Clio Con Clips 2025 – Jenny Dingus – E07

Transcript

Robert Hanna  0:00  

Welcome to Clio con clips 2025 recorded live from Boston and proudly sponsored by Clio, the world’s leading legal technology company, transforming the legal experience for all. I’m your host, Rob Hanna, and over this special legally speaking podcast series, we’ll be bringing you exclusive conversation with the brilliant minds behind Clio, the innovators, strategists, visionaries, driving one of the most transformative companies in legal tech. Across these interviews, we’ll explore how Clio is uniting brilliance across teams, technology and communities worldwide, from AI and data to leadership culture and the future of client experience, you’ll hear from people shaping what’s next for law and redefining what’s possible for legal professionals everywhere. So whether you’re a lawyer, technologist or leader passionate about innovation, you’re in the right place. This Clio conclips 2025 is where brilliance meets purpose and the future of law take shape. Let’s get into it. You Jen, welcome to the legally speaking podcast recording live here in Boston for our Clio con clips series. 2025 sponsored by Clio, and I’m joined by name, title and organisation.

Jenny Dingus  1:14  

I am Jenny dingus. I’m the SVP of global sales at Clio, and currently don’t have a voice, well,

Robert Hanna  1:21  

yeah, it’s always helpful for a podcast, but it’s an absolute pleasure to have you on the show. We’re chatting off air. Love the energy, love the excitement. And before we get into Clio con and all things Clio, I would love a fun fact from you that folks may not know about you here at Clio con.

Jenny Dingus  1:34  

Okay, so before I kind of dove in a professional career, I love to travel, and I have been over 30 countries, but one of the wildest things I ever did was I hitchhiked with a girlfriend across Bolivia. Wow. Okay, that’s we made it. That

Robert Hanna  1:52  

could be a podcast in itself. To avoid that rabbit hole, we’re gonna move to the intelligent legal work platform that changes how firms actually adopt and use software, because that’s been announced by by Jack in his keynote, which was inspiring, super powerful. How has that actually transformed your sales approach, if at all?

Jenny Dingus  2:12  

So it’s a great question. Obviously, we have been very focused on positioning the business of law right? And so our sales team has, actually is probably the best in the world at consulting with law firms on how to run their practice more efficiently. And now we are diving into the practice of law, and that’s a totally new conversation. And so we are working with the team to kind of give them a bit of a law degree in a very short amount of time and teach them what it means to do legal research and applied AI, and just make sure that they’re prepared to have really consultative conversations with their customers. Yeah. And

Robert Hanna  2:51  

look, one thing Clio is very good at is being client and customer centred like it’s just screams through the business. Every touch point, everyone I speak to, it’s in the DNA of the business. And one of the themes. Well, the theme for this year is uniting brilliance. So how do you unite brilliance across global sales teams to deliver a consistent client

Jenny Dingus  3:08  

experience? Well, I think it actually starts with the culture of Clio as a company. We have a very transparent and aligned not only mission as a business to transform the legal experience for all. But we are very aligned as an organisation, cross functionally around what our company goals are, what we’re marching towards, and that trickles all the way to sales. So the sales team is really connected with our business goals and our broader goals for the legal industry and and I think that’s the difference when working with our team versus a sales team that is just trying to push product. Yeah, yeah.

Robert Hanna  3:46  

I love that. And what I love about everything that Clio does this real strategic thought behind it, and it really shows in the quality of the output and every touch point and every team across the organisation. Of course, we can’t not talk about AI. So how is AI reshaping sales conversations and customer insights at Clio?

Jenny Dingus  4:06  

So you’re asking about our internal use case of AI? Yeah. So we’ve we’ve got a lot of different places where we’re infusing AI into our sales process. Everything from our enablement practices are incorporating AI tools to the way that we do outreach to our customers, to the way that we find our customers and prioritise the outreach that we want to make. But I think the key here is like AI has so much novelty to it, and it’s so easy to get sucked into the trap of we’re not doing enough with AI or trying to, like, keep up with the rat race, and one of the things that I’m really trying to do with the team is make sure that we’re grounded and that we’re very intentional about our use cases of AI, so that we don’t lose our humanity, because it would be so easy to just adopt everything and kind of lose. That special touch that makes us who we are.

