Paul Mackender (00:08):
Hi, I’m Paul Mackender. I’m the Chief Revenue Officer here at Agent3 and I’m really pleased to welcome Lindsey Armstrong to the latest of our Agents of Change call. Obviously, Lindsey, you’ll talk in a while, but I’ll just do a little bit of introduction. Now I’ve known Lindsey for coming up to 20 years now, believe or not, Lindsey. But Lindsey trained as a lawyer, did a bunch of work for the likes of Oracle, both in the UK and ran their New York office, spent a lot of time at combination of Veritas and Symantec in a number of leadership roles and sales leadership roles, then went on to Salesforce, spent time running both AMEAR and the APAC region, at the same time was an advisor to Bluewolf, which was sold out to IBM, and has also had a number of roles at the likes of InsideSales. And I think I’m right in saying today, Lindsey, you have a number of advisory roles and obviously continue to be long suffering supporter of Newcastle United.

Lindsey Armstrong (01:03):
Yeah. And I can tell you which one of those is easiest. It’s not easy to be a supporter of Newcastle United now and that’s ruined the whole thing for me to be honest.

Paul Mackender (01:12):
Oh, well, I’m sorry I introduced that, but I thought I’d inject a little bit of humor into this interview. So, Lindsey, thanks making time to chat.

Lindsey Armstrong (01:19):
You’re welcome.

Paul Mackender (01:22):
So, Lindsey…

Lindsey Armstrong (01:23):
What are we going to talk about? What are we going to cover today, Paul?

Paul Mackender (01:25):
So, I think to start off, with all these interviews, we’ve asked everybody to say what have they personally and professionally seen as the being the big changes in these last 15 months. And then I think we’re going to talk a little about how sales has changed and obviously having run so many different successful sales organizations, both domestic, internationally, and globally, I think we’d have a fun conversation. So, yeah, so that first question is how have you seen things in the last 15 months or so?

Lindsey Armstrong (01:54):
I think trends that were already in progress were accelerated. So, what we saw is this compression of a timeline of stuff that was going to change in any event. But I think the big one for me is enterprise remote selling. Who knew? Who knew that so many of those salespeople could pull it off, do it so successfully?

Paul Mackender (02:16):
Yeah.

Lindsey Armstrong (02:16):
I mean really. It’s been one of those long held thoughts that enterprise is different. It’s about the road warriors. You’ve got to be there. This really in the last 18 months has brought into very sharp relief what you do and do not need to do face to face with a customer. So, I think that’s the first big change that I’ve seen. I think the second thing is what’s headquarters for? There’s always been this idea that headquarters was the center of gravity of everything in all companies and certainly in American based companies, but now what is headquarters for?

Lindsey Armstrong (02:57):
And companies have proved that people can move very successfully to a work from home, or a hybrid environment. And I think that’s going to be very interesting to see how that is. And I think the third thing that I… I’m going to try not to look smug when I say this. But boy, all those headquarters folks now know what it’s like being out in the sticks trying to get stuff done. And that’s been a real leveler. I think the change from the ability from a lot of folks to be able to walk around the corner, or walk to a desk, all of us that were in offices or not, the change of being able to just walk around the corner, divert someone’s attention, and get stuff done… Particularly the more senior you are. The more senior you are, the more able you are to divert total work streams without anyone saying anything. That’s certainly changed.

Lindsey Armstrong (03:54):
I can think of a number of departments that I’ll bet think that they’re a lot more productive without that constant interruption. I think we hate to call the C-suite an interruption, but it is an interruption that they dealt with day by day. So, I think a lot of those things have been super interesting as we see what the next 18 months is going to bring.

Paul Mackender (04:13):
Yeah, fascinating. So, looking at that accelerated change, you say it’s been lots of things that were already happening and it’s just a case of they just really ramped up.

Lindsey Armstrong (04:22):
Yeah.

Paul Mackender (04:24):
One thing we talked about previously is this buying cycle, this change you’ve seen, the influence of self-served buyers and the impacts on the sales. Can you just maybe give your views a little bit on that? What do you see happen there?

