Live footage of 1-on-1 meeting with sales leader (behind the scenes)

In this behind‑the‑scenes vlog, Ryan Shank opens by celebrating a record‑breaking four‑day sales week, highlighting multiple high‑value deals and rapid MRR growth. He then explains why regular one‑on‑one meetings are crucial, emphasizing that they serve employees by providing dedicated time with leadership, fostering accountability, and turning discussions into concrete, deadline‑driven actions. Ryan walks through a live one‑on‑one with senior account executive Jim, reviewing weekly metrics (demos, SQLs, upgrades, MRR) and adjusting terminology (relabeling demos as SQLs) to better track the sales funnel. The conversation shifts to negotiation tactics, referencing a hostage‑negotiation podcast and the importance of asking “how” questions and allowing prospects to feel in control. Ryan stresses the need for relentless top‑of‑funnel activity, noting daily YouTube videos as a primary lead source. He discusses pricing strategy, citing recent price increases that boosted average deal size and arguing for positioning high value while tolerating some price‑sensitive churn. Throughout, Ryan shares leadership philosophy inspired by Simon Sinek’s Leaders Eat Last, advocating trust, team cohesion, and celebrating small wins. The vlog blends performance data, operational advice, sales psychology, and cultural guidance to model a high‑velocity SaaS growth engine.
Chapters
Oh, hey, second day in a row. What's up? Welcome to the vlog. We're back to creating videos because one of the things that I'm starting to find, you know, at first I was like, I like doing it and I like the idea and I 100% buy into the fact that like, you know, doing videos, creating the following, creating the content, you're gonna one, just document what you're doing, but then you're gonna humanize your brand and I think that, uh, that is happening. It just takes like years to pay dividends and stuff. So one of the things I actually want to flip, because I was actually recording something else and then I got all these notifications on my phone. So I want to flip to few, uh, to past Ryan when he got the notifications on his phone so you can see how excited I was. Because we're having the biggest week in company history right now. We're having like a ton of sales, and it's a 4-day week, by the way. So we're having the biggest week in company history in a 4-day week, which actually on a per day basis is like blows away any other week. So I'm gonna go to past Ryan. You're gonna see me on my phone getting the notifications. Take it away, past Ryan. Uh, just looked at my phone. So anytime we get a new sale, get a notification from Stripe. I get a notification from like a dashboard app called Kontroll, and then I get a notification from Slack because we push our Stripe sales into Slack. I just looked at my phone and we just closed, uh, this franchise deal that we've been working on, uh, for a while. They just closed for $175 a month. Right before that, we just had a guy text me. He's like, hey, upgrade my account to $375. So from $225 a month to $375. And we had, before either of those, pretty big sales for us, because our average customer pays like $100 a month, even though we do have, you know, a bunch of customers pay like $1,000. Anyway, those are big sales for us. And before these big sales even happened, we're already having the biggest week that we've had in company history. So I literally just looked down at my phone and it's just like, boop! Boop! Just like brrr, like all these notifications for these sales. So that's freaking awesome. I'm super excited. We're having the best week, and it was only a 4-day week. We're having a 4-day week and we have people out this week, and like the wagon is just rolling. So super excited about that. Back to you, historical Ryan. All right, so now, now we're back. That was past Ryan. You saw me get the notifications on my phone. So one of the things that I want to show you guys today, uh, is basically the value of and just the like why you should do one-on-ones. So I do one-on-ones. I was doing one-on-ones with like everyone and it just like was, it was a lot of time and it's like, and then I would move on. And the thing is with one-on-ones, what I've found is the one-on-ones aren't for me necessarily. They're actually for the employees because it gives them the chance to like have your time, right? But the thing that I like to do is have it on the calendar. It's recurring every single week, either 30 minutes or an hour, probably 30 minutes. You know, if they want to move it, let them move it. You as like the founder, manager, or whatever, Like, don't move the one-on-one because that is their time, you know. What we found is that like they wanna be able to get your ear if they have something that they wanna talk about. The thing is that I like to do is like, look, what can I do to help? You know, I'll sit there and try to help them and hold them, you know, accountable and, you know, make sure that we're pushing things forward and look at the metrics, make sure that the numbers are getting hit. This is not a brand deal for Nike, by the way. Peeking out, there we go. Hugely valuable, get their time. They're gonna have like ideas. They're gonna have things they wanna say, and then also, like, it's a chance to, like, just put, like, pen to paper and to put deadlines on stuff. So it's like, hey, we wanna do, you know, this activity, this project, this action, so then let's put a date on it. And then let them agree to the date, and then put the date on the calendar, and then, like, you know, if things come up, you should know well ahead of time if they're not gonna hit