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August 14, 2019 · 20 min read

Better Sales Conversions with Next-gen Software Demos with Greg Dickinson of Omedym

Do we take software demos for granted? Should we be investing more energy and attention into demo UX? CEO and founder of Omedym, Greg Dickinson, believes so. Omedym’s solution helps companies craft interactive software demo experiences, intelligently delivering answers to would-be buyers’ questions in real time.

As Internet culture wreaks havoc on our attentions spans, would-be customers ashew the traditional solution evaluation process. Customers demand instant understanding, and rapid results. Omedym achieves this by using analytics to dissect customer data and unpack the intent of buyers with instant fractional demos that answer objections on the fly.

If you want to understand the buyer’s journey, and the best way to connect with customers, this episode is a great place to start.

Greg Dickinson

CEO and Founder of Omedym

Greg Dickinson is the CEO of Omedym, a software company transforming the customer engagement experience.
Greg has an exceptional track record of creating business value out of disruptive technologies. As a serial entrepreneur and resilient visionary, Greg has spent his career piloting and converting startups into world-class corporations that enjoy hyper-growth and investor return.

Greg served in the United States Air Force, where he was the recipient of both the Air Force Commendation Medal and Humanitarian Award. He holds a master’s degree in information systems and a bachelor’s degree in computer science.

Read transcript

Ledge: Hey, Greg. It’s great to have you on. Thanks for joining us.

Greg: Ledge, my pleasure. Looking forward to it.

Ledge: I know from our offline meeting that you are an expert in demoing and selling software. Actually, taking that so far from your career to develop an evolutionary product in that space, you’re talking to a lot of product people, a lot of engineers, people who develop and sell software for a living.

This is very pertinent to us. We’d love if you’d tell your personal story just to get us kicked off, and then dive into what you and your company are doing.

Greg: Sure. Thanks a lot.

You hit the nail on the head. I’ve been in the software industry for 30 years now. I got out of the Air Force and I got right into it. Computer science was my background.

The first job I took with an enterprise company was as a pre-sales engineer. It was my job to demo the software and make it dance, and make all the customers understand and solve problems. Went on and did a lot of other jobs with that first company called Ariba.

After leaving Ariba, I did another startup and another startup and another startup. When you are the founder and you’re selling software, someone has to give the demo. I’ve always been, for my whole career, it seems that I’m the one. I love doing it, giving the software demos.

To your point we’re seeing a shift and a real big change in the way buyers are buying products today. Let’s go back 20 years ago when I was a pre-sales engineer at Ariba, the product was later in the sales cycle. In order for the buyer to get any information about your company, they had to come to you. They were very dependent on Company XYZ giving the information.

Today, all salespeople use the internet. Well, guess what, all buyers do too. They’re much less dependent, more independent. As they’re independent, they’re looking for that product experience much sooner in their buyer’s journey.

Some companies – to draw an analogy – like Aspire, or Zoom, or Expensify have actually gone to trials. Allowed you to do a self-demo by just, hey, I’m going to download the software and I’m going to play with it. That works for a very small subset.

But those buyers that may buy Spotify, tomorrow try to buy a software that’s more complex and, unfortunately, the demo process is stuck in the 1997/1998 timeframe where you’ve got to go to a person and you’ve got to have that process.

That’s what we attacked. We said, if the buyers want the product sooner – and gosh darn it you’re a software company, you’re selling software, that’s your most important asset – is there a way that we could augment the existing demo process by making the software available to a buyer much earlier in the buyer’s journey, and get them engaged that way?

That’s what our technology is about. Very simply, I’m not going to get here and get into all the details, it’s not fair to audience, we’re here today for them. Think about taking a demo today, recording it and putting an Alexa-like experience on top of it.

What our software does that’s unique is it allows Greg or someone else to walk up to a user interface and ask it questions; does your software do this? How does it do this? Where does it add value? It find the right video and it finds the right minute in the video where that is being demonstrated. It allows that user to get in, get their five or six questions they want answered, and get out.

