Scaling Up Sales Managers: 5 Mistakes New leaders Make (Video + Transcript)

If your SaaS business has a sales team, there’s no way to grow 100% year-over-year without also growing your sales leadership. In this talk, CircleCI VP of Revenue Jane Kim will talk about the 5 mistakes all new sales leaders make. Knowing the common pitfalls won’t stop you or your team from making them, but it will help build the most important skill any manager can have: resiliency. Come and learn how to build great leaders so you can grow your team, and ultimately, your business.

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Jane Kim | VP of Revenue @ CircleCI

FULL TRANSCRIPT BELOW

Let me start by telling you about my first role as a manager.

I’m going to really step out and share some vulnerable moments with you. When I was first promoted to manager, I remember being so overwhelmed. As a rep, I had been responsible for my own deals in my own pipeline, but now I was responsible for a whole team’s. Overwhelmed. I would spend all weekend long stressing out and scrutinizing every aspect of everyone’s deals, and I would be in early on Monday mornings, ready to dig in the second people got in, full of helpful suggestions on how everyone could improve. At least, I thought they were helpful.

My director finally pulled me aside in order to give me some feedback for which, to this day, I am still eternally grateful. First she said to me, “Jane, you’re doing a great job.” See? Eternally grateful. She said, “Your team really needs to get to know you. They will trust a leader more that they get to know, so why don’t you start by asking people about their weekends on Monday mornings?”

I realized then that I was so focused on my own needs that I was forgetting the first rule of management, it’s all about the team. So I really took that advice to heart. I actually put in a reminder in my calendar to ask my team about their weekends just so I wouldn’t forget.

Clearly I’ve made a lot of mistakes, but I’ve grown a lot as a leader in the 10-plus years that I’ve been in this business. Over that time I’ve hired over 150 people, my time at SuccessFactors, SAP, Optimizely, and now at CircleCI. In case you’re not familiar, CircleCI is a mission-critical tool for SaaS businesses. We allow your engineering teams to deliver higher quality product and features to your customers at a faster rate. If you’re interested in learning more about how your engineering teams can speed things up, come talk to me afterwards. Sorry, I’m a sales leader, I can’t help it.

SaaS = Software that scales. But, your people have to scale too

I’ve also scaled global teams across every region, and enabled them to generate over $200 million of annual revenue growth. But most importantly, I have promoted and developed over 20 first-time managers, which I believe is the most critical part of your organization to invest in.

At every SaaS business, there’s an emphasis on speed and scale, and while we sell software that scales, your people have to scale too, and as a leader, it’s your job to create a system to develop leverage within your organization through those managers. I give a version of this talk to all of my first-time managers in order to set them up for success as they start their leadership journey. I walk them through the five mistakes that all new leaders make, which I will also share with you, but I want to emphasize one very important point. The point of me sharing these mistakes is not so that you can try to avoid them. Let me say that again, the point is not try to avoid these mistakes. You will make them, your team will make them, it is inevitable, so don’t even try.

But the point is to learn these mistakes so that you can prepare for how to recover when they happen. It’s actually really important to understand this before I jump into the five mistakes. If you’re able to build resilience on your team and with your managers, then when problems arise you can get back on track quickly. But what does that mean? Resilience means the ability to recognize problems so that you can get into recovery mode quickly, learning from those mistakes so that you can be heading in the right direction no matter what, which ultimately builds trust within your organization and allows you to grow stronger together.

Why is resilience so important? In sales, we all know that you hear “No” more often than you hear “Yes,” but unfortunately as a leader, no matter how much you want to enable and empower and build up your teams, you also say “No” more often than you say “Yes.” And sometimes being a leader can feel really lonely, you can feel solely responsible for the success of your team, and if you don’t have resilience, the ability to recover and learn from your mistakes, it can be even lonelier. And as your business and your teams grow, you want to make sure that you have confidence to make decisions, even when the path isn’t clear or success isn’t assured. Making decisions is hard. You will make mistakes, but that’s okay if you can correct them quickly. So let’s get into it, the five mistakes that all new leaders make. The goal is to leave you with some perspective on how to recover and build resilience so that your business can continue to thrive.

