Episode 474: People-Centered Leadership: Coaching Sales Teams for Sustainable Revenue Growth
What if the fastest path to revenue growth isn’t more activity, but better leadership? In this episode of Making Sales Social, Brynne Tillman is joined by Kelley Hippler, Chief Revenue Officer at Briefly Legal and former Chief Sales Officer at Forrester Research.
With more than 20 years of global commercial leadership experience, and a track record of driving over 50% revenue growth, Kelley shares why people-centered leadership is the foundation of sustainable sales success. Together, Brynne and Kelley explore what it really means to make sales social in today’s AI-driven world, where technology can scale outreach, but can’t replace trust, rapport, and human connection.
Kelley breaks down the difference between managing and coaching, why focusing on outcomes beats managing activity, and which KPIs actually matter if you want to build meaningful pipeline. They also dive into aligning sales and marketing around the full buyer journey, creating content that supports buyers before they ever raise their hand, and building resilient teams that can thrive through economic ups and downs. From celebrating wins to removing “sand from the gears,” this conversation is packed with practical insights for revenue leaders who want engaged teams, loyal customers, and long-term growth.
If you’re a sales or revenue leader looking to reduce burnout, improve performance, and create a culture of ownership, this is an episode you’ll want to listen to more than once.
View Transcript
Kelley Hippler | 00:00
You don’t drive revenue—your people do. To get the best out of your team, you need to build trust, be authentic, and be transparent so they can show up as their best selves every day, understanding the role they play.
Bob Woods | 00:15
Welcome to the Making Sales Social podcast, featuring the top voices in sales, marketing, and business. Join Brynne Tillman and me, Bob Woods, as we bring you the best tips and strategies our guests are teaching their clients, so you can leverage them for your own virtual and social selling. Enjoy the show.
Brynne Tillman | 00:39
Welcome back to Making Sales Social. I am so excited about my guest today, Kelley Hippler. She’s the Chief Revenue Officer at Briefly Legal, where she leads marketing, business development, and client success with a people-first approach. Kelley brings over 20 years of global commercial leadership experience, including her time as Chief Sales Officer at Forrester Research, where she helped drive revenue growth of more than 50%. She’s passionate about people-centered leadership and building empowered teams that drive sustainable growth through clarity, collaboration, and accountability. Kelley, I’m so excited to have you here. Welcome to the show.
Kelley Hippler | 01:18
Thank you, Brynne. It’s such an honor. I know we were chatting a little bit beforehand, but I love your IP and your work, and we’ve been using it with our team. Thank you for everything you’re doing to help elevate the sales profession.
Brynne Tillman | 01:30
I appreciate that. I can’t wait to dive into your people-centered leadership approach because it aligns so closely with what we talk about in the trust-based world. Before we do, we ask all of our guests the same first question: What does making sales social mean to you?
Kelley Hippler | 01:50
That’s a great question. When I think about making sales social—or sales in general—it comes down to building relationships. As technology becomes more prevalent, focusing on relationships first is incredibly important. The social aspect is really the first step in seeding that ground: building your brand, being authentic, and letting people know who you are so you can identify the right time to reach out. I think a lot of people confuse LinkedIn with just another email channel or outreach tool, rather than a place to establish a brand, build connections, and lay the groundwork for long-term relationships.
Brynne Tillman | 02:37
I love that. In our world of AI, the one thing AI can’t do is build rapport and relationships. Thank you—that’s an awesome answer. Let’s jump into people-centered leadership. When I was doing my due diligence before today, that theme kept coming up—people-centered leadership and Kelley Hippler seem to go hand in hand. How do you define people-centered leadership, and what are some practical ways it fuels revenue growth and team success?
Kelley Hippler | 03:17
For me, people-centered leadership is about recognizing that as a leader, you don’t drive revenue—your people do. To get the best out of your team, you need to build trust, be authentic, and be transparent so they can show up as their best selves, understanding their role in the company mission.
It also means viewing my job as removing roadblocks that slow the team down. Anyone who has worked with me will tell you I’m maniacally focused on getting the “sand out of the gears.” Time is money in sales. Every hour spent on administrative work is an hour not spent with clients. When you’re people-centered, you focus on improving the employee experience, knowing that it ultimately improves the client experience as well. Those principles are core to how I think about leading teams.
Brynne Tillman | 04:17
I love that. It creates a strong connection with team members and real loyalty. Is there an overarching concept you focus on in one-on-ones or team meetings to strengthen people-centered leadership—not just from you, but so everyone adopts it?
Kelley Hippler | 05:02
That’s a great question. This is something I’ve learned over time. I used to be very go, go, go, but the pandemic taught us all to pause and really understand where people are. Taking a few minutes to understand what’s going on in someone’s life—not just at work, but at home—matters. You have to know their goals and ambitions.
