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The Sales Summit: The trends and challenges shaping the future of sales

Over the last month, we’ve hosted leaders from today’s most innovative companies for lively discussions to debate the trends and challenges shaping the future of sales.

Inspired by the release of our book Intercom on Sales, we wanted to take a fresh look at three big topics – speed, automation, and growth.

We wanted to know: what are sales leaders doing to bring velocity to their sales cycle? How are they using automation to bring new efficiencies to their sales orgs? Finally, where do they see the biggest opportunities to accelerate revenue and what obstacles stand in their way?

For the final episode in this series, we’ve woven together our recent conversations on speed, automation, and growth. We’ve compiled our favorite insights from all three discussions along with additional material we’re airing for the first time. You’ll hear from:

  1. Dialpad’s Chief Strategy Officer, Dan O’Connell, and Sherlock’s CEO, Derek Skaletsky, on speeding up and slowing down deals to deliver value to your buyers and your business.
  2. Slack’s Manager of Mid-Market Sales, Maggie Hott, and Guru’s Senior Director of Sales, Halid Ibrahimovic, on the power and pitfalls of accelerating sales with automation.
  3. Aircall’s VP of Sales, Collin Cadmus, and Glofox’s Director of Sales, Patrick FitzGerald, on scaling efficiently as you pull new growth levers and introduce new sales motions.

A huge thanks to our partners at Dialpad, Sherlock, Slack, Guru, Aircall, and Glofox for sharing their many insights. And of course, a big thanks to all of our hosts on the Intercom sales team.

To hear each of these conversations in full, check out earlier episodes of our podcast. You can also subscribe to the show on iTunes, follow us on Spotify, or grab the RSS feed in your player of choice.


Dialpad’s Dan O’Connell and Sherlock’s Derek Skaletsky on the need for speed

In sales, we’re constantly asking ourselves: how do we move faster? Speed is our solution to hitting ambitious targets and increasing our efficiency. In a study we conducted, 91% of sales reps said responding instantly to a lead has helped them close a deal. But when it comes to the buyer experience, faster isn’t always better. Intercom’s Sales Manager Dave Bennion spoke to Dialpad’s Dan O’Connell and Sherlock’s Derek Skaletsky about how sales teams can strike the right balance.

Dave: We all place a premium on speed, knowing that time kills deals. The faster we close deals, the faster we grow as a business. How has your team approached accelerating the sales cycle?

Dan: I think, for us, it’s about having a tight process. We care a lot about how we monitor everything from “Do people know what they’re talking about?” to “Are they following a consistent process?” That gets into call recordings and voice analytics on that front.

I think a lot comes down to qualification, too. As you start to scale reps, whether it’s BDRs or SDRs or AEs, do people actually know how to best qualify things? Because, a lot of times – I remember this early on in my career – I just didn’t qualify things well. You get dragged into bad deals, they take a lot of time, and you get heartbroken at the end because they don’t win or don’t close. Then you look back and say, “Oh, I should’ve seen that way ahead of time.”

In terms of processes, we also monitor speed to lead. When a lead comes in, how quickly down to minutes can we get back to them? We do some interesting things in terms of implementing automated text messaging and leveraging chatbots and things to that nature. So, the three things that we care a lot about are process, good qualification, and how we leverage different tools to actually get back to people faster and in more automated ways.

Dave: Awesome. Derek?

Derek: We’re a product led company, so most of our leads come through a free trial. When we think about speed, first of all, it’s how fast we can get someone to value in the product. It isn’t necessarily how fast we can get a sales reaction to that person. So, that’s really important stuff for us to track and make sure we know exactly where everybody is and when they get to a point of value, and that’s when we’re going to activate our sales team.

“When we think about speed, first of all, it’s how fast we can get someone to value in the product”

To that end, our sales team needs to be able to react quickly. They need to know when someone reaches that point, and they need to be able to react because, to us, that is momentum. There’s momentum when you start using a product and, if you let that lag in this day and age, it’s kind of deadly. With today’s attention spans, you’ve got to be able to take advantage of that momentum in the product. So, that’s a big deal for us.

Dave: A lot of times in sales we want to have our hands on everything. We just want to get at everybody. How do you signal, “Hey go talk to this leader, this person”? But also, how do you make sure your salespeople hold back?

