Leading Sales Teams to Year-Over-Year Growth

If you’re struggling to unite your team, maybe it’s time to get back to basics.

In this episode of “How to Sell More,” host Mark Drager is joined by Chris Costello, an executive leader with a remarkable track record of turning around struggling teams and driving significant growth. Most recently she led multi-billion dollar revenue bases and built teams that excelled in even the most challenging environments. 

Chris is known for her ability to meet customer needs through innovative solutions and for her bold, result-driven leadership style. In this episode, she shares insights on building trust, creating clear goals, and leading both small and large teams to success.

Be yourself: Being open about both professional and personal aspects of your life helps build relationships where team members feel valued and understood. This significantly increases their engagement and commitment.

Be present: Your physical presence in strategic locations, such as industry conferences or special executive gatherings, can lead to accelerated deal-making and partnership opportunities.

Be the fixer: Successfully resolving issues, especially those that significantly impact business operations or customer satisfaction leads to increased business opportunities and trust from both clients and team members.

“It's really important to have a good culture and leaders that trust you and leaders that you can trust.” Chris Costello

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Links to This Episode

• Apple Podcast
• Spotify
• YouTube
• Audible

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Key Takeaways

• Authenticity is key for great leadership - To really connect with your team, you need to be your true self. Forget the corporate mask—being authentic builds trust and strengthens team dynamics.

• Make your mark in executive circles - Show up and engage in C-suite and top-level events. It will give you a chance to network and communicate directly with key players.

• Empower by solving problems - Focus on tackling challenges for your customers and your team. Being a problem-solver shows your dedication to making things better for everyone involved.

Top 3 Reasons to Listen

Leadership authenticity: Learn why authenticity in leadership fosters trust and improves team dynamics, as Chris discusses the impact of being genuine with her teams and how it helped build a positive work environment.

Executive networking: Gain insights into the strategic importance of attending C-suite events. Chris explains how attending these events opened doors for her and how it can do the same for you.

Problem-solving strategies: Understand the role of a leader as a fixer, someone who actively solves problems for customers and their own teams

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Follow Chris Costello on Social

LinkedIn: https://www.linkedin.com/in/christinacostello1/

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More About Today's Guest, Chris Costello

Executive, AI and Digital Strategist, PE Consultant, Board Member, Author

Chris Costello, is renowned for her ability to tackle "impossible" challenges and deliver extraordinary results. With a distinguished career in leading transformative initiatives and crafting intricate sales and product strategies, she has positioned Fortune 25+ companies as front-runners in emerging industries. Her passion for meeting customer needs and driving revenue growth through innovative solutions has been a hallmark of her success. As an executive leader, Chris has demonstrated exceptional capability in building and managing large teams, overseeing up to 600 direct staff and a client base in the millions, while handling multi-billion dollar revenues. Her career is marked by numerous game-changing transformations, earning her recognition as a top executive in the industry and numerous accolades.

Chris's early career in the competitive telecom market earned her the nickname "Cloud Guru" for her pioneering work in launching groundbreaking solutions in hosting, application management, and cloud services. These innovations enabled customers to enhance their capabilities without substantial infrastructure investments. She has been featured in over 60 publications and received honors such as Best 50 Women in Business, Top 10 Women in Wireline, and the Leaders Quadrant Cloud and Hosting by Gartner Group. Known for her outspoken nature and relentless drive, Chris Costello continues to be a formidable force in the business world, inspiring and driving industry innovation with her leadership and vision.

