E26: Building a Culture of Teamwork and Growth with Steve Singer | RVP Anaplan, ex Zscaler, Talend

Steve Singer is a high-performance sales leader who has worked with iconic cloud companies like Salesforce, NetSuite, Talend, and Zscaler. He has scaled teams up to 150 people and was named number one global RVP of the year at Zscaler. So today we're in for an absolute treat. So let's jump right in. Steve, thank you so much for joining us today. I am so excited to have you on this podcast.

No, it's a pleasure. We've had lots of chats, Priya. I'm looking forward to this one. They, uh, they never disappoint.

Thank you. Now, you have had an amazing career with some iconic cloud hyperscalers. When I think about Salesforce, NetSuite, Talend, Zscaler, looking back, what are some of the Thanks for the compliment.

I've picked a few companies and picked lucky on a couple of them. So, it has been a wild ride. And I will start by saying I'm not an expert in anything and I'm always looking at getting better. So, I'll share some experiences and things that have worked for me and some areas where I've also fallen flat on my face. And you can take and choose what you like and what you don't like. And so, When I think back of some areas that stick out in my career, my first would be Salesforce. And so that was my start into cloud software, almost the world's start into cloud software. I started with Salesforce when they had 800 to 1,000 people and cloud was brand new. And I wasn't getting objections on CRM or how to use a CRM tool. It was, is my data just floating in the cloud out there? Where's my data? I don't trust it. And I was just a young kid doing that. I was in my early 20s and I started as an SDR doing inbound lead qualification. And the pathway to success there was do really well in inbound lead qualification and you move into a sales role. And so I did really well at inbound lead qualification. I was the 2nd SDR globally in the history of Salesforce to go to Club in Hawaii and met Marc Benioff. And then before I got promoted, They created another role called EBR, Enterprise Business Rep, where you have to do outbound prospecting, making cold calls, building pipeline before moving into a sales role. And, you know, I was, I was a young kid in my 20s. I had really fast early success in my first 6 to 8 months at Salesforce, and I expected to move into sales. And so they created this new role, and I had, you know, I'm ashamed now, but I had a pretty bad attitude about it. I wasn't happy that I had to do another role before moving into sales. I thought I knew everything. I thought I could conquer the world. And I actually got put on a performance improvement plan, not because my numbers were bad, but because I just didn't have a good attitude. I wasn't helping the team. I wasn't contributing in a positive way in team meetings. And they knew I could do a lot better. And I went on this performance improvement plan. I looked inside of myself and wanted to think about the type of person I wanted to be, whether I work with the team or I'd take away from the team. And I turned it around and I eventually got promoted. I moved into sales and then my career shot off from there. But when I think back about it, you know, and I was young and immature, but when I was going into this new role, I got promoted to an EBR and I had a bad attitude because I thought, hey, you guys told me I would go into sales. Now there's this other role in the way of it that's outbound prospecting. And it wasn't explained to me why, right? It was just, you have to do this company policy, new role. This is what you need to do. But I think the why is really important. If someone sat down with me and said, hey, the reason why we created this role is that every sales rep in the world, no matter what company or what you're doing, you're going to at some point have to create your own pipeline. You're going to have to pick up the phone and you're going to have to make some cold calls or warm calls, whatever you want to call them. And this skill set and this experience is going to help you be more successful quicker in a sales role and will give you and will help you throughout your entire career. If someone sat down and explained to me the why, the benefit to me, the benefit to the company versus just this is what it is, this is what the company is doing, you know, kind of sit down, shut up and get to work. You know, I'm sure I would have had a much different attitude, but you know, you You live and you learn.

And it felt like a broken promise at the time rather than actually an opportunity to refine your skills at a higher level with enterprise.

