLB Pitching Coach

    • NCAA Head Coach

  • Absolutely.  The Connected membership is an investment for both your career and your company.

    Majority of our members get the first 6 months sponsored or leverage their personal development funds gifted by organizations. You can check with your direct manager or HR leader to learn more about the policies and access to funds.


    We also have a one-pager that we can share with your decision maker.

  • Think of it as your new locker room with teammates not on your direct team but now YOUR team. IN service of YOU.

    Each session includes a combination of group discussions, individual sharing, practical exercises, and coaching from the facilitator. Sessions are designed to be interactive and focused on real-world application and connection at the core.

  • Yes. Depending on the needs or shared purpose co-created by the team. i.e. One meeting takeaway may call for a session centered around developing a leadership brand or how to effectively block time to be productive.

    In addition, we'll roll out a 30 minute speaker series influenced by wants and needs of members. This may include a professional athlete, fortune 100 sales leader or military veteran excelling in their career/life.

  • Charlie is remarkably patient and thoughtful and his energy and positive demeanor is contagious.

    Ryan Wagner - SVP @ Datasys

  • Charlie's ability to command the room, he quickly created comfort and steered us toward success.

    Elisha Lahiri - Sales & Ops @ Atlassian

  • I was able to be more productive and efficient, enjoying more free time. It feels powerful to regain control.

    Casey Weathers - Pitching Coordinator @ Cincinnati Reds

  • After a single session, I felt a huge unlock, helping me move past a professional blindspot that had been holding me back for years.

    Reyana Fayyaz - Head of Product @ KudoBoard

  • His coaching gave me what I needed to lead my team during a tough transition, while setting expectations with leadership.

    Adriana Soliz - Customer Success @ Contentful

  • Charlie's "less is more" mindset has simplifed my communication style and improved my sales skills.

    Mike Kowalick – Director @ Edo

  • From day one, Charlie created a safe space with his contagious energy, making sure everyone's voice was heard, especially those who may be shy.

    Marc Baselga – Founder & CEO @ Supra

  • Working with Charlie has been a beacon of clarity in a murky phase of my career.

    Chris Lee - Founder @ Scout

  • Charlie has an exceptional ability to notice subtle details, allowing him to truly understand each team member's motivations and concerns.

    Emily Rooney - Strategy & Community Engagement @ Chicago Bears