the date, but they committed to the date, you're holding them. The date comes, hey, where's the deliverable? Let's talk about it, what prevented you from hitting it, which shouldn't happen. The case should be they just hit it, awesome, and then we're just moving things forward, moving things forward. I think a lot of times people fall into the trap of like things aren't moving forward. They're like, ah, I'll try to do that. There's no trying, that's the thing that I've eliminated in our vocabulary. We're not trying, we're doing shit, right? We're doing something, I'm going to get that customer, I'm going to do this many demos, I'm going to get a sale, we're gonna land this partnership. So the one-on-ones, again, it's like, you know, you're just, we're not gonna try, We're gonna do things and we're gonna put a date on them, so we're gonna hold ourselves accountable, uh, so that we can, um, just again be the most productive people. The thing is, like, I want us to move at a speed that no one else is moving at, especially the competition, but also just like other companies, other people. Like, I want us to have more output than other human beings, right? And then the way to do that, one is to keep healthy, uh, mindset, but then also just the systems that we put into place, and not even like intricate complex systems, but really just holding yourselves accountable. Little goals. Let's tackle little goals, get those wins under our belt, celebrate those little wins. And the power of just celebrating little wins with your team is really going to pay off. So anyway, that's the— that's like why one-on-ones I think are so important. It gets you on the same page as well, and it also gives, gives your time to them. I'm going to show you an actual one-on-one today that I did with Jim. He's like one of our senior account executives. He's been with us for over a year. He, he was originally first or second, like real sales rep that we have. He originally came in, he was like cold calling, he was self-sourcing everything. We went through a lot of changes. He joined the company when we were doing like $7,000 a month in monthly recurring revenue and maybe like 70 customers, something like that, right? And we're like almost at like 500 paying customers. Like we added 75 last month. So we're at a different place than we were now. And our sales team now is like a lot more evolved. So anyway, he's— so he's like my top sales guy right now and he kind of manages the rest of the sales team. So did a one-on-one today with him, went over his metrics, went over the team metrics, and then just like higher-level and then just talking to him about some things that, you know, I'm reading, that I'm learning about. He's telling me some stuff that he's learning about. We just kind of are in this just like real, more like, like discussion where we can just exchange ideas and everything. So anyway, follow along, follow the journey. Hope you guys are out there working hard, being pioneers, being Wagoneers. Here's the one-on-one that I had with Jim today. Peace. Alright, so do you have, do you have your last week's numbers? Like last week's numbers and this week's numbers? I'm just gonna fill out our one-on-one doc right now. I mean, this is probably your best week ever with that $1,600 a month sale. Yes, by the way, we've done more in September. We've doubled the amount of MRR in September, and it's only September 6th, September 7th, than we added in all of August already. So we're like pacing for like, like 10K in net new right now.
I like that.
I like it as well. By the way, that, that like podcast that I was just listening to, I thought that was like super interesting about like negotiation strategies and like when they were talking about how like, look, when you try to, you almost want them to feel like they have power. And that's where I think like when they're talking about in the hostage situations, You know, it's like, you don't want to talk over them and you don't want them to feel like you have all the power. So a lot of times, you know, it's like trying to figure out exactly what they want, why they want it. Tell them that like, ask a lot of how questions. So it's like, I need a car in 60 seconds or I'm gonna like, you know, take this person that I have as a hostage. Well, it's like, how do you expect me, you know, how should I get a car in 60 seconds? Like, that's crazy. You don't say that's crazy though, by the way. But there's a lot of how questions. Like, how can we do this? And then you kind of like stroke their ego, which I think we talk about a lot when we're talking with like these customers and stuff, how we talk about like, look, you're obviously like killing it right now. You have amazing reviews. You look like you have a ton of clients. Would love to work with you. So you stroke their ego and like, you know, that whole thing. And then the— so anyway, I thought it was really good. That's why I think like it's just interesting. So I think the team should listen to it, but also for like negotiating. By the way, the things that I've been doing, we're gonna have to— the things that I've been doing when they're like saying they're gonna go to a competitor, I feel like we should all do that. Like, I'm almost being cocky at this point, but every single time I'm saying it, it works. I'm like, look, totally get it, you're gonna go to them, they're not gonna answer you, they're not gonna be responsive, and then you're gonna come back to us. So why don't you just I mean, which is fine. Like, you know, just let me know, just hit me up when you're ready to come back. And then a lot of times they're like, they're like, all right, let's just get it done now.
