Grow Your Sales Team With Better Training

[00:01] Michael McNary: Welcome to Mimeo's Talk of the Trade. I'm Mike McNary. In addition to leading the sales organization here at Mimeo, I'm also interested in unlocking the secrets of sales and marketing. In each episode, I talk with creative leaders to find out how they approach problems like motivating sales teams, structuring the revenue cycle, and fitting product to market. At the end of the conversation, you and I have new takeaways to apply to our everyday life. Let's jump into today's episode.

[00:29] Michael McNary: Hey, everyone, Mike McNary here with another episode of Mimeo's Talk of the Trade podcast. Today's episode is grow your sales team with better training. And our guest is Rachel Green. Rachel is the head of sales at Playground. Rachel, it's really great to have you on the podcast. Welcome.

[00:48] Rachel Green: Thank you. I'm so excited to be here.

[00:50] Michael McNary: We're excited to have you, and you have this interesting background where you have experience and success in both sales training and now leading a sales organization. So I think you're going to bring a lot of unique content and value to the conversation.

[01:03] Rachel Green: Well, I'm excited to get into it.

[01:05] Michael McNary: Yeah. I kind of jumped the gun on a little bit of your background, but why don't you tell us a little bit about yourself to start?

[01:12] Rachel Green: Yeah, absolutely. I've been a sales professional for about ten years. I started on a pretty traditional path SDR straight out of college and then worked my way into sales training and sales leadership. I hail from New York. Originally, I spent time working in Virginia, Maryland, and now I'm back in New York.

[01:30] Michael McNary: And as a fellow sales leader, I always love a story that starts with I began as an SDR, the idea of kind of homegrown talent starting at the beginning, learning the whole sales process. I think that's incredibly valuable in this day and age. So you work for Playground for folks in the audience that don't know about your organization. Why don't you tell us a little bit about it?

[01:51] Rachel Green: Yeah, absolutely. Playground is a childcare management software company. We manage the entire childcare lifecycle from enrollment and billing to attendance and parent engagement. Basically, the software was founded with the idea that childcare providers should focus on taking care of kids and let software pretty much do everything else.

[02:13] Michael McNary: All right, what's your favorite thing about your job day to day? What do you enjoy doing most?

[02:18] Rachel Green: Yeah, so we're a startup, so what I really enjoy about the job is I get to do a little bit of everything, and it's never boring. Some days I'm in Excel doing data and reporting, and other days I'm stacked with one on ones with my team. I'm doing sales training and enablement. We attend conferences. I work really closely with products, so really every day is different, and I'm exposed to so much, and all the people I work with are nice and fun, so it makes it even better.

[02:47] Michael McNary: So we're going to be talking today about growing your sales team through better training? Let's start with a big question that I always have. Why should sales managers, as opposed to say, L&D professionals or partners, care about training their teams?

[03:04] Rachel Green: It's a great question. First and foremost, L&D, they are awesome. They come in with curriculum, they specialize in teaching different topics, going really in depth. Having an L&D team to partner with is absolutely amazing. I believe, especially having been both a sales trainer and a sales manager, is that management really has the full person perspective on their sales team. So what do I mean by that? The manager understands the individual on their team. They understand what motivates them, why somebody would be interested in being 1% better at their job, why they would want to attend an additional training. And also at the end of the day, as a manager, I'm responsible for my team's performance. So it's a direct reflection of my own. So naturally I'm going to care about how these individuals perform and performance. It starts with proper training. I also believe that you probably shouldn't be in management if you don't care about your team's growth and success because your job is literally to pull performance out of your team and get them to be the best that they can be.

[04:07] Michael McNary: I agree with everything that you just said and I'm also hearing more of this. But I want to ask you, SDRs and new sales folks that are interviewing for roles at Playground, do you hear them being more concerned with training at an earlier stage of their career than maybe we saw historically from newer sales professionals? I feel like I've seen that, but I wanted to ask you yeah, that's.

