Jaime Diglio

inFirst Consulting

Clients hire my team and I to train their leaders & sellers on how build a Moneyball Mindset™.

We give leaders and sellers a competitive advantage by training them on how play a different game, so they are less predictable and more memorable.  We teach simple yet unconventional practices grounded in behavioral science, psychology of selling & neuroscience (brain based coaching) to quickly get your leaders and teams in sync working better together. We then combine this with Gen AI tools and practices because the secret weapon to help leaders and sales teams WIN is not just artificial intelligence it’s elevating emotional intelligence. Think AI + EQ = WIN

CEO | WIN Room Programs | Master the New ROI: Return on Interactions

TED Conferences

I deliver keynote presentations & immersive workshops on topics that will give your teams the mindsets, skillsets and toolsets to get out of the WAR Room and into the WIN Room

Most Requested Keynotes:

- The New ROI: Return on Interactions
- How to build a Moneyball Mindset
- AI + EQ = Your Winning Formula

TEDx | Keynote | SKO Speaker

Harvard Business School

Coaching MBA students at Harvard Business School on entrepreneurial sales.

Sales Coach 

Slalom

Delivered WIN Room sales, leadership & employee engagement programs to 600+ employees. Results include: Increasing connection scores by 16%, reducing attrition by 12%, pipeline opportunities by 22% over a 12 week period.

Future of Work Lab

Senior Sales Director

SomethingNew LLC

President & People Officer

Microsoft

National Sales Leader: Banking, Capital Markets, FinTech & Insurance

Gartner

▪️Eagle Award top 1%
▪️10X Winner’s Circle 2006 - 2016
▪️Top 1% Sales Team in North America consistently getting 90% of my team to Winners Circle.

Sales Leader | Financial Services, Capital Markets & Insurance

Business Development (BDR) - Investment Services

Event Marketing Manager

Fairfield University

Masters in Industrial Organizational Psychology 

Lebhar-Friedman

Marketing Coordinator

NBC News

On Air Promotions

Winning starts in the mind.

We get ambitious "forward-thinking" professionals into The WIN Room™, performing their best by teaching them how to measure what matters.

We don’t solve problems by doing the same things the same way and expecting a different result. We "Moneyball It" (just like the movie), which means we drop the outdated, one-size-fits-all playbook and use self-data, new insights, and practices differently to turn underdogs into champions.

Our WIN Room Programs focus on:

- Looking at the problem differently
- Uncovering hidden value in you, your team & clients
- Mastering the new ROI: Return on Interactions

When you learn to "Moneyball it", you’ll go from losing money to making money in every conversation.

Most leaders don't realize it, but their outdated leadership practices are costing them money every day. It’s not their fault; it’s what they were taught. The problem is that they do the same things every other leader has been "trained" to do.  

So they're predictable but not memorable. 

And if you're not memorable, people won't listen to you or buy from you.

The good news is that there is a better way. When we get you into The WIN Room and train you on the Moneyball Method™, you quickly learn how to play the game differently and shift from missing the mark 75% of the time to hitting your target 100% of the time.  

This is why 98.4% of people trained on Moneyball Leadership™ and Moneyball Selling™ principles become top performers who hit their quotas and highest-priority professional and personal goals.

We're proud of our stats because we know our proven Moneyball Method™ works. 

How we Deliver:
- In-person or virtual
- Combined group and 1-1 coaching 

Signature 12-Week WIN Room Programs:
- Moneyball Selling
- Moneyball Leadership
- Moneyball Teaming

Specific Focus Areas:
- AI + EQ = WIN
- Deal Coaching 
- Self Data/ Self Leadership
- Executive Presence / Communication
- Building Trust / Confidence
- Mindset / Resilience

If you're ready to get your team in The WIN Room, let's talk.

CEO | WIN Room Leadership & Sales Team Training | Keynote Speaker

Clients hire me to deliver my WIN Room programs for teams during times of transition, disruption and change. 

Focus on psychology of selling, neuroscience (brain based coaching), emotional wellness, soft skills, leadership and self-awareness coaching and training combines with Gen AI tools that is a proven secret weapon to help leaders and sales teams WIN.