The other problem is, our attention spans are no longer 60 minutes. The average time on YouTube is 2 mins 37 secs. That’s kind of what we’re working on but it’s all about, how do we help companies get people – the more people that experience your product, the more customers you have.

Ledge: You know about the demo-to-sale conversion then, from your experience. How critical is this for every type of software? Maybe a B2C or a less pro experience, you could give that free trial. All you need to do, “Give us your email and just sign up and give it a shot,” because it’s a simple UI and we expect it adds value, then maybe we’ll get you to upgrade later. That’s premium model, well tried, well played.

I imagine the more complex the system gets, particularly in the B2B sphere, you’re going to have to have a constellation buying process where a bunch of different stakeholders are getting in. Hard to get at that one table, do a screen share. “We’ll get everybody who might care in the room and get on the Zoom and I’ll share a screen and walk you through it. I’ll answer all your questions for three-and-a-half hours.”

It’s not going to happen, right?

Greg: That’s a three-month journey right there. Just trying to get more people on the same calendar itself.

Ledge: Right. They all don’t care and they’re working at six other vendors. That’s the human condition you’re trying to deal with.

Greg: Yeah. You’ve hit on a whole bunch of things so let’s peel it back a little bit.

First of all that trial, I draw the analogy that in the late ‘90s, early 2000s, Salesforce came out with Software as a Service. As soon as it starting taking hold, every company wanted to go that route. Every company couldn’t go that route. It took time for you to, A, make your technology SaaS, and, B, make your business model SaaS. Then, C, make your company organize around that model.

That’s the same thing that happened with trials. It’s working really good for Spotify and Zoom and Expensify, but the other statistic that says companies that have gone to trials, their conversion rate is 2 to 4%. That’s not good.

It’s because, A, the software road isn’t ready to be self-trialed or self-demoed, number one. Number two, the support infrastructure is much different for what they call a product led trial company. That was the first point you made.

I don’t really think that matters whether it’s B2C or B2B. If the company and the product are not at a point where Ledge can download it and get the full breadth of that… You may be able to download it and use one function, but if it doesn’t help you understand the whole breadth of value, you probably won’t buy it. You’re not buying software to solve one simple problem, you want to understand the full breadth. We see that quite a bit, conversion rates.

You hit the nail on the head specifically for two reasons. One is, in B2B, the buying teams now – according to all the research – are anywhere from six to nine people. Coordinate six to nine people on a one-hour demo. Okay, great. You finally get it accomplished three weeks later. Half of them forget why they signed up for the demo, the other half are doing text and tweeting and all the other things; because the finance buyer says, I really want to understand the ROI, the person never talked about the ROI; the technical buyer has like two questions, tell me about your security, tell me about this. The business buyer…

When we were selling software 20 years ago and the accounts payable person was buying it, the accounts payable person was on the phone, yes, 60 minutes was relative to that person. It’s no longer that way, because so many people use technology the buying teams are quite different.

You hit a few things that the impact, the overall demo process in general. Forget my technology. Just overall, how do you sell productively?

It’s interesting, I don’t know if you’ve seen the research, but Gartner put out a great study and one of the stats was that, today, when a buyer is going to a journey the seller only gets 5% of the buyer’s time. That means 95% of the time they’re on their own. Discovery, justification, validation, consensus.

Gosh! If your product is only available during a controlled Zoom meeting, who’s representing you at the table when they’re making the validation decision? Ledge and Greg are talking and say, “Gosh, is that company ?” “No, I don’t think they did.” “Okay. They didn’t. cross it off. Let’s move to the next one.” Bad. Very bad for you.

Ledge: Next. Right. Well, everybody’s setting up their own grid in a spreadsheet, and they’re checking the boxes. “It’s hard to find on their website if they do this thing. Let’s just call it a maybe and give them one point instead of five.”

