A League for Ambitious Professionals Ready to Lead with Confidence
THE WIN LEAGUE
The WIN League is a high-impact membership community for ambitious professionals who want more: more clarity, more confidence, and more momentum in their careers.
This is not another leadership course or peer group. This is an exclusive space where ambitious professionals get in the practice of practicing like athletes, building the mental and professional edge required to lead with presence, purpose, and influence.
Membership is $197/month and includes direct access to Jaime Diglio, live coaching, structured development, and a curated community of high achievers. Whether you are in the early stages of your career or preparing for the executive level, you will learn to master the New ROI: Return on Interactions™ and start making measurable progress in every conversation.
WHAT YOU GET INSIDE
THE WIN LEAGUE
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Live
Curriculum-Based
Training with Jaime Diglio
Bi-Weekly Live Group Coaching
The Highlight
Reel
Access to a Private, Professional Community
Twice a month, Jaime leads a live 60-minute training focused on building critical leadership, communication, and influence skills. These sessions are practical, high energy, and designed to help you apply what you learn immediately.
This is the only WIN Room offering that includes real-time group coaching. Twice a month, members have the opportunity to ask Jaime questions, get direct feedback, and work through real scenarios in an off-the-record setting.
If you miss a live session or want to review a key takeaway, you’ll get access to a curated library of the most valuable insights from each session.
As a member, you will join an exclusive online space where you can connect with other high-performing professionals. This is your space to share wins, ask questions, and receive ongoing support from peers and from Jaime.
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2 hours of new content every month
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Instant access to past content
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Ongoing support in an engaged online community
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2 hours of live group coaching each month
If You’re Feeling Stuck, You’re Not Alone
You might be thinking:
I should be further along by now
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I feel invisible or overlooked
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I don’t know how to lead with confidence
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I’m doing everything right, but it’s not adding up
You are not broken. You are not behind. You are just undertrained in the skills that matter most:
how you lead yourself and how you communicate with others.
The WIN League Is Built for Professionals Who Are Ready to Move
If YOU WANT TO:
Lead with more clarity and confidence
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Build a reputation as someone who communicates with impact
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Earn trust, influence, and new opportunities
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Stop overthinking and start taking intentional action
THEN THIS IS YOUR PLACE TO GROW
The Three Pillars Of
THE WIN LEAGUE
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CONTENT
COMMUNITY
COACHING
Every month includes two live trainings with Jaime focused on building mindset, skillset, and leadership presence. These sessions are designed to help you apply what you learn in real time.
Live group coaching calls offer direct access to Jaime for personalized feedback, clarity, and problem-solving. This is the ONLY program where you can access group coaching.
Join a network of high achievers who are committed to personal growth and professional excellence. This is a place where you are seen, supported, and surrounded by others who are doing the work.
FREQUENTLY ASKED QUESTIONS
Will I have access to all the content, or just the current month?
As long as you’re an active member, you’ll have full access to the entire content library — including all past trainings, highlight reels, and tools. You can revisit anything, anytime.
What happens after I join?
You’ll get immediate access to the membership portal and all past content. You’ll also complete a quick Value Builder Assessment to help set your baseline and track your growth. From there, you’ll get fresh content and coaching every month.
I’m early in my career. Is this still for me?
Yes. The WIN League is built for professionals who are ready to lead, no matter their title. If you’re ambitious, coachable, and committed to growth, you’re in the right place. You can also book a call with Jaime to make sure it’s the right fit for you.
Can I cancel anytime?
There’s a 3-month minimum commitment to start. After that, you can cancel by the 15th of the month effective the following month.
I still have questions. Who can I talk to?
We’ve got you. Email jaime@thewinroom.com and we’ll make sure you get everything you need to make a confident decision.
Ready to Step Into The
Win Room?
The WIN League is not for everyone. It is for ambitious professionals who are ready to get in the practice of practicing by owning their strengths and lead with clarity and conviction.
Apply now to join a community that helps you practice with intention and perform at your best.