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A Transcription of The Talk

Mark Drager: So Chris, in your previous role, you led a multi-billion dollar P&L segment at a massive global organization. And when I was reflecting on your career, the real reason that I wanted to have you on, is that in that role, you saw year-over-year growth. And then, if we take a step back, the role you had before that, you led a team of 600 salespeople and delivered a massive year-over-year growth plan. It was the fastest-growing segment in the multinational organization across a multi-billion book of business. Now, if we take a step back to the role before that, you led 450 professional salespeople through a major turnaround. And if we take a step before that—and so I think the audience sees where we're going with this part of— I think why you've been so successful in your career. What I'd love to be able to dig into with you is you are an executive who has had a tremendous career over the last 20-plus years, seeing turnarounds, seeing action plans put into place, seeing year-over-year growth. How is it you've been able to—I mean, I was about to say you've gotten so lucky, let's say.

Chris Costello: I think some of it is pure luck. Some of it is having a work ethic, having a can-do attitude. I think the number one thing is being authentic with your teams, being accessible, and running into the fire with your teams. And I've got some really good juicy examples that hopefully we'll go through today.

Mark Drager: Although I say it jokingly, though, you know, this is not just luck, right? What do they say? Luck is the crossroads of preparation and opportunity. So clearly, as you were able to work through your career, I am curious because as an executive, as someone who's responsible for so many headcounts, such a large book of business, and attending, essentially, a publicly traded organization, you're also responsible for your segment's growth back to the shareholders. And so, I'm curious as an executive, it often looks like you're responsible for everything but unable to directly control or influence anything. Has that been your experience? Or is that more of an outsider's view of what it's like to be an executive in these large organizations?

Chris Costello: Mark, I would agree with you. It doesn't matter what job you have; it doesn't matter if you're the CEO or the floor sweeper; there's always a need to influence others. And if you take sales as an example, if you're running a sales organization, there's always a customer that wants something that's outside the lines. And I think of an example when I had an opportunity to win a large complex deal, but it needed custom development. You go to the product teams, their product roadmap is full, they don't have the funding, they don't have the headcount. And in that example, ultimately, you've got to speak through the lens of the customer and the customer's need. You can't go to team members that you need to influence with one-offs or complaints; it's got to be something that looks like it's sustainable and replicable to other customers. Ultimately, in this example, we were able to convince the product teams to build a custom development, showed the ROI, and showed that other customers would be able to use it; it took six months. So, it takes patience, it takes data, it takes fortitude. Ultimately, we were able to get them on board and got them to invest in it. The other important thing, which is probably even more important than the business case that you have to build, is getting the team excited, getting them to feel like they're part of the project. And then, ultimately, when you've got to, recognize those team members.

Mark Drager: And so when you say we—is this you leading, sleeves rolled up, strategy, and action plan, and you're delegating to people, or is this where people are kind of checking in with you every once in a while? Interesting, very high level, or are you literally leading the account and leading the presentation for these kinds of large deals?

Chris Costello: It depends on the deal. It depends on the complexity, depends on the customer. In the example that I just shared, I personally got engaged and had a discussion with senior management with the CTO of the company, who had some really tough decisions to make and basically said, "Well, what do you want to fall off the roadmap?" And so in that case, I personally engaged; I helped the account executive, I helped sales managers, etc., and I helped to coach them to build a rock-solid business case that would get the attention of leadership to make that decision.

Mark Drager: You mentioned the business case twice. How important is that, at the end of the day, to have a strong case that has a clear risk-benefit analysis done, that clearly has proven benefits, and that you have a proven process for? I'm just thinking off the top of my head about everything that might go into a specific business case to have people move forward with it. But for these large, complex engagements, are they quite rational and logical because that's what's required for the decision, or is it like, "This is all safety, let's clean this up in case something goes sideways later, at least we could say we did due diligence"?

Chris Costello: I mean, I think at the end of the day, you've got to get it roughly right and go. You've got to use data. But if you get into analysis paralysis, and you know, are looking for perfection, and I mean, you've got 80% of the data, you've got to partially go with your gut, and you've got to go after the market opportunity, or you're going to miss the opportunity. It's not just about accounting and leaning up and perfection, but it's got to show a return.

