This week, Kavitha is joined by Neha Gupta, CEO and founder of Breakthrough AI, which recently launched a practice-first coaching platform powered by role play scenarios with AI voice tools. Neha explains that part of her vision was to provide real-time quantitative and qualitative feedback on effective communication: particularly for individuals who may be highly technically skilled, but need targeted practice to improve the soft skills that win over clients. She and Kavitha discuss empathy as a cornerstone of client relations, the role of gamification for incentivizing user engagement and self-improvement, and why Neha feels it is imperative to "keep a human in the loop" when interacting with AI coaching tools. In particular, Neha emphasizes the importance of pushing back on the "quick fix" and "life hacks" culture that is rapidly developing around AI-human interactions. Instead, she encourages Kavitha to see AI coaching tools as an opportunity for engaging in unique, targeted practice to prepare employees to meet high-stakes scenarios with confidence and meaningful preparation.

Transcript

S3Ep8—Neha Gupta Transcript

Links and Resources

Information on YGELP and Yale SOM Executive Education:

• Yale SOM Executive Education Homepage

• Certificate in Professional Coaching Program Homepage

• Sign up for program updates

Resources Mentioned in Today's Episode:

• Breakthrough AI Homepage

• The Way of Excellence by Brad Stulberg

About Today's Guest

Neha Gupta is the founder and CEO of Breakthrough AI, a practice-first AI coaching platform helping teams master the high-stakes conversations that shape performance, client relationships, and career growth. Combining AI role-play, behavioral science, and manager visibility, Breakthrough AI is reimagining professional development by turning communication skills from "soft skills" into measurable business capabilities. Her vision is to make personalized coaching and deliberate practice accessible at scale.

Prior to founding Breakthrough AI, Neha built her career across startups, nonprofits, and global consumer brands, with experience spanning growth strategy, brand marketing, product marketing, and business development. She held leadership roles at SaverLife and previously worked at Clorox and Unilever, gaining experience in brand strategy and customer engagement at scale. She also founded BellyFire Branding, where she and her team advised mission-driven and early-stage organizations on growth strategy, positioning, and sustainable growth. Known for blending sharp strategic thinking with deep empathy for users, Neha has spent her career building brands and systems that create meaningful behavior change.

The daughter of immigrants and a first-generation corporate leader, Neha's work is deeply informed by her own experience learning the unspoken rules of professional communication and leadership. That perspective fuels her belief that confidence, executive presence, and communication should not be advantages reserved for a select few. She holds an MBA from Yale School of Management and a BA from Stanford University.