First mistake, you will micromanage. Raise your hand if you’ve made this mistake. Let me start by telling you the story of a rep on my team when I first became a manager, but in order to protect the innocent I’m going to use some different names, so let’s go ahead and call her Cher. When I was a rep, my strength was being organized and always being on top of my deals in my pipeline, and I was promoted because that strategy was really successful for me. So naturally I believed for my team to be successful, that they had to be like me, but Cher didn’t sell like that. As you can probably imagine, she was a master at building relationships, sort of a classic stereotype of a salesperson, who knew every intimate detail of her clients’ lives, including their kids’ birthdays, what type of restaurants they like, their pets’ names, but while she was good with customers, she lost more deals than she should have. She was sloppy with her notes, she was erratic with her pipeline generation activities, and she would feast or famine depending on whether or not she would win a deal.

I mandated that she change her entire process and follow all the rules that I set. No surprise, she resented me, and her performance got even worse. I realized that I wasn’t going to be able to help her until she felt empowered to own her own success. You will micromanage. It’s the most common mistake that I see new leaders make. It’s easy to think, “I was promoted because I was successful, so to be successful, be like me,” but micromanagement is the fastest way to disempower and demotivate your team, so get to know your team in order to build trust.

As my former director said, your team will trust a leader that they know. Each person has their own unique set of strengths, weaknesses, and experiences that they bring to the role, every person is different, but it is your job as a leader to help each individual find their best way to their highest potential. There really is no one way to hit a target, and there is no greater reward as a leader than seeing one of your people get that light bulb moment where they really take something that they’ve learned and make it their own.

So with Cher, I actually had to go back and restart our relationship. I had to prove to her that I was a partner to her, and not a drill sergeant ready to criticize her every move. Once I was able to gain her trust, we were able to collaborate to leverage her strengths, while also incorporating my feedback into… To allow her and the team to be more successful. I almost shed a tear the first time she submitted an actual forecast report.

Mistake number two, you will hire the wrong person, and this one’s a biggie because at any fast-growing SaaS business, your ability to grow and scale your team quickly is critical. So let me start by telling you about a story of a new rep I hired, and let’s call her Mariah. I’m actually a huge Mariah Carey fan, I don’t know if there are any others in the audience? When I first started as a new leader in a previous role, I had the mandate to double the size of the team from 20 to 40 within a year. I was nervous about my first set of hires, including one new rep, Mariah. But it was clear in the first month, frankly the first few days, that she was not going to be successful, but I was not going to let her fail. It felt like a representation of my own success, so I poured my heart and soul into her development, and over three months I spent two hours a day training her, quizzing her, practicing with her, before finally admitting that it wasn’t going to work out.

And it was only after she left that I realized that spending two hours a day, 10 hours a week with one single individual, meant that the rest of my team, the people who were the right fit, suffered as a result. No matter how many questions you ask or references you check, if you hire at any type of scale, you will get it wrong. Every hire is a decision, it’s a bet that this person is going to be successful on your team, and sometimes you get it wrong. But it’s not about the person, it’s about fit. It’s that person in that environment, in the time and place of your company’s growth.

I actually ended up meeting up with Mariah about a year after she left, and I remember being really apprehensive about it because I was embarrassed that I was unable to make her successful. But when we met up, she told me how happy she was in her new role. I realized then that trying to keep her afloat was doing her, my team, and myself a disservice. Rather than taking the sole responsibility of one single individual, should have been investing across the entire team to make the organization successful. Like I said, when hiring you have to recognize that sometimes you get it wrong, but the real mistake is thinking that one or two bad hires makes you believe that you are bad at hiring, or that you have a bad hiring or training process, or what I did, take focus off of your real priority, which is the success of the overall team.

Look, I believe investing in everyone. I think you should give every person every opportunity to be successful. But at a certain point, you have to recognize when it just isn’t the right fit, and compassionately manage them out of the business. It is right for the team, and actually it’s right for that individual as well. So remember to focus on the overall health of your organization. Trust the process, it’s not about one or two hires. Focus on training, development, and the performance of your overall team. Know your high, low, and mid-performers so that you know how to invest overall.