Mark Drager: That makes so much sense. Now, I'd like to go back to when I first kicked off our conversation. I said, "You know, if we go back, if we go back, if we go back," There was a time in your career when you were leading a turnaround, specifically for a division within a large telecom company. And in this turnaround, I'm curious, what were the challenges that you were able to identify? How did you develop a strategy? How did you achieve that strategy? I'm curious just what your team makeup looked like, and what your process looked like. Because I've heard it said a long time ago that a leader who can lead to growth is a great leader, but a leader who can turn something around, the 'J leader', talk about the 'U leader' that has a totally different skill set, because you almost have to reverse negative momentum, make some positive gains, and then turn everything around. So I'm curious, how did you handle that?

Chris Costello: Sure. There was one role that I had taken on, and I quickly determined that there was poison in the water; it was a pretty toxic culture. There was no cohesion; no one was sharing best practices with each other. There wasn't trust; people were working in isolation. They were in kind of like protection mode. And the previous management, I think, didn't bring them in much on decisions and make them feel part of the decision-making. No one was asking for their opinions or explaining the why, bringing the outside in and explaining the why. And so step one was being authentic, me being authentic with them, showing them who I was, that I was enlisting their feedback, that I wasn't perfect, that I was going to learn from them, explaining the why of the strategy and plan. And then getting them to weigh in on strategy and tactics to make the plan. So they felt part of it. Step two, I did have some cleanup to do; there was a person that I needed to move out of the organization, and then ultimately create a culture of trust with the team and start to help all tides rise and encourage the team members to share best practices; they didn't have to hold their cards close, that everyone would do better if they shared best practices. And then step three of the turnaround was a little bit more operational and communications-oriented. And that was a leaderboard, getting a leaderboard out there to get the teams excited and motivated. I established monthly what I called to grow the business calls with skip levels.

So I would meet with like eight different regions, eight different teams, and we'd go through their results. And ultimately, it was a carrot and a stick, but it helped me to get to know them better. And it also helped us as leaders to glean best practices that we'd share with the broader regions like great tips for selling that we learned that one particular seller was doing successfully. Ultimately, I became viewed as a leader, one who holds a high bar, but also one who gained trust with the teams by advocating for them by moving rocks out of the way, by escalating, and also by recognizing them and giving them exposure to upper management. That was another problem. They weren't getting any exposure or credit for their work. And you know, teams that trust you are going to deliver 150% if they're treated with respect, and the good spread about this one is we started out as last in the nation, and within six months, we turned into number one in the country. So it's good. It was a rough lift.

Mark Drager: Okay, so what do your leadership and peers say about such dramatic results? Because I mean, going from last to first over the course of two quarters is dramatic; it's a dramatic change. Were they tapping you on the shoulder and wondering, "What the hell are you doing?"

Chris Costello: My peers, you mean?

Mark Drager: Yeah, your peers and your leaders.

Chris Costello: Okay, yeah, my peers were like, "Show me your playbook," which I was happy to share, and some of them had been there longer than me. I looked for their playbook, and so we were comfortable enough with each other that we shared best practices with each other. We operated as a unified leadership team, not just competitors of one another. And my leadership team was happy. The very first thing that I learned from my leader at the time when I walked into that role because I remember the first month I gave a horrible forecast—not that the number wasn't a great number, but it was wrong. And I remember him telling me, "Results are awesome, but forecasting is even more important." And so I ultimately got the forecasting right once I got the culture right, and then the results followed.

Mark Drager: What I'm curious about with this story is I've never led such a large team; I think, at most, I've had 24 people on my team. And I found that challenging to lead 24 people in a fairly flat organization. And when we think about large organizations, leadership skills are leadership skills, it sounds like there's not actually much of a difference between being a great leader of a very large team—maybe the stakes are higher—and being a really great leader of a small team. Because the skills are still the same; you're still required to show up with vision, you're still required to hold people accountable, to set a path, to include people, to collaborate—all of those types of elements. I would have thought that in your role and your situation, it just would have been different, less personal; you may have been more up at a very high level, very high vision, not quite as responsible for holding people accountable, leading these monthly calls, managing through the kind of three-step process you mentioned. Is leadership the same at all levels at the end of the day?

