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Sales Poker with Matt Wolach

SaaS scaling expert, Matt Wolach, talks us through playing poker at the office. He shares some great ideas about cross-functional contests and the secret to selling software.

You can find Matt on LinkedIn and at

Episode Transcript

Andrew Phelps: Today, my guest is Matt Wolach. He's the founder and head coach at Xsellus, a sales consulting firm built on Matt's, perfect deal process, which he developed over the course of 10 years in sales leadership at the director and vice-president levels. Today, Matt's system has helped several startups scale to over $1 million in monthly recurring revenue and led to multiple software startup exits Matt, thanks so much for coming on the show.

Matt Wolach: Thanks Andrew. Appreciate you having me.

Andrew Phelps: So, Matt, your specialty is the SaaS world and specifically working with SaaS founders. What's one of the biggest misconceptions about selling software as a service?

Matt Wolach: Well, I think one of the things that happens, a lot of SaaS founders are product or technical based and they think that in the selling process, they really need to unload everything about their product on their prospects. And so, they just tell them everything they can possibly think of about how amazing the product is because they're so proud of this product they built and it's amazing it's going to solve everything. And so, they tell every single little piece about it to that prospect. The challenge is Andrew is that that is a very wrong way to sell. The person on the other side, perceives that as just getting, I call it being thrown up on it, you throw up the product all over them. And so, they're getting an onslaught of information and it overloads them to the point where they think that it's too much and it's not going to be a very simple process. It's not going to be a very easy product to get into and the whole method of getting into it's going to take quite a long time. And so, it actually is counterproductive to what you're trying to do. The much better way is to really dive in and learn as much as you can about that prospect to really go through a really thorough discovery, really understanding all about their needs, their goals, their pains, everything you can, and getting them really, really emotional, getting them feeling the pain, feel the burn, so to speak so that they realize that they need a solution. And then the actual showing of your product can be much simpler, much quicker, and really just focused around what their pain is and by that time, you should have them emotional enough that they know that they need a solution, and they see your solution as the answer.

Andrew Phelps: Well, that definitely hits close to home for us from, you know, coming from the SaaS world and designing a bunch of products, you know, we're always so proud when something works well, so I can see why founders would be stumbling over themselves to sing their own praises. And you know, I think a lot of folks who, software is almost always about automation and efficiency to things that aren't, you know, very emotional and even if we know we need them, that barrier to entry seems so high to get into any new system, even if it's really easy. Obviously, each and every company is different, each product is different and there's a lot of nuance to what you do but is there a good rule for helping people feel how easy it would be to get into your software product?

Matt Wolach: Well, I have a fun analogy that I use for this question, Andrew and because you're so right. When you're a software buyer, and you're thinking about getting into software. When you start to think, hey, this could be a solution. You then realize, what do I need to do to get it set up? What am I going to have to go through in order to learn it? What is my team going to have to do to learn how are we going to connect it to the rest of our systems? And you start to think about all of these annoyances and frustrations that you're going to have to live through. And that's what you don't want to have happen if you're on the sales end, you do not want them to start to get scared. I liken it to they're in the road, they're trying to move forward on the road. They see your product down the road, as heaven, as Nirvana, as a beautiful, wonderful place that they want to get to, and they see the product so good that it's going to be perfect for them. However, in the road in the way is a giant scary monster. That giant scary monster is your onboarding, the training, the integrations, the setup, all of the nastiness that is making them not want to go through that monster to get to the promised land. And so, the real challenge, Andrew, and you brought up a great point is how do you make that monster smaller so it does not look as bad. You make the onboarding, the training process sound much more smooth that you're taking care of them, you're holding your hand. And then what you have to do also is get them to look behind them or at their current situation more accurately and make that monster big and scary and make them feel like the current situation that they're in. What they're dealing with. What they're living with now is so bad, so horrible that they've got to go through your tiny now little monster to get to the promised land.

Andrew Phelps: That's really interesting. So that's all about probably creating some strong comparisons and helping them understand how much time they're wasting without your product.

