The Bowery Capital team had a conversation with Brendan Berry, a Director of Product Management at Ripple, centered around the current state of cross-border payments and what the blockchain-powered future means for international payments.
This is a transcript of the Bowery Capital Startup Sales Podcast – Making the Most of SaaS Trials with Will Batson
MB: Episode one of the Bowery Capital startup sales podcast. Welcome listeners, I’m in the studio here today with Will Batson. Will spent a very long time at ClearSlide. He’s going to talk with us today about making the most of SaaS trials. Welcome, Will.
WB: Hi. Thanks a lot, Mike. I’m really excited to be here.
MB: So give me a little bit of a background in you and ClearSlide, and just for our listeners set the framework for who you are, where you’ve been, and what you’re going to talk about a little bit today relative to your company.
WB: Yeah, sure. Again, excited to be here. I graduated school, I moved out to San Francisco. I think a lot of people move up there with the hopes and dreams of joining a great startup and really making it big, and I got lucky enough to join a company that had some co-founders who’ve done it before. So I joined some other first employees, we two or three customers that agreed to sign on just from a quick… credit card down and this is what we think we’ll have, and they agreed to it.
And so since then, we’ve raised 90 plus million dollars. I’ve started multiple teams for my customer success to adoption to team to enterprise sales team and then business development and definitely very exciting and, I think what we’re going to talk about today is a relatively new space or change because of cloud technology and SaaS trials. They’re very different than how you could sell previous products because of the barrier to entry and just how easy or hard it was to get someone into your product and truly experience it. So yeah, I’m very excited to go for this.
MB: And just set the framework for the listeners, so you started very early on. You are a, if I remember correctly, first revenue-related hire that they made, right?
WB: Yeah. So came in purely sales. So this was pick up the phone in a room about this size.
MB: We’re in a very, very small room right now.
WB: Yeah, you could… I could lean back and slap my my other co-worker give him a quick high five my other co-founder Jim what was in the room was well. And so it was pick up the phone, dial, pitch… revisit sales, and then you get 10, 15 minutes of feedback afterwards.
MB: Sure. And from a customer standpoint, you guys very early on implemented the concept of trials outside a few POC customers or people who you knew that it was really the way you started the business plan.
WB: Completely, completely. And I attribute a lot of our success, I mean obviously the product has to work and has to be great. But the trial has been… when you start off the brand, you have no… the inbound leads aren’t exactly flowing. We haven’t raised the money at that time. We were completely bootstrapping and made 42 grand in my first year out of college.
We were purely dialing for dollars and the trial allows you to not have to completely sell someone in the concept without proof, right? I think that’s fair. Only true tenants of SaaS technology is you can… the product has to work, right?
WB: It doesn’t have to improve itself in the first two weeks’ usage that you’re closing more deals or you’re converting more leads or whatever your product’s trying to do. But eventually, it has to prove itself. So the customer’s going to cancel in six months or a year or two months if it’s not going to work and so yeah, the trial’s critical to winning more customers and everyone in quickly.
MB: Sure. How did you guys think early on about is a trial right for my company? We obviously see a ton of business software that comes in trying to think about free or freemium or trial-based businesses. How would you encourage entrepreneurs to think about is this right for my business?
WB: I think some of the obvious things to think about are how long does it take for the customer to experience a relatively large portion of a value. It doesn’t have to be 100% of that value but 70% or 60%, whatever gets them over that threshold of wow, I need to commit to this business because it’s better than my existing solution or the hodgepodge of solutions I use as a… anyway, in midst of it.
So definitely, how long does it take to get value? So if you’re a founder, how long or how short can I make that time to log into our solution and getting that wow moment and instant gratification that can instantly get someone hooked and what. It’s just like the apps, right? If you’re not getting someone to immediately experience value and then be able to quickly send push notifications that… the welcome back and experience the solutions, you’re shooting yourself a foot. The other thing is does your solution actually work in very short period of time to prove value.
WB: The CRMs are… even kind of e-signature solutions, DocuSigns. They’re not really needing to do trials per se because the end user doesn’t really matter at the end of the day. Yeah, the user has to be able to use it and usability is always going to be important in any technology, but the level of importance and usability for a DocuSign or CRM has always been much lower than the solution that sales reps are in everyday using, so like LinkedIn sales solution, right?
WB: People didn’t find that usability very easy. And so if the end user doesn’t really matter. Your CFO is not going to decide to go at EchoSign, DocuSign, based on… end user feedback, right?