Absolutely. Absolutely. I was, you know, another time I think back to at Salesforce, once again, I was just learning about sales. I was just getting into this world of selling software and technology. And it just seemed like another step in the way of me making big commission checks, which was another problem for me in another area. You know, I've embarrassed myself a little bit is I would go into meetings and I swear if you were the customer, you could see dollar signs in my eyes. All I was thinking about is how can I sell them the most software, the most expensive software, whatever it is to get a commission check, right? And anyone who's been in this game for a while knows that's not the best way to work with your clients. To set the stage for the types of conversations you're having, building trust. And so, it was another area where I had mentors and people who were much more experienced and older than me at Salesforce who would help me learn as I was presenting, as I was going into these meetings, as we were setting up strategies for these meetings. And my strategy was, how can I sell them software that will lead to a big sell versus how can I figure out what their problems are? Can we solve their problems? And is there a good fit between our companies? And it's a much better way of building trust and confidence and working together. And those stick out to me because those were some embarrassing moments when I look back at my past, but great learning opportunities to help build upon a career.

Oh, absolutely. And I can't think of one person who started in a sales or leadership role that's always got it right. Those people don't exist. I think we're all grateful for the mentors. Some of us learn through our mistakes. And sometimes you just win, sometimes you learn. So, I think that that just absolutely underlines a very typical process. So, I'm hearing you talk about starting with why and communicating, that becoming really, really important. And then having a you know, a problem-solution focus with the customer rather than what you want to achieve out of that meeting. How has that— these have— how have these 2 things featured in your leadership and your selling and your even your enablement career as you, you know, were in an enablement role with NetSuite? Tell me a little bit more about that.

Yeah, great questions. So I've done the full sales cycle from SDR, EBR, sales, enterprise sales, 8 figure deals. I've done sales enablement, sales leadership. And one of the biggest challenges I see in the companies I've worked for and the different positions I've interacted with is communication, right? Communication is the fundamental of whether something goes well or something is more difficult, whether it's change management inside of an organization, it's selling software, it's training people on new product releases or new sales plays. Communication is the key to it. And, you know, it's not just sharing what the change is or what the new product feature is, what's the new sales play, what's the value proposition. It's the why behind it, right? It's the reasoning behind it. What's in it for the person you're speaking to? What's in it for your team? What's in it for your company? What's in it for yourself? And being able to communicate and articulate that why. And so, you know, when I look at my teams and I look at making decisions, whether it's around territories or quotas, which are always 2 very fun topics, or it's around changing a process or sales enablement, helping people understand the why behind it. They still may not agree, but at least they have a better understanding of where you're coming from and the benefits that tie back into it. for everyone involved. And so when I, when I think of communication, the big area that comes into for me is one-on-ones, understanding not just the why of what I speak to, but the why of the team, right? Why are they doing what they do? Are they trying to buy a new house? Are they saving to get married? Are they going to have kids? Do they want a Ferrari? Do they want their partner not to ever have to work again? What is their why? Do they want to make the world a better place? What is it? Do they want to get promoted? And if you understand the why of your team and explain the why of why things are being shared or why they're changing, it really makes communication that much easier and for people to be speaking with the same knowledge and understand where different people are coming from.

I'm so glad you've put it the way you have because 2 things. Number one, in the first 10 years of my career, I was a quota-carrying rep, worked with 2 Fortune 100 companies, and then moved into sales leadership. And I saw so many managers who basically demanded what they wanted from you, you know, how much activity they wanted from you, what numbers they wanted from you. And it was almost like, you know, my way or the highway. And they just didn't get the level of engagement they could. You know, you, you could rule by fear for a quarter or 2 or 3, but if a better opportunity came along, they just couldn't hang on to their people. I also talked to reps who are leaving managers all the time who will say, oh, fill in the, the fill-in-the-blank name is all about themselves. It's about how good they look. It's how— and, and you know what? It's actually the minority who say, hey, I will work for John anywhere John goes because John looks after me and helps me get what I want. Right? So, I think that that is such a fundamental switch that leaders need, whether it's from the goodness of their heart or just being smart. I wish there was more education, training, and enablement around that.