Greg: Yeah. There’s a reason why 40% of all sales cycles end in a loss. A loss doesn’t mean you lost it, it means 40% of the time it’s no decision. They couldn’t come to a decision because the buyer didn’t have what they needed at their disposal to come to a good conclusion.

It’s really this digital buyer that has access to the internet, that has the propensity to want to learn and do it on their own.

The other thing that’s really interesting is that we do a lot of work with businesses that are selling, more B2C almost, but B2B companies selling to small SMB business. The gym owner, the dentist’s office. The doctor’s office. The florist. You know why they’re struggling? If you’re a doctor you cannot buy anything from 8:00 in the morning to 6:00 at night. You’re doing office calls. You don’t have time to buy anything. If you’re a gym owner – I talked to one the other day, she’s like, “Yeah, they schedule the demo for two o’clock. That’s my busiest yoga class. That’s when I make my money. I don’t make my money early in the morning before…”

So if you’re an enterprise company, you’re trying to sell to that market, you’re struggling with the fact that, how do I sell to a buyer that’s running a business all day. They have technology like the internet, they think they should be able to learn from you at 10 o’clock at night or 11 o’clock at night, or 4 o’clock in the .

Try scheduling the demo at that time, right? Or, “Hey, I want to do a demo with you at 8:00 a.m. Saturday.” You’re like, “What? Saturday? You’re kidding me.”

Ledge: Right. But the entrepreneur who is an operator is going to think that way. “I’m working. You should work. You want my business.”

Greg: Exactly. It’s not easy. A lot of that is really… When I started Omedym, I thought about this question of, I kept hearing about the buyers change and the Gartner research. I kept saying to myself, so what? Until you can connect the dots on why it matters to me, I don’t care. Now we’ve found that this buyer only giving 5%, the second thing is 77% of all buyers say that you as a vendor add complexity and frustration to the buying process. Well, guess what? Human nature says, if it’s hard I’m going to do something else.

So we’re really starting to feel the effects of this buyer’s world. The fact that customer acquisition costs are about 55% in five years really puts it on the table that it’s harder and harder to be running a SaaS software company successfully. Easy to start them – or easier – because the cloud makes it cheap and inexpensive, but making them successful and scaling is harder and harder.

I think that’s where companies are starting to try to figure out, how can I enable the buyer to buy? Which is what we’re focusing on.

Ledge: I’ve been the human sales rep and I’ve sort of done the demos. We all hate doing it. What we want to do is get in there, we want to close the deal with a well-informed buyer.

How do you work with clients on, okay, the product is going to step in here and take a lot of that demo crapiness off the table and make it more effective. Where does the human, people buy from people, where does the rep then step in? How does that workflow go? It’s a change of mindset then, if you’re doing demos all day.

Greg: Think of it as, we’re not in any way shape or form – and based on my background I hope you agree – I’m not trying to replace the demo. What I’m doing, I’m trying to augment.

Let me give you three simple examples. Today, if you and I said, “Hey, let’s go out and get some really cool podcast management software,” we’d go to a website, we’d read a little bit about it and we’d say, “Gosh. I wish I could see it.” You click on the ‘Request a Demo’ button. What comes up? A form. 85% of all buyers abandon that process. They bounce.

What we’re saying is, hey, if you make the demo available there then you’re going to get a wider funnel of opportunities. You’re going to get opportunities you didn’t know about because they were leaving in the past. Let’s open the funnel up and allow the product to be a customer acquisition tool, drive your MQLs, your, whatever, but allow that demo to be a part of that early buying process.

Now, let’s move it a little bit further down the line. They do engage in that and they do want to learn more, and finally they talk to the salesperson. The salesperson could say, “Hey, listen. You’ve experienced our demo online. I want to build my relationship with you.” Then the sales cycle moves to, “Hey, we need you to do a 60-minute, 90-minute, fully scripted custom demo for our organization,” you do it.

