Sales Engineering discussion with Greg Holmes

Published on: June 3rd, 2021

Guest Speaker


Greg Holmes

Regional Vice President of Presales at Apptio

Greg Holmes is a sales engineering leader with more than 20 years of expertise in presales. Greg has helped founding the leadership collective at PreSales Collective and is instrumental in providing various resources to the presales community through his articles and Clubhouse interactions.

About the Podcast

In this week’s episode of Proof is in the Pudding podcast, Vik is joined by Greg Holmes, Regional Vice President of Presales at Apptio. Greg shares his views on the evolution of presales, best practices for POC, product evaluation process, his contribution to the PreSales Collective, and more exciting topics.


Vik: [00:00:31] Hi, today we have a guest in our podcast, Greg Holmes. Greg is the Regional VP of Pre-Sales at Apptio. He has worked in pre-sales leadership roles for many years, and he has been pretty active in PreSales Collective and he helped founding the leadership collective at PreSales. Hi, Greg, how are you?

Greg Holmes: [00:00:51] Hi there, Vik. Good to meet you again.

Vik: [00:00:54] Good to meet you too, Greg. I think we have been discussing for a long time and finally we managed to join here in the podcast. So, thank you so much for your time.

Greg Holmes: [00:01:02] Yeah, absolutely. It’s good. Good to be here.

Vik: [00:01:05] Sure. Uh, how about we start with, uh, your journey in pre-sale. There is always an interesting story there. Um, how did you get into presales?

Greg Holmes: [00:01:13] Yeah, for me, it was, was back in the depths of time, of course, but, uh, it was quite exciting. Um, I was a graduate from University of Sydney. I’d worked my way for university doing coding.

And, you know, I felt I was going to be an application engineer. Right. So, when I graduated, I found a local software company in Australia, um, who was looking for people for graduates to join them. Uh, but I was joining as a consultant and it was funny because I got through the interview process and everything really well, you know, it was quite exciting.

They were using some of the latest Windows features there, Windows server features to launch software deployment and things like that. But, um, when I joined, they were asking me on, you know, just as I was

[00:02:00] joining the organization, do I want to be, um, more of a presales consultant or a post sales consultant? And I didn’t really know what the difference was or what it meant at the time. So, I just, I thought for a few seconds and leaned on the presales, since it was little bit more exciting. Um, I don’t think it came with any, major differences as opposed to just the kind of work that I’d get exposed to at the early, early time.

But for me, it was really exciting because it was more about meeting people, you know, selling the software for the first time going in and discovering what the challenges for our customer was. Um, and I did my fair share of, of post-sales work as well. Uh, but I, I did find the, the pre-sales aspect really interesting and a great way to get started.

Vik: [00:02:46] Yeah, that’s a great story. I have known you for a while, and I know that you are pretty active in the pre-sales community. And like we talked about you are a, you have helped founding leadership collective at PreSales Collective, which is amazing community. I also know that you write on the, and there’s a lot of content for the people who are listening here.

How, how have you seen the pre-sales evolving over the years and, um, the kind of attention it is getting now, how do you see it now?

Greg Holmes: [00:03:15] Yeah, I feel like there’s been massive change right. Now, there are plenty of resources for people, right? You can listen to podcasts, you can read books. There’s plenty of websites to look at, you know, there’s organizations to join and help you build yourself up.

Uh, which is great. I encourage people to try all of those things and build themselves up as in pre-sales and make it a, an exciting part of your career. Um, but, but I’d say back in the beginning for me, there wasn’t much. Um, you know, outside industry things to help you. Right? Um, some of my favorite books I did read and, and helped me along the way.

So, I I’d call out the Great Demo book by Peter Cohan. Uh, say, call out the Mastering Technical Sales book by John Care as two of the things that really got me going and in the early days and, and understand what the role was about. But I think you, you had to do a lot of the learning yourself as well.

Right? That’s why I started a blog eventually was, was to really help myself get my ideas out there and straightened out and get comments back from, from, you know, the, the internet at the day. Uh, but, um, I, I think at the time, you know, as I was starting and in the first few years, the organizations were starting to see a need for a formalized role.

