Hot Takes

The Enterprise Sales Cycle Just Got Long AF with Brian Gerrard


We are living in an unprecedented time of SaaS! Needless to say, the Enterprise sales cycle has changed for the foreseeable future.

Now, we will have to lean in deeper than ever before and ensure whoever we hire is not only technical but respectfully persistent and organized to drive a deal to closure—which is exactly what you’ll learn in this session with Brian Gerrard, Sales Director at Outreach.

[Transcript] The Enterprise Sales Cycle Just Got Long AF

Joe Aicher

We are back live. Looking forward to our next speaker. Brian Gerrard. Hi Brian, looking forward to your presentation, “The Enterprise Sale Just Got Long AF,” right, so let’s have you take over. I’m curious to see where this is headed.

Brian Gerrard

All right, thank you. The reason that I chose this topic is I’ve been at Outreach for about eight years, all the way, I think, since 2015, and so when I got here, we weren’t really in Enterprise sales yet. 

We had less than a million dollars in ARR, and now we’ve grown over to 250 plus, and so it’s pretty insane the changes we’ve seen and how long the Enterprise sales cycle took, even in a growth market. Anywhere from probably one to three years, and I now see that extending as I’m still trying to figure out what’s the best way to actually do this sale and all the new changes that have come and that are coming. 

Before I go into that, an interesting fact about me, I graduated college in about 2006, and I joined 11 different startups through San Francisco and LA before I actually landed on Outreach. It gave me a pretty good basis of what are the different ways to manage, what are the different products that I need to sell, what are the different objections I got to get over. Hence, it helped set me up for all the different things that I was going to run into at Outreach. So it was a good training ground before I found my footing. 

Now to go into what I’m seeing in the market that I am getting used to or maybe still trying to figure out why these things are happening is, there are a lot of numbers that are being called that are making our jobs incredibly difficult, especially as things change. 

I’ll give you an example. Some of the goals are so high that I question how they actually came to that number, and I’ll tell you a story. Yesterday I was on the phone with my boss, and he basically told me he had a face-to-face with a big Enterprise company. He asked the sales leader, “How did your number get called this year?” and he was told that the board was looking at what is the price per share that they actually wanted to get and then went down from there.

This, to me, is difficult because it’s not looking at the historical facts of what’s actually happened throughout the last five years but also in the last year as things change. So I know we want to get to a particular growth number, but if we don’t make it realistic, it’s going to cause a lot of cultural challenges.

The other aspect of that is it creates people to call pipeline numbers that are inflated. We’re being asked to do these sorts of things which is good. We do want these high-value deals, but if we don’t have the mechanics in place to actually get the deals done, it’s really hard to call that number after one or two calls. 

So, for example, if I actually want to call one of these larger numbers, do I have the executive alignment? Have I gotten to the right people? Do I know how to do an ROI analysis? Have I worked with the subsidiary that has used our product? All of these different elements are very difficult to get to until you can call that massive number and then actually make it real. 

So I think some of the changes in how we call numbers and our sales stages are coming, in regards to what is considered something that’s going to close within the next year. 

The last thing is these sales cycles are being tracked based on what was the last closed won opportunity, and sometimes those opportunities only last maybe one year or eight months to a year. If you look in the actual Salesforce, you’ll probably see 10 different closed lost opportunities. And so when you start to look through those and figure out the duplicates, the sales cycle was really two to four years.

So if we start to look at all those things, we can see how the sales cycle is massive. We really need to do a lot of work and build the right relationships to get it closer to the way we want to.

The Enterprise Sales Cycle Just Got Long Af With Brian Gerrard

Okay, so we’ve gone over specifically, I think, how to look at the close lost opportunities. I have an Enterprise client that took us four years to close. When we even had a leader from this Fortune 100 company that had come over to Outreach, and so it still didn’t change the work we had to do to get this through and prove all the exact steps to make it happen. 

Secondly, if you’re working with your champion or your influencer and they won’t get you to the budget holder, then we really have no idea how long the sales cycle is going to take. They could be telling you what they want, but they haven’t approved those priorities or those initiatives with the people above them. 

Lastly, if we are dealing with all these competing priorities within this new market and we don’t have a clear list of what are the top three or the top five, everyone’s going to have their own agenda around how they match to those.

If you don’t have that with every single sort of persona that this is going to touch, it makes the deal very difficult because there’s going to be a blocker that comes up that’s working on something else. So we got to try to map this out and get ahead of it to be able to make sure we get to where we want.

Okay, so in practice, how have I run my business? Some may agree with this, and some may not, but I tend to underpromise and over-deliver. Not trying to do it too much. What I mean is I try to call the opportunities that I know are going to close based off the things we just discussed.

The Enterprise Sales Cycle Just Got Long Af With Brian Gerrard

The other aspect of it I was on LinkedIn this morning, and the co-founder from Catalyst mentioned something about Jira and how they got to 100 million dollars with the most efficient sales and marketing budget ever. They were at like 19%, where everyone else is up in the 49 to 60%.

So they did that by doing an analysis to see that it is better for the customer to land and expand. It’s better to get the small land or the medium land, let them figure out what they need to do so that we can help them with adoption, they can get the resources involved and then to make sure that then they can scale from there for a very large deal down the line.