They're like, yeah, I use that on a demo earlier. Cause I saw that. I think you said it in live chat. You were like, hang up with me, call them, see what happens. And then call me back. That's not going to answer. And I literally just said that to somebody. He kind of like laughed. He's been using a competitor for a year. Or so, and he kind of like chuckled and was like, okay, I'll make my mind up in the next week or so.
Yeah.
But he was like, yeah, he was super receptive to that.
I was like, that's so good. I mean, I'm walking the line now. I'm going to go on the cocky side, but I think we should go on the confident side as a company. Yeah. So by the way, Arad's killing it. I just think top of the funnel, top of the funnel, top of the funnel. That's why YouTube videos are going out every single day now. No excuses. There's gonna be one going out today. There was one yesterday. I actually got a bunch of people, two different people that watched the video said, oh, I'm like, 'cause I said like deep in the video that I was in Maryland and I didn't say where in Maryland. And I said, I didn't say in the title or anything or thumbnail. And then people like watch the video, they're like, oh, I'm in Maryland or I'm 30 minutes from in Maryland, whatever. And then they like ask me something, but it has like, but anyway, and then I thought it was good. So top of the funnel, top of the funnel, top of the funnel. Okay, so your metrics, last week's, this week's, any hurdles, anything stopping you from putting up $3,500 in MRR this month? Fuck 3K, we're going $35K.
So you're going $4K. No, not at the moment. I mean, I'm pacing good. I feel comfortable with where I am. I got a—
How many payments have you had so far this month?
So demos, little low. Um, actually I need to go through. I don't know if I updated for yesterday or not. Uh, demos so far I have 3, 4, 4, 4 so far. 4 demos complete. Yes. 4 demos complete so far. And then I have, I guess I can look at just at the dashboard.
Yeah.
4 demos complete so far. 6 sales.
$1,901. Okay. That's really good. Uh, in terms of sales and MRR, we just need to, uh, figure out how to, how to feed you a little bit more. Um, 4 demos in 4 days though. Yeah.
And I did, and that's not including today. I just did one earlier that I self-set from an inbound.
And then it was basically 4 demos in 3 days. Yes. Um, yes.
Uh, last week it looks like I did— last week it looks like I did 2 demos. 2 demos, um, and brought in 6 sales and 2 upgrades for $1,152.
Okay. So demos are done, but so you're basically just working upgrades and working pipeline and stuff. So you're not getting like new demos.
So yeah. So that's, I mean, that's the other thing too, is that what we were talking about the other day kind of overflows as far as like MQLs, SQLs, and then expansion within the company. Right. Cause that big upgrade and a couple of the demos that I did, are like the same company, but it's a different group at the same company.
It's like technically it's a—
I mean, it is a demo, it's just not a new demo because it's not a new account.
I'm gonna get a radi at that one live chat. Um, do it. Yeah, and I think, I think like we gotta just maybe move a little bit away from this notion of demos and into just an SQL. You know, it could go leads, SQL, sale, or even like niche if we don't want to go like SQL and be super like fancy. But either way, start putting down demos as SQL. We can change the label on it. Okay. Just so I know, like, look, I want you to— I want to know, like, if you really only have 4 this week, or was it really like 8, but only like 4 actually did a screen share demo? So it's truly 8, because if we look at just the 4, to me I'm like, oh my God, I need to like feed them, you know? Cause like, the thing is you guys are killing, you're killing it on like, once you're in conversations with someone, it's like game over. Like we're going beast mode right now. Um, yeah. So maybe just change, maybe just change the, uh, let's change the definition from demo to SQL. Okay. And then we'll still just do close rate on SQL. We'll do close rate on SQL and then we'll do like conversion from like lead, lead, top of funnel to conversion.
