At SaaStr, we love advice from the best of the best in Sales on hiring your first rep to the building your first SDR team. From SMB to enterprise, we love it all. And it’s no secret that closing selling into the enterprise is a different beast that it comes with its own set of unique challenges and triumphs.

We were extremely fortunate to have three sales veterans (with decades of experience between them) together on stage this year. Shep Maher, SVP of Sales at Guidespark, sits down with Andrea Austin, VP Enterprise Sales at InsideView, and Marc Jacobs, VP Sales at Greenhouse, to discuss the ins and outs of negotiating, handling, and closing whales.

They delve into the evolution of enterprise sales over the last 20 years, the importance of making sure your solution is a painkiller rather than just a vitamin, tools that help shorten the sales cycle, and traits to look out for when onboarding an enterprise SDR.

Check out the full transcript below! 

If you want to see more sessions from 2016, we’re releasing a new one each week. Subscribe here to be notified. And be sure to grab your tickets to the 2017 Annual NOW.




Shep Maher:  I got to start off by letting you all see my sock game. If you’re in the front row I hope you can appreciate that. We got the Golden Gate Bridge going on today. I’m really excited to be here. I’m here with Andrea Austin from InsideView. I’m here with Marc Jacobs from Greenhouse.

Andrea, let’s start off with a quick background for the audience. Tell the audience about yourself.

Andrea Austin:  Absolutely. I always like to say that anything past 20 years of technologies is just 20 plus years. 20 plus years in technology. Started my career in college at IBM. I definitely worked for the man. I’ve been working with InsideView for the last two years. I’ve dabbled in some of the Valley companies. 20 plus years.

Shep:  Great. Marc, go ahead.

Marc Jacobs:  Thank you. I’m not quite 20 plus, but close to 20 years of enterprise sales experience. I am really thankful to be here, and I appreciate everyone coming. I am VP of sales at Greenhouse. Hiring is one of the most important initiatives at a company, hiring really good talent.

We provide the tools necessary to help everybody within the organizations to more effectively source, interview, hire, and onboard the best possible candidates for a given role. I’ve been with the Greenhouse for almost a year and a half now. We’ve grown our sales team from 10 to over 60 people. Like I said, I’m really excited to be here.

Shep:  Welcome, Marc. Just to get everybody the lay of the land of what we’re going to do here, I’m going to start off with a few questions for Andrea and Marc, to get the juices flowing. I see a few people in the audience that, I know, will have some good insightful questions.

We’ll turn the mic over to you all very quickly, so that you all can get your questions answered. We’ll get started with a couple of structural questions. Andrea, maybe you can start us off? Tell us how you define enterprise at InsideView.

Andrea:  Enterprise, and every company does it a little bit differently, we treat the enterprise at the size of the client, and we base it on companies with 2,500 employees and more. We operate that at our business level. We have a channel sales team. We structure that very similarly.

We have an SMB sales team, and we have an enterprise sales team. The cutoff is very similar. We go on employee size.

Shep:  Marc, maybe to add some color to that, can you give us some perspective? I know your background, you worked at VMware. You worked at Thomson Reuters. You worked for some very big companies. Now, you’re working for a startup.

Can you give us some perspective on how the enterprise role might have been treated differently at prior companies you worked at?

Marc:  It is very different at a startup. Not only because it’s a startup, but the SaaS inside sales model, that we have, is very different than what you have at some of the larger companies that I’d been a part of.

When you look at how we define enterprise right now, for our company at Greenhouse, we’re defining it based on the number of the employees that the companies have. We segment based off of 0 to 100, 100 to 1,000, and above 1,000.

At larger companies, you could be dealing with just the Fortune 500, or even the Fortune 100 that are considered enterprise in a way that they deal with it. The way we dealt with it there is very different.

In fact, you have a lot of folks, I think Andrea is someone that did this as well that have maybe one or two accounts and an enterprise sales rep. That’s what they’re focusing on. They might have a huge quota based off of that one account.