All right, mistake number three, you will fall into the likeability trap. So let me tell you a story of a newly-promoted manager on my team, and let’s call him Elton. So Elton, like most new managers, was promoted because he was successful as a rep, and when he became a manager he decided to be the ultimate champion for his team, to single-handedly solve every problem that he suffered as a rep. The thing that was most important to him was that his team liked him, that they were loyal to him, and that they felt supported by him. Every decision was a team vote, and he never rocked the boat. His team loved him. But you know what? His team was failing, and over time they became resentful. It’s no fun being on a low-performing team, even if your boss is your friend, or Elton John.

Wanting your team to like you is an easy trap to fall into. New managers struggle with the transition of going from a boss or a friend to a peer to a boss. “Will they see me differently? Will they like me?” These are the common questions that run through their minds. They don’t want to rock the boat, but they end up passive-aggressive, kind of like David Brent from The Office. As a leader, it’s not your job to be liked. Don’t get me wrong, I’m not saying to be mean or terrible, but your ultimate goal is not likeability, it’s the success of the overall team, which sometimes means having to make the tough call or the unpopular decision.

So in order to recover, take your ego out of a vision of success for your team. Remember, it’s not about you or your likeability or your popularity, it’s about them. Trust that you’re making the right decisions for the right reasons, even if nobody can see that or understand it. Ultimately, I want my team to be successful even if I’m not there. My goal is to build an organization with a structure and a team and a process that can thrive long after I’m gone. That’s the ultimate testament of a high-performing, resilient team. They will respect you more, even if they like you a little less. Everybody wants to be on a high-performing team with a resilient leader that they can trust to get them there. So what happened with Elton? Well unfortunately, he burned out as a manager and went back to being an individual rep. It turns out that heroically diving and catching after every problem ended up burying him in the likeability trap.

Okay, mistake number four. You go into an important meeting with a giant piece of spinach in your teeth. Actually, no, that’s not really what I want to talk about. You will do that, but the fourth mistake is you will give bad advice to your team. So let me tell you about a rep who asked me to join an important customer meeting, and let’s call him Bono. Luckily, I didn’t have spinach in my teeth when I went to this meeting. Bono asked me to join an important customer meeting to help close a large, competitive deal. The customer had been hemming and hawing, and he didn’t know how to approach the meeting. So when he asked me for my help, I immediately jumped into action and told him that we should be very direct and challenging in the meeting in order to secure the deal.

We traveled all the way to Berlin, came in hot, and we got shut down. I know, I know, classic American story. The customer feedback was that we were too harsh, and that we didn’t understand their needs. It was because of me that we had lost that deal. Ouch. But the real pit in the stomach moment was realizing that I had told him the wrong thing. He knew it and I knew it, and until I fessed up to it, we wouldn’t be able to fix it. I jumped fast to a conclusion without knowing enough. I should have slowed down, gotten curious, and dug deeper with Bono. I might have learned some more context in order to give him the right guidance.

So again, you will give bad advice. It may be because you want to be helpful, or you just don’t want to sound stupid in front of your team. Sometimes the most terrifying, deer-in-headlights moment is when you have your team come to you and you don’t have a freaking clue. In those moments, you have two options. You can either jump to conclusions, which is what I did, or two, admit that you don’t have all the answers. Sometimes it’s okay not to know the answer. In fact, it’s better to take a beat and recognize that before barreling headfirst and sending your team down the wrong path. Your team can smell BS a million miles away. The more that you pretend to know something when you clearly don’t, the faster your team will stop trusting you.

But sometimes admitting that you don’t have all the answers can feel really vulnerable.

It’s uncomfortable not to know which direction to take, especially when you have so many people depending on you, and this is where resilience in a leader is so important. By admitting that there’s more to learn or that you made a mistake, the faster you can get to the root cause issue and find a real solution. Often the best thing to do is take a step back and diagnose the problem. Whenever I get stuck, I ask myself and my team, “Do I really understand the root cause issue? Do I really know where we’re trying to go?” And if not, I spend time listening and learning instead of immediately jumping to an answer. That’s really hard for me, I’m incredibly impatient, as I’m sure all my teams would attest.

With Bono, even though we lost that deal, we actually got another chance a few months later, but this time I invested the time to ask questions and collaborate so that we were ready to show that customer that not only did we understand their solution… Sorry, understand their problem, but that we were the right solution for them. Luckily we ended up winning the deal, but not after… But only after recovering from some serious mistakes.