So when you were a rep, are you telling me you didn't love the constant questions around how much pipeline have you created? How many meetings have you done? How many phone calls have you made? You didn't enjoy those conversations?

Oh my gosh. Yeah.

I had a rep maybe 8 or 9 years ago and we butted heads. all the time in one-on-ones. And, you know, you do profile analysis, there's DISC analysis and there's different profile analysis. Are you a high red or yellow or green or blue and all these types of things? And we would come into a one-on-one. I wanted to understand forecast and deals. They wanted to tell me about their weekend and their friends and what food they ate. And we just never aligned. They were a high yellow. I was a high red. I wanted to get to the point. And It was good learning that everyone around you isn't going to change to be like you. You need to adapt and modify to the people you're working with. And so we actually had an open conversation around expectations for our one-on-one in that I'm happy to spend some time hearing about your weekend. I'll tell you about my weekend and my wife and we can have a chit-chat and I'm good with that. But we have to have X amount of time So we can go through, you know, your week, the meetings you're on, let's strategize, let's get into some deals that are tricky. As long as we have time to do those things, we can balance it so we can work together. But it was, you know, it was all about me at the start until I took off my ego and looked at, you know, we need to be adaptable to the people we work with to make sure they're getting what they need out of our meetings and our interactions while still driving the business forward.

That is so insightful. What would you say is your current framework or best practice around one-on-ones?

Yeah, that's a good question. And they're going to change, right? So, I think every one-on-one is going to be fluid within the lines of some parameters because every week there's different things going on in the world of business, in the rep's life, in your team's life. And so it's setting some parameters of the things you want to uncover. I believe it's not— if we're having a one-on-one, it's not my one-on-one, it's Pri's one-on-one. And so when we sit down and have these conversations, we set some expectations at the start around what's important to you to get out of a one-on-one. I'll share some of the things that I typically like to achieve in these meetings. And although it is business and although it is, we need to get into deals and figure out what are the roadblocks, how can I help remove your roadblocks? It's also understanding the person and not just being all about business. And so when I talked about understanding the why of your team, that happens in one-on-ones, that happens in, you know, you do a walking one-on-one or you go for a coffee or you have a lunch or you do it over Zoom. But getting to know what motivates and what drives your team so that you can relay things around that. Or if they're having a bad week or a bad month, it's not just, pray, why aren't you making more phone calls? Why haven't you created X amount of pipeline? Why aren't you closing deals? It's, oh my God, I'm so sorry to hear about your kids or losing out on a house or whatever it is that's going on in your life is understanding some of that context. And then, and then it's what are, what are the top of mind things in Pre's world that are giving you heartburn, right? So if it's a deal that you don't know how to move forward, if it's an objection you don't know how to handle, if it's conflict with another department, your sales engineer or your SDR or the marketing team, it's I want to make sure that I remove those things that are the top burning priority things at the top of your mind so that we can get back to kind of our operating rhythm and our operating cadence of week in, week out of how are we driving this business forward, which to me is very, very different to a forecast call, which once again is very, very different to an opportunity review. A one-on-one isn't a forecast call. It's not me ripping apart a deal unless you want a deal to be ripped apart. We can do that together. But a one-on-one is, it's pre one-on-one. And then on our next one-on-one, we follow up with the actions. What was I supposed to do to help remove roadblocks? And what were you supposed to do to help whatever it may be to drive your business forward? But it's, you know, often people get stuck in a one-on-one as a forecast call or as just a pipeline review call. And to me, it couldn't be further from the truth. You know, it will happen. Because sometimes that'll be top of mind for you. But that's, that's not the just of the, of the one-on-one.

I think just the switch from it's about you and what you want to achieve to it's about us itself is a change that would be beneficial for so many leaders, just that much alone. But tell me a little bit more. You've, you've given me some great detail and best practices. Tell me a little bit more now around You know, how do you create a culture where, you know, you win more together? You talked about deal reviews. I know you've done a lot with medic as well. Tell me a little bit more about, you know, how do you build that rhythm cadence into your culture?