[04:29] Rachel Green: A really good question. I'm finding that really great candidates that I speak with are the ones that are invested in their growth and learning and have a mindset of continuous growth. They don't walk in thinking that they know everything, but that admitting when you don't know something is actually a very powerful characteristic to have and pretty indicative of being a high performer because you want to continue to learn and grow and take feedback and take coaching. So I find that those are some of the best candidates that I speak to.

[05:03] Michael McNary: I think that's really well said. They have a sense of where they are now, like you mentioned, not knowing everything. Right. And then if they're a great candidate like you're mentioning, they have an idea where they want to go. Right. And they know in order to get there, it's going to take probably a village, so to speak, and a lot of effort and resources.

[05:23] Rachel Green: Right.

[05:24] Michael McNary: And I think that wherewithal and knowing that early on is definitely a good sign and has been indicative of potential high performance in the future.

[05:33] Rachel Green: Yeah, absolutely.

[05:35] Michael McNary: So Rachel, how should sales managers be driving sales training initiatives versus partnering with L&D? Are sales leaders best as, say, subject matter experts or should they be designing the curriculum too?

[05:48] Rachel Green: Yeah, that's a really good question. It's a tough question because it depends on the resources that you have. So I think as much as a sales manager can lean on L& D, they should. Sales managers, they have so much responsibility, they could be in charge of over ten reps. They're the ones that are driving performance, they're driving morale, employee engagement. They have to champion new processes that come out. They do so much. So as much as you can partner with L& D, it's going to kind of help you be able to be as effective as you can. Now, I think that an effective way for a manager to help train and grow their talent is by acting like a coach. Like I said before, they know their employees as individuals. They know where they should be spending that one on one time specific to that person's needs. They can also use technology to help them do that. I love, for example, using Gong because it really helps me hone in on what specific sales reps need extra support on. So technology is something that they can definitely take advantage of and from that, that's where the sales managers can see different trends within their team and then roll that up into L& D and figure out what larger trainings and content should be addressed to the entire team.

[07:11] Michael McNary: Yeah, and I really like the point you made about the technology component, too, because it's changed everything. Not only in how we're designing the ongoing we'll call it instructional design or training content, but also where we're focusing our efforts role by role, day by day.

[07:27] Rachel Green: Right.

[07:28] Michael McNary: Having that granular understanding of how your rep is handling a very specific part of the sales process or when a very we'll call it specific topic or word or just maybe obstacle presents itself in your sales process and you see how maybe one rep versus another is navigating it better or worse. You can take these best practices and funnel them back into the entire process from day to day but also to that ongoing component in partnership with training. Right?

[07:59] Rachel Green: Right. Absolutely. And you can actually take recordings and show L& D, hey, this is what's going on. This is what we're hearing on the phones. This is how prospects are responding to what we're telling them to say. How can we tweak this or how can we make this better?

[08:14] Michael McNary: Yeah, I love that. And I think one of the things I've heard from a lot of other sales leaders recently when it comes to the technology component, Rachel, is with so many more remote teams, this tech is really helping and showing the new team members what good looks like. Right? It's not like the old days when you had a pit five days a week or some internal office set up where you could build off of the energy of the room, you could understand what the best person on the team or highest performer was, doing what best practices to make your own, et cetera. In some respects, you're on an island, right?

[08:50] Rachel Green: Yeah.

[08:51] Michael McNary: So something like a gong or a chorus can really drive. I think the idea to these new folks, hey, this is what success looks like and these are what folks that are getting it done sound like, right?

[09:03] Rachel Green: Yeah, exactly.

[09:04] Michael McNary: So, talking again, I like to focus on the newer sales folks. The more tenured folks, of course, always have stuff to learn, especially if they're introspective and looking towards the long term. But the newer team members tend to be this fun challenge because they're unique in so many respects. But you need to get them kind of rowing in the same direction. Right. So let me ask you this. Why is onboarding so important for sales teams specifically, in your opinion?