Where we look at it now is different. It’s a company that has a more complex buying process. It’s going to take a little bit longer to get through the process. You have to navigate through it.

That’s the difference how we look at whether something is enterprise or not. It could be a large company. It could be a medium company. It could be anything that takes a longer, more sophisticated, complex buying process.

Andrea:  To add to that, enterprise accounts, we have found that whatever it is, if it’s at 1,000 or 2,500, the procurement process and the number of influencers that get involved in the deal, intrinsically changes. A cutoff in the selling motions are sometimes different for a more transactional sale, than when you get into that more complex environment.

You have to understand how to preserve something for procurement, understand how to appease IT and then, obviously, coach your business buyer through their own internal processes. That’s a craft that happens, typically, with a certain type of seller.

Shep:  That’s a great point. To put a specific number on that. I think what you were saying, when we are prepping for the session, Andrea, was that you found that that cutoff point is about 400 employees. Is that right?

Andrea:  Yes. The team Enterprise, at InsideView, is actually, 400 employees. It goes 400 to 2,499, and we, technically, consider that mid market. Rather than having that sit closer to SMB, we found that at about 400 employees, that buying complexity changes, and it becomes much more like the very large organizations.

The bigger that company is getting, they’re starting to say, “We need to not just buy departmentally. We need to buy for the company.” When you’re at the level of buying for the company, IT gets a little bit more involved because there’s vendor consolidation that goes on. When you get to the 2,500 markets, it becomes a little cray cray.

Shep:  That’s the technical term, cray cray. That’s C R A, C R A, and a Y. Go ahead Marc.

Marc:  It’s also how you’re going after that organization itself. If you’re going after a small section of GE, that might not be an enterprise account, although they’re an enterprise company, obviously.

Whereas, you can have a mid market account, that you’re trying to get the entire thing at the same time. You need to get everybody involved, and that becomes an enterprise deal, even though they may not, necessarily, be an Enterprise account.

Shep:  Good point. Another question for you, Andrea. We’ll have you weigh in on this one too, Marc. It would be helpful for the audience to get your perspective. What are a couple of key ways, that you’ve seen, Enterprise selling evolved over those about 20 years that you’ve been doing it?

Andrea:  20 plus years.

Shep:  Sorry.quote1-austin

Andrea:  When I started selling, back in the not 2000s, it was definitely you’d go to your business buyer, or your IT buyer, and you just move. Procurement has taken a seat at the table. In the industries, where you’re focusing upmarket, the procurement department and vendor management gets very engaged now, and they need a win.

They need to be able to show back to their leadership, within the organization, whether they roll up into finance or IT, typically, it does go that way. They need to show that they got something out of that deal. That has definitely changed.

That’s a norm right now. I have this conversation with my teams all the time; you need to save something for procurement, because if they don’t feel like they’ve won, then they’re going to try to hold your deal up, and it’s going to continue to delay.

Shep:  Great point, saving something for procurement, besides a kick in the shins. Marc, what about you?

Marc:  How is the change? Is that the question?

Shep:  What’s one or two key ways that you’ve seen enterprise selling evolved?

Marc:  I’ve seen it evolve more from the difference between selling into the small accounts, into the larger enterprise accounts. The processes is much different. Navigating through the buying process.

As you think about these complex buying processes, you have to think about two or three main things. The first is getting a good understanding of what that buying process is. What I mean is, it’s not just from a surface level. It’s from digging deeper.

Example, I worked recently with one of my sales reps who had a meeting, had the presentation, did the demo, spoke afterwards, came back and talked about how the meeting went. We talked about it and the first thing I asked is, “So what’s the next steps? What’s the timeline?”

The sales rep said to me, “They want to move forward by the end of March and they just have to get approval by the CFO.” Great, so what happens between now and getting approval from the CFO? “Well, I don’t know.”