Okay, mistake number five, you will pursue the wrong strategy. No need to change names on this one, because this story is all on me. As your business expands, it’s always difficult to know when to enter a new market. In a previous role, I had made the decision to jump into the enterprise segment. Our business was growing fast, and the opportunity was just too enticing, but as I’m sure a lot of you will recognize, selling into the enterprise is very different than selling into SMBs. The sales process is much more complex, and hiring a enterprise sales team can be a big investment. So I hired a phenomenal enterprise… Experienced enterprise sales team, and spent months with my product team to ensure that we were enterprise-ready.

But what we didn’t anticipate was that the enterprise wasn’t ready for us. Even though we had the best product in the market, large enterprise companies had trouble implementing us because of the immense technical and organization debt that companies like that tend to carry. Within the enterprise, unfortunately the best product doesn’t always win. But I now had an expensive enterprise team with a territory that was too narrow and a product that didn’t fit the market, and nobody was close to hitting target. I was terrified.

Like I said at the beginning, the stakes only get higher as you grow your career. As you go from leading one team to multiple teams, to growing an entire organization, the decisions get harder and bigger, and the consequences get scarier, and as a leader, you may set the wrong strategy or take the team down a bad path. Sometimes the right direction is unclear or the signals were wrong. Hindsight is always 20/20, but foresight can make you blind as a potato.

Being a sales leader is kind of like the Goldilocks of SaaS, everything has to be just right. But ultimately, you have to be resilient as a leader in order to get your business back on track. You can only make the best decision with the information that you have at the time. You have to build trust in yourself, and your team, so that even if you pursue the wrong strategy, you can learn from those mistakes and head in the right direction no matter what.

With my enterprise sales team, I had realized my mistake and had to move fast to shift our strategy. Fortunately, the product investments we made allowed us to actually grow much bigger in the mid-market, and we’re actually able to close seven-figure deals with much smaller companies. But that pivot was hard, and some of my enterprise reps was able to shift focus, but unfortunately most did not. It was really difficult to manage that type of turnover, but we were resilient. By recognizing the mistake early, we were able to recover and stay focused so that the business continued on track.

Here are the Five Mistakes!

Okay, in recap, here are the five mistakes. Micromanagement. You will hire the wrong person. Falling into the likeability trap. Giving bad advice. Pursuing the wrong strategy. These will lead to the ultimate mistake, which is that you will doubt yourself. Trust me, we’ve all been there. Now raise your hand again if you’ve made this mistake. We’ll probably all be there again in the future. But in the moments that you doubt yourself, you can trust in your ability to be resilient.

I don’t know if you guys have caught on by now, but this talk isn’t actually about the five mistakes new leaders makes. It’s about the importance of being resilient so that you can face any challenge, and here are the things that allow you to be resilient. Be focused on where you’re trying to go, no matter what bumps show up in the road. Allow yourself to experiment, and be ready to learn from those mistakes. And always, always put your team first, then you know that you’re doing right by your team even if you’re making mistakes.

I’ve been at CircleCI for two and a half years, and when I first started there were seven people in my organization. I had one office and an unproven sales process, in a market that was only starting to gain traction. Since then, I’ve been able to grow my organization by 7x to 50 people globally, and the company to over 200 employees overall. We’ve increased revenue by 4x, and we’ve launched three additional offices, and we’re actually going to be doing a big launch here in Europe later this summer, so come talk to me afterwards if you’re interested in learning more about that.

All while growing our platform to over 25 million builds per month, and 30,000 customers every day. It’s not bad.

But there were some really tough moments along the way. Over those two and a half years, I also had to redirect our team’s focus, change our segmentation, shift the products that we’re selling, and our pricing multiple times. I had to rebuild our team with a new hiring process, and we’re actually in the middle of re-architecting our sales process yet again, all while balancing all the growing pains that comes from explosive revenue growth, trying to stay ahead in our market, and international expansion, and there are going to be so many new challenges as we continue our journey.

But my core job is to make decisions, it’s the number one thing that my team looks to me for, and while I may have decision fatigue at times, I do not have decision paralysis, because I’m resilient as a leader. Honing your ability and your team’s ability to be resilient is one of the most critical things you can do to ensure your success and your team’s success overall.

Thank you.

Published on November 14, 2019

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