Chris Costello: It isn't, it isn't. It is a little bit harder to get the message out the larger the team. I made a concerted effort to travel to all the different regions, spend time with the teams, act like a human being, bond with people, ask people how they're doing, and share things about my personal life. The grow-the-business calls with the skip levels took a lot of time on my calendar. But I thought they were so important in terms of having the team have exposure to me, but also all the best practices that I was gleaning as a result of it. But I think the number one thing, regardless of the team size, is your direct reports need to be in the boat with you. I had one point where I thought he was in the boat with me, but he was almost like pocket vetoing, and I later found out through a discreet phone call from one of his team members that, you know, we were sharing one message, and then he was sharing another message which was kind of contrary to what the mission was of the leadership team. So, it's really important to have a good culture and leaders that trust you and leaders that you can trust.

Mark Drager: I'm just pausing slightly between us talking because I'm absorbing this information. Because I think, listeners, you agree this is something. Now, being as results-focused as your career has been, with the wins and year-over-year growth, I was wondering, given your level of operations, your seniority, and the global business that you're running, what types of results and KPIs matter most? It was interesting that you said your leadership mentioned that results are good, but forecasting is what matters. And so, even with that, I'm curious whether the KPIs and metrics you use and prefer to focus on as a leader, are more trailing or leading KPIs. What do you look for to ensure that you can manage results?

Chris Costello: The first thing that I would say when it comes to KPIs, especially the ones that you roll out to your team to measure, is to pick a few important ones. I've seen teams get weighed down and have seen organizations want to measure too many stats and fail, because the sales teams are then playing the salesforce.com activity game, and they're not out selling to customers. And so, some people like to roll around in tons of data. And it's really not fair to burden the sales teams with all that data. I look at things like top-line revenue, deal size, cycle time, profit, and industry trends. My team members, teams that manage other team members, and individual contributors will also look at productivity metrics of their teams, such as the number of meetings, and close rate—not in a micromanaging kind of way, but to get a sense of trends and to be able to perform accurate forecasting. I also, as an executive, will deep dive at least monthly into a much more detailed set of metrics for myself, to manage the business and pick out trends and insights such as, what are the top services that are selling? Where are dealing margin trends? What kind of credits are we issuing out to customers and why? What are my top accounts? What are my bottom accounts or loss reasons, what are win reasons, but you can't put every single one of those on a leaderboard or you're just going to stress your teams out, and they're going to do nothing? Well, in terms of, you know, is it just a leaderboard? Or do you get strategic insight? You know, I could probably share some feedback on that as well. An example is that I mean, obviously, there's a leaderboard that goes out on a weekly basis, on a monthly basis.

And it's a great motivator for team members. I've had that in every sales assignment I've had, and every leadership assignment that I've had, but I remember a story that I'll share where one time we were really heavily incenting a certain product, and we really wanted to go big with the launch of the new product. And the sales weren't materializing and we were really nervous and really paranoid. And so we dug deep. We were trying to determine what insight we could glean out of this, and why is it not selling like hotcakes, so we did the press release. Everybody loves it in concept, and nothing's happening. And so we dug deep to determine if there was a problem with the product. Is there a lack of customer need, are there supply chain issues, or macroeconomic problems, or is there a competitive pricing issue? What we learned in deep diving is the sales comp plan motivated sellers to sell long-term contracts, and what we had launched was a pay-per-use product without a long-term contract. And so ultimately, the leaderboard and the stats and the insights gave us the intelligence to change the comp, so that salespeople would be motivated to sell it.