[09:33] Rachel Green: Salespeople are the ones that interact with your customers every single day. So first and foremost, they are a representation of your brand, of your company. So you need to tell them what to do, what to say. Without that, your customers will not have the best possible buying experience. So an unknowledgeable salesperson who is not ready to hit the phones does your customers, and therefore your brand, a disservice. The other thing I want to add is salespeople, they are some of the hungriest, hardworking employees. They eat what they kill is what we say. Right. So you really owe it to your employees to make sure that they're actually equipped to do that for their own livelihood and also for your companies.

[10:20] Michael McNary: Yeah, I really like that. And I think sometimes being the first line to your customer, to your audience, is incredibly powerful. Right. You can torch a considerable portion of your total addressable market if you just put it in front of or calling and emailing to untrained new sales professionals that are not quite capturing the value proposition and maybe are going about it in a way that's not strategic.

[10:49] Rachel Green: Exactly. And especially today, customers know each other, they talk. We're a very connected world. There's groups for everything. It's very easy to share if you've had a bad experience with a company. One bad interaction, unfortunately, can have a compounding effect. So it's really important that before your salespeople, as talented as they are, when you hire them, because obviously in the interview process, you vet and make sure that you're hiring really great people, you need to make sure that you're equipping them with the tools they need to succeed in the job.

[11:25] Michael McNary: Yeah. Common sense only so far, right?

[11:28] Rachel Green: Exactly.

[11:28] Michael McNary: I think we'd all like to think that we're screening for that at an early stage. But the reality is it's a stressful environment, especially for folks who haven't done it before. And now you put them in this sometimes adversarial, or we'll say off putting environment of cold calling or reaching out to folks that don't have much awareness of you or your company. And it's high pressure. Right. So bad things can happen, and as you said, they can have an impact potentially longer term. Right?

[12:00] Rachel Green: Yeah, exactly.

[12:02] Michael McNary: So thinking about that. Right. I love that you're concentrating on how things can go really well and why it's important to really target sales folks early. What are some success or maybe even failure stories you've seen in onboarding?

[12:18] Rachel Green: I'll start with the failure and then I can end on the high note. So I think when it comes to failure, the biggest failure that I've seen or experienced is when a company does not prioritize onboarding and they don't have staff ready to train and focus on this. So maybe they think that they prioritize this and there's one day that's really welcoming and really great, and then you leave the employees to kind of figure it out from there because they just don't have adequate staffing to continue the training process. And also they assume that, okay, well, I've hired top people. They should be able to figure it out. They have maybe a Rolodex that they walked in with. And you say, okay, well, they know customers. It shouldn't be hard to get them up to speed, but we're missing some sort of knowledge gap. That's really what I find to be the most difficult. It's sort of this figure it out, trial by fire model. And of course, salespeople, they should be able to think on their feet. Anyone, any employee you hope should be able to think on their feet. But if we don't have clear expectations, if we don't arm our employees or our salespeople with verbiage and scripting and the right value prop and all of that, it can be a really bad experience for your employees. And as we talked about before, a bad experience for an employee is ultimately a bad experience for a customer. And take it even a step further. I've been there before too, where, I wonder, they were so excited about me in the interview process. Is this what's expected of me? I thought that this was the right fit, but I'm just not really sure because I have no sort of idea if I'm hitting the mark because there are no marks to be hit. The best companies I see are the ones that are really prioritizing those first few days, the first few weeks that onboarding and getting your salespeople ready to succeed on the phones, I think that's really well said.

[14:12] Michael McNary: And thinking about what not to do, what are maybe some ideas or experiences that you had that are maybe in line with the success or we'll call it the best practices.

