Why The Founder Has To Be The One To Create The Sales Playbook

Oh, thanks for having me. Appreciate it.

My path into sales, I discovered sales at the ripe age of 15, which was the day I got a worker’s permit and could get a job. So I was fired up to get a job and make some money. So I applied for a few retail jobs in my hometown and the owner of two kind of neighboring boutiques met me and said, you’re hired, start tomorrow. So was so excited. So I marched in on my first day ready to get working, and he said, here are the keys to the other store.

Go open it up. There’s a shoebox of cash in the back. Use that for the cash register. I’ll show up in a few hours and teach you what to do. And I was terrified. So he’s like, open the store and get going. So I’m like, all right, I’m going to do this. I go and open the store. And soon after opening the door, customers started coming in. So I had to start selling. I did a terrible job. I don’t think I charged sales tax to anyone that day.

I’m sure there were some very good deals made, but what I got from it was the energy of working with customers. And I stayed in retail throughout high school and college. And then fast forward, I graduated from college during the recession in the early ’90s. So not a lot of jobs. I was still working in retail. And I was at a barbecue and talking to my oldest sister’s friend who had been in the workforce for a number of years ahead of me. And she said, hey, Lori, I work at a software company.

We’re doing kind of this group call interview for salespeople. Are you interested? And I was like, both hands up. Let me get a job with a career path. Sounds good. I knew nothing about the company. I didn’t know what they sold. I didn’t know how they did it. I didn’t know anything about the market. I just really wanted to just get in and get a firm job. So I went to the interview. I got the job, and that company was Remedy Corporation, which was later, you know, became part of BMC.

I think their software still on the still askew of BMC, which is amazing. It was a formative part of my career. Super fortunate to experience an IPO with them, So just saw, like, what high growth was all about from the start. So that was my story. That’s how I got here.

Honestly, I think it’s the latter. And I say that even though that wasn’t my experience, because I think there’s a perception sometimes about sales that it is just this, like, kind of robotic anyone can do it. Go and run a script. Go there’s there’s not a lot of humanity to it. And I think when you really learn that there’s an art and a science to it, that it’s about genuine connection with people, that it’s about really like, listening, then I think you can really learn to love it.

So I think it’s actually more the latter, even though my experience was that instant energy.

The real takeaway there is the importance of building, like, genuine connections to do great work. You can’t do anything on your own at Google. It is so big. It’s so complex. There’s so many layers, crossover of teams and initiatives and budgets and structures that you have to learn quickly that the stakeholder partnerships you make are critical to how you get work done. And so from the start, you’ve gotta get out there and and not just stay in your lane. You’ve gotta go learn about the neighboring businesses.

You’ve gotta learn about the partnerships that are gonna help your business grow and learn about what are their motivations. It’s not just about me. I was in Google Cloud. What’s happening outside of Google Cloud? What’s parallel to us? How can we work together? And if you do that in a genuine way, there’s so much that you can take that to. That’s an applicable skill skill and talent that carries over into any role. So that would be my takeaway from Google.

Facebook was, I would say, focus on impact. They do a lot of work in really small teams and focus on just the impact you can make. So narrow your list down to the three things that are to make the biggest impact and carry that forward versus getting of diluted across a long list of to So definitely and you see that the way the company operates.

Sure. Two would be be really comfortable with moving fast and being really comfortable with ambiguity. We did not have all the answers, but we were moving fast we were figuring out as we went. And not just like being comfortable with it, but finding energy in it. Like, getting excited that you don’t know what’s next. So what do you craft to build a plan that could go in a few different directions and that could morph and change? So that kind of flexibility, but definitely learned the speed and the ambiguity there.

That was probably a favorite place of mine. One big learning that has been kinda core to the way run the company from the start is to be an owner. Really believe that we collectively are the company. It isn’t someone else. It isn’t above you, below you from the sides. It’s from the way you put your attention into an email you’re sending a prospect to the way you’re navigating big operational organizational change management. You’re part of it. You’re doing it with a team. It’s not happening to you.

You’re help getting it done. And that’s really something Aaron just has built and made core to the culture, and I’ve carried it forward in every place I’ve been since. Is that why it was your favorite? It’s one of the reasons, definitely. You really felt that you were part of something at Box. You were part of the build, and and that meant for the goods and the bads. Right? It’s not just the highs, that everyone was in for all of it. And you really felt it. You felt it, and you could get that energy inspired across a team of SDRs or sales rep coming in.

Like, the energy that creates is just it’s palpable.

