#035 Sales Leadership in K-12 Education Market with Lydia Winn

A Guide to Thriving in Transactional Sales

Guest & Host

Lydia Winn & Thomas Miltschuh

Welcome to Speak Revenue, the podcast where we emphasize that revenue is not just a goal; it's a result. In this show, we shift our focus from the output to the inputs. We engage in conversations with sales leaders and entrepreneurs about their remarkable journeys. Our mission? To uncover the true root causes of success. Join us in this episode of Speak Revenue as we dive into the world of sales leadership in the K-12 education market with our guest, Lydia Winn. With extensive experience in driving sales growth, Lydia shares valuable insights on developing sales teams, mastering customer retention, and tackling challenges unique to the education sector. Learn her secrets to accurate forecasting and team development strategies that have led to success in highly transactional sales.

November 6th, 2023


Thomas Miltschuh: Welcome to our new episode of Speak Revenue. Remember, revenue is not a goal. It's a result! But a result of what? In this show, we turn our eyes from the output towards the inputs. We speak to sales leaders and entrepreneurs about their journeys. Join us on our quest to uncover and learn the root causes of success. Let's unpack what works for them. And what didn't today with our guest, Lydia Winn. Welcome Lydia. So great to have you here. Thanks for taking your time.

Lydia Winn: Thomas, thank you so much for having me.

Thomas Miltschuh: Great. So, let's get started right away. Tell us who you are. What do you do? Why are you so successful?

Lydia Winn: Great question. You're giving me a chance to do my favorite thing, Thomas, which is talk about myself. And I've really built my life around growing relationships with great talent. Professionally speaking, I spent the last, or I have spent the last six years. Selling into what we in America call state, local and education. First at a company called GoGuardian, and now at an incredible company called SmartPass. We sell into K-12 education and at GoGuardian I had the privilege of seeing us grow from 35 million to 175 million, and seeing my own team grow from 6 to 32 people. And I also saw talent grow from BDRs all the way to enterprise reps and managers, and that was really the privilege of my life. And now I have the opportunity to do that same thing at SmartPass. And we sell digital hall pass solutions to K-12. We allow administrators to regulate and track movement that used to be done through paper or physical hall passes, and we're growing really quickly as well.

Thomas Miltschuh: Right. Seems like there really is something demand in this, in that sector. Very impressive. Growing is from 6 to 35 people within which time range.

Lydia Winn: From about 2018 to 2023, five years.

Thomas Miltschuh: So many challenges to cover there. Let's go into this a bit in more detail in a minute. Maybe it could give us a quick overview on your current goals. Goals of this year, goals of next year.

Lydia Winn: Absolutely. Our real goal at SmartPass was to take our company from, I would say, truly small to maybe the first year of three years of hypergrowth. And so when I started at the company, we had just taken venture capital from extraordinary experienced investors, and they were starting to bring on their first sales team. We started with a team of five people and it was their very first year. And so we saw growth just about 4 x year over year from 2022 to 2023. We're really tasked with continuing that growth trajectory, expanding our impact, and of course taking over market share. And to do that, we're looking at marketing channels that make sense, where are the leads gonna come from? Who are the ideal hires for this team as we continue to grow, and where does it make sense for them to focus on as we go into 2024?

Thomas Miltschuh: Alright, so that's a lot of different tasks to cover to really achieve hypergrowth. Very challenging. How far did you already get with your sales process from lead generation? Are we closing to upsell? Is it something dynamic? You're still working on, or is it already an established process?

Lydia Winn: Oh, great question. Part of the reason I love working at growing companies is that I can essentially live many different lives and see different processes work at different times in the company's lifecycle. When Smart Pass was starting out, our sales process really relied on simply showing people the product. That was the biggest barrier as people had never thought about replacing physical hall passes, but there was product market fit, there was adoption, and we simply had to have more people see it. And now because we are starting to get adoption, we've grown very quickly. More and more people are familiar with it, and part of our sales process now leans more on district level expansion. So essentially if your neighbor is using us, you're gonna get a call from SmartPass, we wanna share it with you. Whereas in the past, every single school in the United States was pretty much greenfield that has changed our lead generation process and our sales process has changed because we're now doing something slightly more consultative, a little bit more based around the decision process as opposed to education, like strict education, like this is what our product does. And that has been an incredible journey for the company and for the operations team as I work with operationalizing that in HubSpot, which is our CRM.

