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Mastering the New ROI: Return on Interaction

A Blend Masterclass with Jaime Diglio
Event Location
The Capital Grille
Event Date
March 24, 2026
Event Time
6:00 pm - 9:00 pm
About this event

Traditional ROI no longer reflects how value is created in today’s enterprise environment. As buying decisions become more complex and consensus-driven, leaders must rethink how influence, trust, and alignment are built.

This masterclass invites Blend’s Boston community to explore Return on Interaction: A modern framework for growth and decision-making. Led by Jaime Diglio, founder of The WIN Room™ and a leading voice in B2B growth strategy, the session challenges transactional models and shows how intentional, insight-led interactions drive faster decisions and long-term value.

Jaime works with enterprise leaders across technology, professional services, and complex B2B organisations to help teams win in moments that matter, by designing interactions that build relevance, trust, and momentum.

Designed for senior leaders across revenue, strategy, product, technology, operations, and people leadership, this session is for executives responsible for influencing outcomes in complex stakeholder environments.

You’ll leave with a practical shift in perspective and a clearer understanding of how interaction design can become a strategic advantage for both your business and your leadership.

Our speakers
Jaime Diglio
Founder, Team Performance & Engagement Expert

Jaime Diglio is the founder of the WIN Room™ and author of Moneyball Leadership. She has a background in organizational psychology with proven methods in sports psychology, social intelligence, and competitive knowledge.

After 20 years leading top-performing sales teams at Microsoft, Gartner, and Slalom, she hit a wall and couldn’t find the support she needed to push forward.

That moment became her wake-up call. She walked out of the WAR Room and built the WIN Room: a space where purpose leads, and performance follows.

Today, she helps leaders trade hustle for purpose and lead from within. Her WIN Room programs have transformed Fortune 500 companies and high achievers around the world.

Key themes & discussion topics

Why traditional ROI falls short in complex, enterprise buying

What Return on Interaction means for growth, influence, and engagement

How the WIN Room framework creates clarity and momentum in critical conversations

Practical ways leaders can elevate interactions across teams, partners, and customers

Event agenda
01
Registration & networking

6:00 – 6:45 PM

02
Masterclass & discussion

6:45 – 7:30 PM

03
Dinner

7:30 – 8:45 PM

04
Event wrap-up, reflection & networking

8:45 – 9:00 PM

Why should you attend?

Learn why traditional ROI no longer fits complex, multi-stakeholder decisions.

Discover how intentional interactions shape outcomes in enterprise buying and leadership moments.

Take away practical frameworks you can use right away with customers, partners, and internal teams.

Engage in Blend’s cross-functional environment designed for candid, high-quality executive discussion.

Event Organizer
Emily Osgood
Venue
Event Location Light
The Capital Grille
900 Boylston St.
Boston
MA
MA 02115,
United States
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