Think of it as a more of a GPS. So it doesn’t have to be a script. Like each step down to the minute detail. Think of it as a guide. So depending on where you are in a sales process where they’re very early and you’re doing discovery, or even earlier trying to get a meeting, and then down to doing discovery and carrying it all the way through, I think a playbook is like, what’s the successful motion in this stage of the cycle that you should go lean into and flex your strength or get the support around in order to have a successful outcome.

So I think it’s all about like, thinking of it as like, drawing on the experience and the success you’ve seen from previous sales engagements and building that into, like, a guide that can help you navigate through, but enough that still gives that level of creativity and flexibility that accounts for the style of that salesperson.

Yeah, good question. The founders are the right folks to create it for a few reasons. There’s where it started, right? They had the passion. They had the idea. No one has more passion than them. No one can better articulate the story. So they start from that place of like, this is my belief. This is my idea. This is my baby. So there’s that that you’re grounding from. And what that creates is the person that knows the why and the what in in such a deep level that they can anticipate things like, what problem are we trying to solve?

And then when they get that customer feedback pivoting, so, like, is that really as important a problem as I thought it would be for the customer? And if it is or it isn’t, how do we change our playbook to amplify how our solution solves that problem? So I think that them being the closest to it allows them to pivot just not only the playbook, but also like feedback back to product. You know? So for example, at WorkRamp, you know, Ted is a go to market leader and also has an incredible product background.

So what’s great about that is his him setting the playbook, which he did here, is he knows. He knows how customers respond. He knows what really matters to them and how our story fits in. And then if we get some feedback, even now where he’s less connected, less as close to the playbook as he was in the early days, he still knows, like, hey, Ted, here’s what we’re hearing. We need to adjust this. He’ll take that feedback. So I think it’s great formatively in the beginning, but then it can carry through as your company grows as well.

Like, how do you coach them and how do you guide them?

A couple reasons. I believe, especially in the early stages, there’s a huge opportunity to not only like, identify and sprout new talent in a startup, but also you’re looking for someone who’s demonstrated drive and ambition and all that good stuff. But that doesn’t just translate into a huge logo person. What gets them energized? How do they navigate through ambiguity? They don’t come in with it like, this is the only way to do things. There’s an openness to like, I am in it because I’m passionate and I believe in this and I have all the talent to go navigate challenges and to go build something, but I’m not so set in a way that there’s only one way to do it.

There’s a mindset, there’s a grit and a scrappiness that can help you really accelerate through that energy of that team. So I’m a big believer in you can really do great things with maybe a more junior talent because of the creativity they can bring and they don’t have kind of a bias from a previous experience.

I think it’s all about thinking about scale. So if the founder’s doing it, and let’s say you’ve got 10 to 20 customers, like how much more can they do? Like just in their straight daily capacity, you know, how much can they get done in addition to growing and scaling the company through all the other disciplines? So I think it’s that moment where you’ve got enough customers and you find enough of a repeatable process that can take your good work and grow it and have feedback. I think also just someone that you can work with, like, hey. we’ve been trying this for the first X number of customers.

Let’s tune that a little bit. I’ll go try that and come back to you with feedback. There’s huge value in having partnership, you know, the kind of how many people do you hire at a certain time. There’s huge value in being to learn from someone that’s that’s next to you. So I think it’s a combination of customers, how many you have, and just thinking about the CEO or founder needs to now scale beyond and focus on other things, and this person can help them do that, but they can still stay close.

I do. I think you should hire more than one at a time for a few reasons. Less about the competition. I think that’s of gonna happen maybe naturally, but it’s more about you know, work work for scale. I think if you’re onboarding one person, onboard as many as you can because just that time and investment in onboarding, you know, is a big commitment. So if you’re onboarding one, there’s huge value in onboarding more. I think there’s goodness in creating a team and having a place for those first sellers to collaborate and say, hey, I’m to try this message, this motion, this sales play.

Maybe let’s tune it a bit. You try this. We can test and see what’s working. That first like of group founding team, there’s nothing like it. You know, there’s there’s learnings, there’s energy, there’s culture that comes from that. So there’s just so much positive byproduct from building a team through having, you know, a small group that starts that you get that carries through and just reverberates through the company culture and is very foundational.

From a process perspective is you break down an interview process into kind of chunks, if you will. So the first part would be just vetting for and this is a term I learned at Google, which the way just they framed it is really helpful. It’s like vetting for just role related knowledge. So it’s like, do they have knowledge that relates to the role that you feel would say, yes, I want them to kind go through to the next phase in the process. So do they demonstrate the characteristics?

