Sell Like A Leader – Episode 26
In this episode, we dive into:
– Building high-performing sales teams: Hiring the right talent, skills to look for when hiring, tailored training and development programs, measuring the impact of sales training, effective sales incentives, cross-functional collaboration, quarterly realignments, transparent compensation.
– Rapid fire Q&A
About Jessica Klek
David Kreiger chats with Jessica Klek, the CRO at User Interviews. For +20 years, Jess Klek has worked and led teams in B2B SAAS organizations like LinkedIn, SalesLoft, and 6sense. She has also been a fierce advocate for women in technology often speaking on panels, and was voted the Best Female Executive in tech by Women In Sales America.
Podcast Key Takeaways
- Jessica discusses her approach to building successful sales teams through focusing on talent, training, and incentives. She emphasizes the importance of hiring talented individuals, providing comprehensive training, and designing motivating incentive plans.
- She looks for inherent traits such as curiosity and grit in her salespeople. She believes that while sales skills can be taught, these intrinsic qualities drive success and can’t be easily instilled.
- Jessica underscores the significance of recognizing not only sales achievements but also the unsung heroes within the organization, like finance and billing departments, that contribute to overall revenue success.
Connects
Connect with Jessica Klek: https://www.linkedin.com/in/jessicaklek/
Connect with David Kreiger: https://www.linkedin.com/in/davidkreiger
Subscribe to the podcast and follow our Podcast LinkedIn page so you don’t miss any episodes!
Transcript
David: Welcome back to another episode of the Sell Like a Leader podcast, the podcast for revenue leaders who are on a mission to cultivate a high performing sales team within their organization. I'm your host, David Kreiger, founder and president of SalesRoads, America's leading appointment setting and lead generation company.
Today, I am bringing you another great revenue leader. Jess Klek, who is the CRO from User Interviews. Jess has over 20 years of working with B2B SaaS organizations like LinkedIn, Salesloft, 6sense, just to name a few. And now she is, as I mentioned, leading up User Interviews in their whole sales motion as their CRO. Also Jess is an amazing advocate for women in technology, speaking on panels and was actually voted Best Female Executive in Tech by Women in Sales America. [00:01:00] Wow. Welcome, Jess. Thanks so much for being on the show.
Jessica: Thanks for having me. Excited to be here.
David: So let's dig into your approach on cultivating high performing sales teams. What I'd love to understand first is just some of the key elements of why you choose to invest in certain things as you're leading your organizations forward.
Jessica: Yeah, for sure. The way that I think about building high performing sales organizations is like these three tenets. The first being talent, then training, and then incentives. I think talent is the most important thing, right? It is the lifeblood of any organization and your talent can truly make or break your success.
I tend to really focus on referral or what I like to call repeat hiring. I've been very fortunate in my career to have folks that I've worked with at multiple different organizations that have trusted me enough to follow me to different places. And so that repeat hiring just accelerates my ability to impact and build a high performing team.
Secondly is training, right? Like any high performing athlete or for the other F1 fans out there, like a high performing race team, training is so vital to our success. And so I really build full customized, holistic enablement plans for my organization that really help us hone in on the red in the business and allows us to tweak those things to optimize success.
And then lastly is compensation. At the end of the day, we'd like to think that our employees are working with us because they just love us and love our companies. But at the end of the day, they want to get paid. And so I feel like building truly empowering incentive plans is what really motivates teams to perform their best and give the best to the organization. [00:03:00]
David: Yeah. So I love how you put that in and you create three clear buckets. I feel like for sales leaders, there's so many different things we can think about and trying to figure out how to prioritize is important. And giving just an easy way to think about the key tenets of what you think about when you're building that team is really important.
So let's dive into each of them a little bit. So with talent, first of all, I love that you think about how you can bring talent along with you and whatnot. I think that's a great strategy and that's how over 20 years you can continue to build great talent because it's a 20-year interview in some ways with the people that you're working with.
What are some of the attributes that you look for in those people that you want to bring with you from job to job? What to you makes a great salesperson, somebody who you want to have on your team?
Jessica: Yeah, I think there are a lot of things I look for. I think certainly past performance. But two things I really focus on—versus a lot of people talk about personality traits, introverted, extroverted—I really tend to over index on folks that are naturally curious. Because that is an inherent trait. You can teach that through good discovery. But having that natural curiosity I have found has really been a defining characteristic of the most successful reps.
