Episode 089 : How to Pivot and Master Sales during a Pandemic with Gessie Schechinger

Gessie Schechinger is the laziest salesman in America as well as Vice President of Sales for OnCourse Sales Engagement Platform. Gessie is passionate about leveraging technology and automation to surpass revenue targets so he can help protect golf and bar time for the salespeople of the world.

Gessie won annual sales awards at 2 different Fortune 500 companies. His 20+ years of sales experience began in an outbound call center where he averaged 450 calls per week and blew out his quota by 297%. Unsurprisingly, he moved to field sales where he travelled 300 days a year convincing the biggest companies in the United States to open their wallet. He now spends his time educating sales leaders to utilize the most effective sales tool in the world and co-hosts the mediocre podcast, TechTales.


  • Could you just share with us a little bit about your journey, how you got into sales in the first place? Is it something that you realized you were born for or were you just thrown into that initially when you started your career?
  • So you are the Chief Revenue Officer at OnCourse Sales Engagement Platform. Brilliant, brilliant platform. Could you tell us a little bit about your platform or what it really does for an organization and what types of companies can use this type of platform?
  • Could you share with us maybe one to three things that you think a salesperson needs to be successful, especially in this space that we’re in currently globally? Sales is definitely changing, how do you see the really successful salespeople being able to manoeuvre through this time?
  • Could you share with us how you think the future of sales is going to look when we come out of this pandemic? Do you think things will change much in terms of how we sell to each other? Or do you think we’re going to return back to that face to face experience?
  • How is it that you manage to stay motivated everyday?
  • Share with us what’s one online resource, tool, website or app that you absolutely cannot live without in your business?
  • Could you share maybe one or two books that have had the biggest impact on you? Maybe a book that you read a long time ago or a book that you’ve read recently that’s really had a great impact on you?
  • What’s one thing that’s going on in your life right now that you’re really excited about? I guess something that you’re working on to develop yourself or your people.
  • Where can our audience find you online?
  • Could you share with us now as we wrap up one quote are saying that during times of adversity, you tend to revert to this quote. It helps you to refocus and maybe re strategize if you’re having a challenge or an obstacle. It’s just a little quote that kind of helps you to stay on track.


Gessie shared that it’s really interesting in the sense that what really drove everything for him was this constant yearning to try to cut corners, which typically isn’t great. But when he was a kid, he lived down the street from a golf course and he would go find golf balls. And then he would sit at this hole that had a big lake on it and he would sell his “experienced golf balls” to the golfers that were coming by.

And as soon as he started making money doing that, he was like, “Oh, this seems pretty unique.” And then as things progressed in his career, he just didn’t love listening to bosses, he wouldn’t say he was crazy rebellious but he just hated people telling him what to do. And so he was really just looking for like, “Okay, so how can I not be told what to do and still, you know, pay my bills?”

So, how is he going to figure this out and sales seems like one of those things where you’re up against a number. They give you a number that you have to hit and then you go out and you hit that number, as long as you hit that number, then you’re going to be good. It’s like the one hand you have; you want some independence and stuff.

But the one thing you do learn very quickly on is that you always have a boss and that boss is the customer. And they’re going to be the ones that really dictate your level of success or not.

Gessie Schechinger

And so, being able to kind of cater to customers and keep people generally happy it kind of saved him and giving him some independence as his career went on.

Me: Amazing, amazing. So, sales is where the game’s at. And you’re right, as a salesperson, you are pretty much your own boss, because at the end of the day, as you said, you had a target. And once you met that target or exceeded it, then you are levelled up and given a new target. So to some extent, you managed your own schedule.

Gessie shared that OnCourse is a sales engagement platform. And it’s a CRM, but it’s a CRM with a couple added functionalities baked into it. So, they were at ZIB Tech, which is the company that owns OnCourse, as it started was not a very large company, very much a small business. And they were paying for Salesforce, they were paying for Outreach they had tons of these independent tools.

And one, the spending was just getting kind of crazy because everyone’s adding users and there’s a cost and everything just got kind of out of hand. And they also didn’t really talk very well to each other. And so they wanted to create a platform that gave you all the basic functionality you would need to really take advantage of automation and sales without having to sign up for several different companies. And so, where they are really strong is everywhere, from entrepreneurs to businesses that are doing that 20, 30 million in revenue or maybe have like 10 man teams or less.

Their tool is very good because it gives you a lot of flexibility. And so, inside the tool, you’re going to have the CRM functions, so that’s your client record information, that’s your opportunity management, pipeline management. And then also, the tool has a dialler software in it. So, you have your phone system, it can do SMS text messaging, it will also do LinkedIn automation. So, if you’re selling via LinkedIn, they have a lot of great automation around how you can get that LinkedIn outreach going very effectively, as well as doing bulk e-mail, kind of that MailChimpConstant Contact type functionality.