Do they know enough to be dangerous, right, And some experience that they can lean on to go forward from enrolling with the company. And then the next deal in the process is the how. So how have they been successful? What stories can they lean on to tell you how they’ve navigated through a win or a loss? Most importantly, a loss. Who like, how did they bring in different resources? How do they navigate change? Because you know, a lot of folks will say, oh, yes, I to be part of a startup.

I’m ready for it. I’m ready for all the the crazy and the chaos. But like, are they really? Do they really want that? So really kind of peel back those layers and ask questions that can help you reveal how they’ve navigated something really hard. And does that energize them, or does that make them go, run away? so

Oh, they do. They do. You’re absolutely right. Because there’s some great people can interview really well and tricky. Right? So the things to dig in on is I like to ask about, like, a loss and less about like, tell me why you lost, but what did they do? So they’re not pointing to someone else. They’re not saying, oh, it’s this person’s fault. It was my territory. There’s something else other than me, but it was like, what resources did you bring in to help you? Like, give me an example of what you learned from that loss and how you brought it to your next win.

And what that demonstrates is not only, like, an ability to of reflect and, you know, take an experience, learn from it, and turn it into action, but also how do they work in a team? Because I think especially in a startup, like, the team is so critical to the success. So how do they partner with other resources in the company to go get something done? So I think vetting for that is really important. And then I think, you know, if you hear too many mentions of iii I I mean, of course, it’s it’s sales and you want folks to be proud of their performance.

But if it’s too much on just what they did independently, for me, that’s a red flag because I think no one wins, you know, independently. It’s a team sport.

Exactly. And they, And it also demonstrates that they’re proud of that. Right? So it’s like they’re sharing that data with you because they’re proud of what they did to get there. So there’s two really interesting parts of that answer.

So I think, you know, if you’re to go through the steps of having them maybe present to your team or get do some sort of mock discovery, mock sales call, whatever case study work that you do, I think that’s an important step in the exercise. I don’t think it is like incumbent that it has to be on their current solution or it has to be on yours. I’ve seen it done both ways. I like putting in front of the candidate about the company they’re gonna come join, not because I’m looking for, like, the perfect answer, but more I like that they just do go and do homework.

Like, are they curious? To me, it’s like a critical characteristic of a great salesperson is curiosity. What they go learn about us? They they might find something in our story that we aren’t leaning into as much that we should amplify more. So I like to have some sort of case study discovery call, whatever it might be, that has that’s on the company that they’re gonna interview that you’re representing, and so that they can come and kinda tell how they interpret that. You know, that’s not an easy situation to be in also.

So it’s of high stakes. So how do they operate in that? Like, are they comfortable being uncomfortable? Because that’s what a lot of sales is.

They could say anything.

Right?

We wouldn’t know. like, what are you even vetting for at that point? Exactly.

That’s a good one. So on compensation, I think you learn a lot in that moment with the candidate. So you learn a lot about them. And especially if it’s competitive and they might come to you and say, hey, I’m getting, you know, 50k more OTE over here. And then you ask, okay, well, what does that mean for you? What does that represent? What is it in equity? Is it an OTE? What is it? And what’s driving that ask? So I think with compensation, it’s an opportunity to really understand what motivates that person.

And also, like, a startup, like, do they really believe they’re taking a risk? Are they excited about that future opportunity that shows up in equity? You know, what are their questions around equity? Do they you see an excitement in those questions? And if it comes down to just dollars on ot, I’m always a little bit like, it’s not a full red flag depending on, you know, where the conversation goes, but it’s something that concerns me because that will come back, you know, in the future where someone’s gonna be, maybe, you know, you have a hard quarter.

How do they navigate that? You know, if things don’t come together, do they have the staying power to work through the ups and downs that can happen in a startup? So I think it’s a moment to really understand what someone’s motivations are and also just like, see kind of where their research went. You know, how deeply do they care about the opportunity in front of them? Is it just a OTE, or is it they really care about the mission of the company and they to be a part of building?

I’ve done that. I’ve said, you know, when someone’s really like, this OTE is so I can’t step away from this. And maybe you could get closer and bridge it enough. But if that is all they’re talking about, sometimes you have to you have to walk away and say, you know what? That sounds like it’s a better fit for you. And if that changes, let’s you know, I always leave a door open. I think it’s important the valley’s small. Right? You just cannot, you know, shut a door.

And so I think it’s okay to leave it open, but it’s okay to sometimes walk away. And I’m trying to think if there’s anyone that we walk away from there, was like, that got away, and I no one’s coming to mind. So, you know, that tells me that those weren’t the wrong decisions.