Lindsey Armstrong (04:40):
Yeah, I think one of the things that we’re seeing is that there are a lot more people in a buying cycle now. Firstly, there are a lot more complex buying cycles. So, there are more cycles that involve four or more departments and 12 or more people. So, there are more of those cycles. And within those cycles, the average number of people has increased. And a lot of those cycles now look a lot more like collaborative processes, the ability to run these complex processes by consensus.

Lindsey Armstrong (05:17):
Now I think a couple of things matter out of that. Firstly, that consensus and collaboration in a lot of different departments is quite difficult if the thing that you’re selling is disruptive, or you’re in a category of one. That actually makes your job much harder. And this number of people I think, also the idea that in the past, there was… I know how many times I used to say this. “Well, who’s the decision maker?” I don’t think there is a decision maker anymore.

Lindsey Armstrong (05:44):
And a lot of our constructs and sales constructs are around getting to the decision maker, access to the decision maker, how will the decision maker make that deal happen. And I think that’s, if not gone away, certainly dissipated dramatically and certainly in these complex sales. And when you have a lot of people that are involved in these complex sales, obviously the time that you get face to face is less, right? If buyers are spending, whatever it is, a hundred percent of their time on a deal and there are now four times as many internal people, that reduces the amount of time that they spend.

Lindsey Armstrong (06:26):
Then you look at the competitiveness of deals. That in itself, if there are three of you in a deal and you’ve only got 20% of time to share between you, that’s even less. So, the impact that you make when you get to a customer, or a potential buyer, it has to be really impactful. It has to be really meaningful. On the plus side of that, Paul, what I think is… Again, there are a lot of downsides to work from home, but one of the things that this kind of environment forces us into is an opportunity I think to contract timelines, because we’re not trying to organize 20 people in a room together anymore.

Lindsey Armstrong (07:06):
Now what you’re trying to do is just get a time slot for a Zoom meeting and get them all there. And in many ways, that is a lot easier to do. And you can do that a lot faster than flying people in from four different locations to a spot where you do a presentation. So, I think there are swings and roundabouts on it, but I think it’s going to be very interesting.

Paul Mackender (07:26):
Yeah. And with this then, so in terms of the sales infrastructure, if you like, adjusting to this…

Lindsey Armstrong (07:34):
Yeah.

Paul Mackender (07:34):
I don’t like the term new normal, but one of our colleagues is turning it to never normal, because this constant change. Do you see this as a combination?

Lindsey Armstrong (07:42):
Yeah.

Paul Mackender (07:42):
Is it more of a people or process of technology challenge? Is it all of the above? Again, if you were in this situation let’s say 10 years ago, with what you know, with the infrastructures in the likes of the Oracles of this world and the semantics, et cetera, where do you see the most pronounced change where you would focus your time, or have your reps focused?

Lindsey Armstrong (08:04):
Well, I think it is all three. It’s obviously all three. But I think one area that we’ve got to look really hard at is the infrastructure by which we manage and measure our sales people. And I think if you look at these multiple people in multiple departments, selling now is no longer anything resembling a linear process. There’s no linearity to it.

Lindsey Armstrong (08:29):
It turns into a very recursive process with a number of people at different stages in the sale. And they loop back, they move forwards, they loop back again. And you are constantly having to resell, and in CRM or sales terms, go back a stage. You go back a stage, you go forward a stage. So, the movement within what a traditional sales funnel might look like, I think it’s now completely different.

Lindsey Armstrong (08:54):
And certainly no CRM system that I can see that’s widely used is supporting that. They’re very linear systems and that doesn’t help. So, you have sales managers that are trying to force a sales process to be recorded in a very linear way and yet express a very non-linear process, the nonlinear circumstance. And I think that’s going to create some problems as we go forward in terms of the measurement of how we measure our sales people, how we know where we are in a deal.

Paul Mackender (09:26):
Interesting. And so taking the human side of it then, again, I’ve seen some data from the likes of the Gartners of this world where customers, especially with this shift toward digital transformation, I got in an interesting conversation with a good friend of yours, Eric Berridge. And he talked about that actually a lot of the challenges of digital transformation are cultural and not technological.