Derek: So we track the activation rate of all our trial leads that come in. And we have our salespeople react based on where a lead has gotten in terms of using the product. So, for example, if it’s a big company that comes in, say, someone from Intercom, and signs up for the trial, sales is going to know that, and they’re going to react to that quicker than they’re going to react to a small startup that started to use the product. In that case, they may not react to that at all, or they may wait until they get further down the line, say, 80-90% activated with the product.

Dave: So, segmentation definitely plays a part of it?

Derek: Oh, absolutely. And it’s a combination of product activity with firmographic information.

Dan: We do something similar, which is we start to segment the market. It’s not just geographical or bi-vertical, but it actually gets into tiers. We call them tier zero to tier four companies. Are they basically cloud first or are they kind of legacy, more old school? That has a different implication in terms of sales process and probably momentum that you might see in that deal.

Dave: Yeah. I think it’s something we’ve had to think a lot about as well as, as we segment our customers. What type of experience do they want to have? Some people just want to go online and sign up by themselves, and they don’t want to talk to a sales rep. How do we make sure that we’re nurturing an onboarding and activating those people correctly? At the same time, for people who do want to talk to a salesperson, how do we get to them super quickly? Especially those companies that have large wallets – we have to make sure we’re prioritizing those and providing a great experience.

Dave: It’s also interesting to think about it from a buyer’s perspective. How do you think speed from a salesperson affects the buyer? If a salesperson comes in too quick or too slow, how does that make you feel?

Dan: I think it depends on where I am in my own cycle. I was doing a refinance for a house and Better Mortgage – I’ll give them a shout out – immediately texted me back. Literally after three seconds. I was on a flight going through the mortgage application, and they texted me. I was blown away. Pinged our CEO to tell him that this is amazing. This whole experience is amazing.

I got off the flight, called them, and literally asked them, “How are you compensated? Because you sent me an email, you called me, you sent me a text message. I’m just kind of blown away and we’ve been trying to figure out how to move faster.” They’re like, “Oh this is just part of a part of our process.” And so for that, going through that, I wanted to lock in a rate. I was very much like, “Hey I want to move really, really quickly on that.” And that was great.

If that’s not where I’m at in the cycle, it can also be somewhat off-putting if this person is literally berating me. How do I get them to slow down? I’m just trying to get some information. I’m trying to shop rates. I don’t even know if I’m going to go do a refinance. Again, it comes back to how you can slow down and understand where that person is in their own process, which, David, as you highlighted earlier, becomes really important in qualification. The better you can qualify anything, you then have the gauge of “How quickly do I need to move?” and “How can I perhaps match that cadence?” Or even, to Derek’s point, be slightly ahead of their cadence to try to best manage it.

Dave: Yeah, having that conversation around urgency and understanding the urgency of your buyer is super critical.

Derek: That’s interesting. I think software buying is becoming a little more like mortgage buying where the competition is crazy. There’s like a jillion places you can go look for a mortgage. So, for them, capturing you as fast as possible before you have a chance to go to four other sites and check things out is super important. We’re certainly not there in software, but we’re closer than we were 10 years ago when there was one option for what you wanted to get done. Now there are 12 options.

Dave: Yeah, immediate response times are pretty critical still. We’ve all seen the graphs of how first response times affect conversion rates. And it looks like a waterfall. So, you have to be there almost instantaneously and responding. That doesn’t mean you have to be hounding somebody, but you need to be there if they want you, in order to engage and start that process.

“You have to be there almost instantaneously and responding”

Dan: That’s why – we were talking about metrics a little earlier – we manage speed to lead. We know speed to lead matters within our business, business communications for Dialpad. That stuff matters whether we get back to somebody within minutes or if we take hours. I can tell you the ones where, if you take longer than a few minutes, they’re going to move on and talk to the next three people. We do some interesting things and just go shopping to test out how quickly competitors will get back to leads And you’d be shocked at how fast some people are.

To Derek’s point, I think a lot of walls get broken down in selling B2B software these days. There’s a lot of competition, a lot of markets, and this stuff actually starts to have some pretty significant implications for how quickly your business can scale.

Dave: Yeah. I’m even thinking about how, even though our products don’t necessarily compete with each other, we’re all competing for budget at some point. So, if multiple people are running multiple projects, you better be responding to your person quickly because, if they’re the first one that asked for budget, you’re going to have to be there.