WB: Here she’s thinking how does it help me sort contracts more easily. Is there a workflow that I can put into place easily that guarantees I’m not going to screw up, right? They’re thinking about themselves and not the end user that much.
WB: How hard is it or quick to be able to experience that value and then probably the 501 is you can actually approve that value pretty quick. If people just get in, take it’s cool, but don’t really get much from it, then it’s probably not the thing you want to do.
MB: Sure. And relative to ClearSide, what were some of your… so you guys obviously launch the free trial and you’ve come a very long way from this point. What were some of the learnings early on or you eat that dog food, if you will.
WB: Yeah, yeah. I think the real learning that took place early on is how important it was to truly understand the workflow of your customer that you’re selling to. Yeah, I think… maybe this was a naivity of being out of school. You think, “Hey, I’m going to pitch you this products and you’d be like, “Wow, this is awesome. You should instantly see it and buy it and use it.”
MB: That’s not the case.
WB: That is not the case. Until you’ve learned every aspect of their process and where you fit in between, you really can’t convey that value as well as probably, I mean as well as you need to. And then understanding that any aspect of… and you’re end users using your product that outside of maybe your perview that can effect of impact the trial is actually your problem, right?
WB: So if your a automated dialing technology. Well now, part of their solution is you have to give them 200 email addresses and phone numbers. Well, their technology might be great at connecting your people, but if your phone numbers are terrible and the emails are terrible or the context are terrible, the other technology’s not going to work. So who they go partner with instantly… all the data companies.
WB: Because they know if you’re not getting phone numbers, the trial’s going to be worthless.
WB: And so I think a very similar thing can be said about a lot of other companies. You got to make sure that every input that’s a part of your… the end user using your solution has to be spot on. So whether you’re partnering with other players or you’re building it into your solution, you got to make it so you can control that whole demand. Or just take a step back and don’t even do the trial because yeah, you’re just going to shoot yourself in the foot.
MB: And how did you guys early on really understand that workflow of an end user because it isn’t like a founder would have that knowledge built in. So…
WB: Completely. I think that’s… a lot of it effuse that first deal that you thought you had them back.
WB: You lose sleep over it and you trace the steps back and say, “You know what the hell happened here?” I think the other part of it is – and this is why I highly encourage founders to not even bother with enterprise sales rep early on or the more senior salesperson – you got to hire and even just a salesy person in general. You got to find someone who’s truly inquisitive. It’s not about the money or short term. It’s all about how many deals can I close or how many case sneak past the customer.
It’s got to be that very… very interested learning, again really inquisitive, wanting to ask tons of questions. It would be really friendly to get the customer open up and share what’s going on, what’s not going on internally. That is where you truly can learn this is where we were faltering in the process, which is why actually early on, we try to do this group call at the system. We will do a group training call and you could realize you get everyone hates conference calls right.
WB: Even if you are in person, everyone dozes off.
MB: But just walk the listeners through that.
WB: Yeah, sure.
MB: What did you guys do specifically as it relates to that?
WB: Yeah, I mean so early on… anyway, I think… the thinking was, “Hey, we’ll just get the sales leader on the call, they’ll bring up, “Hey, I really like this technology. I want to try it out, yada, yada. We have two, three weeks, whatever.”
We would just walk them through the product and how you use it and we found that A, no one pays attention to calls. B, that explicitly telling someone where in our sales process they should use our technology or if we’re in another technology, where in your day to day life you should be using this. They don’t connect the dots. Maybe 2% would connect the dots and you can call those people and get them to tell the whole group that, “Hey, this is how you should be using it” but you’re going to understand that stuff before you walk into a room and present to 10, 50, 500 people.
WB: And so we really learned early on is don’t do group call unless a couple of things: A, you have an internal champion who’s going to pause the meeting whenever they have a point of like, “Hey, this is where you should use this.” Or just don’t even bother with the group call. What we like to do early on was one on one calls, you’re able to… obviously your price point has to justify that at that time.
WB: But if you can… your price point justifies at that time and I would say I think it took to win enterprise software, you need a price point that justifies that time these 5 and 10 or $15 user price point.
MB: Sure. That’s challenging, right?
WB: All those solutions sell to one person. They saw the ops, IT, marketing, head of sales. And then they just pitch and walk away.