Yeah. So I think that it’s honestly like a discovery call in sales. It’s like, what’s the why behind the title? Are they looking because they to demonstrate a certain level of progression on their LinkedIn profile? Is it that they wanna demonstrate scope? Is it someone who’s maybe and I’ve seen this, like, gotten stuck with title at a big company where titles get a little murkier and are a little more flat and they come out. they’re like, I need to break out of this kind of big company title level conundrum that I’m that I’m trapped in and I want something to demonstrate my scope.

It’s a very individual conversation, but I also think it’s important to keep in mind, and this is hard to do, what you’re setting up for will impact the future. So if you get too aggressive on title, then you’re a couple years down the road and your next person comes in and they’re like, well, wait, why am I not a senior director? Maybe that first person wasn’t. You know, and so you’re like, okay, now we gotta unwind this a little bit. So I think it’s okay to be comfortable with some of that in the beginning, but I think you just have to be aware of, like, right, this might be something that we have to navigate or walk back a bit as we grow.

Exactly. You’re using it to go accelerate growth. That’s a good answer. Right? Yeah. So yeah. 100%. Yeah.

People People can interview well if the answers just are shallow. If they’re just very canned and shallow and you feel like, okay, Anyway, I could play back, you know, a bunch of different LinkedIn posts and collect a bunch of these and this would be an answer. know, if they can’t connect to an actual customer engagement. I like it when someone’s like, to your point, the stats, they’re really showing you, like, passion behind the work they did, and then a real, like, customer story and team story.

If there aren’t enough of those, like, there’s not enough depth. You know, that means you might get some performance for a while, but that’s gonna fizzle

Yeah.

Yeah, that’s a good question. I’ve had folks that, it came off in an interview were super ambitious. Right? They’re like, I’m to do this. I’m to build this iii. I And they had this energy about them. But when you really peeled back how they’re to do it, you know, not vetting the how enough. I’ve had that happen in the past where it’s like, it looked really good, but we didn’t go deep enough on that how. And then I think another piece is I don’t think you need to do a million references because people are to send you the references, of course, are gonna say all the good things.

But I do think if you can get some connection to people that have worked alongside with some sort of, you know, reference backdoor that shares a little bit more insight is helpful. And I think in places where we be moving too fast because we really had to get it done and and couldn’t get some of those additional touch points that that we could have maybe seen around a corner in advance. And I think, you know, again, a lot of it is folks want to say they’re ready for a startup.

You know, And, like, I’m all about it. It’s to be great. I’m in for the journey. And then they get there and they’re like, wait, what? You know, so I’ve made some mistakes there. It’s it’s hard to vet, honestly, because it’s hard to say, like, you can anticipate everything and prepare someone for that. But there’s been some places where it’s like, this is just too fast and too ambiguous and too crazy, and I I can’t. I think you should expect one of those every once in a while.

Right?

Right. 100%. I 100% agree with you. And it’s it’s not about that.

Yeah. One One of the most important characteristics in my opinion with a great salesperson is being curious. So what active listening means, it’s discovery. It’s someone who can ask a question, who can ask the next question that’s connected to that first question, really listen to the first answer to inform the next question, and listen not just for the answer you want to hear, but the answer you maybe don’t want to hear, which is, you know, some red flag roadblock that’s to slow down or make the selling engagement difficult.

So it’s listening for the places where there’s alignment and it’s listening places where there isn’t alignment that we need to go build that alignment through a really tight sales engagement. The way you teach that, I think you have to shadow a lot and listen a lot, and it’s a practice. So you have to prioritize that as the sales team and make sure that those questions are happening. So you have to enable around it and then you have to listen for it. So for example, with my current team, we do a lot of relistening of calls and we publicly, in a Slack channel, mark them when they’re perfect.

And we say this is a perfect call and we to highlight why this is perfect. Now, perfect. doesn’t mean you get every single piece right, but it means that you were really demonstrating the activist of those links. So we demonstrate with our leadership that this is important and matters and we’re gonna teach you how to do it by giving you an example of one of your peers who does great. That’s how that turns into action beyond the warm and fuzzy.

This is bad. I think when a salesperson is just going through a script and maybe we inform them through enablement, like, here’s some great questions that can help guide a call. And instead of asking them and pausing and listening about where that question takes that, they just go to the next question. So it’s like and it’s more of just like a checkbox. You know, it goes back to that perception sometimes with sales of being just a, you know, kind of robotic method. It’s like, no, no, there’s a list, and we might give you that to help guide you.

But that is not meant to be just something you kind of check, check, check, check, check, Because what then what then you’re wasting the customer’s time and you’re wasting your own time because you didn’t get anything from that experience.