Slack’s Maggie Hott and Guru’s Halid Ibrahimovic on accelerating sales with automation

Sales leaders have a full plate, but one thing they all need to understand is how their reps spend their time. According to a Salesforce study, 64% of a typical rep’s week is spent on non-selling tasks – things like updating contact information and scheduling meetings. That’s why it’s crucial to have an automation strategy to eliminate low-value work. Intercom’s Director of Sales Operations Shriya Ravikumar sat down with Slack’s Maggie Hott and Guru’s Halid Ibrahimovic to discuss how they’re creating new efficiencies with automation.

Shriya: The brute force way of driving more sales is to simply hire more salespeople and increase your overall capacity, but that’s expensive and not scalable as we are all too familiar with. Another other way is to free up your existing capacity by automating work that’s high touch, low value. In your mind, what’s the next area of sales work that is ripe for automation?

Maggie: This is kind of a weird one, but for me it would be automating meeting preparation and presentation creation. I can’t tell you how many years of my life I’ve spent creating presentations. Before I was a sales manager at Slack, I was an Enterprise AE for a few years and I was also an AE for five years before coming to Slack. I have just learned that it is so time-consuming and manual to not only have to do the research but also build up the presentation.

At Slack, our sales cycle is very consultative. We sell into every single line of business, so we do a lot of personalized presentations and demos. Sometimes, it can take days to put together and research the companies. We also like to come to every single first meeting with our hypothesis on that company’s goals and a solution overview on how Slack could help them. It takes a lot of research to really nail this, but it is usually quite effective.

My dream for automation would be to have a way where a rep can go to an extensive pick list and click the different topics to cover, input some basic company information. It would somehow do a lot of the research for them and then spit out a beautiful presentation deck and demo within a couple of minutes.

Shriya: I’d love to connect you with our EMEA Sales Director, Stan Massueras, as this is such a passion of his. He absolutely loves beautiful presentations. It would be such a great way to scale our teams. Halid, how about yourself?

Halid: I wouldn’t say it’s necessarily next for everyone else, but it is absolutely next for us. In an effort to support a product-led strategy, we’re now testing live and AI-assisted chat when prospects are hitting our website. We’ve learned that the odds of us converting people into sales are exponentially higher when a prospect trials our product. So, we want to do everything we can to really encourage that experience and get them to trial as soon as possible. The hypothesis is chat, and especially AI-assisted chat, can help with that. The early findings have been AI-assisted chat is actually outperforming humans when it comes to yielding new trials, which is great.

“AI-assisted chat is actually outperforming humans when it comes to yielding new trials”

Shriya: Conversely, are we at risk of removing the personal element of sales with too much automation? I’d love to hear a little bit more about your thoughts on that, Halid.

Halid: I have a strong opinion on this one. I disagree. I think, if anything, it should do the opposite and actually has to be the opposite. And the reason I say that is I think there are a couple of real important macro trends that need to be considered versus the pace of innovation. All of us work for companies that are probably bringing new ideas, new features, new products to market really, really quickly. And so sales reps need to keep up with that. The barriers for entry for competition keep getting lower and lower. Just go to a G2 listing for any product category and you’ll see how many different vendors fit into that. So there’s that to consider.

There are two other considerations, as well. First, the world is becoming much more real time. Consumer apps have influenced how buyers think about their experience when it comes to B2B scenarios. And the buyers, they want to see something that is real time. They want to engage as quickly as they can and across many different channels, too. Finally, think about how much more educated buyers are. They’ve done probably 60% of their research before they’ve even engaged with a sales rep.

So, you bring all of that into play and what you’re really asking your sales reps is, on the flip of a switch, they need to be able to get in front of a prospect and add value to that conversation because that’s what people are expecting. They need to be the consultant. So, how can you eliminate all the other things that sales reps need to think about through automation? So that they have more time and capacity to be an expert in their arena and really bring value to what the prospect is looking for.

Shriya: That makes a lot of sense. Maggie?

Maggie: I agree with Halid with the caveat that I see a lot of companies who have sales reps sending out email blasts that try to look personalized, but it’s very obvious it’s a blast. There’s actually a time we’ll never forget when myself and the management team were all in a room, in a meeting, and every single one of us got the exact same email. Someone brought it up, in the sense that they were like “Hey, oh this interesting email just came in.” We were all like, “oh yeah, we got that exact same thing”. I personally would never respond to one of these and it, to me, just comes across a bit like junk mail. It’s very obvious when something’s personalized versus a template, and I’m a firm believer that, even though it takes longer, I think prospecting emails should always be personalized. It would take a really advanced email tool to write out custom emails per prospect. Hopefully someday, that comes.