[14:24] Rachel Green: So again, it really comes down to having people who are deployed to make sure that onboarding goes well with proper training, proper enthusiasm around the idea of onboarding and processes. So I'll give an example. My first job at the college. I was an SDR. As I mentioned before, we had an entire L&D team. They were focused only on onboarding and training. So their entire mission was to get us up to speed on when we first started, we did not meet our managers. We didn't learn about territory until two months of training. And as SDRs, we begged and we said, oh, we really want to know who our manager is going to be, and really wanted to understand these things. And they said, no, your sole focus is to understand your job responsibilities as an SDR, how to prospect, how to talk to customers. To give you sort of an analogy, I was a sprinter in high school track. I love to run really fast. Right. And that probably part of the reason why I'm in sales now, is sort of the energy that comes with that.

[15:25] Michael McNary: Yeah, there might be something there.

[15:26] Rachel Green: Yeah, there's a little something there. So we spent the last week with four championships tapering and basically we were at the point where we hardly were allowed to run. And that meant we were so ready to go. We had so much pent up energy that we just couldn't wait to run as fast as we could. So when it comes to hitting the phones as an SDR, we had so much built up anticipation that when we hit the phones, we just had so much energy. And that translated into our customer interactions pretty much immediately. So it was really strategic of how this company did this. I don't think that everywhere you go needs to be two months of training. Obviously, I was fresh out of college, it makes sense. But another company I went to, we had two weeks of training and then we had a three month ramp and that worked really well, too. There was some continued training in the three month ramp, but we had two really strong weeks. And the common theme was that both of these companies had a department that had a curriculum. They had people that were ready and engaged and training us on the curriculum and they were excited about the curriculum. And that is the common theme between these two organizations.

[16:34] Michael McNary: I truly believe that it can be contagious right. If someone's coming into a room and treating it as just another meeting that they've got to get through and kind of presenting it as if it's content that isn't having a huge impact on this audience's, professional development, or the early stages of a career that they're excited about right. That comes across and it can totally impact the onboarding experience and the morale of a new team member. Right.

[17:03] Rachel Green: Definitely.

[17:04] Michael McNary: Let me ask you one question about that two month example. Was there anything about the two months that psyched any of the team members out? Because I can imagine, like you said, it would build up this energy right. This anticipation. And that would be very positive in a lot of instances, but I can also see it being almost too much and get in somebody's head a little bit. Did you see any of that occur or am I kind of making something up in my imagination?

[17:27] Rachel Green: No, it's a great question. So in this specific company, we had probably 98% retention. I mean, people that's great loved it and stuck it out. I have been at other places before where maybe we had a long training. It might be two weeks of training, but sort of a six week probationary period, if you will, where you had to make X number of sales. And if you didn't make that, you essentially could not graduate from the sales training. And we'd figure out next steps from there. And that situation, I think, would sometimes psych people out or maybe they would say, okay, I'm not even pacing. Maybe this isn't really the right fit. So I think you have to be careful with what outcome you want from this. And when it was a really positive outcome, it was get you so excited that you can't wait to crush the phones. And I think it's just making sure that you have an outcome and that your training is set up to help people achieve the outcome.

[18:25] Michael McNary: Yeah, I totally agree with what you're saying. I also think that if you have a proven hiring process and you understand the attributes that you're looking for and the type of contributions to culture you're looking for from new team members and all those things are kind of proven, you're likely picking the people that are going to come out of that two month training program and do pretty well.

[18:45] Rachel Green: Yeah, right. Exactly.

[18:47] Michael McNary: So, yeah, really good points. I love that. Rachel so we talked a little bit about the early stage, right, the onboarding let's touch on for a moment or two, we'll say later stage career development. So how can managers think about ongoing training to keep and retain their top performers?

[19:07] Rachel Green: I think that we have to acknowledge first that doing the same thing over and over again after a while can become boring. And that's not a bad thing, right? If your employee is bored, especially a top performer, it's really good to know that as a manager, because if we don't know that and acknowledge that, then that's where we run into retention issues, for example. And for high achievers, this is especially true, right? The high achievers are probably the ones who are doing great and getting bored first. So we need to make sure as managers that we are really finding ways to expose top performers to new opportunities that keep them interested and engage in their job while learning new skills. I think a really common example is a top performer that has expressed interest in management. What are we doing about that? Do we have an LDP program? Do we have a new hire mentor program? Can they do these things and then also decide, do they actually enjoy this mentorship component of sales management or do they just think that management is the only next option to grow? Because there are so many ways that you can grow as an individual contributor and not everyone needs to go on the management track.