You have to really dig deeper. How many times has this buyer, this guy actually gotten approval from the CFO? Have they made a purchase similar to what we’re selling them right now? What happens after the CFO approves that?

Are they signing at that point or does it have to go in front of board approval? If it’s going in front of board approval, that may not happen that often. That’s the complex buying process. Getting through that, it’s important to understand all of the steps that you need to. The second thing is being able to map out the different stakeholders.

It’s important to understand, within the organization, which stakeholders are actually getting involved. I read somewhere recently that something like 25 people in a typical Fortune 500 company will touch the decision making process or the proposal, for even just a $50,000 purchase.

How do you get to know these people? Which ones are the economic buyers? Which ones are the technical buyers, champions and coaches? We can talk about that later, the difference between those things. Those are the things. Lastly, is my favorite tool that I use and that’s a reverse timeline.

We’ve all talked about reverse timelines before. When you understand and fully understand that sales process, the buying process, and you understand all the stakeholders to be able to reverse timeline it back from when they want to move forward to now and all the steps that are in between, that’s an invaluable tool.

One of the things that I’ve seen that made people successful is when you take that and you get the buyer to agree on it and to approve all of the steps. You use it as a living document as opposed to just a document that you’re going to look at and help yourself through that sales process.

Andrea:  Shep, I think with the different constituents in that process and by doing that reverse timeline, backing up from the date that it is going to close, one of the dilemmas is that, frequently the business buyer doesn’t even know what their own buying process is.

If you can help them lay it out and coach them through their own internal processes. Sometimes at the enterprise class level, you have to go and help them build that relationship with IT, and build that relationship with procurement.

If you actually do back into a deal and understand all the steps that can go on, you’re sometimes educating that business buyer because they’re not always doing a purchase like that. They’re not always engaging with the CFO for that type of purchase.

Marc:  You get to learn if that is really something that is forecastable. If they’ve never done it before, you can have a lot less confidence that they’ll be able to get it done this time.

Shep:  Great points. I love that point about, Marc, focusing on the buying process, their buying process as opposed to the selling process and the concept. I think for many of you in the audience, you might have a pretty new solution that they can’t pattern recognize.

They haven’t bought something like what you’re offering before. That concept of helping them understand and navigate their own buying processes are a really important point. I’ve got plenty more questions for the panel.

Let me turn it to the audience and see if we have a couple of questions. I see a gentleman back there with some glasses. Go ahead. We got building a sense of urgency, go ahead. You’ve got to turn it on.


Shep:  This better be a really good question.


Audience Member:  [off mic question] .

Andrea:  Yeah.

Audience Member:  [off mic question] .

Shep:  Let me repeat the question for the benefit of the folks who didn’t hear. The question was around building urgency. We just heard Marc say that in a typical enterprise sale at a Fortune 1000 company, you might have 25 stakeholders involved.

How do you build urgency and momentum? Especially if you have a timeline, like end of quarter or end of year, that might not mesh with the prospect’s timeline. Marc, let me turn that one to you first for some thoughts and then Andrea, we’ll come to you.

Marc:  That is one of the biggest challenges, it’s making sure that the buyer has the urgency that you have. The discount that you mentioned before, the discount for moving forward by the end of December, whatever that is, that’s only going to work so well.

It doesn’t work so well at the higher levels, as you mentioned. The most important things are, first of all, understanding the timeline from the beginning, so that you can continually be going through that timeline with the customer.

The second thing is figuring out what business impact, that that customer is going to have if they move forward on time and what negative impact they’re going to have if they don’t move forward on time.  It’s about digging in, figuring out what that impact is.

Whether it’s financial impact, productivity impact, whatever the case may be and leveraging that in order to make sure that it moves forward in the timeline that you’re looking to move forward in. It’s about them achieving their goals, not about a sales rep hitting their quota for the month or something along those lines.