WB: Maybe do a short trial or whatever, but it’s not real change in workflow and real optimization of workflow. So in a one on one call, you’re going to get to know the people, you’re going to have to ask a lot of questions by the fifth call. You could hand off the training to someone else because you know there are process so much. You get on the vernacular for selling to an ad sales team. You’re going to be able to talk about RFPs, you’re going to talk about the need to be able to get the analytics on whatever, whatever that usually otherwise wouldn’t know.
WB: And so when they… when you have trained that six, seven, eight person, you can bring up, “Hey, here’s in your workflow how you should use our technology versus just here’s our product and this is what it does.” Talking about product stuff versus how to change your workflow is a completely different talk.
MB: Right. And so you would abdicate especially in trial environment’s one to one conversations between sales person and prospect.
WB: Into… one… a big thing to say is you can sell anybody. You should be able to sell any company if your roommate worked there. If your roommate works there and your technology is worth half it’s weight in gold or whatever. You should be able to sell it because you’ll know the entire process. You know where in cross you’re going to sell them, paying where… what the terms are called, what’s actually important in solving versus not important in solving.
MB: But what if your rommate doesn’t work there.
WB: Yeah. And so if you really just working, and that’s the value of the one on one call, right?
MB: Right. Sure.
WB: So it’s one in ten… I used to say one in five, one in ten of the first people that you get into that trial whether… it doesn’t matter if technology. One is people has to be your best friend at the end of it.
WB: If you’re not, I mean every time we would pick up the phone to start that trial, it was what make best friends… one of these people has got to be my best friend because I need to call that person to get me proof points later. Hey, this is why it was so helpful. I’m going to need this person… some of these people to give me intel on who’s the major players in company who’s… how does this process actually work. You can’t get that from a group call.
When you… and also when you do group training, you don’t actually get people in to the technology, and any of you do get into technology, there’s kind of laxidasically going through it.
MB: Right, yeah.
WB: If you do group call, you run a risk of… when you call them back to actually walk them through it then saying, “Oh, I saw the demo. I’m good, I’m fine,” versus you get them on the phone, “Hey, what is this thing? I never heard of it perfect.”
WB: You get the chance, ten chances to screw up your pitch. Whereas in the group call, you’re all in that one call here.
MB: Sure. So ClearSlide launches, you had some concept of SaaS trial in place. You start to have let’s call it some success. What do you know or what’s… how did you guys determine wow, this is working or…
MB: This might not be the best use of our time or…
MB: … paid in capital type of situation.
WB: I think very early on and even just the start. We’re always very lean, it was always… you’re going to pay for yourself in the first three months. I think it was a pure revenue number. I talked to a lot of co-founders that will scoff at that like, “What? You need to pay for yourself instantly?” Some of these stuff that I think too many founders hire too early or they’re tired too many too early. I’ve no problem hiring two or three sales people however relatively junior, but still fairly good to go figure out what works. Before you’ve cracked that code, you written that cookbook that you can repeat fairly regularly. No point really, no hiring folks.
So I think it’s… when you can tell, “Hey, I need to pour more gasoline on this fire is none of your leads are inbound or a large portion of leads aren’t inbound. It’s not friends of friends hooking up with deals. You can count… almost fully sustain a new person coming in, purely outbound sales without… yeah, its awesome if you have ton of inbound leads and…
WB: … with people and then start closing deals. Well, yeah. Yeah, you should bring them in.
WB: But I really think that’s the critical pieces. Can you bring in someone new, and no need to go hire ten people for yourselves. Hire one or two and have them sustain themselves in two, three months and be closing deals right away.
MB: But what about on the trial side?
WB: Oh, we got some trial side. Yeah.
MB: What was success for you guys or how did… assume you’re a founder, you listen to Will’s advice.
MB: You go out and you start a free trial. You look back in three to six months and you got a bunch of numbers. What did you guys use that’s parameter for success.
WB: Yeah. I don’t even think we ever looked at we’re not going to do a trial. I think part of that was… and people just like our technology. The end users love it, and that’s probably our biggest strength is that users love it. If that’s not your biggest strength, then the trial might not be for you.
WB: And so…
MB: Maybe literally translating what were you benchmarking then? What were you using as a framework? Was it trial to convert… conversion or what were some… give the listeners some idea of what to think about when they’re…
WB: Yeah. I mean… so we were looking purely at MRR can a rep hit 3 or 4 K or… per month in revenue number off of trials. It doesn’t have to be all deals that you close that month, but from the growth of those trials I had just started. I’m on three, I’ve only closed one deal but that deal I closed is also… the deal I closed last month is growing 2X, and so it’s… I think it’s just can you sustain… I think early on, all you really care about is revenue.