If you want to support and motivate people, you have to know them. When leaders model that behavior, it increases the likelihood that others will do the same, creating a multiplier effect. It comes down to relationships, trust, and making conversations a dialogue, not a monologue. There’s a power dynamic in leadership, and if people don’t trust that you’re asking questions to fix problems—not to blame—it’s hard for them to open up.
I used to tell my teams, “I can’t fix problems I don’t know about.” It takes time, investment, and genuine interest in making the employee experience better.
Brynne Tillman | 06:46
That bridges nicely into the difference between managing and coaching. What shifts do you see when a sales leader adopts a coaching mindset instead of a traditional management approach?
Kelley Hippler | 07:08
I have a lot of sympathy for sales leaders today. We see stats showing how short CRO tenures have become. That pressure can lead leaders to manage to dials and activities instead of outcomes.
Coaching is about helping people become their career best and achieve the outcomes they want. It’s not about spreadsheets and telling people how many dials or emails to send—especially when we know that kind of volume is often just white noise. Coaching means training people so that when they do have an at-bat, it’s impactful. They’ve done their homework and can bring relevant insights to the conversation.
The real pivot is focusing on how to do the work, not just telling people what to do.
Brynne Tillman | 08:18
That’s interesting. If we’re shifting away from volume, what KPIs should we be measuring to coach people to success?
Kelley Hippler | 08:42
That’s a great question. For me, it’s about whether people can set meetings. If they can, it means their outreach is compelling and high quality. Then, what percentage of those meetings convert into opportunities?
Those two metrics tell you whether outreach is impactful enough to build pipeline. Everyone’s approach is different. Junior sellers may need higher volume early on, while senior sellers can be more strategic. Measuring dials alone often leads to gaming the system—ghost data in CRMs, calling friends or family just to hit numbers.
Focusing on meetings and opportunities keeps the emphasis on outcomes and eliminates a lot of those issues.
Brynne Tillman | 10:24
There’s a book in “the metrics that matter.” Measuring what truly drives outcomes is powerful. Shifting gears, we’re in a roller coaster economy. Some people are thriving, others are struggling. What lessons have you learned about keeping teams aligned and motivated during periods of change?
Kelley Hippler | 11:18
Sales isn’t for the faint of heart. It reminds me of that scene in Parenthood where they’re riding the roller coaster—that’s life in sales. The rate of change is accelerating, and rejection is part of the job.
You have to be honest with your team about that and focus on building resilience. When you do win, take time to celebrate. Too often we ring the bell and move right on, even when a deal took a year or more to close. Reflecting on wins helps people stay resilient during tougher times.
AI, shifting buyer behavior, and constant change make this even more important. Look for people who have overcome adversity before—they’re often better equipped to handle the resets that are constant in sales. Growth isn’t always straight up and to the right, and leaders need to reinforce that reality.
Brynne Tillman | 13:29
That’s incredibly powerful. A supportive culture helps reduce uncertainty and keeps people from feeling paralyzed. You lead both marketing and sales, which have traditionally been siloed. How do you break down those walls and get them working in sync?
Kelley Hippler | 14:51
It’s definitely been a challenge. One thing that’s helped is aligning around the revenue bow tie. Marketing isn’t just about filling the top of the funnel—it’s a partner across the entire customer journey, working alongside sales and customer success.
We look at the full customer lifecycle and ask how marketing can help expedite and amplify the work at each stage. Buyers now complete about 80% of their research before ever talking to a rep. That means sales and marketing must be aligned, using the same language.
Whether or not they sit under the same leader, alignment is table stakes. Marketing has to be present at every stage of the journey to win in today’s market.
Brynne Tillman | 16:34
You said something I want to double down on and go a little deeper into: marketing has to be part of every stage. At each stage, different content is needed. It’s not about features and products. So talk to me about where you start. I’ll give a shout-out to my buddy David Newman, who taught me, “Start before they know they need you.” What are they Googling two steps before you show up? Walk us through the buyer journey and the types of content needed to help sales move prospects through the funnel.
Kelley Hippler | 17:24
Universally, one thing you can never get enough of at any stage is case studies and testimonials. They’re incredibly helpful for building trust. Taking your key personas and industries and creating client stories—attributable or not—that show how you helped solve a problem is especially valuable early in the buying process.
As relationships progress, a client may come in with one pain point, but there are often multiple ways you can help. Marketing can then help surface those additional opportunities. People love stories. They make things real. Beyond feature and function descriptions, focusing on who you’ve helped and how builds pipeline.