Right? So, it changed from being, let’s just grab the best-looking techie or, you know, the, the person who can string the words together so that business people get it and explain, you know, in plain terms or in layman’s terms, what the products are able to help with and listen better. Um, you know, someone who can repeatedly do that as opposed to just picking the next technical person up and just expecting everyone to do the

[00:05:00] same job in a pre-sales scenario. So, I think really came formalized and then people in that role started to see that there was a need to get paid in a, an incentivized way, like our account managers do so that you can focus on the deals and focus on winning business and realizing that you actually are in sales, right? Your, your job is not just to be an advisor or a technician it’s to actually help sell the software.

So, you have to realize that that is your role. And I think that that transition has happened a lot over the last 20 years or so. Um, you know, I’m sure there’s people before then, you know, who, who realized that’s what their role was and all of that, but I think it is something that’s emerged much more as a formalized role in that period of time.

Vik: [00:05:48] Right. Right. Absolutely. And with someone having experienced, as extensive as yours, I am interested in knowing how do you, I mean, without going any specifics of the organizations. Well, what are the, some of the metrics that you find very effective in tracking? What are some of the things that you do on a, on a day-to-day basis, from your perspective at the leadership level?

Greg Holmes: [00:06:13] Yeah. So, there’s several different kinds of metrics here, Vik. So, I’d suggest you know, for me, the most important things are actually the outcome-based metrics. So, are you winning more deals? Right? So, and, and it could depend on what industry you’re in as to what is a good win rate. Well, first and foremost, if you’re in a very competitive space, a 20%-win rate might actually be good, right?

Depending on how much effort you put in, but in a very non-competitive business, like where you’re the only player in a space, it might be about, you know, that you should expect to win most of your deals. It’s then more, a matter of how much effort, and how much time go into those wins. So, I think, you know, if you break down your business by the

[00:07:00] different offerings you have and work out what your win rates are and track them, um, then that becomes a very important kind of thing to compare, uh, either between different pre-sales team members or different sales teams, even.

Um, and, and also over time, right? If you think your win rate is going up then, is that because you’re getting better at what you’re doing or you’re presenting better materials? Or if it’s going down, does that mean that there’s competitive influences that are stopping you or hurting you? I really prefer those kinds of metrics.

Way more than say, just looking at how busy people are, because if you ask people to be busy and you pay them or just to be busier, chances are people will find their way to, to have a lot more meetings. Right.

Vik: [00:07:47] Right. Yeah, absolutely. And, um, you know, as, as the pre-sales process itself has been more, getting more structured.

And last you know, for last some time, there are different parts of the pre-sales process. You know, it starts with qualification demos in discussions engagements with the customer, goes into product evals, the different names where some people know POC’s, POV’s depends on what is the coverage pilots, uh, in your experience while you know, talking to other people and how have you seen this, the product eval process or the POC process? How often do you see companies doing it? Is it something they do all the time in every deal or do you see this happening sometime? Not, not always. What’s your experience on that?

Greg Holmes: [00:08:35] Yeah, there’s different models, right? So, it, you don’t necessarily need to do a proof in order to sell a product.

You know, these days, especially with SaaS products that the trial motion or the pilot kind of motion, let’s sell you an introductory period and let you get on with things, uh, that works for a lot of products, particularly more at the consumer level or at the small business kind of level.

[00:09:00] If, if you have the right product for that kind of offering, um, most, most companies where there is a significant amount of work into showing how the product performs the need for the customer though, they will probably want some kind of proof point before they agree to make a big upfront investment or a long-term commitment on it.

And it’s, it’s those situations that I feel like good pre-sales teams, uh, are most effective when they can help. Establish what, what the business case for that customer is. And I think often the business case needs to come first, then, you know, show what the main proof points should be and agree with the customer on those.

And before you even get started, agree on what the follow-up to a successful POV or POC should look like. Right. So, what, what is the customer going to do when you show them that it does what they’ve asked for?