▪️Facilitate Leadership Workshops
▪️Communication & Team Dynamic Strategies
▪️Leading & Selling through Transition
▪️Career Coaching
▪️Speaking Engagements

Focus Areas: Coaching leaders and their teams on EQ & self awareness, deal coaching, organizational & culture change, authentic & courageous leadership, self sabotage, diversity & building strong people focused teams.

What did your dad teach you that you’ll never forget?

Mine taught me the importance of hard work and what it means to show up.

He worked at the same grocery store for over 50 years. Every Sunday morning I’d help him get the produce section ready before customers arrived. 

Back then, grocery stores didn’t open until after noon so people could go to church.

I spent those mornings learning the difference between Granny Smith, Fuji, and McIntosh apples 🍎 - how to stack the fruit just right, water the greens, and make fruit baskets around the holidays. 

He always gave me a job to do and as a 7 year old it made me feel important.

My dad took pride in the smallest details and that pride showed up in everything he did.

Looking back, I realize I wasn’t just helping him at work. I was getting a real-life lesson in consistency, humility, and purpose.

My dad turned 83 today and it’s funny what memories stay with you. It isn’t the big things, it’s the little things. 

The quiet lessons. The ones you didn’t even realize were shaping you. 

👉 What did your dad teach you?

Jaime Diglio🥇

Get your teams in the WIN Room by mastering the New ROI: Return on Interactions™ | Author, Moneyball Leadership | TEDx + Keynote Speaker | Harvard Sales Coach | Former Gartner, Microsoft

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Nine years ago today, I closed a chapter I spent 13 years writing at Gartner.

At the time, I didn’t know exactly what was next.  I just knew it was time to bet on myself.

It's funny how you can only see the meaning of a chapter once you’re no longer in it.

—————————

Looking back now, I can see how much that season shaped me.
- The reps
- The pressure
- The people who believed in me before I did
- The lessons I didn’t know I was collecting

What I've learned is...
- Every chapter gives you something
- Every inning leaves a lesson
- Every season teaches you how to play the next one.

—————————

What chapter are you in right now? What is it teaching you?

—————————

Here’s what I know about chapters, innings, seasons (I ❤️ a good metaphor).

They don’t just end. They hand you something to take with you.

They give you:
- A new way of seeing yourself
- A skill you didn’t have before
- A lesson that shows up when you need it most
- A reminder that you’re stronger than you thought

—————————

And eventually, without even realizing it, those chapters become your foundation.

- Your courage
- Your voice
- Your ability to step into what's next

I’m grateful for the chapter I closed nine years ago and even more grateful for the one I’m writing now. 📖 ✍️ 

—————————

👉 What chapter in your life has made the biggest impact on you?

#thewinroom #gartner
#selfleadership

Most people wouldn’t have the guts to do what you did.

To the hundreds of students I met, coached, and role played with a few weeks ago at the Northeast Intercollegiate Sales Competition , I’ve been thinking about you and wanted to share my reflections.

Watching you compete was genuinely impressive. You put yourselves out there to be coached, judged, and challenged round after round, and I’m confident I couldn’t have done what you did when I was in college. The courage you showed was real.

What stuck me most was how open you were to feedback. You didn’t take it personally or pull back. You listened, adjusted, tried again, and walked right back into the room for another at bat.

That mindset, the willingness to treat everything as practice, is something that will take you incredibly far, and I know this because it’s what I coach new (and tenured) sellers on every single day. 

Most people avoid feedback. 
You leaned into it.

I hope you realize what a gift it is to have access to sales coaches at your universities who care enough to help you practice this early in your journey.

Most people don’t get this kind of support until they are already in the workforce, and many never get access to this kind of coaching at all. 

They end up learning in real time (with real customers) and no reps behind them. You’re putting in the reps now, long before you “have to,” and that early investment in your inner game will pay off in every room you walk into.

Keep surrounding yourself with people who want to grow the way you do. Stay in rooms that stretch you and keep choosing courage.

As I tell everyone I work with - practice makes performance and it’s already setting you apart. I am proud of every one of you and excited for what’s next.

👉 If you competed at NISC, what did you learn about yourself from the competition?

#futureleaders
#sales

I get teams in The WIN Room by mastering the New ROI: Return on Interactions™ | Author, Moneyball Leadership | TEDx + Keynote Speaker | Harvard Sales Coach | Former Gartner, Microsoft

What I love about traditions is the way they make the little things feel like the big things.