“If reps can just spend one hour less a day doing manual tasks, they’re going to have a lot more time in their day to talk to prospective customers”

I do think, though, if reps can just spend one hour less a day doing manual tasks, they’re going to have a lot more time back in their day to talk to prospective customers. We’ve already seen a ton of improvement in just a few years. Implementing tools like Guru, Troops, Gong, CPQ, etc allow reps to find and take action on some of their day-to-day tasks in a much faster way. My team and myself are often on the road, about every other week, so anything that can be accomplished very quickly via mobile, like an approval, is a huge time saving for everyone. I think really everything should be built with a mobile-first strategy.

Shriya: I really couldn’t agree more. Here at Intercom, we use automation to help prospects and customers get a better overall experience. Automating certain parts of our acquisition process and workflows allow our reps to provide an enhanced and personalized experience for those who actually need extensive and consultative purchase decisions, while doing quick assists for customers looking to move faster.

Aircall’s Collin Cadmus and Glofox’s Patrick FitzGerald on the challenges of growth

You’ve likely heard the truism, “what got you here won’t get you there,” and this is exactly the case in sales. In our study of B2B sales professionals, 6 out of 10 of them reported the tactics they used last year were less effective this year. So, what can sales leaders do to maintain their momentum in the market? Intercom’s Sales Manager Will Holden sat down with Aircall’s Collin Cadmus and Glofox’s Patrick FitzGerald to uncover their secrets to scaling revenue.

Will: What levers do you have at your disposal to drive growth? As opposed to just throwing heads at the issue, which actually is a fairly valid approach to the problem to begin with, but now you’re at the point where that’s no longer reasonable. How are you continuing to drive growth, and how do you wrestle with that challenge?

Patrick: It’s a very critical challenge for us at the moment. As a Series A business, we have teams in Sydney, Dublin, and LA, and a mixture of inbound and outbound now. We’re focusing on two core priorities for the next six months. The first is recruitment and finding the right people to come in and keep doing what we have done. But, for every single person that we do take in, we have to make sure their ramp time is shorter than the last person that joined. We need to make sure everything good that has been done is something we are recording and we are making available and visible to the rest of the team, and standardizing everything the team is doing.

“For every single person we take in, we have to make sure their ramp time is shorter than the last person who joined”

Will: So many people forget about that metric. It just sort of filters away. It’s like, “Hey, we’re moving really quick. We’re growing. Let’s just get on board. Let’s get this figured out.” It’s such a key metric. How long does it take for this person to approach productivity? And that needs to be socialized across the business, right? Finance needs to be aware of it. The enablement team needs to be aware, all of the hiring managers need to be aware. You can very quickly run a muck by growing fast but, ultimately, not producing for nine months.

Patrick: Absolutely true. Salespeople don’t generate demand, right? It depends on your definition of a salesperson, but, ultimately, salespeople don’t generate demand. They help close it out. So, what can they do? They can maximize the value of the demand they have, right?

And so, we brought on a call recording system, which enables us to see what high performers do that other people perhaps don’t. It allows us to create that kind of competitive element across the team, view the topics that top performers speak about that others don’t. It allows us to see the type of language that they use.

Will: It specifically unlocks value for them?

Patrick: Yes, exactly. So, you set your metrics, you set the topics you think are valuable to the sale, you identify the language that drives toward a closed deal. And then, it also assesses other things like whether you let your customer speak or whether you bore them to tears with your own monologue. It records how often you interrupt or how much time you actually allow someone to finish their sentence before you jump in. It’s an amazing tool which helps us standardize, helps us work towards the perfect demo, the perfect call.

Then, the next step is process, right? Post-demo process. How do we standardize the 10 contact points that drive toward a closed deal in 10 days? How do we make sure everybody is doing that? How do we enable them with the right materials for the right prospect to close the deal as quickly as possible?

Will: I’m going to jump to you now, Collin, particularly on that point around knowing what to optimize and when to optimize it. Could you give us an overview of a few levers that you guys are pulling to drive growth outside of growing headcount? Then, let’s talk about the sales process that Patrick was alluding to and optimizing stages of it. I’d be really keen to get your take on how you plan and how you approach optimizing a sales process.

Collin: For me, operations ties into one of the pieces. We’re putting rev ops in place. A lot of, I think, optimizing a team and making them more efficient is having dedicated teams whose job is to actually do that. And of course, you’ll lean on your VP of Sales, you’ll lean on your Director of Sales, your sales managers. But when it really happens best is when you have people who are dedicated to doing it, whether they’re implementing it or just helping you identify opportunities.