WB: And this is thing growing. So if you’re not… we’re closing… our close rate historically has been 50 or 60%. But then it gets even higher as you get more users in. so if we had… I think we’ve only lost one deal that had over 100 users in a trial. Whereas if two or three people or five people… I think it all goes back to this, which is the… it’s where I probably got SAS. You’re not… it’s pretty obvious if not going to work out, right. And so very early on in the trial, you can pretty much tell.
WB: When we talk about closing calls and SaaS, the work should already done. At that point, it’s just posturing for deal size and price points versus we signing up or not.
MB: Sure. So maybe just to transition a little bit on that point, how did you think about that nuclear option? What were some of the issues you faced? Think about when do you pull the plug, someone’s just definitely not going to use the product thinking about how long do I let them stay in this free trial world.
MB: So I don’t know if you guys had thought a lot about that
WB: It actually was a very much evolving thing. We… the head of our company early on a couple of big trials like if you got a… just getting shut off. And so maybe I should learned trial by fire that back to urgency by the customer from my boss doing my workshop …
MB: Ended up resulting in some way.
WB: In some great wins. It’s the, “What do you like? I’m here to help you. We’re in this together. I feel like, especially in SaaS, you’re in it together with the customer, how you’re pretty much married because if it’s not going to work out in six month, we’ll then I don’t want to waste my time with you. And same thing, you’re not going to waste your time with me if this in invaluable.
So we learn very quickly was you go them, if you put urgency on them like you got to sign by the end of the month and my boss is pulling the plug there’s usually some urgency, right?
WB: But you’ve got to have people and using it, right? And so I think the real thing we learned was no need to even discuss pulling the plug until you have them hooked, right? if they’re not hooked, don’t even bother. And so when people talk about how long should a trial be, well you can give them a two, three-week number. You want to make sure that that’s not going to inhibit a rep from… or whoever user from going in and using it because it’s on so quickly.
So you definitely keep the length long enough that they’re like, “Hey, I can get some value out of this even if it goes away.
MB: And we give grant extensions of…
WB: But… and so there’s… that’s how you sell it, right? It’s all how you sell it. Its look, I understand… you go push on them… like it was only supposed to be through your trial. We agreed on this last week.
WB: But then it’s the relationship with you and that business owner. It’s look, well it’s out of my hands. Out budgets are frozen or whatever, you need to believe it. And if you don’t, then you have to push back. But then again, you always has be in a relationship thing and you push on them if they don’t have a good reason and it might… it’s probably because they’re just not bought in. But if they’re bought in, then they either come or committed to sign or they will give you a legitimate reason. Then you go back to your boss and what do you actually do go back to your boss or not, you get that extension.
It’s a very transparent process in terms of they’re either bought in or not and we… we’re either showing off or not. I think the one time we turn someone off too early completely backfired. People are mad that they spend this time in your service and then maybe turn them off. I think it should always be the… “Hey look, I don’t want to turn this off but man, my hands are tied here.” And so you’re just getting them to help you out.
MB: Would you have the monitoring process or trial review process internally that would allow you to surface people who had…
MB: These people who are 30 or 60 days into their trial, what’s going on here, can you…
WB: Yeah, I mean I think once they bubble up to the your committing this deal or it’s potentially closing, so once the committee’s getting a value out of it that it can bubbles up to management radar then yeah, you’re going to be and it’s going to be… getting brought up in meetings. Sales leaders always going to want to close your revenue and the reps trying to make sure the deal actually closes without…
WB: … the customers saying, “Hey look, you said you could give me more time.” They’re just not ready, whatever. It’s just manning the process.
MB: And was there a sort of indicator from a day standpoint or a time standpoint? I mean you usually tell if there’s certain period of time now that they were or they were not going to buy.
WB: Yeah. We definitely had a lot of great, I mean every sales company should build… start to build, start with, or before they even get trials going, have amazing internal metrics on usage and how, when, and what products people are using and how often so that you know who the people are that love your service and you should focus on. And so usually have that info, and then we even have an internal dollar amount based on usage and the hour in we came together.
MB: From… in terms of cost of ClearSlide.
WB: Less cost of ClearSlide and more, “Hey, we think based on how they used the product what we think they’ll be worth or they’ll pay us. What they’d be willing to pay us.
MB: Got it.
