Jennifer Dulski is the founder and CEO of Rising Team, which she describes as an AI leadership and effectiveness personal trainer for people at work. Its AI coach, RT (she calls it Arty), learns your team and coaches you on how to lead it. Jen joined us in Episode 52 (September 21, 2026).
She started as a high school teacher and founded a nonprofit helping first-gen students graduate from college. Then came 25 years in tech: ten at Yahoo, several each at Google and Facebook, and five helping run Change.org. She also teaches at Stanford GSB.
As a division leader, Jen got human executive coaches and expensive training, but nothing that scaled to the hundreds or thousands of people on her teams. She bootstrapped Rising Team in 2020 to fix that. It began as team-building software that any manager could run without an outside facilitator, and the AI coach was added on top once LLMs arrived.
That order matters. Because the team-building sessions teach RT about each teammate, it can say that Tom likes his feedback straight while Debbie wants some encouragement first, and write a different script for each.
At 11:09 Jen showed the product. RT starts with an intake about your experience, challenges, goals and which company value you want to work on. It then summarizes what it learned and builds a one-of-one growth plan; hers covered leading through change, making the team feel valued and accelerating AI adoption.
Each track breaks into working sessions, coaching sessions, role play and team-building sessions. RT finds time on your calendar and sends reminders, like a trainer would. On demand, you can pick a teammate before a hard conversation and practice it with RT.
So this is, again, one way that having a tool like this is so different than a standard LLM because it already knows my team.
— Jennifer Dulski, Episode 52
And the BCG data says 70% of whether your AI transformation is successful or not lands on whether the people are able to adapt to these tools and still work with each other.
— Jennifer Dulski, Episode 52
In the news segment on Siri in iOS 27, Jen, a self-described ex-Googler who carries a Pixel and an iPhone, said the best AI is the kind you don't notice. She then asked us whether an assistant that remembers everything is helpful or creepy, a question she is weighing for RT. Jordan said helpful: he wants his phone to ask whether he needs his alarm set. Sam's complaint was that his Nest Hubs still don't have Gemini.
For more on AI at work, see our pages on AI in recruiting and HR and AI in productivity.
Rising Team calls itself an AI leadership and effectiveness personal trainer. Its AI coach, RT, learns about you and your team, builds a personal growth plan, schedules sessions and helps you practice real conversations.
Jennifer Dulski founded Rising Team in 2020 and bootstrapped it herself. She previously spent ten years at Yahoo, several years each at Google and Facebook, and five years helping run Change.org, and she teaches at Stanford GSB.
Jen says RT already knows your team from team-building sessions, so it can tell that one person likes direct feedback and another needs encouragement first, and write a script that fits each one.
No. Executives see anonymized insights rolled up by level, location or function, never by individual or even by team. RT also won't help with firing, hiring or rating decisions.