Yeah, great question. When I think about all the reps I've interviewed and all the managers I've interviewed with, One of the most common questions is, why is this company better than the competition? Why is your product or service better than the competition? And every answer I've given to every rep I've ever interviewed is, it's not because our technology is great. It's not because our company is the best company in the world, even though I may think it, right? You could have the best product and the best company. It's the people in the company that you're working with. And so many companies I've worked at, they've had the 3 Rs, meaning we focus on recruitment. So recruiting the best possible people. Then the second R is retainment. How do you retain the best possible people? And then the third R is revenue. And it's no mistake the first 2 Rs are people and you get that right, the revenue, the revenue follows. And so if people are the most important thing in the company, how do you build a culture of teamwork and not just teamwork, but of improvement and coaching and helping everyone get better as a team. And so I'm a huge advocate of open feedback, giving feedback after every meeting, and not just downwards, but upwards. Everyone should have feedback after that meeting to me and me to whoever I'm in the meeting with, as long as the intent is to help people improve, not to make someone feel silly because they did something wrong or they said something wrong in a meeting. with the intent of helping everyone around us get better. And so, you know, being vulnerable and, you know, at first people are sometimes hesitant to share feedback to someone who may be higher in the org chart, but it doesn't matter. I'll call out my own mistakes and hopefully we get to a point where that feedback is back and forth and all around with the team. The other area is You talked about having those meetings around numbers and forecast reviews and pipeline and how many phone calls have you made. At my previous company, we had a ton of leading indicators. How many activities are you doing? How many of them are leading to opportunity progression? How many of them are discovery calls? How many lead to new business meetings? How many new business meetings have you had? How many of those turn into opportunities? We have all this data open to everyone, the reps, the SEs, the management leadership. And at first it was used as a stick, right? You haven't hit X amount of activities, you're doing bad. You haven't created X amount of new business meetings, you're doing bad. And so it was creating the culture of all of this data and all of these numbers are being used as a scorecard, whether you're good or bad. And no matter what I do, there's going to be some area that's not perfect and I'm going to get beat up over. And the data was great. How it was being used was in the wrong way. And so all of this data, if you break it apart and we'll use pre again as the example, you've done, you know, you've done 100 discovery calls. Let's just call that, that's what the check is. That's the threshold. But it's only led to 5 new business meetings. And it should have been 20 just based on the thresholds. It's not, Pri, you're failing. You've only done 5 new business meetings. It's, wow, this is great insight where me as a leader can coach Pri because he's doing a ton of discovery calls, but they're not converting. So where in that discovery call can I help Pri get better? Right? So it's used for helping the team around you continuously improve and you as a leader figuring out how can you help your people. Right? Because they're not failing on purpose. Everyone wants to be successful. And so instead of using it as a stick, it's a coaching tool to figure out where are the gaps in your business so you can get people back on track. And then the third one, this is a long-winded answer. I'm sorry about that, Prey, but I love the topic of teamwork and bringing people together. The other area I did was Figuring out what other people are motivated by—not even motivated by, but how they're KPI'd. So, in software sales, to be successful, you need an SDR helping to qualify leads. You need marketing to generate leads. You have sales working the sales process. You have a solution engineer hand in hand with the with the sales rep. You've got strategic architects. You've got business value analysts that are helping prove the ROI and TCO in the negotiation. Then you've got delivery of professional services. You've got customer success to make sure the customer is adopting and deploying. And it's a circle, right? Everyone gets involved to make sure the customer is successful. And by creating transparency for all the departments around how people are KPI'd and paid, not how much they're paid, but how they're paid, right? What's important to them? And what are they measured on by their managers? And this way it gave everyone a chance to understand once again, why, why is marketing acting this way? Why is customer success doing these things? Why are they asking these questions? Well, if you understand how they're KPI'd, it makes it much easier to work as a team and step in someone else's shoes and understand their behavior and why they're potentially doing the activities that they're doing and asking you for things. And so Some of those areas really helped to bring together the team and to be able to win together. And we mentioned this before in a previous chat. I think we've all been in a scenario where you've gone to a sales kickoff or a QBR and your team has had a bad quarter or a bad year and everyone around you is celebrating. Maybe there's one or two people on your team celebrating. It's a humbling experience versus you and your team and your surrounding team all being successful, going into those meetings with your head held up high, getting called up on stage for those awards, it's a much better place to be.