And then just grit and money motivation. The folks that want to come in, that are willing to work really hard, that can identify problems within an organization and bring solutions to the table while also doing their day jobs. Those are the types of individuals that I always over index on hiring. I think you can teach a lot of sales, but there are inherent skills that you look for that are sort of unteachable. And I think curiosity and grit are two of those things.[00:05:00]
David: Yeah, I love how you start with curiosity because I think it cuts in a few different directions. One is just as—the best salespeople are those that continue to try to want to get better. Learn how to get better. And when they're curious and they're listening to podcasts, they're talking to people, they have mentors, whatever it might be, and they have that curiosity on what can make me better, what is a new technique I can use, that helps them to improve day in and day out.
And then on the flip side, when you're selling, if you can be curious about your prospects, curious about their problems, that's what drives great discovery, right? And so I love how you started there. I'm right there with you.
So the second part was training and development. And so maybe can you talk to us a little bit about what initiatives maybe you're currently running and what are some of the things that you really feel work when it comes to training your team and developing your team?
Jessica: Yeah, I think training and development are really in and of the moment. So for instance, last year we rebuilt our entire revenue organization. And so we deployed new sales processes. We deployed new infrastructure, a new tech stack, a new way to do all of our processes internally, a new way to collaborate with our peers. [00:06:00]
And so the training and development last year really focused on the basics. It was really about: how do we do great discovery? How do we push the sales cycle forward? How do we deploy MEDDIC? And how do we coach our leaders to coach our reps through the sales process?
And through that, we were able to get this high performing outbound motion going. And as we look to reset for this year—we have really high growth targets, like I'm sure everybody else does—but this year is really focusing on more of the refinements and less on sort of the building and infrastructure of training and refinements and looking at, okay, where was the red in our business?
We had trouble really at late stage, stage three, stage four, where a lot of the negotiation, a lot of the procurement navigation of the sales cycle happens or more so more often for us is selling to the CFO. How do we get their buy-in? And so really developing our enablement around the needs of the business at that time in the moment.
And so one of the things we're really working on refining is our business value assessments. Something we built and deployed last year, the reps were not really ready for those types of conversations. And so it's, how do we scale that back? How do we make this muscle memory so that they continue to build these business cases that will help elevate us to get above the line, help us sell to the CFO, and also when we talk about our champions, how do we help them help us go get budget for what we're selling? [00:07:00] And so I really look at our enablement as "of the moment" type training.
David: Yeah, I think that a lot of times people feel that training doesn't work. They're not sure they get the results they're looking for. And I think something fundamental in what you're saying is something for sales leaders to think about. Sometimes choosing what to train on is the most important decision and really figuring out what is the need in that moment, in that year, in that quarter.
Because if you choose the wrong thing and you try to train on the wrong thing, maybe you could have the best training, you have the best follow-up on the training, you do all those things right, but it's not going to move the needle because you're not training on the most important thing.
I'm not sure if this applies or not, but just curious, is there any role in team dynamics that plays a part in the way that you're either choosing what training you're needing in that moment or the way that you are delivering the training? How do you think about the team and thinking about what's best given the way that they are or they work together?
Jessica: Yeah, for sure. I think team dynamics plays a big role for us. We have segmented our go-to-market team on acquisition, and then account management, and then customer success. And so when we think about deploying training and enablement, there are things that we want to do holistically so we're all speaking the same language across the customer journey. [00:09:00]
For instance, we just rolled out Challenger methodology, and that is a change for our organization as we have relied heavily on relationship building. And so this is going to be a new motion, but we want to deploy this methodology across the customer journey.
I think where the team dynamics comes into play, there are tweaks to that specifically in the role. Acquisition side of the house, it's a lot easier to want to teach, tailor, take control throughout the process. Where account management, there's different scenarios where we're dealing with, you know, high-value customers and customers that we've had for many years. And the way that we sell to them or continue to strengthen the relationship might vary a little bit.
And then certainly the CS team has a different skill set, right? They're not so much in that mind frame of selling, but really increasing utilization and driving customer value. And so, um, there are things that we can deploy org-wide and then have to sort of refine that based on the role or the team dynamic.