Now this is also a way to do it because the switching cost is really high if you’re working with a competitor or if you’re going against a competitor. So when you think of it that way, if we think about the stickiness of our product, they’re not switching because they can’t; we should be making them switch because they see the value of why to do so versus the other one, which is a really long sales process to get into because you have to get really deep into a certain type of gap analysis. 

The second part of that is we’ve seen the studies all over the place from Mary Shea, for example, of how the average stakeholder amount is above 20 people. It’s getting to 25-30 people that you have to convince to be able to move a product in this market for the Enterprise sale. 

Even when you think you’re okay, keep prospecting. Don’t stop, and when I say prospecting them, I don’t mean so much to go cold after just a bunch of different personas.

We have to figure out the exact message from having multiple conversations of what they’re running into on a day-to-day basis for main users, from managers, from directors, and have very personalized emails to the people you need and the stakeholders you need to get this through. And so they feel that you understand what they’re going through in their day-to-day, it takes a lot of time. 

And then the last thing is there are typically sellers that have a more technical analytical mind, and they can get fairly deep in the product itself in relation to the workflow, and so what I’ve seen, at least for myself, is I’ve tended to call a more realistic number instead of having 4x to 5x, 6x my pipeline number, just to have that number out there to make sure that I have pipeline coverage.

Instead, I focused on the ones that I am getting deep with because that’s a sign to me that I have a good way to close, and I can bring back the problems that we’ve run into specifically that we’re going to solve. So I always call quality over quantity.

And the last thing I’ll say is just a quote, “Trust is maintained when values and beliefs are actively managed. If companies do not actively work to keep clarity, discipline, consistency, and balance, then trust starts to break down.

If we don’t have that trust, it’s really hard to work as hard as we need to to get these Enterprise deals through the door. 

The other thing I’ll offer is I am now doing one-on-one consultancies. That’s it; I’m not trying to scale; I’m just trying to learn about what’s out there in the market. It also helps me in my role to see what others are running into. So if anyone’s interested in talking one-to-one, please send me an email directly. And now on to the Q&A.

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Hot Takes Live


Catch the replay of Hot Takes Live, where 30 of the top SaaS leaders across Marketing, Sales, and RevOps revealed some of their most unpopular opinions about their niche.

These leaders shared what lessons they learned and how they disrupted their industry by going against the grain (and achieved better results in the process).

Joe Aicher

Perfect, thank you, Brian. That was awesome. Look, I just love this track that we’ve been on all day long because all these sales leaders and sales folks that have all this experience are just bringing up these things that we’re constantly encountering.

I think this idea of multiple stakeholders, parallel tracks, and making sure that we’re addressing a larger group in the buying process is so key now to getting deals over the line in a quicker amount of time.

And I’m just curious, how you’ve seen that actually develop over time from your start with Outreach, you said in like 2015-ish or so. I’m sure that the buying process was simpler, right, and it was a very straightforward buy, but like, man, how is that developed now to this point for you?

Brian Gerrard

So back in the day, I was doing a lot of transactional business, and so that was a lot quicker, but what I’m seeing in the Enterprise space is a lot of times, you’ll have a conversation with one persona, it goes well, and then the conversation stops, and then it goes quiet for a bit, and then another conversation comes up, and it goes quiet, and then two conversations come up, and it goes quiet, and then an inbound lead comes in, and then it goes quiet. 

There are just a lot of pieces that are put together to make sure that you’re tying all those together and that you’re talking to the right people so you can get that group together as one at some point to have a way to move forward to bring this up the chain. 

Joe Aicher

Yeah, for sure, and I’m curious if you have strategies that you’ve been working with your team on to quicken that in the early part of the sales cycle. For us, for example, asking for direct conversations with other stakeholders and not shying away from that ask, not feeling like you’re end running your contact, but really trying to bring more folks in, are there strategies that you guys have developed, or ways to help bring that conversation together amongst multiple stakeholders?

Brian Gerrard

I mean, part of it is using our technology Outreach which we’ve done a really good job building. The right content and sequences for that. There’s no silver bullet. It’s asking your stakeholder, getting face to face with them, and making sure that you’re personalized through video or other means of LinkedIn,

Yeah, there’s no silver-bullet way to do it. Still, if you have the permission of everyone you’ve spoken to and verify to be very specific with what you’re writing to those other people and have approval, it tends to go a lot faster because you’re speaking their language.

Joe Aicher

Yeah, and I think it’s just persistence, right, and just making sure that you’re not letting that drop off because look how many times have we been towards the end of the sales cycle and there’s somebody else that pops in and just totally derails what have you guys built to that point. And that’s what we were trying to avoid by doing this.

Brian Gerrard

And that’s, honestly, what the executive alignment is for, at the end of the day. If that does happen and you’ve built enough relationships with the top, they know exactly why we’re doing this so they can make sure everyone gets in line. 

Joe Aicher

Yeah, for sure. Well, Brian, thank you so much. I love this topic; I’ve been loving all of them today. This has been like a total treat sitting in this chair; if anybody has questions, they can obviously get a hold of you and find you on LinkedIn.

Feel free to go back and take a look at what his slide decks were. He had that offering on there, so feel free to go back to that. Brian, thanks again; I hope to contact you guys soon, and best of luck out there.

Brian Gerrard

 Thank you all, have a good day.