And then so you want to change the label in the report and in Close.io or just in how we talk about it. I got another big one I'm working on.
Really? So is he friends with any of us on like Facebook, LinkedIn, anything? Like, like we have to be top of mind. Like he's not just gonna like, yeah, I mean, yeah, he wants to be like, unless he's on us and then it's like his need was like matched to us. But I feel like, I feel like something triggered him to come to us.
Something obviously triggered, but I'm saying, is it Well, I know Eric reached out to him at one point.
External triggers and internal triggers.
I don't know.
Oh, the habit loop. There's like external triggers, internal triggers. Anyway, that's different.
I know Eric reached out to him recently because he's been digging through some of my old leads to try to revive and re—
Huh. Look at this painting behind me.
I know, I noticed that actually.
Riding bike. It's like riding bike.
Where is that painting from? It looks like a river. And a light post. Some birds. Nice hipster sleeping on the bench. Yeah, they're all wearing black. It must be New York. You leave New York, New York follows you wherever you go.
Um, all right, cool. So how have the one-on-ones been going? Uh, uh, with the team? I saw you do that with Eric the other day.
Yeah, I did it with Eric and Rod as well. Been doing them both. Um, I guess I haven't been filling out the form as well as I should be probably, but we've been going through and trying to work on little things and like coaching them through little objections and what can we work on this, this week type of stuff.
Um, Yeah.
Went through numbers a little bit with Arod and was like, hey, look, you can, you can do this. Like, you're within spinning distance.
Like, we're— Yeah, he's so good. He's so good. Yeah. The team right now, I feel like, like, it feels a little, a little light just because people are out this week, but I just feel like everyone right now is such heavy hitters that it's like, if we just— I've been trying to read so much. It's like all this shit is about is like getting the right people on the team, and I think Like getting the right people on the team, then giving them— dude, you should read this book that I'm reading, especially as you become more of like a leader, like in the company, just like in the world. But like Leaders Eat Last, it's all about like making everyone inside the organization like trust each other, because then it's like, then you're gonna go to war for your like fellow like teammates and stuff. And then it's like, you know, they have your— their back. So then if any like external conflict happens, like, you know, obviously the one I'm thinking of is like competitors and things like that, but if anything happens, if like, you know that your team, like, got you, and then you trust each other. Um, it has a lot of, like, war references, like military references and stuff. Like, you know, it's like if you're in a plane, you're on the ground, and like someone on the ground needs you, you know that the person in the plane above is gonna, like, come down and, like, get you. Uh, and then it's like, but it's like, if you don't trust the people in your inner circle on the inner team, then, like, then you're not gonna fight the outside as well because you're, like, exhausting physically and mental resources because you're, like, you're like negotiating and conflicting internally versus like you're supposed to like pack together. It's just, it's really good. I have the hard copy and the audiobook that I'm reading right now, but I think like—
Leaders Eat Last, that's the name of it. That's the title.
Leaders Eat Last, yeah.
Check it out.
It's really good. It just reminds me, and it's like, you just want the whole team to know that like, the thing that I'm, the way I'm starting to shape, like shift my mindset is like, I work for you guys, you know, it's like I'm gonna do whatever you guys need. I'm gonna try to like set everything up, but like Hannah's running this customer success onboarding implementation. Like I'm gonna help her, I'm trying to guide her in terms of like messaging, like, you know, make her accountable, things like that. But like, that's her, she like runs it and whatever she needs. And that's where I was like, I think picture myself, like I'm trying to SDR for you guys. Like I'm trying to just feed you guys, you know, we can do training. I'm gonna try to give you everything I like know in terms of messaging and then like, you know, hey, let's do these. But it's like, I feel like the team has to feel like they're trusted and that they can run with it versus— there was some example that I thought was really good. It's basically where someone felt like they didn't have the power. So they did something that totally didn't make sense. And they're like, well, why'd you do that? Well, it's like, well, that's what you said to do. And it's like the person just had no control. They're like, they knew that it wasn't the right decision and that it didn't make sense. But they're like, well, you told me to do it. And they just felt like they just couldn't make their own decisions or anything like that. Like, they were just like, like, executors of, like, someone else's, you know, ideas all the time versus, like, being able to, like, own stuff. So anyway, um, cool.