Vik: [00:09:54] Right. And, you know, uh, one more, uh, point that I’m interested in dig deeper on this topic is there are a lot of different, uh, kind of milestones during this whole pre-sale engagement process that we can probably spend hours talking about.

But what I want to focus more on right now with you in this topic is let’s say the POC is done or POV is done. How do you recommend is the best way to close a POV? I mean, you know, to successfully say, give a full stop and let everybody be happy about it and say, okay, we are done. How do you recommend, what are some of the best practices you can, you can offer?

Greg Holmes: [00:10:32] Yeah. So, I think having an agreement of what the scope of that POV is from the beginning helps you close it down, right? You need to set off in the right way with an expectation that can be met in a certain period of time. Um, so that once you’ve done that, you can sit down at a table, maybe across a Zoom meeting or something like that, and run through the results of the POV with the people that are actually going to take action on it.

Right? So, for that reason, knowing who those people to take action will be, is very important. Um, making sure that they know that the person they’re the person who’s going to take action on it. Because you can easily do a POV for the wrong person or for someone who’s not going to take action or not empowered to take action.

But then I guess once you’ve agreed what the scope is and, and, you know, perform that scope. That’s when you have that executive review, you go through what you’ve said, you’re going to show you, show it. And I think it’s good to give them some kind of handout that is a reminder of the POV, right? Because if you, you know, I think it’s ideal that you do take it away from them. Maybe afterwards so that there is a compelling reason they need to, to engage you business-wise with a contract in order to keep using the solution. Because if you let that keep going for too long,

[00:12:00] um, you will end up not having any leverage. Right. And your product is valuable, right. Everyone’s product does something that’s worth doing or else they wouldn’t be in business. So yeah, at some point you need to say, we’ve, we’ve shown what you asked for and we’re ready to move on.

Vik: [00:12:18] Right, absolutely. And I think, um, this is always, um, one thing is for sure, is I don’t think any company or any vendor will go to a POV or a POC if they don’t know that, that they will win. I mean, we, we know that we can do all that has been asked for then only we will go otherwise, why would we do it?

But I think what you said is really important is if we don’t define, what is a skill and what exactly are we offering in the POV, then how would you close it? I think that is. That is a, the key point there. So, yeah.

Greg Holmes: [00:12:51] I would say Vik, everyone thinks they know that they can solve those problems or those issues for the customer, but, but your aim is to make sure that the customer knows that you can solve those problems for them.

Right. And so that, that is part of the buying journey for them is, is telling you where their doubts lie or what they need to be convinced on. Um, cause if they were convinced before the POV, the best action for you to actually go forward would be not to do a POV at all. It would be let’s sign up a contract and move you forward straight away.

If you know, if, if you’re gonna, you know, get a new computer and install an operating system on it. You know, what most of the leading operating systems do, right? You’re not going to go and do a proof of concept of the operating system. It’s a, almost a commodity product. And I think, if you’ve gone very successfully through the early sales process, and you have defensible products that have been worked before in similar customer environments, and they have a strong belief and confidence in your ability to perform, um, they don’t need to have a proof of concept necessarily either.

Vik: [00:13:59] Right, I agree. I have one more question on this topic. A little bit different question. Usually, what do you think is the primary motivation of doing a POC because POC or POV or a pilot? Because like, like you, I agree. I mean, you know, we shouldn’t be doing the POC’s or POV’s just for the sake of doing it. What, what do you think is the primary motivation?

What do you think the primary motivation is to get a quick wins or to do the bake-offs or, um, to show, you know, product features. Uh, because your product is so awesome that you want to show customer everything and you think that will vow them. Uh, but what do you think typically companies do? What is the primary motivation to go into a POV or POC?

Greg Holmes: [00:14:43] Well, I think what it should be is more about, um, reduction of risk, right? So, they’ve seen, you know, things that they want, they they’ve seen you talk about the business value that you can deliver. And hopefully they, they believe in that to a strong degree.