Thomas Miltschuh: Okay. When it comes to onboarding and customer retention in my experience, it's sometimes not easy for a very young company to really focus on retention. It's in many cases. Just about getting as many clients as quickly as possible. How are you handling this? Is there a solid customer success team?

Lydia Winn: Great question. That was actually part of the conversation I had before I even came to SmartPass was what does your retention look like? I have seen so many companies come out of the gate with an incredible promise and a great offering, and then they'll see a churn of 50%. And it makes customer acquisition cost and lifetime customer value, it completely distorts that ratio and makes the business unsustainable until that churn is resolved. What I see when I hear you have 50% churn is you have great go to market, but maybe your product market fit is fundamentally lacking when it comes to user adoption. So, SmartPass already had very strong retention even without a customer success team in 2022. We have the privilege of bringing out a brand new customer success team this year. And now we're in the process of experimenting. What does it look like to give people an extraordinary experience that is gonna leave them raving about SmartPass? While not overburdening them with information, getting them the right information at the right time. And because there are so many school sites and now we have so many customers and we only have a six person team, how can we automate that and send people through an academy so they can get the right information at the right time? And they don't have to wait on a human being to deliberate.

Thomas Miltschuh: That sounds interesting. Would you say in your, especially in your business ICP is not a very big issue just for me, looking into it as an outsider would be all schools basically. But the more narrow your ICP is the less customer retention, probably. Would you agree with that? Or is it something you're I see wrong. So maybe it's even more challenging than I expected.

Lydia Winn: Great question. The ICP in K-12 can be a little bit of a mystery if you're coming from B2B and you know the personas CFO / CTO / CEO. That being said, I always urge people not to get too intimidated just because it's a vertical SaaS situation. For SmartPass, again, Ideal Customer Profile is evolving. We're starting to sell as much to individual school sites and really hardworking forward thinking principals as we are to hardworking forward thinking district administrators. And the question of what that looks like in terms of decision making is still something that we are figuring out. And that's a challenge compounded by the fact that most school districts have actually never bought a digital hall pass solution. They've certainly purchased the curriculum. They have purchased other tools. They've purchased security, they've purchased networking. This is just a new category, and so a lot of what the sales team is learning, what the customer success team is learning is. What is that decision making process, what is the project of rolling it out look like at a district and what does it look like at a school site? If we're selling to a district, typically we're selling to a CTO or a superintendent. If we're selling to a school site, we are selling to confidentially my favorite people in the whole universe, which are principles.

Thomas Miltschuh: Awesome. That's a nice , very nice position for you. It's interesting that it's a very new market obviously, and not a lot of educational things or tasks you're covering with your go to market approach. Did I understand that correctly?

Lydia Winn: What we're really thinking about is what does education at scale like? What does branding and awareness look like for a new category? Something that is distinct about K-12 is, and part of the reason I really love K-12 is that it is inherently non-competitive. And so when one school finds something that they love, there's no disincentive to share it with everybody they know. They love going to conferences and sharing their ideas with their peers for the same reason. There are no secrets in K-12 because there's no need for there to be secrets, right? We're just trying to support the education of our student body wherever we are, and K-12 events are huge. It's a great way to educate people at scale, and part of the reason I knew SmartPass was gonna be a good fit was because I saw the response at conferences. We had so many people huddled around the booth. What we're working on now is how do we improve and build out our SmartPass Academy, which is our online training and distribution. How do we create videos, social media posts? I think the biggest thing we can do is create evangelists within school districts who can educate their peers in the language of that district with their district's unique situation in mind. And that's an ongoing project especially creating, I would say ambassadors or evangelists. And getting them potentially certified is something we're looking at as they go out and they share what we're about and support their own district in getting started.