Yeah, no, then I’ve seen that definitely have had that happen. So that that is a you know, I think anyone who’s led any sort of sales development team or the team right after the sales development team has experienced that. And I think the way to mitigate that is a few ways is having a qualification criteria that has to be met. So if it’s a BANT, if it’s, you know, whatever the structure is that identifies kind of the core drivers of that call. But, also I think what can validate if that’s quality is to have some sort of checkpoint, if you will, of sales stage progression.

So let’s say you set a meeting the opportunity is early in stage, but we’re gonna incentivize when that opportunity goes to the next stage. So when the seller takes over, but they move it forward because that is a vote of quality. That demonstrates that that opportunity that you created for that salesperson moved forward in their funnel. And that think that’s a moment of like, yes, we had stage progression off this. this. wasn’t just like, to your point, like fluffy meeting that didn’t went anywhere checked a box got the list on the dashboard, all that good stuff.

It actually is turning into something. So that’s another way to just counterbalance and mitigate that. But I think you have to have some sort of structure. So, you know, I’ve used Bant in the past, I’ve used Anim investors, all sorts of different ones you can use. But something that says this person is giving a signal that they want to continue the conversation with us, and there’s a timeframe and there’s a budget and there’s and they have some understanding of the buying process.

I think it’s activity. You have to put in the activity. If you’re not having enough conversations and you’re not working to accelerate the pipeline you have or create the pipeline that you need to have, then what are you doing? So I think you have to go back to pipeline acquisition and pipeline acceleration. What are you doing on both? Most of the time going to be on acceleration, right? Because the intention is they’re not creating all of their own pipeline. But I do think it’s very important for sellers to create the sum of their own pipeline.

They’re not fully responsible for it, but they have to have skin in the game on creating pipeline. So I look at those two metrics, it’s acceleration and acquisition, and how are they taking feedback? So let’s say they have an opportunity that doesn’t progress. Let’s dissect that. Let’s do some postmortem and then learn in the next one. If you’re not seeing that learning pickup, you know, after giving the right coaching and resourcing, then that’s a sign to have a conversation.

So So the first question would be, did you have mutual agreement with the prospect on when we would execute? So did you work on a mutual evaluation plan or some sort of joint evaluation plan that had milestones that said this is the timeframe that we both agree to? If the answer is yes, and the circumstance that pushed it is something like, you know, we’ve seen this in 2023 and the end of twenty If there’s some internal event, let’s say there’s a rift, you know, like, hey.

We were going down this process. We were all in with you, but we just had a reduction of force. We have to pause. We have to reassess, but this is still a priority, then that’s you know, it’s hard to anticipate that. Right? Like, an external person can’t anticipate that. But if it’s like, you know, I was told this was the timing, my person agreed, okay. Maybe you never had access to the economic buyer. You really were just working with a champion that didn’t have the power to really understand the buying process.

So a lot of the core of that, like, if it’s a result of the salesperson’s engagement, it’s because there wasn’t access to the economic buyer. That’s usually like the number one part of Medic that makes it fail is you’re just not you’re not there.

Yeah. Well, I think you start from doing the discovery with your champion and coach to understand, like, who are the stakeholders? Like, who ultimately signs? Whose budget does it come from? And how does this fit into their priorities? That’s super important because especially right now, you know, when a lot of companies are looking at saving, you know, and cost cutting, where can they consolidate? If you haven’t sold to the economic buyer that really understands the true value of what you’re bringing, it’s very likely that you can be consolidated away from.

But if you have built value and connection with that economic buyer and they understand how that’s solving a problem for them, you’re mitigating that chance of being of being consolidated against. So I think it’s really understanding, like, who’s the ultimate person where this impacts? And if they are looking at their p and l, and this is part of it, they, you know, thumbs up, I’m not changing.

trying to build your stakeholder, ma’am.

Yeah, exactly. How do you

Because we can know. In fact, I that’s so funny. I was just having this conversation this week. You know, if you’ve got a great champion, it’s like there’s such opportunity with that. Letting them know that like if we partner to share this story on what we’re doing together inside your organization, how can that make their experience and life and goals and career path and exposure, whatever it might be that they’re looking for, get amplified? Right? So first gotta get the buy in with the champion. instead of, like going around I’ve trying to meet a bunch of people, you know, going on LinkedIn to figure out who else in this company do I know. like first get the buy in for the champion of why.

Like, it’s so important in every sales engagement. Explain the why. Explain why you’re doing it and then get some of their buy in. Could you refer me to like, for example, is there another department that we might partner that might be using our solution? How would they interact with it? Could I get a conversation with them just to better understand their goals? And also always say, I’m not to take an hour of their time. You know, make sure you’re you’re also setting the stage that you’re to be respectful, that they have a job to do and other priorities that don’t include you.

