The moment Jenny said “Nobody has led a sales team in 2026 before,” I stopped and smiled.

She’s right. None of us have. That hit hard.

We’re all leading into uncertainty. Learning as we go. Balancing AI, performance and empathy while trying to keep humanity at the centre.

When I sat down with Jenny Dingus, SVP of Global Sales at Clio, live from Boston at #ClioCon, it didn’t feel like a conversation about sales.

It felt like a conversation about leadership.

About trust. About humility. About how the best leaders aren’t just setting targets, they’re building people.

Jenny’s approach is the kind we need more of today.

💬 “AI has so much novelty, but we have to be intentional so we don’t lose our humanity.”
💬 “Leadership is about creating community, not control.”

Be human. Stay accountable. Lead with intention.

She’s uniting high performance with high compassion, using AI without losing authenticity, and leading through connection, not control.

This episode is about what leadership really looks like when the map is still being drawn.

🎧 Episode 7 of Clio Con Clips 2025 is now live here or on all other major podcast platforms as part of the Legally Speaking Podcast™, sponsored by Clio 👉 https://open.spotify.com/episode/2BXpX9rxS5YawBxJiQMSgG?si=f1SaWWYcQUeTDoycN_2SZg

If you lead a team or aspire to, take 10 minutes for this one. It’s worth it.

#ClioCon #Leadership #AI #FutureOfWork #Sales #LegallySpeakingPodcast