Shep:  Thanks, Marc. Andrea.quote2-austin

Andrea:  It’s the proverbial, “How do you become a painkiller and not the vitamin?” The vitamin is optional;, the painkiller has to handle something acute. If you’re not able to tie it back to the business value, then it frequently becomes optional and then you’re just a product…You’re a hammer looking for a nail.

You have to get that buyer to understand what the storyline is. How do they become a hero in the storyline of going against business as usual? When you’re getting a customer to buy in to the storyline and they’re seeing themselves as that hero, they need to look at business as usual as the villain.

In every story there is a hero and a villain. If they don’t see themselves as solving that business problem and being the hero within the organization, it’s optional and you’re a vitamin.

Shep:  That’s a wonderful point. I love that visual imagery of vitamin and painkiller. The one thing that I would add would be, make sure your reps are really, really frank and candid and have the rose colored glasses taken off.

If there isn’t a business impact and that prospect can’t articulate a business impact because there is none, then you might be a vitamin. It’s not a deal that you should be counting on or banking on because there isn’t that hard ROI.

Andrea:  In SaaS, it sometimes is OK and easy to take down revenue with momentum, but in SaaS, how do you keep that customer if they don’t understand how to measure success? I think that’s the death knell for SaaS, because that recurring revenue has to be tied to something of value.

I think we all get a little caught up in the top line revenue, top line revenue. I don’t know about you, but InsideView measures success on the lifetime value of that customer, and we don’t always make it back in the first year, but we do make it back in subsequent years. If you lose them after the first year, whoops.

Shep:  That’s a great point. We’ve got a question over here. Go ahead.

Audience Member:  Hello. How are you guys deploying account based marketing for your named accounts when you’re going whale hunting after some of your biggest potential clients.

Shep:  Great question. Andrea, I’ll pass that onto you to start.

Andrea:  Those of you who don’t know what InsideView does, we provide bulk data, insights, and connections. Tying, in account based marketing, it to something that’s relevant to them versus making it all about you.

If you’re trying to pitch your product and pitch your product, but you’re not tying it back to some intrinsic business value, you’re going to continue to be that vitamin. Account based marketing is just very tailored for the specific customer that you’re looking at.

If you can create watch lists or provide insights on that specific customer’s business needs and tailor a campaign to them, then you’re actually going to be able to much more precision oriented and you’re not shot gunning messages out there, you’re rifle shotting them. Sorry, I’m from Texas.

Shep:  Marc, anything you want to add on that?

Audience Member:  By the way, I’m sorry, if you have an example, I would love to hear how you guys have tried to deploy with a particular campaign.

Andrea:  I’ve got a great example. If you’re a real estate broker and you’re trying to sell them on mergers and acquisitions, you want a watch list that’s going to tell you that they just bought a division and they’re expanding an operation in a certain geography.

Why don’t you tailor a message and your product solution, especially if you’re going after some type of HR or people base solution, what a great opportunity to tailor and do an account based marketing campaign to that business driver, which is their business driver? It’s not about your product and offering. It’s about their need. Does that help?

Shep:  Good. We got a question over here.

Audience Member:  What’s your sales rep profile for an enterprise sales rep?

Shep:  That’s a great question. I think we talked about traits. What’s the profile or traits that you look for? Marc, we’ll start with you.

Marc:  In all sales, you look for a lot of the same types of traits like being able to ask a lot of questions, being curious, being intelligent, those sort of things. When it gets to the enterprise, there’s some more things that you have to really focus on.quote3-jacobs

The thing that sticks out to me is if you think about it from a quarterback perspective, it’s about being able to not be a person that can just do everything and get through closing a business, but being able to corral all the necessary resources that you have internally within the organization and put the right people in front of the account at the right time.

That’s a little bit of a difficult thing to look at. That’s why it’s important when you structure the process and you go through the interview process to be able to test if they can do these types of things. I think that would be something that stands out to me as that’s very different.