Me: So, it’s extremely robust and it definitely can serve a great purpose for anybody who is trying to level up their sales game.

Gessie shared that the funniest thing is in sales, especially his team. So, he is having the exact same challenges that everybody else is at and so they have the traditional channels which are face to face meetings, phone and email. And those three channels have been worked. But then all of a sudden you start feeling like, “Okay, well, I’m getting a lot of noise and email.” They’re always like, “What’s that new channel, what are the things that are going to help?”

Now, LinkedIn is really good because where your email outreach but he gets all these emails every morning he wakes up and there’s a part of him that just gets happy deleting them all. He has this big number and he can delete all his easy ones first. And it just makes him kind of happy, it makes him feel productive. And so, you’re hoping that your sales outreach doesn’t become one of those emails.

And so, the first thing is really trying to focus in. He thinks what a lot of people get caught up on is that they think they need to be good at every single channel. And that’s not necessarily true. He will always believe that the phone will win. He thinks that the phone is the only way that you actually close business. And so the phone is something that you always have to have an outreach is something going when it comes to cold calling or your phone game.

Your phone game’s got to be good, but then you just need to pick one other channel and be really good at it. Now, as per your point, they don’t really have that face to face option, they don’t really have the trade shows like all of that stuff is done. And what he would say is, figure out how you can stand out above the noise and get that LinkedIn game.

And he thinks the good news about LinkedIn is that you actually know that you’re reaching the person that you’re looking for. And the funny thing is that he over the course of his career, he has been hung up on, he has been cussed at, he has had people send horrendous emails back to him. Very, very rude is, anybody in customer service, we’ve all been there.

Something about LinkedIn, it makes people polite. He doesn’t know what it is, he thinks maybe it’s because you’re like two clicks from their boss, not really sure how exactly it works, but everyone’s super polite. He’s like, “Oh, no, thank you.” “Oh, appreciate you reaching out.”

And so, that has been very, very good for them. They’ve got to double down their efforts there and that’s really helped. And the problem is, is that he kind of thinks of sales in a lot of people do, is like fishing. And so, you find like this new little spot at the lake that you think’s got a lot of fish at it.

And so you go and that’s LinkedIn. And so you’re kind of coming in but now all sudden, we see like lots other boats showing up. So now tons of people are showing up like, “Oh, boy, it’s starting to get noisy.” And one of the things that their company pivoted to and their sales outreach was, first of all, if you’re a person out there listening; don’t ever just write somebody a three to four paragraph message.

Nobody’s going to read it and they just know that you’re trying to sell something right away. And then you have like everybody, all of a sudden, everybody’s concerned with his business and wants to learn how things are. He’s like, 

I kind of don’t think you are concerned. I think you’re trying to sell me something from the start.” 

Gessie Schechinger

And so he thinks that you need to be very authentic. And then what they ended up doing was, they ended up starting doing embedded video in their LinkedIn because you might have something to say and it might be a complex value proposition, there might be a product or a service that you’re representing that does take some explanation in order to convey those thoughts. And he just knows himself; he’s like one of the worst people ever, he only reads the news headlines, like only the bold, even in college, it was just the bold words.

It’s got to be super interesting for him to get the details. So, what he found was but almost everybody will watch your video. So, if you can give it to them, get your message under two minutes, put it in a video, put it on LinkedIn, and you’re going to stand out way past everybody else. And it’s going to really help you cut through a lot of the noise that we’re experiencing today.

Me: I agree with you. Actually, when you spoke about video a while ago, I was thinking to myself, I hope he says the video is going to be short because typically, if I look on it and I tap and I see 9 minutes, 15 minutes, I’m like, “Whoa, that’s just too long.” So 2 minutes is good and whatever you’re going to say, if you can capture it in 2 minutes and capture the attention of the person then you definitely have a winning tool right there.

So you said video helps to cut through the noise. And we have to definitely take a different approach as it relates to sales and we have to try and be more authentic. I like the fact that you mention that we shouldn’t be sending 3, 4 paragraphs to somebody who we don’t know on LinkedIn. And as we know, LinkedIn has what, the first connection, second connection and third, some of the connections if they’re not connected to somebody you know, sending a note is definitely a good thing, a good place to start. But as you said, I think maybe one really powerful statement is good enough.