I can just see that the moment there is a greater appreciation and understanding both to your left and to your right, that's to the cross-functional team that you're a part of, you're going to improve outcomes anyway. You've mentioned in the past when we've, you know, you have an approach called No One Left Behind. Tell me a little bit more about that.

Yeah, so it's actually at a previous company and it was called No Sales Rep Left Behind. And so the meaning was, you know, you're going to have your star performers, you're going to have people that are consistently at 70 to 90%, and then you're going to have, you know, the trailing tail. of reps. And it was making sure that we're helping all of those sales reps get to a reasonable number, achieve their targets, make commission, feel proud. And that was the motto, leave no sales rep behind. And to me, it just, it didn't make sense. It was just madness to me thinking that we're talking about this in massive meetings with the company there. And I can only imagine if I wasn't a sales rep and I put myself and I'm there as a sales engineer or I'm there as an SDR or the channel team or customer success or professional services and everyone's only talking about leave no sales rep behind, I'm sitting there thinking, well, what the hell? What about me? What about my team? And so, you know, I just, I stopped it. I just, I wouldn't ever use that. And instead it was just, Leave no one behind, right? Leave no one behind. So our team in ANZ, it was leave no one behind. And that means, once again, you go into a meeting and, or you're sitting as an SDR, you're sitting with your SDR and he's struggling doing cold calls. He can't get the message out. He's getting hung up on. Step in and help. Give him some feedback, do some role plays, um, and vice versa. And so anyone who's having a tough time, You can ask anyone on the team for help, right? No one's better than anyone, no matter where you sit in the org chart, no matter what your name is or what your title. We're all here to succeed as a team. And so, you know, forget about just the sales reps, because if the sales reps are successful but no one else is, they're going to run out of leads. The channel is not going to be happy. The customer is not going to get deployed. They're not going to be happy with customer success. We need everyone to be successful for that circle of business to continue. And so it was We can't just be talking about sales reps all the time. It's the interaction and the ecosystem and the culture that everyone brings with different experiences to drive the business forward. And it was, you know, some things seem so obvious. And to me, that was obvious. And there's been other things that are so obvious that go right over my head. But that was one I jumped on right away.

Fantastic. Well, I'm listening to you speak and I can just see Consistently the difference between the different types of managers and leaders that I encounter. And often the reps, I've probably interviewed over 10,000 people in the last 15 years because in a day, as you know, right? With at an easy, you know, yeah. The point I was trying to make was that It's very easy when you ask people, who was the best manager you've worked with and why? Or who has had a significant impact in your career? It is always someone who came alongside, saw them for where they were, saw them in a darker moment, and was able to shine a light on something that could help them you know, do better, whether it was be better, do better, integrate and work better so that basically everyone was rowing in the same direction. And I have countless stories. So everything you've said to me today, I can just tell that, you know, it would create for an amazing environment. So thank you. This has been an amazing conversation, Steve.

No, I've really enjoyed it. These are— hopefully you could see topics that are close to my heart and I believe in, and it makes It makes working fun, right? When you're working with a bunch of people that are aligned, enjoy working together, rowing in the same direction, so to speak, in terms of goals and outcomes. It's not work when you're doing that. It's fun.

I believe with all my heart, if you hate Mondays, then you're absolutely in the wrong job. So, yeah.

Agreed. Agreed.

Thank you so much.

Awesome. Thanks a lot, Pri. Have a good one.