Paul Mackender (09:48):
He talked about calcified structures and this idea of getting leadership to change. And this is like in some organizations turning an oil tanker. So, in terms of if you are a rep, or you’re a sales manager, then what’s the role they play? As I say, I’ve heard some people say they need to bring a market perspective. They need to coach the customer more as opposed to overtly selling. Do you agree with that?

Lindsey Armstrong (10:11):
Yeah.

Paul Mackender (10:11):
What’s your take on that?

Lindsey Armstrong (10:15):
Here’s what I think is going to happen with buying. I think this is about how buying is changing, not how selling’s changing.

Paul Mackender (10:20):
Right.

Lindsey Armstrong (10:22):
And I think successful sales people are not going to be the people who can sell most to a customer, but who can enable a buyer to buy the most without regret and to do that successfully. I think that’s going to be a real change. One of the things that I do think is… Let’s look at what the role of a sales manager is now. They have a very tricky role, because they are trying to arbitrate these nonlinear processes within these linear environments.

Lindsey Armstrong (10:51):
They’ve got a lot of employees. Some of them they’ve never even met. Think about being onboarded at this point in time. They never met half of their employees with the turnover. That’s pretty tough. You see some incredible leadership. You talked about the calcification. The opposite of that though is leaders, not necessarily senior people, but leaders who stepped up and have done some really creative things to break that calcification, to make this so-called new normal actually just feel like normal, not a new normal, just normal.

Lindsey Armstrong (11:24):
And I think some of those guys have done a tremendous job. But I think that the unit of coaching for a sales manager now is less about coaching the individual, looking for the strengths and weaknesses of an individual, which might be a more traditional way of doing it, but I think in the environment that we have at the moment, the best coaching that those guys have now is the deal.

Lindsey Armstrong (11:46):
And I think there’s a lot of data that shows that sales managers who use the deal as the unit of coaching are the ones that not only get the best out of their people, but they get the best out of their whole organization, the deal itself. Bringing the ability to scale, bringing advantage to the deal is what I think will make sales managers super successful as we roll this out in the future.

Paul Mackender (12:17):
Interesting. So, what would you say the archetype of a successful sales rep would be today? Because listening to you, it sounds like it’s quite a different skillset. And I don’t know. If you’re in sales and you’re seasoned, and you made your quota, you made a good living. Over the coming 4, 5, 6 years, do they need to ultimately change their skillset, or how do you see that? Because it sounds like quite a drastic change.

Lindsey Armstrong (12:47):
Yeah, I do. I think there’s a couple other… Sorry. I think there’s a couple of things that sit around that. I think the first thing is that the way that we’ve traditionally sold is all about differentiation, right? Now what we’re taught to do is focus in on that very narrow thing, that very narrow differentiation. Yes, 95% of it’s the same, but we’re going to make the whole argument is about that 5% that is different.

Paul Mackender (13:11):
Yeah.

Lindsey Armstrong (13:12):
And I think that’s a false way of going about business now. I think if you’re a buyer, the web’s democratized everything. I think there’s a ton of data that is out in a public domain. I think if I’m a buyer and I’m trying to choose between, for the sake of argument, Salesforce, SAP, and Oracle, it all looks credible, right? All of it. None of them are lying. It all looks credible. It all looks reasonable. It all looks choosable.

Lindsey Armstrong (13:42):
So, how, if you are a buyer, do you navigate all of that kind of data and information? And I think that’s the role of the new emerging sales person in this. And it’s going to be to make sure that the buyer has performed all of the things that enable them to make a low or no regret decision. You help the buyer make sure that they’ve asked all of the right decisions, help the buyer that you make sure that they’ve got confidence in the vendor that they’re working with, help the buyer to understand that they need motivation for change as well.

Lindsey Armstrong (14:22):
It’s not a one way street. Help the buyer articulate what the benefits are so that as you come to renewal and as you get into expansion, they are able to look back in a really… And I don’t just mean a solid business case. I mean something that is proposed and helped, and run by the sales rep. So, I think that’s a very… It’s a little bit like the old consultative selling in the past. But I think that’s going to be the role of the new sales rep. I think it’s going to be about enabling the buyer to buy, not selling this narrow, differentiated solution that you have.