[20:30] Michael McNary: It's very true. And listen, a lot of great salespeople don't make great managers, right?

[20:36] Rachel Green: Yeah.

[20:36] Michael McNary: And I think we've all probably seen some of that. But let me ask you this, right? In trying to offer this ongoing kind of development opportunity to your top reps, what role, if any, can third party training opportunities play in that accessibility for, say, your top 10%?

[20:56] Rachel Green: I love third party training. I hired someone last week at Playground to do this for our team and every single person walked away absolutely loving it. We not only had sales in the room, but we had pretty much everyone that was working on product marketing, all of that. Everybody benefits from it, even though it was really specifically a sales training. I think sometimes we need to shake things up and bring in a new voice and a new perspective. We can get really tired of hearing leadership say things. Obviously leadership needs to set the mission and the stage and everything, but sometimes we just need fresh and different voices. And that could be third party trainings. That could also be peers. Peers showing what they do really well and leading the other reps to learn something new that's working for them, that allowed them to blow past their quota, for example.

[21:58] Michael McNary: Yeah, I think the new voice thing is something, right? I think you really hit something there and I think it's the same also, sometimes if you have a broader sales leadership team and you're having trouble coaching a particular team member or there's maybe a topic or a skill set that they're not buying into your particular approach, sometimes it's so valuable to get another voice, right? Pair them with another leader or hear it told in a different verbiage. I think sometimes that's a way to break through. I think the same thing can be a set of training, right?

[22:36] Rachel Green: Definitely.

[22:37] Michael McNary: So I really like that. I want to touch on the leadership development component really quickly because like you said, some are going to want to pursue this, right? Some are going to want to hone their skills as selling into maybe larger markets or more complex deals or work on various stages of the sales cycle. And that's what's going to really get them juiced in terms of development. But there's going to be the folks that want to become leaders, right? So what role does training play in identifying salespeople who should become leaders?

[23:08] Rachel Green: So I think that a lot of sellers believe that the natural next step for them when looking to grow is to become a leader. And I think a lot of that's actually because they don't realize how much impact an individual contributor can have and how much there is to learn and grow as an individual contributor. So I think it's really important for organizations to have some sort of leadership development program to help people assess if these are really the skills that they want to focus on and if this is the track that they want to go on. I was part of a leadership development program at a previous company and a lot of people would join and realize, I actually don't really think I want to do this component of leadership. They didn't actually want to be managers. And I think it's really helpful to let individual contributors know that being a leader doesn't necessarily mean being a manager. You can be a leader in so many other ways on a team, but without training and exposing individual contributors to what, quote unquote, leadership or management looks like, they'll never really understand what's being asked of them in the management track and really decide if it's something that they want to do.

[24:39] Michael McNary: Very well thought out and executed, LDP can kind of take the place of what the team lead role did for many organizations for a long time, which was try to give somebody this intermediary exposure while they're still an individual contributor to some management responsibility so they could see, hey, is this something I want to pursue? Do these sort of day to day skill sets and expectations align with my goals and interests and my personality? I think there's a much more effective way of getting that screening done, right?

[25:13] Rachel Green: Absolutely. And when I actually think back to some of my best experiences at work, I would say that it was some of the individual contributors who I looked up to the most. The people that were amazing individual contributors that were blowing past their quota every single month, but also took the time to stop and check in on their peers, to take the time out to maybe lead trainings, whether formal or informal, or sit with you if you were having a bad day or a bad month. Those are the people that really brought the culture and brought the energy of the team up and really allowed the team to be successful. They were just leaders in a different way as individual contributors.