Robert Hanna  5:02  

Yeah, and look, I always talk about the era of no longer B to B, B to C, but it’s the H to H that human to human connection even more so in a tech enabled tech first world that we’re living in, what does sales with purpose mean to you at a very mission driven company like Clio? I mean,

Jenny Dingus  5:19  

I think that’s it. It’s being authentic to our mission and not giving up on the fact that we are trying to close the access to justice gap. And the way that we do that is we really surface our customer stories, often with the sales team and the broader business, so that we can continue to connect the impact we’re having on our customers with the team. I think you know, when you when you work anywhere, it’s really easy to forget what you’re doing, and it takes moments like this, like Clio con, where you’ve got, like, very precious opportunities to talk to people and hear how they’re implementing our technology and practice and the impact that’s having on their clients, that that goes a long way. Yeah, it

Robert Hanna  6:05  

really does. And I feel it also when I’m here, like the whole impact of Clio and everything that you do, and the whole Clio con experience, which I want to get your highlight in a moment, how do you balance performance and empathy in leading your teams so sales, you know, it’s a business, and so sales, they need to be met, but that needs to be an element of empty as well. So

Jenny Dingus  6:26  

how do you do it? Totally I actually think Jack might have asked me that exact same question. And so I have one of, one of our values as a company is human and high performing, yeah. And I think I balance those two things really nicely. I’m very human and transparent with my team. I don’t really care about the titles, like I’m always accessible. I’ll respond to anybody on my team at any time of the day, but at the same time, I hold them accountable and I know what, or I make sure that they know what is expected of them at all times, we run our business with a lot of rigour. We have a really tight operating model with our marketing and revenue operations partners, and there is accountability at every touch point, which by managing that internally so well, we’re able to turn around and service our customers efficiently and with humanity.

Robert Hanna  7:19  

And I love that you talk about self accountability, because people who join Clio buy into the mission. I remember a mentor said to me very early on, Rob, it’s meant to be it’s up to me. You have to take self accountability. And I love that you do that, but you know, you’re hopeful, comfortable doing that, because everyone who joins Clio is a believer in the mission. They see the value and why they want to do it. And I think that’s testament to recruitment process as well. But what traits define top performing sales leaders in an AI powered environment.

Jenny Dingus  7:43  

So I think that one thing that we as leaders have to keep in mind is humility. Right now, nobody has led a sales team in 2026 before. No, nobody. And it doesn’t matter what your background is, what your experience is. This is new for all of us, and something that I’m doing, personally is creating a lot of community with peers like myself in the industry and revenue organisations across tech to make sure that I am continuing to be a student of best practices and not only things that are working well at other companies, but things that aren’t working well. That aren’t working well, and I think that we have to really come together with community to ensure that we’re implementing best practices with AI and frankly, everything else go to market in a way that is going to tie us back to achieving our mission,

Robert Hanna  8:39  

which absolutely Clio is doubling down on, for sure. And that’s loud and clear this Clio con, okay, so you mentioned no one’s Sales Team 2026 but what excites you most about the future of sales in legal tech?

Jenny Dingus  8:52  

I mean, I think Jack said it yesterday, like we are defining a whole new category of legal tech, and now Clio is the first company in the world that can combine the business of law with the practice of law, and, you know, be the world’s leading intelligence platform. And that’s such a good opportunity. But it’s also like going back to the humility piece, like a big responsibility. We have to do that in a way that is customer centric and continues to keep law firms in mind.

Robert Hanna  9:29  

Yes, and look, I just think it’s brilliant what Clio has achieved this year, and it’s just phenomenal coming back. We were at Clio con in Austin last year, and prior impact, Clio has definitely done that. Let’s zoom out before we close. What’s been a highlight moment for you of Clio con 2025

Jenny Dingus  9:45  

oh gosh. Look, we’ve been working our butts off ever since we made the decision to pursue this acquisition of Velux. The Clio team has been working literally around the clock for months trying to make sure that we. And we could announce the things that we did yesterday. And so I was sitting up in the rafters, kind of in the nosebleeds, just like looking down on the audience as they were consuming Jackson keynote. And I didn’t see one person on their phone. I didn’t see anybody distracted. Everybody was just locked in and totally transformed by the message Jack was delivering, and I think Jack has done an awesome job at talking about the vision of Clio, and yesterday, it really felt like that vision came to life.

Robert Hanna  10:30  

I couldn’t agree more, and it’s super exciting, and it feels like we’re at the beginning of this new era of what is going to be possible in an AI powered world. Jenny, it’s been an absolute blast having you here on the leading speaking podcast live in Boston, if people want to know more about Clio or indeed, get in touch for yourself. What’s the best websites or social media handles for them to get in touch?

Jenny Dingus  10:49  

Yeah, so cleo.com and if you’re interested in working with us, cleo.com/careers and my LinkedIn. Jenny dingus, please reach out anytime. Happy to chat.

Robert Hanna  10:59  

There we go. Jenny, thank you so so much for joining me here live on the leaders dream podcast, sponsored by Cleo, but for now, over and out. Thank you for listening to this week’s episode. If you like the content here, why not check out our world leading content and Collaboration Hub, the legally speaking club, over on Discord. Go to our website, www.legallyspeakingpodcast.com as a link to join our community there, over and out.