Hand-in-hand with that, I like to move in cycles. I look at 2019 as a growth cycle for us. We did a lot of hiring; our main efforts were towards hiring. Of course, you’re always trying to optimize and perfect the process but, really, you can’t do a whole lot of both at the same time until you’re a much more mature organization and you have teams dedicated specifically to hiring and training. Whereas today, it’s our directors and our managers who do the hiring. And so, they’re going to be limited on how much they can do to change the process while they’re training 30 new people and constantly recruiting.

I look at 2020 as more of an optimized year for us. It’s where we are going to do less hiring than we did this year. But we’re going to aim to perfect different metrics in our funnel, different aspects of the sales process. And so, I look at it in a couple of ways. Because I have directors and managers, the way I split it up is I have the managers focus on the individual reps, focus on identifying a metric with each rep every month that you’re going to put a strategy in place to improve. Pick one and go all in on it.

Then I have the directors focus on picking a metric every quarter for the entire team. And so, you have a director who’s spearheading this one big initiative. An example for us earlier this year was, “Hey, we want to increase our percentage of deals that prepay us annually versus monthly.” And we put a whole strategy in place and it was a 90-day initiative. We executed it and we got it to 4X of where it was. It’s because we had a laser focus on it and it was led from the top. That was me before we had a director. But going forward, that’ll be a director-type initiative.

“If you can significantly improve four key metrics a year, you will have a significantly different team at the end of every year”

Each quarter, every 90 days, you pick a metric and you really focus on it. Of course, if it takes longer than 90 days, keep going. And then, you have to obviously sustain that. But I think if you can significantly improve four key metrics a year, you will have a significantly different team at the end of every year. And of course, that’s hand-in-hand with the managers also focusing on the smaller details with each rep.

Will: I think yearly planning and getting the group together to define what we’re going to be working on are absolutely key.

Will: Moving forward at Glofox, what are some of the key challenges to growth that you foresee over the next 12 months? We’ve dipped in and out of a few different areas today, around alignment, around tools and processes. Are there any big rocks that you are going to try and break over the next 12 months?

Patrick: Absolutely, there are two key priorities for us over the next six months or so, which are around talent acquisition and enablement. We’re not at a stage like Aircall, like Intercom, where we have a multi-tiered management structure. The responsibility for all of those things lie with a narrower pool of people, and so what does that mean? Our ambitions are no smaller than either of your businesses. So rather than just bleeding all of our team dry, we have to think about very scalable ways that will enable us to achieve the growth you already have.

On the acquisition side, recruiters are a necessary part of this, but they are not the answer. They provide valuable service in many ways. But any person that is going to want to join our business is going to want to have a much more personal experience than they would get through a recruiter. So I’m using an account based marketing approach, essentially, for my talent recruitment, which has transformed the pipeline by a factor of about a hundred in the last week alone. So that’s pretty exciting.

Will: Before we wrap up, Collin, to you with the same question, any big challenging rocks you’re going to try and break over the next 12 months? And these aren’t necessarily opportunities, these are the things that really pain you today and you want to fix quick.

Collin: For us it’s maintaining all of the organization and efficiencies that we have to-date as we continue to grow into these new channels. Expanding things like channel sales and then, moving forward, we have some strategic partnerships that are in the works. For example, if one of our partnerships takes off, we would probably need to hire 20 to 30 people just to handle the influx of leads that will come from that deal. And it can happen really, really quickly. It’s exciting, but it’s also a bit scary because a lot has to change and it’s not just on the sales side.

If we start 10x-ing our influx of leads through one strategic partnership and those leads start converting at even the same rate we convert regular leads – they should actually convert at a higher rate – we now need to be able to support those customers not only with salespeople but also with onboarding, with support. Those customers could be located anywhere in the world, they could need 24/7 support.

I would say, if there’s a big rock, it’s that you need to be prepared, and it’s hard to be fully prepared, because you can’t hire 30 people and have them just sit and wait. You have to be ready to move fast when that happens. And, if you screw it up, you can kill that whole initiative pretty quickly. That’s something I’m thinking a lot about – how to prepare for those things while also not taking focus away from everything else that we need to be working on.


If you enjoyed The Sales Summit, then make sure to grab your copy of our book, Intercom on Sales. It’s jam packed with proven sales plays from our journey scaling a billion dollar business

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