Like the annual 7am Turkey Trot with my sister. Quality time with family and tons of great home cooking.

Happy Thanksgiving everyone. I’m grateful for you.

🦃 What’s your Turkey Day tradition?

I’ve spent the last seven years coaching leaders and high performers, and one thing keeps showing up. Most people aren’t lacking talent; they’re lacking a place to practice the things that actually move them forward.

A place to talk it out.
A place to get honest feedback.
A place to feel seen, not judged.

And truthfully… everything I teach is what I’ve had to practice myself.
Every mindset shift.
Every conversation skill.
Every confidence reset.
I’ve lived it first.

That’s why today means so much to me.

I’m finally introducing The WIN League, a community for people who want a competitive edge by learning unconventional skills nobody teaches you, but everyone needs to win in their career and life.

If you’re ready to grow, lead, and communicate with more confidence and clarity… this might be exactly what you’ve been looking for.

I’ve been waiting a long time to share this. After years of coaching leaders and high performers, I kept hearing the same thing over and over again: “

Open article: Where Practice Becomes Performance: Introducing The WIN League by Jaime Diglio🥇 • 2 min read

Where Practice Becomes Performance: Introducing The WIN League

I was talking to a CRO a few weeks ago who was frustrated.

He’d invested in executive presence training for his leaders… and after 6 months, nothing changed.

I told him that it’s common. It’s what happens when the training teaches one-size-fits-all skills and tactics but doesn’t tackle mindset.

I explained that if a training program is not personalized and practiced with the individual, it won’t stick because they’re not bought in.

This is why in The WIN Room™, we always start with mindset BEFORE skillset, because it’s the foundation that everything else sits on.

You can coach someone on what to do, but they still don’t do it. You show them again. They make the same mistake. It’s easy to think it’s a skill prob

Open article: Mindset Before Skillset: Why Training Fails Without EQ by Jaime Diglio🥇 • 1 min read

Mindset Before Skillset: Why Training Fails Without EQ

Feeling like you’re underwater? Most people think it’s their to-do list, but it’s actually the “I have to” loop running on autopilot in your mind.

That tiny phrase pulls you straight into the WAR Room, quietly weighing you down with pressure, noise and doubt.

Break the loop and the whole feeling changes.

Replace “I have to” with “I get to,” and you’ll feel your energy shift instantly.

I break it down here.

I hear it constantly: “I have to present tomorrow.” “I have to figure this out.” “I have to work out.” Those tiny words, have to, are heavy. They make

Open article: Shift From Self-Doubt to Self-Leadership (In One Simple Move) by Jaime Diglio🥇 • 2 min read

Shift From Self-Doubt to Self-Leadership (In One Simple Move)

Leaders, here’s a quick practice drill you can start to increase your sellers confidence in meetings.

#thewinroom

Self-leadership starts with the story you tell yourself.

Because unlike what many will tell you, performance doesn't just happen from action - it starts with what you believe about yourself.

The story you tell yourself becomes the story you live.

Let me explain what I mean with a lesson I learned five years ago during lockdown.

My family drove to South Carolina to get away, and one afternoon I was in the pool with my son Landon. He started playing with a few other kids, and one boy caught my attention.

He was wearing a hat that said Lucky Fin (like from Finding Nemo). Then I noticed this kid had one arm.

But what first stood out wasn’t what he didn’t have, it was his energy. He was full of life, joy, and confidence. Completely owning who he was.  His worn in hat said it all: Lucky Fin. 

———

What one might see as his setback was his superpower.

That image is etched in my mind because it’s the opposite of how most people think and show up.

That boy wasn’t focused on what was missing, he was focused on what he had and it always makes me think about how often we let smaller moments - a missed goal, a setback, something that feels like a loss throw us off our game.

We forget how far we’ve come, and how much we already have to celebrate. 

———

I shared the Lucky Fin story recently with a client who was struggling after not getting a promotion to VP. 

I helped him see that maybe not getting the promotion was the best thing that could have happened, because it opens him up for something even better that's waiting for him. We reframed it for him to see how far he had come and how others see him and value him.

Sometimes when you lose, you really win in your career and life.

When you practice gratitude and self-awareness daily, you lead yourself better.

When you lead yourself better, you perform better.