[00:15:01] And usually what a good proof of concept is, is to show back that and repay that risk. Right? We we’ve taken your data. You’ve, you’ve seen that this works with our fake data in our demo and, or you’ve seen another customer use it. So, you’ve had a reference and you, you have a high degree of confidence that we can do it sometimes what you want to see is that it works in your organization with your data or with your servers or, you know, in your environment.

And so, I think it’s about the reduction of risk so that they don’t go and, you know, do a big implementation with a lot of people or they don’t go and roll out a new system to a lot of users that won’t be happy with it. They want to see and reduce that final bit of risk.

Vik: [00:15:46] Yeah, that makes sense. Um, now, uh, let’s change gears a little bit.

Do you have any favorite tools? That you personally like to use, to, you know, manage the pre-sales or, or even to be effective in the pre-sales role? Like maybe, uh, some productivity tools or some tracking tools. What do you usually use in your day to day? Some of the tools that you really like to use them?

Greg Holmes: [00:16:12] Yeah. So, you know, I’ve looked at a lot of tools in the past, and I know there’s a lot of presales tools coming in into the market these days as well.

It’s, it’s now, uh, a sector in the, in the sales market place of different kinds of tools. So, it’s an exciting category. Um, what, what I’ve used mostly, um, today is, is tools that are aimed at the overall sales organization. Right. So, Salesforce naturally, you know, is, is one of the main CRMs I’ve ever been dealing with.

And for me, it’s about managing, some kind of link from pre-sales activity to the opportunities. So, I, I feel like it’s good to link them in. It’s good to have some kind of record and, you know, ability to communicate with the sales team to record what has been going on in a

[00:17:00] given opportunity, because there can be a pretty big gap sometimes between some of the pre-sales activity and when a deal actually gets closed, right. You can do a proof of concept many months early. If, if you’re unlucky, um, I’d be waiting to see what happens with the result afterwards. Right? So, Salesforce or the system of record, if you like, should have some touch from the pre-sales team to show, what, what have you been working on? What is your influence?

And I think that’s important. Um, other things that my organization has been using a lot, you know, we use a lot of the sales tools like Gong and HighSpot to record, um, you know, the different materials you might share with customers and, and to be able to track their usefulness and things like that. So, linking that activity also back, uh, to the opportunity records is pretty good, right? So, that you can see, uh, the customer was interested in this product. They saw this demo and they, you know, downloaded a few

[00:18:00] documents and they’re all included in that record. So, you know what they’ve looked at and, and I, in an ideal world, I’d love to see the, the, the causality kind of link between which documents seem to cause the most, you know, happy customers in the long run, because that would be really useful.

Um, it might even help you run a more efficient organization, um, what I’d love to do, a better job on myself, right, is, is how we manage the actual, uh, big proof of concept kind of activities. Right? So, one of the big things we do, we, we manage a lot of documents that, you know, document that process and agree on success criteria and things like that.

Um, and presentation materials around that. But I think where we could do better is actually managing, what stage and being consistent across a global team of what stage is this proof of concept in? Is it in the planning stage? Is it in progress? Has it been completed? Has there been a deal closure based on that activity?

[00:19:01] Because all of those things, um, can be different steps. And I think that they actually offer a lot of value back to the sales organization as a whole and the finance organization, because it could be a good indicator of how close are you to doing business with those customers as well? And even knowing how quickly you go through those steps.

Right, right. They talk about sales, velocity being important? Right. So, how quickly do we go from a discovery meeting to a, a first demo meeting to a contract and to closing that contract, all of those things might be very interesting. If we could also look at how quickly did the customer wants to go through the technical paces.

Right. Did they, did they drag their heels going into a proof of concept or were they very eager to do that proof of concept? Because I, I I’m sure that more eager ones are actually the ones who buy quicker as well.

Vik: [00:19:54] Right, right. No, that’s, that’s amazing. Uh, I think it, it kind of aligns or it, it, you know, uh, I see a very similar, like, questions, answers when I hear from other leaders as well.

I think, um, you, you put it in a perfect way. What I want to do now is to talk about the Clubhouse, the presentation or the, the room that you run. Can you talk a little bit more about the Clubhouse activity that you’re doing? I know you are on the Clubhouse every Friday at 12 noon central, uh, and you cover for the PreSales Collective, but can you give more detail about what the intention is? What do you cover usually?