Matt Wolach: Exactly.

Andrew Phelps: But I feel like we could talk about this for a couple more hours, but the reason you're here today is to talk about your favorite sales game, poker. Can you tell us how to play?

Matt Wolach: Yeah, exactly. Well, I have loved poker. I was taught by my grandpa a long time ago and I've always loved poker myself. And so, on my sales teams, when I was growing SaaS companies, I would love to play poker. And essentially what you do is you come up with some sort of hurdle that they need to cross to get a card. You can, depending on the role could be a different thing. If you have an SDR, it could be they book a meeting if you have an account executive, it could be that they sold a deal, or they crossed a certain threshold in revenue, whatever it is, make it something that should happen a few times a month. And you can even do this. I like making sure that the whole team feels involved.

So, admins or coordinators for their role, they should have some sort of benchmarks. Essentially, once somebody crosses the benchmark, they get a card and you just out of random, pull a card out of a deck and hand it to them. And throughout the month, they're getting these cards at the end of the month, you get everybody to reveal their cards, their hand, and whoever has the best hand, or can make the best hand out of what they have, wins. And you have some sort of fun prize, depending on how you're set up. It could be cash. It could be, you know, a gift certificate or it could be whatever you want. But essentially everybody has a fun time trying to accumulate as many cards as they can so that they can try and get the best hand. And, you know if you have five cards, you have less of a chance. If you have 10, 15 cards, it gets a lot easier to have a flush or a full house or a straight flush when you have more and more cards. So, you find people starting to get really, really motivated to try and get more cards and you get them really excited about more cards. They start comparing to each other and they realize, hey, I'm behind that guy has a full house. This person over here has a flush. This person over here has a straight, I better do more if I want to beat them. And it gets to be pretty fun. People have a good time with it.

Andrew Phelps: So, you mentioned a month, is that the recommended play period for a poker game?

Matt Wolach: I would say yes, because if you go any longer then people start to lose interest. So, within a month, it's much easier to kind of capture, even if you're based on quarters in terms of your sales numbers, which would be more of an enterprise type focus deal but within a month you can still put in parameters. Maybe they had this many meetings, maybe they got this many follow-up calls, whatever it is, you can figure out what the right parameters are. That would give them a few cards a month and at the end of the month, let's put our heads together. Let's figure out what it is. And maybe your first sales meeting of the next month. Everybody revealed their hand. Who's got the best hand. Boom, there's our winner.

Andrew Phelps: Gotcha. So, there's a lot of different kinds of poker. Are there any community cards like Texas hold them or does everybody just have their one hand to themselves?

Matt Wolach: I think that's the beauty of this. You can kind of have some fun and say, hey, I am taking a seven. That's going to be the community card. You can play off of that if you want or not. I haven't done that myself, Andrew, but I think that's a fantastic idea. And you can always kind of move things around and play with it a little bit to see what's best for you and your team.

Andrew Phelps: Great. And so obviously one deck of cards would limit you to how many people can play. But if you have multiple decks of cards, is there any limit to the number of people that can play? What were the size of teams that you like to play with?

Matt Wolach: Well, I've had teams of 20 or 30 people. So, you need multiple decks of cards in order to do that. It's totally fine. Yeah. You're going to have three, you know, queen of hearts. Oh, well, it's more about what hand can you make yourself?

Andrew Phelps: Yeah, I really love it because it is infinitely scalable. So, you know, one of the things I love about this is you said you could have a cross-functional team. You can have salespeople playing with admins, playing with customer service reps. You know, do you have any tips for how you might make sure that, you know, goals are fair across different roles?

Matt Wolach: Yeah, absolutely. I think that's a big question, but just to make it a bite-size for this conversation and the game stance which you probably were thinking about, I would say you have to look at before you create the game, hey, I'm trying to find, I want to make sure people get somewhere between five and 10 cards a month or five and 15, somewhere in there. What in each role needs to happen for them to get that and how can I incentivize them to do things that we need them to do as a company so that they get this many thresholds crossed, this many cards and it motivates them to accomplish that? Yes, it's going to be a little weird because you have, like you said, some cross-functional stuff happening, but if you can figure that out and get it to be about right where everybody thinks it's pretty fair, it can be a really, really cool motivator.