Mark Drager: That is so much. Now, when you say you dug deep, if you can recall that situation, does that mean digging deep in terms of turning to your sales leaders, turning to maybe the comms department, the product department, like who do you bring around the table to figure this out? Or is it literally like, let's just look at the sales activity, and insights and make a decision because this is simply just a sales issue?

Chris Costello: On the surface, it was looking at the leaderboard and the stats and salesforce.com and things like that. We also had a strategic adoption team that was doing outbound calls internally to salespeople to help them make the sale and also some calls directly to clients. But ultimately, where we got the most insight was talking to just honest salespeople who weren't going for the pressure. Like, "I don't care what headquarters says, this is the situation." And so it was ultimately some trusted salespeople that said, "Chris, I can't retire my quota this way, this is not going to fly. I'm not selling pay-for-service." So that's where we got the real data, talking to honest salespeople who care about how they're retiring their quota.

Mark Drager: I love that so much. The greatest breakthrough I've had in business for myself and my clients, and we've talked about this a lot on the podcast, listeners, it's the gap between marketing, sales, and the customer. Or if we take a few steps even further back, anytime you have one or two areas of removing yourself from being able to speak directly with the very people that your work is affecting, you're always going to get these political answers. And you're going to spend a lot of time and a lot of energy. Yet if you can have the types of relationships, and I think back to when I first started my career, I was 23, I was extremely young. But I started working at a medium-sized organization where, because of my work, I was situated in the C-suite. So I sat with all of my internal clients, as a shared service where the executives, I sat with legal, I sat with accounting, and I had the ability to walk into the CEO's office at any point. Often, we had this great dialogue, because he could ask me questions about what was happening, and what were people thinking on the floor. And how did this presentation go? And I worked in marketing communications, so I was analyzing it. But that direct relationship, that ability to—I've done it myself—go to a trusted client, go to a trusted prospect, that you may never win the business with the team member. And then vice versa, them coming back up the channel, being able to have those conversations without worrying about jeopardizing your career, or the politics, when you could just get down to the basics, you're going to get the answers so much quicker. Makes sense? And so when you look back over your extremely impressive career again, what would be the two to three leadership lessons that you really picked up along the way that you can help share with me and, of course, all of our listeners?

Chris Costello: Sure. I used the word 'authentic' earlier. And this was a learning for me earlier in my career. So the first leadership lesson is to be authentic. And this is based on what could have been a fatal flaw for me earlier in my career when I had taken this Myers Briggs and part of it was getting 360 feedback from others. And a couple of the verbatims in the report that came back to me is, "We don't know the real Chris." And when I got that feedback, I realized and I reflected on myself I was young in my career. I was being guarded. I was so worried about being taken seriously that I just had this work persona that was just so buttoned up that nobody could access the real me, so I've worked literally ever since then. And this was in my early 20s. To just come across as me, the real me, what's going on in my business life, a little bit about what's going on in my personal life, and to just be me.

The second leadership lesson is to be accessible, and to be accessible to all levels, and to move rocks to serve customers quickly and so escalate for your teams. I don't care if it's some floor sweeper, the CEO, whatever level it is, the junior aka the telemarketer, the senior sales leader, a new different function in the organization, there's a subject matter expert, they know what the problem is, they should feel comfortable being able to come to you, you can't stop what you're doing every second of the day and fix everything but my team always know. So they can come to me to escalate a problem or run into a fire with them to solve a problem with the customer. The third leadership lesson is to empower and recognize teams, if teams feel as if you have their back, they feel like they're trusted, and they feel like they're not being micromanaged. Salespeople, in particular, are motivated by money, but they also appreciate recognition, it goes a long way, and knowing that you trust them and that you have their back.

Mark Drager: I do have one bonus question. We are coming up against time, but I would be really remiss if I didn't ask this of you. Are you game for it? Bonus?

Chris Costello: I'm in.