Gessie thinks you can just have one little statement. He also thinks that you got to make sure it’s personal. So, here’s the thing, you can send out a message to somebody and say, “I’m trying to expand my network, love to have you connect.” It’s like, “Awesome, let me help you sell to more people.” which you know is fine but if you can lead with, “Hey, I saw that we have Bill Smith in common, love to get to know you as well. Are you familiar with Bill? Do you know Bill?” Whatever, it’s this much more organic and natural because if you and him (Gessie) were at a conference and Bill knew you, he wouldn’t just come up and say, “Hi, Yanique, I’m trying to expand my network, want to be friends?”

He’s never going to do that, that’s a weird thing to do. So, he’s definitely going to come up to you and say, “Hey, Bill told me about you, you’ve got an awesome podcast. I’d really like to talk to you about it.” That’s a much more organic way of cultivating relationships. And he thinks if more people just thought about it, if you are in a bar and you had to approach somebody, lead with that line, don’t lead with this, “I’m expanding my network.” If somebody came up to him off the streets and say, “Hey, I’m very worried about your business and think I can help.” Like, “Well, what are you worried about, is there a problem? I didn’t know that I had a problem. You’re telling me I have a problem? Oh, my goodness. Tell me about it.” It just got to be real.

Gessie joked that he thinks the robots are going to take over everything. But the interesting thing and again, take it for what it’s worth. He’s a software guy; he’s into all of this kind of stuff. But what he sees is there’s some really cool stuff about pipeline management, sentiment analysis. And so, sentiment analysis, basically, people these days use the term A.I. (Artificial Intelligence) pretty fast and loose.

Really what we’re talking about is robust algorithms that weight certain pieces of data heavier than others. And as they see success, it just learns to focus on weight on those things differently. And so, one of those things that we’re going to start seeing in sales tools is because you have a tool like OnCourse, for example, shameless plug in. So, you have a tool that’s going to capture all of your action. So it’s going to see that you had these meetings with them.

Then it’s going to see the notes of how you responded, of your summaries of those meetings. It’s going to see how many calls that you made with them. It’s going to see how many emails it took before it goes. And then anyone who’s ever used a CRM tool knows that, when you get an opportunity, you have like a percentage of closes. You’re like, “I’m 80% confident that this deal is going to win.” Well, they’re going to stop doing that.

And the computer’s going to start telling us, “Hey, this guy is 70% of the way there. You need to focus on him.” And they’re going to start being able to collectively look at what they’re doing and use it as a guide. And that guide’s going to be like, “Okay, this is what has been working for this type of customer.” And he doesn’t want to get crazy because there’s nothing that’s ever going to be better than the personal connection of a sale.

There’s a couple of things that happen when you talk to a salesperson. And the first thing is,

“Can I trust this guy?” You’ve got to be trustworthy and you’ve got to be relatively friendly. It’s like,

“Can I trust this guy? And do I want to talk to him for the next year of this business?”

And so, there’s going to be a lot of credibility about your reputation and how you hold yourself. And all of that is extremely important but we can use it as an assist to that to be like, there’s a certain amount of work that he’s going to do in every single prospect in order to get them to a place that they’re going to buy. And the challenging thing for salespeople right now, he comes from a whole family, they’re just all people who just talk and sell stuff all day.

So, his father was a sales rep/entrepreneur. His father was a sales rep for Dupont back in the day. So, when he tells them that computers would be taking over sales, like, “How dare you? You don’t know what it was like.” Yeah. Because when his father and grandfather sold, most consumers were getting their information from the sales rep, they didn’t really know about this stuff.

Now, he’s got customers telling him about new competitors he has. And so, the buyers are extremely smart and so we have to kind of pivot our game to make sure that, like, okay, well, they’re smarter than ever before. They’re getting way further into the buying process than ever before by the time we’re interacting with them.

And so, being able to track and just know some of the necessary things, the boxes we’re going to have to check in order to get this person to actually buy is going to be critically helpful and he thinks technology is going to help a lot with that.

Me: I agree that the average consumer now is way more informed than they were before. And traditional marketing, at least for me personally, I don’t think it’s as effective as word of mouth. Like hearing feedback from somebody who had the experience and it was really good for them. I’m more likely to consider buying from that company or that person if somebody I trust and somebody I know and somebody I value their opinion gives me feedback on their experience versus an ad that I saw on TV or some YouTube thing that popped up while I was watching a video. Because at the end of the day, I just find that it’s just annoying.

Gessie shared that first of all, it’s certainly annoying. But secondly, they have a rule, and that is

If 30% of their leads are not coming from referrals, then they have a service quality problem. So, that’s what they kind of use as their measuring stick to make sure quality in service is good.”

Gessie Schechinger

Because to your point, you have to be having people refer your service and business to people. And if you’re not seeing at least 30% of that new inbound leads coming from them, then there’s work to do, there’s improvement to be had there.

