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Hi, I'm Jaime Diglio.

I'm an organizational psychologist, a mom of two, the founder of inFirst Coaching, and the creator of the WIN Room.

By all accounts, I had a lot of success as a Sales and Marketing Leader. I built a 40 million dollar business from the ground up, and managed a 500 million dollar business selling technology transformation to some of the most competitive firms on Wall Street.

But after 20 years of being over-connected - my body sent me a physical wake-up call and went numb during a client lunch. It was a physical response to the constant stress of being over-connected. Today, we call it "burnout."

Following my recovery - I got back to work. But this time it was the work of disconnecting from the things not serving me and re-connecting to my mind, body and the things important to me.

I took everything I knew about mindfulness, change management, neuropsychology, and the power of positive psychology and translated those ideas into a new method for working with professionals.

And the WIN Room was born

named so that we never lose sight of "What I Need" and "What's Important Now."

I give professionals a unique leadership language to feel and BE more confident and connected at work.


For the last seven years, I've helped thousands of professionals and teams learn how to identify and disconnect themselves from what isn't working in order to reconnect with more meaning and intention so they can have a successful career and life.


By focusing on the individual performing a job or the individuals that make up the team, I help people look in first and stand in their strengths so that the individual, the team, and the organization WIN. 

The Foundations of the WIN Room

Better connections build better culture, community and confidence across co-workers



Feeling safe to be seen as yourself builds trust, enables creativity, and fuels discussion.




Embracing diversity and seeing value in the uniqueness of others creates a culture of belonging.



Building friendships and community unlocks growth potential.




Leveraging the strength of individuals and bringing out the best in others inspires teams to reach shared goals.

Join a WIN Room

Sellers value their time and experience with the WIN Room

WIN Room

Your toolkit and roadmap to improve performance and engagement in your current role.


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Individual Coaching

Dive deep into your development with personalized guidance.



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Executive Advisory

Keep your organization winning with consulting services that focus on your corporate learning and development goals.


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