It’s also about understanding your buyer and the triggers that signal it’s the right time to reach out. And of course, making sure your brand is findable—not just through Google, but through AI tools as well. We’re seeing more leads coming from ChatGPT and other platforms, so marketers need to ensure content is present where buyers are searching.
Brynne Tillman | 19:08
I want to piggyback on that. I’m deep in the FAQ world right now because frequently asked questions are being indexed by AI—Gemini, ChatGPT, Copilot. As a revenue leader, how are you shifting to ensure those FAQs are out there? Are they by sales rep, by company, or something else?
Kelley Hippler | 19:47
It’s a great question, and it’s tricky to find the right level of focus. You don’t want it so narrow that it only speaks to a small audience. We hone in on our top buying personas and the most likely reasons they’d reach out to us. We’ve identified about four or five core use cases where we typically help solve problems, and we double down on content around those areas.
We’re very active on LinkedIn, sharing content that shows how we help. It’s really about understanding what you’re best at and leaning into that, rather than spreading yourself too thin. We focus on our top five ways we help and build content around those.
Brynne Tillman | 20:49
How much of that content is about how you help versus actually helping—checklists, insights, value-centric content—versus “us” content?
Kelley Hippler | 21:02
That’s a great question. Fortunately, we have some great thought leaders who share tools and assets, and we’ve been doing more of that. Offering something tangible can be powerful. Someone may download an asset and use it without you even realizing it—similar to how I shared your “top mistakes reps make” content with my team.
At some point, if they’re using your assets, they’re likely to come back. We’re working to create more leave-behind tools, checklists, and day-to-day resources, with the hope that they eventually raise their hand and ask for more help.
Brynne Tillman | 21:55
That’s powerful—earning the right to have conversations through value. Buyers are researching independently. You mentioned 80%; I’ve been using the old 69% stat.
Kelley Hippler | 22:20
That’s about five years old now.
Brynne Tillman | 22:23
I’m updated now, which I love. With buyers waiting so long to reach out to sales, what can salespeople do to leverage marketing so they’re the ones who get the conversation?
Kelley Hippler | 22:50
It’s a great question. Because buyers know so much more now, sellers need to focus on the buyer, not the product. That means showing up having done your homework and demonstrating a deep understanding of what that buyer is dealing with.
You want to be a resource. You may not even mention your product at first. The more you focus on their challenges and industry context, the more trust you build. When they do have a need, they’ll reach out to you.
My mom used to say about dating, “If you get them talking about themselves the whole time, they’ll think it was the best date ever.” There are a lot of similarities between dating and selling. In this environment, focusing on the buyer is the best path forward.
Brynne Tillman | 24:16
I love that—and I agree, selling really is like dating. As we wrap up, let’s talk about creating a culture of ownership for sales and marketing. What does it take to build a culture where everyone truly owns their results and outcomes and isn’t trying to game the system?
Kelley Hippler | 25:15
It starts with building a clear plan. Most organizations create an annual plan and break it down by department. At Forrester, we used something called a “plan on a page,” which aligned company goals across sales, marketing, customer success, and product.
Each plan outlined key actions, success metrics, and interdependencies with other teams. That helped everyone understand the role they played in company success. Alignment is easy to say and hard to do, but having a shared touchstone helps.
As leaders, our job is to ensure people understand how they contribute to the overall goal. When people see their impact, engagement increases—and that’s when numbers really start to accelerate.
Brynne Tillman | 26:43
If companies adopted this mindset, turnover would drop and motivation would rise. People feel ownership beyond just showing up or earning commission. I’m grateful for your insights. Before we wrap, is there a question I should have asked that I didn’t?
Kelley Hippler | 27:36
Nothing comes to mind. This was a great conversation, and I appreciate the time. We covered a lot of ground.
Brynne Tillman | 27:48
You shared insights that sound logical but aren’t widely practiced. Revenue leaders should listen again and grab the transcript—there are so many nuggets here. Small shifts can have a huge impact. Thank you for the value you brought today.
Kelley Hippler | 28:30
You’re very kind. When you focus on your people, it truly is the best way to build sustainable, profitable sales teams. I appreciate the time as well.
Brynne Tillman | 28:54
This was great. Thank you so much. And to all our listeners, wherever you are, don’t forget to make your sales social.
Bob Woods | 29:04
Thanks for watching. Join us again for more special guest instructors bringing you marketing, sales training, and social selling strategies that set you apart. Hit subscribe to get the latest episodes of the Making Sales Social podcast. Give this video a thumbs up and let us know what you’d like to hear next. You can also listen on Apple Podcasts, Spotify, Amazon Music, and other platforms. Visit our website, socialsaleslink.com, for more information.