WB: Any solution would do this. You’re linked in sales solution, you can call trial. Ten of the twenty users have gone in and done 50 searches. Six have sent inmails, and of those six, five have gotten replies or 10 plus replies, but what does that mean in terms of value. Looks like they’d be willing to pay X.
WB: From historical data. And so it’s all about calling and driving the option from that LinkedIn self-solution rep standpoint to that more people get inmail replies, so that more people get new meetings from inmails.
MB: Sure. I guess final thought to both the discussions where you guys are at now. Ninety million in capital, paid in capital, tons of customers, you just look at the ClearSlide website.
MB: It’s the who’s who of pretty much every industry. How many of those customers or… what has changed, if anything, with that trial piece of business? Are you still… you’re just now closing larger accounts through the trial?
MB: Are you having moved towards the direct sales effort on top of the trial? How do you see the world today?
WB: We…I say this a lot internally and it’s going to sound bad externally. I think our biggest challenge is we’ve had too much success early on. It’s the old saying, or not saying but just a lot of small businesses fail because they’re too successful. They have too many people coming through the doors.
WB: And so they get a bad impression of their service well no one got a bad impression of our service it’s more that we had to run around behind the curtains like crazy people trying to make up for other people at the company or a lot of internal processes in place or too much manual stuff to be done. What I think is changed, we’ve always been able to sign… I think two years in, we signed… or year and a half in, we signed a 500 plus user and bring them in off of the chart.
We started with approved concepts for two or three months with the biggest data company in the world. They went from… we’ve got five people on this on a free trial to selling the head of sales on approved concept for three months for 50 people.
WB: Well, we obviously let them have as many people there as they wanted. You get 250 people training up on the service. It makes it pretty easy for the head of sales to say like, “Everyone should have those because look at the rate we usually got.”
That’s just something that a six-person company can’t do without a trial. They must’ve had connections, and very hard to go out there and hire on connection on your six-person company without funding, right?
WB: So that just shows the power of trial But I think it’s changed to answer your question is it’s a lot of that… it all comes down to just being more official and have more processes. So before it was just pour tons of gasoline on the users, how you run a call, how do you… we used to have – we don’t do this anymore, which I think why my team mind the sharing – when you log in, our phones will ring. I would literally get a call saying, “Mike, from Bowery Capital just logged in to his account.”
I would press one, it would dial you. “Mike hey, how’s it going? This is Will from ClearSlide. One of your co-workers actually added you to the account so that you walk through it.”
“Oh, no way I just logged in for my first time” “Oh, no. that’s perfect timing. Let me walk you through it.”
WB: And I can’t tell you how many deals we got going from that. Just the… maybe they would’ve closed anyway whether it would’ve but the number of people we got on the phone, whether random sales leader or sales in a different department that actually liking the solution more than someone else, that was just awesome.
But what changed now is it’s a much more, especially in enterprise sides, it’s a much more… in codified system, it’s…
WB: Look, we know were going to come and present to you that hey, we’re going to do a free trial for a set period of time, month, two months tops. We’re going to buy in from the tops. We’re going to understand your org so that we get buy in from all levels of sales managers and then when we do the trial, we’re going to make sure we get enough power users to the point where we can really collect those data points that then go back to the sales they represent.
A business case that says, “This is how much revenue I’m going to make for you.” And whether you tweak the percentages from a conversion from this stage or that stage lower than two or three percent, 10%, whatever, it doesn’t matter. We’re still going to make you money. Any time, you’re selling a solution that’s under… even a SalesForce can get away with this 250 / 300 bucks per person. If you’re increasing the efficiency on top of the salary in person or total person that’s making over 150 a year, 100, it’s relatively easy.
WB: Our total cost annually per users five to seven, 800 bucks a year. It’s pretty easy in the grand scheme of things, one rep closes, one extra deal when I deal sizes are worth a $100,000 pays for solution 2X, whatever.
WB: So I just say it’s more codified we do. We do team trainings now. I’m sure we still have the army of folks that help support to make sure that hey, even this one, I get an email from a user I’ve signed three years ago. He was having trouble with… I couldn’t finding something in his account, right? You’re still going to have that stuff, but you just grow up on the process on how you do things. But no need to do it until you’re winning tons of customers, right?
MB: Right. I think we’re out of time.
MB: Will Batson from ClearSlide talking about making the most of SAS trials. Thanks for coming, Will.
WB: No problem.
MB: Appreciate it.
WB: I definitely appreciate, Mike. Thanks.
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