And when you perform better, the right opportunities find you.

———

So, what's the lesson? 
Be careful about the story you're
telling yourself. 

Practice reframing every loss into a lesson:

▪️What did you learn that you didn't know before? 

▪️How does it give you a competitive edge over others?

▪️ Where can you use your unique perspective and lived experience to win?

Because how you talk to yourself is how you train yourself.

And that story will determine how far you will go.

#thewinroom

It’s easy to ignore the roles that aren’t in the spotlight - the ones nobody claps for, but everyone depends on.

Kinda like mopping up sweat on a basketball court.🏀

On the surface, it doesn’t look like much.

A job anyone could do.
Something that has zero impact on the game.

But last night reminded me that the opposite is true.

______________


My son was an on the court helper at for the UConn vs. Michigan women’s NCAA Basketball game and before tip-off, the woman in charge pulled him and the others aside to set the tone.

She said:
Your job tonight is extremely important. You must stay focused and move fast.  Wipe up the sweat and get off the court.

The refs are watching
The coaches are watching
Your effort and attitude matter just as much as anyone on the floor.

She said it with conviction.
And because she took the job seriously, my son did too.

______________


WHAT PEOPLE THINK

It’s just wiping the floor
Anyone can do it
It doesn’t change anything.


WHAT’S ACTUALLY TRUE

It keeps players safe
It keeps the game moving
And it supports every player on the court so they can perform their best.

______________


We all have these everyday moments that seem small at first. Tasks that no one claps for, jobs that feel invisible, effort that looks insignificant from the outside.

But they’re not insignificant at all.
They shape how people see you, trust you, and rely on you every single day.

______________


📝 Here’s your practice drill:

Think of one small thing someone around you does that you usually overlook.

It might be:

- the person who empties the dishwasher every morning
- your co-worker who quietly fixes the tech issues no one else can
- the teammate who always shows up prepared
- your friend who checks in, even when they’re busy

Now take 10 seconds and acknowledge them for it. Let them know you notice what they do (specifically) and that you appreciate them. 

Ex. Text (or tell them in person) and say…I just want to let you know that I appreciate that you ________. Thank you. 🙏

It’s a simple way to let them know they matter and what they do matters.

______________


👉 What’s one “small” thing someone does that makes a bigger difference than they realize?

#thewinroom

Finding your people changes everything.

This weekend I sat down to write holiday cards to every client I coached this year - and it hit me: 
This is my community. 
These are my people.

→ People who choose to invest in themselves. → People who are willing to put in the practice to improve their careers and lives. → People who wanted more.

They’ve put their trust in me, and I don’t take one ounce of that trust lightly.

——————

I started The WIN Room because I wasn’t getting the support I needed. So I created the space I wish I had, and now I get to give that support to others so they can perform at their best.

What began with one client has become a whole ecosystem. New leaders, tenured leaders, sellers, operators, athletes of life, all practicing together to get better. 
And it’s that same spirit we’re building inside The WIN League: a place for ambitious professionals to get what they need to perform at their best, with support, reps, and people who get it.

——————

If this year taught me anything, it’s to continue to trust myself and trust the process. When you find your people, the work takes on a whole new level of meaning.

I’m proud of every one of you for what you’ve accomplished this year. Big things are ahead. 🩷

👉 Who helped you grow in ways you didn’t expect this year?

#thewinroom

Outdated leaders control. 
Modern leaders connect.

Did you know…Great Places to Work found that high-trust companies earn 8.5x more revenue per employee?

Trust drives performance and why so many leaders are struggling to hit their goals is because they are “trying” to lead with control, the opposite of trust.

❌Control leaders lose money in every interaction.

✅Connect leaders make money in every interaction.

If you’re a leader who’s stuck in command and control mode it’s probably not your fault, it’s what you were taught.

The good news is, you can change your play and reset the scoreboard.

WIN Room leaders learn to connect before correct…and when they do, revenue and results follow. 💰📈

Every single time.

#thewinroom #leadership

I’ll never forget one specific quarter-end in my sales career. I had already hit my number… actually, I exceeded it. Quota crushed. Commitments met. M

Open article: Modern Leadership Starts with Trust, Not Control by Jaime Diglio🥇 • 2 min read

Modern Leadership Starts with Trust, Not Control

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