Paul Mackender (15:00):
Yeah. You mentioned post sale there. So, like in a SaaS based world, where do you see the handoff between possibly sales and success, or service, whatever you want to call it, in terms of recognizing value? Because you make the deal, you sell the business benefit, et cetera. You want the customer… Obviously, you want to ideally cross sell and upsell. You want that renewal and whatever time period. The customer increasingly needs to be realizing value from signing that check. Do you see sales playing a fundamental role in that? Or again, is that a hybrid of what has been now possibly a by gone set up in terms of a division between sales and success, or service?

Lindsey Armstrong (15:45):
The way that I view it is that more than ever sales is actually the foundation stone of it. I don’t know whether it’s a handle over. If you’re in a SaaS business, the whole point of a SaaS business is not the ACV. It’s the retention. It’s the returning money. That’s the only point. So, you have to get to retention. In order to get to retention, you have to have sold a low or no regret deal, because otherwise the CSM’s job is unfulfillable. They can’t do it. They can’t make it.

Lindsey Armstrong (16:14):
And the reason that I come back to this consultative sell and helping the customer ask the right questions is now I’ve been in a lot of rooms where the sales rep said, “I didn’t tell the customer about X, Y. Thank God they didn’t ask. Otherwise, that would’ve changed the course of everything.” We got to change that course early. And the reason for that is to get to this renewal, to get to these renewed dollars, you’ve got to provide the thing that they were looking for.

Lindsey Armstrong (16:43):
If the thing that they were looking for comprises of something which is a question that they didn’t have answered, CSMs are going to end up in engineering. They’re going to ask engineering, “Hey, we need feature X, Y, otherwise we can’t keep customer A.” Engineering end up spending their effort and their energy fixing things that have already been sold. And now that bleeds back over. Their ability to innovate gets lower. The roadmap that you should actually be selling to gets smaller and it becomes this terrible circular thing.

Paul Mackender (17:15):
Boiling all this down to looking forward, there is clearly no crystal ball, but what do you think the biggest takeaways are going to be from all of this as you look at sales? You mentioned the next 18 months earlier on. What do you think the real steers and drivers are going to be based on what we discussed today?

Lindsey Armstrong (17:32):
I think the really big things are going to be a recognition that ICP is not a question of score and numbers of employees or revenue sizes. We somehow need to find a way of identifying ICP as customers who will buy from us, be happy, and retain and renew. I don’t quite know how that’s done, but you’re the marketing guy here. I’m sure you can figure this out more. But that I think is the biggest takeaway for me that the way that we’ve striped and scored customers is not an indicator of their success and their attention.

Lindsey Armstrong (18:18):
It is simply an indicator of someone to whom we might be able to sell, not someone who may be able to buy from us. And I think that’s going to be a big indicator. And the second is, for me, that this is really just shift happens. We got to keep moving with it. We can’t look back over and think that we’re all going to get back on planes and be road warriors and sales people, who measure our success by our golf game and ability to understand a wine list. That’s gone. That’s really gone.

Lindsey Armstrong (18:52):
And the new people who want to buy, if they could buy in a completely frictionless world, probably would. And we have to stop treating those people when they come to us as if they hadn’t done anything in the past. An example of that would be a lot of companies that I know when a junior BDR speaks to a customer, a customer is probably 70% to 80% through their buying journey. And yet we give them our most junior person and then we roll them back.

Lindsey Armstrong (19:22):
We’re like, “Yeah, yeah, yeah. You might think you know something. I’m going to set an appointment for you. And then I’m going to qualify you and ask some really basic questions.” So, a customer who thinks they’re 70% through their journey is someone that most vendors will call stage one, at best stage two. We’ve got to stop that. We’ve got to figure out how to place them and how to interact with them where they actually are on their journey, not where we wish they were to fit in with our sales processes.

Paul Mackender (19:51):
Yeah. A very good point. Wonderful. Well, look, Lindsey, I found it really interesting and no doubt that folks that watch this video will do. And I’m sure it’ll create a whole bunch of debates. So, thanks for your time. I appreciate it. And good luck for this football season ahead.

Lindsey Armstrong (20:06):
Thank you very much. That ruined everything for me.