[25:59] Michael McNary: Yeah, I couldn't agree more. And one of the pieces of advice that I give, for better or worse to new SDRs is to find a mentor within the organization that's not your manager. Right. And those particular I love that you said that because speaking from experience and my own career, it's those kind of team members and colleagues that have played maybe an outsized role in my development and success and I'm incredibly grateful to have had them. So I always encourage other people to look for those, the folks around them once they're getting acclimated and trying to figure out, hey, what's next? What's for me? How do I succeed et cetera.

[26:39] Rachel Green: Absolutely.

[26:41] Michael McNary: I really like that. Let me ask you one more question about the LDP. Should there be a barrier to entry for a program like that? And if so, what should it be?

[26:52] Rachel Green: I think that I've normally experienced some sort of barrier to entry. Maybe you needed to be at the company for at least a year and hit quota nine out of twelve months or something like that. So basically saying you've clearly grasped your role, right? You've hit your quota X amount of times, you've surpassed that threshold, and you also have tenure, so you have institutional knowledge, you've shown loyalty to the company. These programs are also an investment in resources, time, money, all those sorts of things. And it can be rewarding to your tenured employees to offer these additional resources to them. So I definitely think that to get the most out of the program for everyone involved, it is good to have some of these barriers to entry, an application, if you will, to really show that you don't want to just do this as a resume item. But it's something that you truly want to learn from and see yourself grow with.

[27:57] Michael McNary: Yeah, I think I agree in the sense that it's probably some sort of proven skill set achievement or tenure and performance mix. Right. So long as it's clearly outlined, I think that's an effective kind of threshold to make aspiring potential leaders kind of meet in order to get into this program, because otherwise I think it loses its luster if it's something that's available to everyone and isn't somewhat achievement based.

[28:29] Rachel Green: Right, yeah. And also it's something that helps you attract really great talent as well, because you can tell people who are newer on the team or even in the interview process that we really value employee development. It's not just going to be about your first few months here, but if you hit X, Y, and Z, you'll actually be eligible for our leadership development program. We're going to invest in you growing your career here. And I would actually go to one on ones at this former company, and my manager would talk to me about, hey, what are some of your larger goals that you want to achieve? Do you want to try to get into this program in six months once you've reached the tenure? Do you want to try this or that? And it really helped me feel like the company valued me as an individual and helping me grow. And of course they were also getting the most out of me as an employee, which was beneficial to them.

[29:26] Michael McNary: Yeah. Win win, for sure. I think if I'm thinking about some of the things that you shared today, most of these strategies that you've put forth, I think you've been really consistent in painting them as win wins. Right. Why it's good for the employee, but also why it's good for the organization. Right. That intersection where I. Think real organizations who are thoughtful about promoting sales growth, sales achievement. Think about it that way, right? Where does the benefit of the company and the benefit of the salesperson intersect? And let's try to live there, right? I think from the outset, you've had some really good ideas here, and these are really thought out and I think experienced answers. So, Rachel, I'm so pumped that you came and talked with us today on the Pod. I'm going to kind of sum up some takeaways for our listeners. One thing I heard was that the most successful training programs prioritize onboarding and outline clear expectations for sellers. Also that salespeople are your customers first interaction with your brand. It's a disservice to your customers and to your organization not to equip them to have good interactions and be poised and ready to promote your value proposition. And then finally, leadership doesn't have to mean management, right? There's a lot of different ways to make an impact and explore this path that can help you as a team member, but also the broader group and organization as a whole. So I think those are really good takeaways for anybody who is thinking strategically about using training to retain top talent. And I want to tell you how much I appreciate you sharing all these ideas and just thought leadership with us today. So thank you.

[31:15] Rachel Green: Thank you. It was a pleasure to be here.

[31:17] Michael McNary: If our audience wants to get in touch with you, Rachel, what's the best way for them to reach out?

[31:22] Rachel Green: They can find me on LinkedIn, Rachel Green, and they can email me directly as well. My email address is [email protected].

[31:33] Outro: Talkofthetrade is hosted by Mimeo. The better way to print. Find out more at www.mimeo.com.