Today, what happens is that the next day or day after someone calls and says, “Hey, so and so wasn’t in the meeting, we need to redo the demo. But they’re an executive so they’re not going to sit through 90 minutes.” This happens, our customers tell us, 95 to 98% of the time. With our software, you’d record that custom 90-minute demo, make it available so that the executive and you can go back and say, “What are the four questions my team asked? I want to know what they asked. I want to know what the answers were. I want to look at the software.” They’re in and out in five minutes and they gave their blessing.

So, what we’re doing is we’re giving really that salesperson that’s worked their tail off, that built that relationship, a connection to the digital buyer that’s going to be doing a lot of the work on their own. If you only get 5% of their time, build the best relationship you can. Don’t waste the buyer’s time.

Now when the buyer is alone, provide that connection with the demo or other information they ask for so they can readily find it, get it and consume it during their decision making process.

We’re augmenting what’s there based on the fact that, hey, think about it this way. People don’t necessarily go to a car lot anymore, so Carvana will bring it to your house. Still buying a car, but I make the buying process either Uber – said, hey, people are frustrated by sitting out in the pouring rain in downtown Nashville trying to get a cab, so I’m going to offer them the same product, but I’m going to make the buying experience much easier. Say if they were Netflix. Same movie, better buying process.

What we’re suggesting is, let’s make the buying process better – same product, same people involved, same amount of attention – but give you another tool, an arrow in your quiver. Make sense?

Ledge: Yeah. Absolutely. You could see exactly where that would be useful for all those people that escaped the funnel before you could even know about them.

I know enough, at least from the enterprise space, a large enough business is not doing that evaluation at the executive level. The executive level is going to be the approver. The evaluation of 10 different vendors or what have you is happening in a delegated fashion, and those are the people that can very easily leave your solution off the list because it was just too much of a pain in the ass to figure out what it did.

Greg: Playing right along with that, one of the companies that does those recorded phone calls and then does analysis – I’m not going to get into their name but there’s two or three of them that do that – they produced a study that said that 75% of all buyers on a sales call with the inside salesperson asked to see the product within the first minute.

Well, if your process is, “Great, I’m glad you asked, but let me tell you about our process in order for you to see the product,” you’ve now frustrated, irritated the buyer. Why can’t you say, “Hey, I need a few more questions answered, but I’m going to give you access to a fully functional demo environment where you could ask your own questions, drive your own content, and you can visit it 24 hours a day, 7 days a week.”

Now, maybe that’s an opportunity that you would have lost. Now you are engaged because, like anything else, if you make that experience better for the person you’ve already started building up a level of trust.

All we’re trying to do is augment and really get past some of those really bad things that are happening because of the fact that the demo is the same as it was in 1997 when I gave my first one.

Video today and to us was consumption around play, pause, fast forward and rewind. I want to be able to consume the video my way. The way I ask my Alexa to get me something, the answer comes right back. How about I ask a video and it comes right back? A much different world for that buyer. Not end of the story, not to replace the later on custom really detailed dive into the demo but, “I want to test drive the car. I want to test drive it now. I don’t want you driving it for me because then you know where all the buttons are. I want to know how hard it is to use the radio. How hard it is to put cruise control on.” That’s why you do a demo. I want to know.

Ledge: Since we have a technical audience, from a technology standpoint, we know video then is at the root of this. You must be indexing in some way and able to click around a video so it’s like a bunch of hotspots, I guess, or something like that.

How are you actually indexing such that you can answer a question about what comes up relative to the question?

Greg: It’s a whole bunch of different stuff that goes into it. At the most basic level, you ingest your MP4 video or PDF, whatever, into our platform.

Yes, we 100% decouple the audio and video channels. Transcribe the audio into text such that I can then make it a searchable text that’s linked back to the video – because I want to know when you said ‘parallel workflow’. Then I put a natural language processing search interface on top of that so that you can ask contextual-type questions.