Gessie jokes that he doesn’t even know if he is. Mentioning that we have a pandemic, he wasn’t doing a great job go into the gym when the gym was open and now they’re closed and they’re starting to get back. And things aren’t even going great there now either.

But in all seriousness, it is one of those things where you have to be doing something that you can see yourself gaining ground. So, the fun thing for them in software is when you launch a new product, he thinks this goes for any service. So, you start your service and then you realize you have all of these problems with your service that you didn’t even know about, you have all this stuff to solve and then you just start solving for them and then it starts getting a little bit better.

And then that part gets a little bit better and then, “Oh, big oopsie. Yeah, we’ll fix that.” and then we fix that, then that gets a little bit better. And you’re seeing that progress and being able to see how things are coming along. That’s probably the most exciting thing that kind of gets you going in the morning, that and fairly highly caffeinated coffee.

Gessie shared that in the spirit of being generous, he would say that, yes, OnCourse Sales Engagement Platform is necessary to all of your businesses and you should sign up right away. But also that he actually love Calendly. Calendly is very effective and it just cuts through a lot of the stuff when it comes to scheduling meeting and stuff. So, that’s a really cool thing to have but then again, he thinks it is important to have all your communication tools in one place, and that’s why they created the tool.

Me: I use Calendly as well when I started this podcast, it was four years ago. I can’t believe it’s been all that time. And it really makes it easier for scheduling, especially for people who are in different time zones across the world. So, it sinks their calendars to the time on dates and everything and then it sinks mine and it’s just brilliant and it just works really, really wonderfully. The automation makes your life so much easier with that one little link that you sent to them and they choose their time on date.

Gessie shared that he’s not going to say that he’s the biggest reader on Earth. He tends to start lots of books, finishing them is a different challenge altogether. But one of the ones that he actually had to because he had took a business class in college and they made them read it, but it ended up being like really practical advice was, The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change by Stephen R. Covey.

And so, they actually had to do that and by chapter level and then maybe it was like osmosis, but some of it just kind of got grained in his system. And so, especially like one of the fundamental things and this is something that has served him really well throughout his entire career. It’s such a little tiny thing, but it’s, it says, “If the task is less than two minutes, just do it right away.”

And just taking that is good; if it’s more than that, plan it. Because time management for him has always just been a disaster, because he tries to schedule things and then like he has great hopes and desires to the schedule, he’s going to keep and then 3 things happen and the entire thing falls apart. And so, it is a constant struggle for him to figure out, like, he can plan a schedule like a champion.

Living to a schedule is a whole other burden. And his approach, if you have something instantly get it taken care of, it’s going to take less than 2 minutes, more than that, plan it. You’ll have these windows of times you could do things made him much more productive than he probably would have been without that advice.

Gessie shared that they are working on a brand new social media management tool, that’s really cool. Basically allows you to just kind of look for articles that will post amongst all of your social media. It’s not coming up for a while. So, probably like the next two months or so. But that’s something really fun that they’re working on that he’s pretty excited about just because again and all roads go to laziness, he can’t be just focusing on every single social media, he needs one place and then just let it take care of the rest.

That and then, they do have a pretty robust product roadmap at OnCourse and so in addition to the functionality, like they’re baking in that sentiment analysis type stuff, branching and sequencing and a lot more that they’re doing around automation, that he thinks is going to be pretty cool. And they’re taking a couple of, not very traditional views about gauging productivity in sales. And so, he thinks it’s going to be interesting to see how it plays out.

Me: So our listeners listened to this podcast. They said to themselves, this guy is really cool, he’s awesome, he’s fun, I really enjoyed the conversation. And I’m thinking of connecting with him because I want to learn more about CRM and sales engagement and how to leverage sales through automation. I want to really be connected with what he’s doing and how that can help my business and my own personal growth as a sales person or even as a business person in my business or a business I work for or for someone.

  • Gessie shared listeners can find him at –


Twitter – @TheRealGessie

When asked if there’s a quote or saying that helps him refocus, Gessie shared that every single morning, he had two parents, his mom and his dad. His mom would come in, wake him up for school the morning. She would turn on the little light, the little light next to your bed, “Gessie, it’s time to wake up,” trying to get going. His dad, a different approach, came in every morning, turned on the big light, which was very jarring, not a comfortable way to wake up. And then he would say, “Today is the first day of the rest of your life. Don’t waste it.” And then he’d go out. That is the signature quote for him by far.

Me: Okay. I’m sure it’s fully ingrained in the deepest part of your long term memory to never, ever forget.

Gessie mentioned, and if you’re a parent, turn on the little light, the big light’s very abrasive.

Me: When you said that I thought of my daughter when I go in her room and I turn on a big light and she’s like, “Mom!” I know exactly what you mean.

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