Greg Holmes: [00:20:33] Yeah. So, I started using Clubhouse around, I guess, around the start of the year. Right. For me, it’s still a very new, um, technology to use for social media and everything. Um, and the reason I found it, interesting, you know, even just with general purposes with other rooms that I’ve been a part of is that it’s a completely audio based, uh, social media. And, what that means is

[00:21:00] because it’s audio based, you have to pay attention, right? You, you are not off looking at some slides, you’re not confused about whether I’m watching, you know, your demo or the disc, this the words you’re saying, you know, I’m not confused because a sales person off on the left is not actually paying attention at all.

They’re tapping out emails or, you know, they seem to be watching something else on their screen, not the same session that we’re watching. So, it it’s without its, uh, visual distractions and all of that. And people pay attention, but it also, it’s very conversational. In Clubhouse, you set up a room, you have moderators on the room and there’s a stage and there’s, um, anyone can join that room.

And so, for the PreSales Collective, we run a Clubhouse room called PreSales Talks. Each week we pick a topic, and, and we make that topic an interesting thing that people want to talk about. And so, a recent topic for instance, was

[00:22:00] on multitasking, you know, is multitasking good or bad? I think we can guess which one I might lean on. Um, But, in this room then, uh, people will just turn up, you know, within an hour we run, we typically run the PreSales Collective one for an hour. They’ll turn up and people can put their hands up. They can ask questions and we generally that the discussion flows. So, we might start out talking about multi multitasking, but we might end up talking about sales engineer to account executive ratios, or we might talk about metrics or tools.

So, it becomes a really interesting conversation, that’s led by whoever’s there. And then in my mind, it’s a lot, like I listened to a lot of podcasts and it’s a lot like listening to a podcast, but one that you can then take part in because you can put your hand up and ask a question, um, or you can, you know, go and tell people how you got into pre-sales or things like that.

So, it’s a really interesting room, um, really great, uh, good way to, to start interacting more. And some of the questions there, I, I, you know, there’s a great mix of people, either people wanting to develop their, their first role in presales, or, you know, learn a bit more about how to do their, their demos better or how to become better at pre-sales. And, and also some leaders who want to, you know, learn how to lead organizations in pre-sales better.

Vik: [00:23:22] Sure. Um, so for our listeners, I would recommend you check out the Clubhouse club that PreSales Collective has created and they meet every Friday at 12 central. And, um, one last question, before we wrap up this podcast, Greg, you already mentioned about some, you know, multitasking and you know, what is the right way or not right way.

We also talked about the book, you know, the Peter Cohan book and, um, and John Care, amazing people. Uh, Presales Collective is building already a lot of good content, but at the, at your personal level, uh, do you have any, any productivity hacks that you follow that you find very effective for yourself?

Greg Holmes: [00:24:05] I’m very old-fashioned, I think the more I try to do crazy things, the more mistakes I make. So, I like to keep it nice and simple. I think, you know, closing down as many windows that you don’t need, uh, when you’re giving a demo and trying to focus on the screen. A good one from my friend, Mark Green, shout out to Mark Green.

I’m in the UK is I, I have a little Lego figure, and I know we’re not showing the video of this, but I sit this little Lego figure on top of my camera. And then I can, if I’m worried about not giving eye contact to people, I just look at my Lego figure and then it looks like I’m looking right at the person.

Vik: [00:24:44] That’s nice actually. That’s very cool.

Greg Holmes: [00:24:46] I could talk to the Lego figure and I’m talking to the customer.

Vik: [00:24:51] Yeah. That’s actually, that’s really good hack because it’s always confusing where to look, especially when you are focusing on a presentation and, uh, so that’s, that’s a great hack, well, uh, Greg, it was, you know, it’s a pleasure talking to you.

And, you know, we had really good conversation. I hope we join again in future in other podcast episodes, but thank you for finding the time.

Greg Holmes: [00:25:11] You’re welcome, Vik. Always a pleasure.

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