Thomas Miltschuh: Okay. It sounds like a very motivating market ecosystem that you are working in. 

Lydia Winn: I think something I have learned over my career is, working in a vertical that I geek out about, there's no substitute for it. It will make me spend the extra 20 minutes each night answering that email or putting together a resource for my team. Because it is fundamentally something that interests me and I think that is why I have spent now over half a decade in K-12 education is because it is something I geek out about. It is objectively really interesting to me.

Thomas Miltschuh: So that's probably some advice you would give to potential team members or probably any person. So maybe we could talk about this a little bit. How do you handle team development, especially sales rep development in a transactional sales environment?

Lydia Winn: Ooh, there are so many things about that. Because we are doing a more transactional sale, I have the distinct privilege of working with a lot of early career salespeople, and so I have the chance to shape and mold people that might be in their first sales job, might be in their second sales job. Because this is a more transactional sale, the great thing is they're gonna get so many at bats and those initial mistakes, those experiments that they try that might not work, wash out. It's okay, you're gonna do 250 deals in a given year and you can always try something else. Where it becomes a challenge is organization. And again, how do we deliver that extraordinary experience to 250 schools as they come through one Account Executive or a BDR that might be booking 250 meetings in a year, which sounds intimidating. It's pretty routine, especially the season for it. And again, a compounded challenge for K-12 is its very seasonal and so what I've worked with from our Ops Team is creating deal stages that are binary. So moving something from, in our case, prospecting to buy-in that simply requires a rep, has a follow-up meeting on the books. The prospect has to have accepted that meeting. There has to be an agenda for it, and it's a yes / no because there's gonna be, in my case, sometimes a thousand deals in the pipeline at any time. I simply don't have the bandwidth to go in and do a more traditional deal inspection like I would an enterprise deal for all 1000 deals. What I need to do as a manager is ensure accountability and adherence to the system. And I will give a huge hat tip to Jaimie Buss at Zendesk for creating what I think is one of the best resources about forecasting.

Thomas Miltschuh: Okay. What's and maybe you could talk about the team development topic just for a minute. Do you have any specific coaching approach?

Lydia Winn: Yeah. I am a big believer in the one thing at a time role, especially when it comes to working with early career salespeople. Something I see newer managers fall into is they just forget how long it took them to acquire the fundamentals of sales. So there's that expert novice gap when they're training new salespeople. And I work with early career salespeople, so I also work with a lot of first time managers, which is . So much fun, and I now see what the most common mistakes are. So when I'm training someone to do outbound, I really think of it as a six part process, right? We're gonna go through a couple of what I call outbound magic tricks, easy wins that you can knock out from the beginning. I wanna talk about cold calls. I wanna talk about messaging matrix, then I wanna talk about emails and sequences, and then I wanna talk about objections and objection handling. And again, like deal stages, it's gated. When I see somebody master those basic outbound magic tricks, like a permission-based opener, I can move them along to the next phase, which is gonna be cold calling. When I see the mastering emails and email sequences, we can talk about objections and objection and handling. Same thing when you move into a closing role. I wanna talk about agenda setting and rapport. I wanna talk about decision makers and upfront contracts. I wanna talk about discovering the pain decision process, negotiation, and then close and post sale. And so we do the one thing at a time rule. When you pass the first stage, you move to the second stage of training. We started working on those skills and tools like Gong have been absolutely instrumental because I can set automatic trackers that help me know when reps are taking sometimes 7 or 8 calls in a single day. Are they adhering to those fundamentals? Are they ready to move on to the next phase of training and continue developing?

Thomas Miltschuh: So that's a very individual and situative approach for each single sales rep, right? 

Lydia Winn: It is. 