So making sure you bring that humanity to the conversation. But it’s back to that checklist question like not doing it just to check the the thing to really understand curiously, like how will my solution stretch across an organization and how to meet the people that are to be part of

I don’t think it’s fully dead. It was the play when I started. Like, that was it. You know, You flew out to Texas, you took them to the steakhouse, you did all that stuff. Right? I think with COVID and realizing what we can do remote, that has absolutely changed the game with how much selling you can do virtually. And I think if you do that right and it doesn’t feel transactional, you can still have a very genuine connection with a buyer. I think it hasn’t died, but I think it’s just been kind of relegated to like a very specific motion that’s happening.

And it’s almost additive, if that makes sense. It’s like you’ve to still do all the work to have that moment, really have strong ROI. It’s just like, how do you use that moment, and what’s the return for the customer and for the company?

Yeah, they might be like, you know what? I don’t to hang out with you after work. I’d rather hang out with my family and friends. So no, thank you.

Yeah, I mean, there’s some dependence on, you know, what market you’re in, how many competitors, all that good stuff. If it’s really competitive market and there’s not as much differentiation as you’d like, you might need to do it to just get a foothold and to make sure you are grabbing market share where you can. So definitely understand when that has to happen. I think it’s all about a trade off. It’s like, what are you demonstrating from a value trade for that? Is there something that, hey, I’m gonna give you this discount, in exchange for that, especially in the early stages, I need references.

You know, I need folks that will speak on our behalf beyond just me, said founder, or or sales leader, whomever the person is that’s in the engagement. So I think you should just make sure you’re preserving value through what that trade off is with the discount. I think in the early days, it’s like customer stories. It’s references. It’s introductions to other referrals you can help me with that can help me broaden my reach that I maybe couldn’t get myself. And then also just, of course, you want not make sure you’re demonstrating what that discount represents.

I’m a big fan of like when you’re even going to proposal stage showing it like this is exactly what’s coming off of this original list price. This is what that means. So you really see it visually and that sits with the buyers. They recognize that the collection of your good work to get to this stage has produced this discount. We’re gonna support it provided we’re gonna execute on the time frame that we agreed to mutually.

me? Yeah. I mean, multiyear deals right now, especially, are a good thing. Right? Because you’re, you know, like, gross retention, gross retention. Right? And so they’re a good thing. I think, again, you can put some financial incentive behind it and make them very compelling for the customer and for, you know, the vendor. So I think it’s a good thing to do. And there’s ways to also incent a sales team to do it well. So you’re thinking about like, hey, if you get a multiyear deal, this is some things we can do from a future pricing perspective or things like that.

Yeah, I worked with him I worked with him at at Navanya.

That’s bold. But I think you have to to say there’s a caveat around that. Like, we’ve gotta prove value. So we’ve gotta prove what we’ve been telling you for whatever this selling motion period is. We’re confident we’re gonna do that. And in exchange for that, we’d like a testimonial. But I think it’s it’s important to ask, but I think it’s important to set the framework. It’s like, we’re gonna meet the mutual goals that we agreed on. We’re gonna get you to what you’re trying to reach from a, you know, organization perspective and say, and at that moment, I’m gonna come back and ask for it.

And I think it’s like it’s a seeding opportunity. It also demonstrates that you’re staying connected to them for the long term. I think when a customer really is in partnership with you and believes that you genuinely are looking for a long term fruitful partnership, they’re to be apt to do that because they believe that that, you know, genuine human connection that you’ve demonstrated and that great discovery and that great listening is gonna prove to be a really good investment long term. So I think if you set that stage, then you can get that testimonial, but you should make sure you’re going back to you’re to prove the value that you said you would bring.

like, do I like that?

Yeah, no, I think you can’t make it dehumanized. And I’m in my role today, I’m responsible from sales through to customer success through to support. And we operate as a revenue organization. So we don’t operate as a sales organization and an implementation organization and a success organization and a support organization. It’s one. And what we prioritize to make that not feel like a handoff is the conversation that happens. We are engaged in each part. So for example, if we’re closing out our quarter and we’re about to plan an implementation and the next phase of that customer’s journey, that implementation manager’s on that last call.

And they meet them, and they say, this is my colleague. These are some of the customers that they worked with. They’re a rock star. They’re gonna carry you through. And I’m gonna join when you go to launch that last call. So it’s like you’ve got to hand the baton off, but say, I’m coming back, and I’m gonna stay connected. And you can also do that with just, like, structure of how you compensate people with upsell and things like that so to make sure there’s an incentive.