You forced me to make, make decisions by not answering me.
Like, just get it done.
I feel like it makes sense most of the time. Not really. Oh, one of the things I got to the point where in the podcast where they're talking about like, get me a car, whatever. This is why the reason I can't be a negotiator is for like, like for hostage situations.
Yeah.
Cause like my question was like, cool. Like, I don't know if I can do that. Let me figure it. Like it was similar to where he was. And then he kept asking about the car in my head. I was like, so you like cars? Like what? Like, what type of cars do you want? Like, what do you want? Like, let's talk about cars.
And just like change the how questions. If you kept listening, he's like, yeah, then you should have asked like, absolutely, I'm gonna get you a car. How do you expect me to get you a car in 60 seconds? I need to make sure that like, you know, the team isn't surprised when you come out and you get the car. So then, and then, but you got to stay composed.
Absolutely.
Because what he said is like, when you're not— when you feel like someone's trying to talk over you, then they're trying to take the power. And like, you want to feel like you have the power. So it's like if you're calm and it's like you let them talk and you let them be assertive, like they still feel like they have the power and then you position yourself as like powerless. Like how do you expect me to get you the car? I need to, you know, okay, 60 seconds is not a lot of time.
Yeah.
Cars, you know, turn them on. Yeah.
Like in my mind I was like immediately like what type of car? What do you want me to call Nick Cage? Like what? Like Gone in 60 Seconds?
Come on.
So I can't do hostage negotiation.
Well, that's been good. I thought it was— they said that a hostage in a bank only happens once every 20 years.
Yeah, that doesn't— it seems like it— I guess TV makes it seem like it happens more often, but, um, crazy.
All right, anything else? Anything I can help with?
Not at the moment.
Um, Not at the moment. Hello?
Hello?
Pay attention.
Sorry, got distracted.
All right, what can I help with?
Uh, I don't think anything at the moment. All right, you did help actually last month by upping our prices by like $15 and $25, dude. That's because that is literally what got me over the hump from $2,800 to $3K.
Oh wow, that's interesting. Right?
Well, you mean if you look at it, you— I didn't— this is more anecdotal, but if you go through and see like, like the 4 or so pro plans that I sold and then the one agency plan to Bob that we sold, that makes up that extra $100, $200. And that's like, it's like monumental.
Yeah, it would have been like 2, 3 sales at the smaller dollar amounts, which you would have had to do like 6 more demos, which is like 3 days of work. You literally just shaved 3 days of work off your time. Oh my God, that's actually a good point. I was— I'm actually— I'm about to do the end of month update for, uh, like investors and stuff, and I, I was not even gonna mention the price increase, but it's like— and that's also— I think we need to prove to ourselves. I remember when I first did it, like, we're kind of like, I don't know, because it's like, dude, yeah, it's like, you're gonna pay $115, like, the value's there, you know. I bet we could even $140, you know, and it's like, as long as like we're netting, you know, we might get a few tire kickers who might not come because they're like purely price sensitive. But it's like, you know, if we just need to position value, like value, value, value, I mean, we're like responding within seconds to these guys. We are full fucking service. We are helping them. We're going into their WordPress, we're purging their cache. I'm going into their like striking the accounts, getting our senior-level developers to implement this stuff. Like, no one else is doing that shit for like this. That's like a $1,000 service, like full, full service. We're basically doing full service at self-service prices, which is why I think we can justify—
none of this hidden fee bullshit. There's none of this extra— yeah, sorry, am I not allowed to say bullshit? You have to edit that out?
No, you can say I don't know.
You got the FCC watching this. I don't know.
Probably.
Uh, your videos look good. I'm excited to see those go live. The one where you're like walking up the dock, that one's kind of sick.
You're like, wait, wait, wait, wait, wait, who else is doing that? No one else is doing videos like that.
It's like the same video as the other one, but the background is just so obscure that it's like, it catches your eye a little bit more. Yeah, because it'll be like, like, like on the computer, you know, this, this like random guy in like an office building or whatever with a weird painting behind you.
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