Thomas Miltschuh: Or would you create cohorts the bigger their team growth? When we were in hypergrowth at GoGuardian, I created cohorts. But again, people are gonna acquire those skills at slightly different times, even if they're all extraordinarily talented. Delivering individual coaching that is still very focused is absolutely key, and I don't think it's actually as much of a challenge as people anticipate it. If you're willing to focus on just one thing at a time. Where I see newer managers struggle is when they're trying to coach to six different things for six different people and they're not tracking the efficacy of their own coaching over time and how much the rep is actually adopting it.

Thomas Miltschuh: Do you also work with individual dashboards for each separate sales rep? Where covering individual KPIs and goals?

Lydia Winn: Yes, I try to make sure that those KPIs and those goals are as similar as possible, but when we have a growing and developing team, there's gonna be people on the ramp. Then there's going to be people who are fully ramped and they're gonna have different KPIs. And this is where I originally came from, I had worked with Salesforce for almost a decade, and now I am fully on HubSpot. And that is where I absolutely love HubSpot. Because creating dashboards that capture these KPIs is incredibly easy. And ideally after I've been working with the team for a few weeks. I empower them to analyze and understand their own dashboards, and then we start every one-on-one meeting with the rep, presenting that data to me.

Thomas Miltschuh: So you've mentioned forecasting already especially in transactional sales and covering the public market I assume this can be really challenging. So how are you doing that? Maybe on a team perspective, but also individually?

Lydia Winn: Great question. I think tools like Clari and HubSpot Forecast are phenomenal. Generally speaking, I have not seen them work for a highly seasonal sale. So for context, most K-12 businesses are done over the summer as preparation for a new school year, right? You have this in a sense, K-12 schools have their own motion, and so our sales motion follows that buyer journey. 

Thomas Miltschuh: Right. 

Lydia Winn: So we can't really rely on automated tools for forecasting and as our sales process becomes more sophisticated. In the beginning it's usually easy because everything is inbound. And forecasting based on inbound just depends on how many of your leads convert and how many leads you got, the prior month. But as more of our messaging is done through outbound or through events, that becomes a little bit more challenging to anticipate. And so what I have really seen, I'll go back to those binary deal stages, is binary deal stages where there's a good understanding of if a school or school district or principal accepts a follow-up meeting and they have actually accepted the calendar invite and they show up because we have so many deals in flight at any time, we can start collecting data on how many of those deals actually close. And then once they move to that second conversation, and maybe they book a time for implementation with a customer success manager, how many of those deals close. What, if there's an agenda, does that improve the likelihood that they'll attend that meeting and that they'll find value in the solution and ultimately purchase it? The more I can create a consistent process, the more accurate I have found my forecasting and the benefit of a highly transactional sale. I don't have to wait months and months to test a theory about how a change to the process impacts something like close rate or success rate. And once that is determined, and it usually takes about six months for me to figure all of that out, at this point I can forecast within 10% accuracy on any given month.

Thomas Miltschuh: Nice. So how do you know the process is consistent already?

Lydia Winn: HubSpot. I love HubSpot for this because HubSpot allows me to see if there is a next meeting scheduled on the calendar. That's a field that can automatically populate. I can also see what the last email to a customer was in HubSpot or to a prospect, and I can see if there was an agenda attached to this. I can see when the last email was. And so instead of spending my time on individual deals or opportunities in HubSpot, I really spend most of my time looking at lists of deals and looking at those key columns in any given report to ensure that there's consistency. And then when I see that there isn't consistency, that's my opportunity to have a discussion about that particular deal with a rep.

Thomas Miltschuh: Okay, so because consistency is the, depending on how complete the sales process is followed how complete data is gathered for each separate deal. 

Lydia Winn: Well said, consistency here is absolutely key, and so when we hire, we look for people that are highly organized and can follow that process successfully.

Thomas Miltschuh: Awesome. That's really interesting. You've also, already mentioned HubSpot, Gong but also Clari. Is there any additional tools or something you would like to highlight that's important for your specific sales process?