David: Was also curious when you think about the training for specific use cases or things like that. Is that something you think about at the beginning of a year and you lay it out for the full year? Or is it just ongoing across the year as things come up? How do you think about that?
Jessica: I would love to be the leader that has [00:10:00] like the entire calendar in the beginning of the year. But I think for us at the stage and size of company we are, we sort of revisit that. And I think that's really valuable that we have that agility because we are able to identify what's working. And then, of course, what isn't, and we're able to then refine and tweak those things to continue to enable the organization.
I think one training that is constant is competitive and the competitive landscape and understanding our place in the market and just being industry experts. So those types of trainings, I think we think about holistically the year.
Okay, every month, this is what we're going to do for competitive intel. Every month, this is what we're going to do to drive market awareness. Every month, this is what we're going to do to become experts in this space. And then the quarterly realignments happen on, "Oh, okay. Wow. The part of Challenger that didn't work out was really in that discovery, that tailor phase."
And so now let's go back and sort of [00:11:00] rework what we can deploy to the organization to optimize that part of the sales process. So holistically, there's some things that I think everybody probably always trains on, and then we tweak it every quarter. And then we also measure that.
I think it gives us enough time, but not too much time to actually see if any of that is impacting what we're hoping that it will impact. And it gives us enough time to tweak and change things to, again, optimize the results.
David: Take into that a little bit, because I think that's awesome that you guys do it. And I think a lot of times people can sometimes want to measure the training or hope to measure the training, but not exactly sure how to do it. Can you just walk us through your process, if there is an example, or just at a high level of how you would roll out training and then try to measure it to see whether it had this?
Jessica: Certainly. And I think measuring training and development has always been this nebulous thing. It's been very hard to quantify. I think there are very specific training programs that we have deployed that we have been able to measure impact.
For [00:12:00] instance, on conversion, specifically with laying out MEDDIC, right? Are we getting above the line? Are we getting the decision process? Are we getting the decision criteria? We focus on a couple elements of MEDDIC and we see—has that affected our conversion rates at all? Have we been able to push deals faster through the cycle? Has it enabled us to increase ASP?
So we look at just like the key KPIs in the quarter following that training to see if that really helped. And I give a lot of credit to my leadership team as well because we are really reinforcing that training in every conversation. When it comes to deal evaluation or win rooms or win strategies, we’re always having those leaders go through those lines of questions that reinforce what we have trained the organization on.
David: That's so critical. I mean, any organization that does the one-and-done philosophy and thinks that you're going to have this amazing sales training and then they walk out and leave them be to try to execute on the sales training [00:13:00] is going to fall flat, right? And that's where the managers come in. So I think that's fantastic.
Jessica: Yeah, definitely a lesson learned. I have definitely deployed training before that you hope it's going to work and then you're like, "Oh wait, they're not doing that because we didn't reinforce it." So the reinforcement, I think, is absolutely the most critical part of any training and development—just like constantly revisiting that.
David: Yeah, I think that's fantastic. So let's transition to the third part. The incentives and, as part of that recognition, can you give us an overview as to why that makes the top three? Why is it so important as part of your methodology for building a high-performing sales team?
Jessica: Yeah, I was a seller myself and still consider myself a seller at heart. And we don't get into this line of business for the good of our health, right? We get into this line of business because we want to make money. And I have always been a fan of really straightforward, transparent compensation plans that really favor the [00:14:00] rep. In all else, when all else fails, favor the rep. Incentivize them. They're the ones out there doing all of the hard work.
And so I really love transparent plans that you can really sit down with a rep and say, "Here's how you're going to overachieve. Here's how you're going to get to your accelerators." We will run some quarterly SPIFs, but I'm such a fan of building out the most impactful compensation plan up front.
For instance, I think I might have mentioned this, but we wanted to sell more multi-year deals. And when we put that into the comp plan, we grew our multi-year deals 500 percent year over year. So we really focus on the behaviors that we want to change or incentivize. And we build those into the plans. We change them annually again to sort of tweak, "Hey, what's the behavior we want to see now? Okay, it's not just multi-year, it's five-year deals." And so there's an accelerator built into your plan.
But I think at the end of the day, sellers want to make money and they want to work for an organization that is recognizing [00:15:00] that. And so when you have a great compensation plan, that's the best way to get overperformance and to retain that top talent.