But I think you’ve got to show it. Like, you actually have to show up to the call and stay engaged. And then let’s say you’re now with a customer you’ve launched. You’re with a customer success manager. I think the account executive needs to join those QBRs. They need to listen. They need to participate. They need to not be maybe the one driving the QBR that the customer success manager is leading, but they need to show up. And what that shows is like, I care about you as a customer.

I’m not just closing the deal and moving on, closing the deal, moving on. I’m staying with you through the life cycle of and seeing your success through.

So quarterly business review and there’s argument to do quarterly or monthly, but essentially a regularly scheduled business review with your customer that demonstrates how they are progressing against the goals we originally set. So let’s say that is you’re to launch in our environment at WorkRamp. you’re to launch a certain number of classes, you’re to build a certain number of guides, you’re gonna hold this many court whatever, you know, certifications, whatever it might be. We’re gonna walk through how’d you do? Like how and how did we agree on those, and how did we set you up to have that engagement?

And how did the engagement go? What was the activity from it? How are your users engaged? So really use data back to your day. Like, show them with data what is happening with their investment, and then show them opportunities. Like, here’s some things that you aren’t doing yet. And we have five customers that look just like you that are doing this really well. We to share that. We think We should try it. Let’s get a call on the calendar to talk through how we can do that.

So it should be a moment where you’re validating the goals of what we originally set, also really bringing the value of what else can you do? Because it shouldn’t just be a checkbox, right? Like, great, you purchased it, you got it Launch, go. What else is happening? How do you activate the roadmap? How do you activate what’s coming in the future? Here’s some insight in what we’re building. We think this could help you reach your goals. So that’s what that moment’s all about. I think there’s arguments for doing it more frequently, less frequently, but the importance is to have it, you know, it’s like at at a regular schedule.

I think that when that happens, it’s probably because you’re just going too fast. You know, it’s like it’s one of those moments where you gotta slow down to speed up and you’re doing back to the checkbox, you know, exercise of like, here’s what we did. We’re to kinda just read back versus actually like articulate and connect. think when it just lacks depth and it usually is because you’re just going too fast.

Yeah. You’ve gotta look for signals. And then some of it is subjective, of course, because anticipation is going to come from a customer success manager connecting with a customer and reading that experience and figuring out what does that mean. But I think you can measure a customer’s health throughout, let’s say a quarterly fiscal, whatever the time frame is. And that could be with data and usage, but it also can be like, hey, we set up these milestone calls. We’re to have these calls to make sure we’re progressing.

Let’s say they miss the calls. Let’s say they continue to put like, back to your question, it keeps getting pushed. Why is it getting pushed? We’re not on the priority. Take that information, marry it with the customer data. If both are down, that’s a signal that you could be stepping into an area of risk. So I definitely think you can, you know, basically measure the health score of a customer and using both data and anecdotal experience and seeing, like, what does that tell us? And then how do we get ahead of it?

Okay, so let’s say they’re not attending calls. Does a leader in the customer success or revenue organization need to step in and say, hey, I understand, you know, these were your original goals. We’re excited to really continue to work with you. We’d really like to get a call. We’ve understood there’s been some challenges. Could we get that? So, you know, go title match, go to their leader and try to get a call and of shake something loose. That oftentimes can do it, because sometimes it’s just the person below who doesn’t have the time.

So they just need someone to kind of bump it up on their priority list. So a lot of times just intervening works or going back to what was their original goal and bringing that up. Like, we were set to achieve this. We see this as risk. We to help you achieve it. So I think it’s driving that activity and trying to get that connection back.

I think what’s important is a good deal review is based on a common framework. So whatever your framework might be, let’s say it’s medic just for, you know, the structure’s sake, the team participating in the deal review knows what you’re to be asking and can prepare. Not that it should be a big exercise and huge prep. You’re not, you know, writing a PhD dissertation to to do a deal review. but, you know, know, what we’re gonna talk about. We’re to talk about the metrics that are important to that customer.

We’re gonna talk about who the economic buyer is. We’re gonna talk about their process from a decision making process and then decision making, you know, structure. So we’re gonna talk about those. So so common language, really important. Second is you use the deal review to learn and diagnose. You’re looking to see, are we on the right track? You’re not looking to just tell someone they’re doing a bad job. Like they’re gonna come in with a defense and tell you what you to hear and make the deal review not as productive.

Also, deal review should not be story time. I always say this. It’s not your time to tell me a story. Like, don’t say, oh, I met with this person who’s connected to this person. I talked to this person. This is what we said. And they said this. was like, no, I don’t. That’s fine that there’s a story, but let’s get back to that framework. Who’s making decision? Where are we in that process? What roadblocks and what resources do you need? The whole point of a deal review should be what resources and support is needed to go make this accelerate and where are the gaps right now?