Andrew Phelps: Great. So, we know that games are a super valuable tool when you need to move the needle. You know, maybe it's the end of the month. Maybe it's a down quarter, maybe it's an up quarter and you're just trying to crush the goals. But you know, we play games at specific times for specific results. If you overplay them, they lose their power. Is there a specific scenario where you recommend, you know, playing poker or another game? You know, what are kind of your triggers when you, as a manager thinking I need to get something going here?

Matt Wolach: Well, I mean, I think at some point it may play out. I mean, when you start seeing the team, not really, you know, not really motivated, like they should be. It's something that you need to recognize, you need to say, hey, the numbers have kind of started to slow. The trajectory is kind of starting to flatten out. Let's get some new life and sometimes a new game can do that or a new incentive. I mean, one of the things that we always did was every time we hit a new record team dinner. Team, we're going to take you out to a nice, awesome, nice restaurant dinner. And every time that the team as a whole, hits that new record and breaks that record, it's another opportunity to do that. So, you're constantly having them work for a fun, you know, dinner and a night out on the town.

Andrew Phelps: We've heard, you know, all sorts of fun prizes on this podcast, breakfast burritos, $1 scratchers, you know, a nice restaurant. Sounds great. Were there any other prizes that were your favorite go-tos with the poker game?

Matt Wolach: We did a lot of gift certificates. So yeah, obviously nice dinners. There's cash prizes sometimes, I think every month, if you kind of mix it up at the beginning of month, you say, here is what the prize is going to be for this next month. Here's something to aim for. That would always be something. I think those monthly prizes, we made a pretty tame, I would say maybe a hundred dollars or a gift certificate, or maybe if you really need a big month, you might put a 250 or $500 bonus out there. Something around that but we would also do big prizes for more annual stuff. Like we would have president's club, we're going to fly to somewhere. We're going to take you on a trip so that you can start to get more and more depending on what you need to have accomplished essentially.

Andrew Phelps: Awesome. So, I'm going to give you my takeaways because I absolutely love this game, mostly for its simplicity. As we've learned on this podcast, it's all about using what you know, and adapting it to, you know, add a layer of interest, engagement, and fun you know, into the workplace. So, the first takeaway, and what I love about poker is that it's easy. You just need a few decks of cards and if you don't have those, they're really easy and really inexpensive you know, inexpensive to acquire.

The second is I love that you've played with cross-functional teams. And the big takeaway you shared with us is when, whenever you're designing game poker or otherwise you should start with your desired results. So, if I want my folks to hit a certain threshold of meetings for the month, then that should coordinate with the number of cards that I want them to get, or the number of cards they may need to make really good hand. And finally, what I liked is that you said a hundred dollars for a monthly prize, and that's another thing that we hear over and over again. It's not about how much you invest in the prize itself, it's about the game play experience. So, if you can go to the dollar store and buy a couple packs of cards for a dollar each, and then just put up a hundred dollars gift card you've spent, you know, let's say $105 and you have a team of 20, 30 or more sales reps, you know, really enjoying themselves, being present, closing more deals, you know, all for the cost of a one person at that fancy dinner.

Matt Wolach: It's pretty cool. Yeah, I'd say those takeaways are spot on Andrew, and it's pretty amazing what can happen with just a small amount of investment.

Andrew Phelps: Well, I really appreciate you coming on the show today, Matt. If people want to find you online, what's the best way to get in touch?

Matt Wolach: My website is probably best. That's, M A T T W O L A C I'm also really active on LinkedIn. So, you can just go to LinkedIn, Matt Wolach, and you will see me there.

Andrew Phelps: Thank you so much. I'll talk to you soon.

Matt Wolach: Alright. Sounds great, Andrew. Appreciate it.