The user can type in a question, can ask a question. The can also look at topics. It will automatically parse out ‘parallel workflow’, ‘credit card processing’, ‘new user’. Some of our customer’s prospects want to learn by browsing through topics, others want to ask questions.

Then the third way to consume is the customer, my customer, can put a roadmap in there, like a journey for you, and be able to say, “Hey, start here. Here are some questions we think you may be interested in as a new visitor to.” We call those recommended questions. Giving that prospect a different way to consume your sales deck that you recorded and did a voiceover, so it’s now fun and interactive. A demonstration. A webinar that was conducted. Your CEO message. All those things.

People like to consume video. It’s nine times more relevant than reading. It’s retained better. People can get it right now like you and I are doing. I don’t have to sit there and get and read it, I can drive and listen. Love that.

That’s what makes podcasts grow so rapidly is, where I can enjoy your podcast is not bolted down to my desktop computer. I can listen to it when I’m working out. I can listen to it while I’m driving. It gives me time to learn when it otherwise would be dead windshield time.

Ledge: Absolutely. Before we go, let’s shift gears to your own entrepreneurial journey to multi-time startup guy. Probably learned some things along the way.

Tips for folks who are on number one, number two, and looking to make some success down the road.

Greg: I think a couple of things I’ve learned – and I will say the hard way. It’s not going to happen as fast as you like, or as fast as you read it happens. It’s always the extreme of; these four companies went from 0 to $100 million revenue in a day. Those are the extreme and that’s not going to be your business unless you’re one of those extremes.

Really understand that it’s going to take a little bit of time. Don’t get discouraged. Don’t lose confidence. It takes time.

Number two. Very rarely – and this is the case for us as well – very rarely is your hypothesis, your thesis you start with, what you get traction with. It has to veer left and right a little bit. If you are… How do I say this politely? If you are stubborn and you’re trying to convince everybody that you’re right, you’re in for a really long haul. Instead, take your hypothesis to your prospects, your audience, your mentors and get some feedback and tweak as necessary. Their perception has to become your reality and not the other way around.

The last thing is, there will be… A good mentoring network that I rely on a lot and two or three of them always tell me, “Greg, make sure you don’t get too high or too low. You’ve got to stay in the middle because you can get really, really excited. But if you do, then as soon as there’s bad news you’re going to get depressed.” Stay in the middle. Understand there’s going to be good and bad days, but as long as you’re continuing to move that up into the right, you’re on the right track.

Enjoy every minute of it, because it’s great. It’s going to go by fast.

Like I said, I’ve done four of five of these now and they’re exciting. As Keith Krach, my mentor from Ariba, used to say it’s all about scary fun.

Ledge: That is an accurate description of startup life. I can tell you that right now.

Greg: Ain’t that something?

Ledge: Cool. So if anybody’s interested in the product, wants to see how this works – I think it sounds really compelling, the experience – where do they go and how do they find out more?

Greg: We named the company Omedym – in case you forget that name, it’s ‘my demo’ spelled backwards. If you go to the website, that’s where you’ll find us. You can grab me there. I’m on LinkedIn constantly, so grab me on LinkedIn. By all means, please let’s have a conversation. I’m out to learn more and understand what your struggles are in growing your business and selling more software. I love to talk to people.

Reach out to me. Let’s have a conversation. Right, wrong or different, we’ll learn something.

Ledge: Great. Thanks, Greg. Awesome. Thanks for the insights. Thanks for joining us. We look forward to more.

Greg: All right. Thank you. Appreciate it.

David is a Managing Partner at Add1Zero where his team provides lead-to-close sales execution for tech-enabled B2B services companies ready to leap from 6 to 7 digits of revenue. He is also a co-host of the Leaders of B2B podcast. When David isn’t working, he spends time with his five kids and frequently travels between Dallas and Nashville to keep his interstate marriage alive.