Lydia Winn: I have become a total evangelist for Notion since I started at SmartPass. It has created a central deposit for information as we train and onboard people. So easy. I was aware of it before I started. I did not realize how powerful it was until I came to SmartPass, so that's been a privilege.

Thomas Miltschuh: Great. Yeah. I also have nice experience with those and especially with Notion. Let me ask you, would you like, or would you please tell us something that did not work?

Lydia Winn: I will go back to forecasting. Part of the privilege I had at GoGuardian was I was there long enough to try a lot of things and not all of them worked. So we tried forecasting based on lead volume and as again, our lead and go to market became a little bit more sophisticated. That became less accurate and more challenging. I have tried using AI driven forecasting through ClarI and HubSpot. We saw some months it worked, but many months it didn't because of that seasonality. 

Thomas Miltschuh: Okay. 

Lydia Winn: Oh goodness. I have tried doing individual deal inspection and we simply didn't have the time. It was stealing time away from my reps. So that lesson about forecasting was absolutely hard. Won and won through a lot of things that didn't work first.

Thomas Miltschuh: It looks like that fits pretty well to our topic, to really check the causes of results and not only focus on results to set the goals of the next results. When and how did you realize that this forecasting approach is not working?

Lydia Winn: I think talking to peers, I realized that accuracy was possible. And hearing that other people were able to forecast within 10% or even within 3% or 2% accuracy each month was so inspiring to me. I was like a dog with a bone. I could not let that idea go. And so then I was able to. Set out and start experimenting. And I didn't have the benefit of a ton of experience in transactional sales at the time, and I didn't know to say look for companies like Zendesk as opposed to Oracle to model my approach. I found that out through trial and error. But once I found a cohort of like-minded people, who had reps who were doing 100 to 250 deals in a given year. They already knew the playbook and I didn't need to reinvent the wheel, and that's where I came up with that sort of linear system from moving deals through deal stages as essentially a series of touch points for the potential customer.

Thomas Miltschuh: How long did it take you to find a solution and to correct the process to improve it?

Lydia Winn: This is why I'm glad I was there for five years. It took me about

Thomas Miltschuh: Okay. 

Lydia Winn: It took me years to iterate on it. I can tell anyone who's struggling through a challenging problem stay the course.

Thomas Miltschuh: Thanks. So maybe the last question. Is there any additional lesson learned you would like to share with the audience? Maybe specifically for aspiring sales reps starting in the business or any other lesson learned you would like to share?

Lydia Winn: Ooh. I'll go back to what I said in the beginning, which is that I've really built my career around growing relationships, and so my success as a leader depends on how many talented people trust me and trust me to get them to where they wanna go in their career. And serve their interests. And so that is what I have built my career around. And I encourage people who are new to sales, whether they're interested in management or not, to focus on those key relationships and hone and develop them over time. Whether it's putting a reminder in your calendar for someone's birthday that you really respect and you have a lot of professional love for, or pinning their contact information. I have iOS. So pinning their contact information in your phone so you continue to think of them and remember them. It is those people that I have kept top of mind and continue to keep updated on my career that have helped me find great opportunities, like SmartPass that have helped me be successful, helped me direct me to the best resources for my problems, and ultimately have success when I step into a new role. So I really cannot understate the value of nurturing those few key relationships over the course of a career.

Thomas Miltschuh: Alright. Very nice. Sounds great. I think that's very important, basic advice for no, not only people new in the business. So that brings us to the end of the episode. Thank you Lydia Winn for joining us today, sharing such valuable insights. A huge shout out to all our listeners. Your support means the world to us. Remember to check out our website: speakrevenue.com for a full transcript and additional resources. If you enjoyed the show, please leave us a review on Apple Podcast and wherever you go for your listening needs, it really helps get the word out. Also, follow us on LinkedIn and Instagram or on YouTube. We'll be back soon with another great guest. Until then, stay curious and keep listening.

Copyrighted © 2022-23 Jaxx Technologies, Inc.

Copyrighted © 2022-23 Jaxx Technologies, Inc.