Mark Drager: Okay, so a common theme that has come up time and again with guests on this podcast is the challenge that certainly junior, but even mid-level sales and business development people struggle with being able to get time in front of the executive or the C-suite, meet with the executive or C-suite and not just throw up a pitch, you know, like benefits, features, benefits, features, but be able to manage that, get the time, get the meeting, make the most of the meeting, sell the concept, and move on to the next step. Now, you've spent a lot of face-to-face time with some of the world's largest CEOs and leaders. You've had to do this in your career. And of course, as an executive, you have had people pitching to you all the time, I imagine. So, what can you share with us? What insight can you give us from your firsthand experience both selling to the C-suite and executives and at the same time being pitched constantly by others?

Chris Costello: Sure, I'll take it from a couple of angles. One is: to be where your customer is. Sometimes it takes an executive to land an executive right to land that well. One of the things that I do is I personally attend executive C-suite events. Depending on the industry, the C-suite is going somewhere at least a couple of times a year. So, make sure you're at that event, make sure you and your sales team are setting up 30-minute power talks, and put them on calendars in advance. Make sure you're prepped, and make sure you've got the bio of the person that you're about to meet with. Once you plan the meeting, if it's one of those trade show events, meet them for coffee, or book a conference room where they can come to you. I once time went to an industry event and I had literally within a couple of days 20 customer meetings, and the learning from that one is just make sure you're in the same place because I was literally running, sweating, trying to get from meeting to meeting.

Don't use handouts. This is a strategic one-to-one relationship-building type of discussion. But you can bet I'm prepared. I know the one or two or three points that I want to land but ask the customer a lot of questions about what's keeping them up at night, and how can we help them with their business but do not go into slide mode. You can't always be at customer events, sometimes you can open the door by sending a personal note via LinkedIn. Sometimes you can have your account executive send your bio to try to open a door. So those are some ideas to get to that C-suite. I once had a role where I observed that my team was selling to middle managers and they were getting small wins. And I knew, I absolutely knew if we were targeting the C-suite we'd get a lot more wins and much bigger wins. We implemented this through a combination of up-leveling talents with getting new talent that had the experience to get to the C-suite too by motivating team members. And three, we actually created an executive positioning program where we lined up some of our own executives with some of our own top accounts and that was super successful.

I also think of a deal example that is an interesting one. I was once working on a deal. It was a very large deal. And we started with the C-suite. We didn't have to ratchet our way up. We landed the meeting right away. I will tell you that the deal was two years in the making. There were lots of meetings, there was a lot of pomp and circumstance. There were a lot of legal red lines on contracts and things like that. But we ended up landing a massive deal as well as strategic partner status versus we could have gotten a little deal in a sea of vendors. The advice on this one that I would say is really important for executives to personally invest time in whale hunting because salespeople have quotas that they have to make, and they can't think whether they're going to make their entire year's quota on whether they're going to win one deal or not. And so I would say executives need to personally take some of the weight when you're hunting whales and going after those large strategic deals.

Mark Drager: Oh, my goodness, that's such amazing advice. One last question for you, Chris. If you were to give us one tip or one strategy to help anyone listening sell more, what would that be?

Chris Costello: It's really simple. It's being a fixer—fix problems for your customers, fix problems for your sales teams. So, let’s say you have a customer who has a long-standing billing issue that you inherited; you're the new account executive. Find a way to fix it. They're going to trust you, and then they're going to give you more business. For your team, unblock issues, and escalate, and they'll deliver strong results. I once had a customer who was surely going to fire us because we created some kind of a service problem for them. And I remember flying out to Arizona, having a dinner meeting with the CIO, getting the beatdown of my life, falling on the sword, leaving completely deflated, figuring well, we just lost that business. Ultimately, I did fix the problem, was able to fix the problem, and three months later, we were awarded a multimillion-dollar contract. So being the fixer has its rewards.

Mark Drager: And that goes back to all the responsibility, not a ton of control.

Chris Costello: Absolutely.

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