David: And I like how you talked about leveraging SPIFs, but trying to build the best plan possible, because I think sometimes, I think SPIFs have their place. But if it is a replacement for trying to catch up on the quarter or creating the incentives that could have been created right out of the gate to keep people motivated throughout the year, that’s a problem. And so I think thinking through that prism is really important for sales leaders. As part of that, do you have any—and they go hand in hand—but do you look at recognition in any different light, or is there anything you do as far as recognition for the team over and above the financial incentives?
Jessica: For sure. We hold quarterly awards for the team and not just the sales org. We also recognize our cross-functional partners, which goes a long way. A lot of them are unsung heroes. Giving them the platform to be recognized in [00:16:00] front of their peers, in front of their managers, for their contributions to our revenue growth has been a game changer.
And so doing those quarterly recognitions. And then of course, we have annual recognition. For our stage and size, we don't have a club trip or a President's Club trip yet, but certainly working on that. I think we do things throughout the quarter. We leverage programs like Bonusly to publicly recognize and thank people for their contributions.
But I do think that recognition comes hand in hand with the compensation. We’re paying you to do a good job. And then those accelerators are a way to continue to recognize your over-attainment. But I love to recognize my team, and we try and make it fun. And we try and make sure that the whole company gets to ride along on that recognition so they'll continue to help push forward certain of the things that we need them to do to win.
David: Yeah, I think it’s so important to be able to call out the full team—everyone who's touching the sales motion. And I know you don't necessarily have a trip, but [00:17:00] I think I saw on LinkedIn a few days ago somebody who also includes in President's Club some of the sales ops folks and whatnot. I think that's really important to recognize everyone, because what we do sometimes feels like an individual sport, but it really is a team sport when it's played best.
Jessica: Oh yeah. I think driving revenue is a company goal, right? And I think every single part of the company is responsible for driving revenue growth. And I really think that way. I think it's a holistic measurement of success. And when we get to recognize our finance and billing team for the collections efforts that they've done that saved us from $100,000 of potential churn, or that PM that really wanted to buy directional integration versus a single-sided that really helped us sell more deals—those are the folks that need to be recognized too so they can feel like they're part of the win.
David: This is awesome. Okay. Thanks for breaking down those three aspects of your philosophy. So what I would love to do at this point though is go into our rapid [00:18:00] fire questions. So I'd love to ask you a few questions. If you can give me your perspective on each one, that would be great.
So first, what is one thing people don't give enough value or attention to in leadership?
Jessica: I think it's their own leadership team development and training. I think we think a lot about the reps and the sellers that are executing, but not a lot about how to actually continue to lead and coach.
David: That's awesome. What's one skill you advise everyone in sales to master?
Jessica: This is retro to what I said about natural curiosity, but good disco. If you can do good disco, you can make up a lot of ground.
David: Yeah. Closing starts with discovery.
Jessica: That's right.
David: Favorite business, leadership, or sales book?
Jessica: It's a little tangential, but I recommend it to everybody and it's Growth Mindset by Dweck.
David: That's a great one. Favorite quote, mantra, or saying that inspires you as a sales leader? [00:19:00]
Jessica: It's one that I heard very young in my career that I couldn't quite wrap my brain around, but now it is absolutely my mantra and it's: "Detach from outcome."
David: Yeah, not easy, but I think in sales—riding the roller coaster—if you're riding it nonstop, it's hard to survive in this business. So, that's awesome. And lastly, what is the most important goal or project you're working on right now?
Jessica: We grew our company by 40 percent last year. We're going to grow it by 50 percent or more this year. So that is what I focus on every single day. So big goal to hit.
David: Wow. That's huge. Jess, this is fantastic. Thank you so much for taking the time to share your perspective today with other sales leaders. If people have questions about the episode or want to connect, how do they reach out to you?
Jessica: Sure. Feel free to reach out to me on LinkedIn. My profile is public and if you want to email me, you can at jess@user [00:20:00] interviews.com.
David: Fantastic. Thanks again, Jess, for being part of the show today. I know I got a lot of great nuggets. I know our listeners did as well. And for folks out there, if you love what you heard here, please subscribe on your platform of choice. You can always reach out to me. I'm on LinkedIn a lot—probably too much—David Kreiger.
You can check me out and reach out with any guests or ideas, or questions you have. But thanks again. Thanks, Jess. Really appreciate it.