So I think that makes a really good deal review.

I think a good reason is like, if there really is just a mismatch in what the customer needs from like a feature perspective and they’re saying they want this and you realize like, we’re just not fit that for them. And we might in the beginning, but then it’s to create churn. You know, so you gotta anticipate, like, is this customer gonna stay with us for long term? Are we really a match? So I think it’s okay to sometimes say, we’re just not going meet their needs.

They want this very specific use case. Yeah, we could put some resources behind it and make this happen. But are we gonna do that on repeat? Probably not. So let’s move on to a customer where that’s a really good fit, like our real ICP. So I think that’s an okay reason to lose. And it’s okay to like, you’re gonna lose some. So you also have to be comfortable with that. Like you’re going lose some, you’re to lose some competitively sometimes. I think first getting comfortable with that and and realizing like, how do you find those ones that are to be really, you know, solid wins?

Bad reason to lose is you didn’t anticipate the competition and how they were engaged or how much the competition was positioning. Like, what really the customer cared about, how the competition could answer that question and how we could answer that question. So it’s back to discovery, like really not understanding what the core goals were for the customer and that a competitor could outsell you in that moment and you didn’t ask the deeper questions on what their top priorities were.

Back to that balance of, you know, you have to set the foundation that there’s that be a level of accountability to the forecast and you have to dig in with the forecast when you are in a high and when you vet in a low. So oftentimes you’ll see like the forecast inspection happens when you’re having a down quarter. Forecast inspection needs to happen in the best of quarters because if you just only pivot to when you’re down, then it’s in a fear based moment and you’re making decisions that are informed by that stress of missing.

You’ve to have that same level of rigor all the time, and you to teach your leaders that. You’ve of demonstrate that that’s really important. You’re to have rigor when you’re having the best quarter and you’re to have rigor when you’re having the worst quarter. And so you learn that and you teach that and that becomes kind your basis for accountability. And I think right now, especially in 2023, it’s hard to anticipate. So it’s back to like having really healthy skepticism about every deal. Like it couldn’t look beautiful, but like, let’s just go in with a skeptical mindset and shoot holes in this because we don’t have the benefit of a buffer.

We don’t have a growing, you know, macroeconomic environment that’s different. So I think that’s really important. just acknowledge that and go in with skepticism.

I would say, you know, selling is an art and a science, but at its core, it’s about really good listening and bringing value. So it’s it’s back to like people buy from people. And so it’s really like, good listening, connecting with that buyer and bringing value in response to their answer. So I don’t think that’s changed.

We talked about it a bit, but I think onsites are dying to death. They’re not gone, but I think we’ve learned how much we can do virtually. And so that old, like, everything must be on-site in person handshaking has really changed. And it’s crazy to see that we’re not all on airplanes like we were just, you know, a few years ago, but it’s changed. So I think that’s definitely I don’t know it’s died of death, but it’s dying.

Setting expectations. I think it’s really important to both have a common, here’s where we think we can go. Here’s where I, you know, like really having a mutual understanding and joint belief in those expectations. But you to set them because if the founder believes here and the first sales leader thinks we can only get to here because those expectations weren’t set, then you’re just to have a mismatch.

I would give them the advice, like really dig in and learn in those first, you know, 90 days deeply, but be prepared to relearn everything in 90 days. So it’s like you’ve to go deep and understand and get in as many customer calls as you can and really work to understand the mechanics and the operating rhythm of the business. But then you will take that basis of foundation and you’re to learn it again because you’re to have all that context and you’re to pivot your mindset and build off of that first to days.

So I think it’s like the expectation is just be ready to keep learning. That’s not to stop. You’re not done after quarter one.

This has changed tremendously in my career, but I would like to see more female leadership at the top. And again, it’s changed so much in my time in sales, but just more female leadership would be something I would change.

And to And to your point, it’s changed a ton, which is great, but we just can’t. Like, we got take our eye off the ball. That has to be still priority.

Yeah, Actually, it’s recently but we recently bought vitally for a customer success team, so a customer success platform. What I was really impressed with is really clear communication the whole way and very direct and engaging. But what I really have noticed is post sale is how they continue to stay connected and care about the success of our launch. And especially in this time where gross retention, you know, is so important and thinking about retaining every customer that you spent so much time earning, they’ve stayed connected through that whole process.

So really clear communication, great sales process up front, but they’re continuing it through all the way as become a customer. So I’ve been very impressed by that.

Thank you. It was a great conversation. I appreciate the time.