I’ve seen great sales reps that have been able to present great, be able to negotiate great, be able to close business. When it comes to closing large enterprise deals, if they haven’t done a really good job of building internal relationships.

If their first call to the head of security at their organization is that I need you on a call in an hour to help me close this business, you’re not going to be able to win a lot of fans and win a lot of business so it’s not scalable. That’s one thing I would say that stands out to be that’s different from an enterprise sales from other things.

Shep:  That’s great insight, Marc. If your enterprise sales rep is like the quarterback, how important is the post game press conference?

Marc:  [laughs]

Shep:  Just joking. That was a Cam Newton reference y’all. Stay with me here. Andrea, you had some great thoughts on this. Tell us about the traits you look for.

Andrea:  For me, it’s really three traits, which definitely the athleticism is one of them. Intellectual curiosity, not just trying to answer the what, but to understand the why. Really working with the customer to get back down to, let’s tie this back to what is the customer’s challenge and business needs, so that intellectual curiosity.

You’re not just surface leveling the internal relationships, but really clicking down into how are you going to have people help you. The second one is resilience, grit. We all hear about grit these days. Enterprise selling, you hit a wall, you got to bounce off, shake it off. Hit the next wall, and bounce off and shake it off and learn and pivot. Then the athleticism, the quarterback. You can lose a deal alone in enterprise but you darn sure cannot win one alone.

You have to have a team player, you have to have the ability to be strong and nimble and pivot very quickly. Those traits, really, the intellectual curiosity, the resiliency, and then the ability to be an athlete.

Shep:  That’s great, good. We have another question over here.

Audience Member:  For early startups with just the founder teams, they don’t have a marketing department, an outbound sales team, what would be your advice for those types of teams that are trying to close enterprise sales like deals zero through five, one.

Two, from a tactical standpoint, has a bottoms up approach been a successful strategy, or is the top down strategy for whale hunting, is that more effective? Thanks.

Shep:  Andrea, do you want to start with that one?

Andrea:  Your CEO has got to be able to get engaged and help you sell those first couple of deals. Again, it is about team selling. If you’re not getting, especially on that first zero to five big deals, they will make your company.

Everybody has to pivot together and put the ego outside the door, be willing to actually craft and hone in on the right presentation. Again, just do not make it about you, you have to make it about that customer. The more you can tailor and, again, make them that hero.  I know I overuse it.

If you make them that hero in that story and get your leadership and your resources to all, understand the flow, and create the arc of the story, and again, put them in the middle of that as a hero. Your CEO has to get out there and sell those first couple of deals, especially in startup mode.

Shep:  Marc, go ahead.quote4-jacobs

Marc:  I just wanted to hit on the top down versus bottom up. I’ve never seen anybody be that successful in an enterprise deal going bottom up alone. It’s just not going to work. The best case scenario is if you can have somebody, an executive, CEO, or seasoned sales rep that can go top down.

Then also have either an SDR, or a more junior sales rep, or even a sales engineer go top up, then they can meet somewhere in the middle. But going bottom up is not a recipe for being able to close enterprise business.

Andrea:  It’s not fast, that’s for sure.    

Shep:  Good. We have a question closer to the stage here.

Andrea:  We got one over there afterwards.

Audience Member:  The question is about the priorities when you’re selling gain, and you convince the buyer and they have a lot of priorities. Like you said, IT gets involved and it’s not on the list of the priority projects, so it gets moved out a couple months.

What are the best practices there to keep that going so that nothing else happens during that time so the project gets thrown out. I’ve encountered that a lot of times. How do you [inaudible 25:53] ?

Shep:  Marc, do you want to start with that one?

Marc:  Just so I understand the question, what can you do in that few months in between where it hasn’t been a priority and you’re waiting for the deal to progress through, but there’s nothing you can do right now in trying to figure out how to keep engaged?

Audience Member:  [off mic question] .

Andrea:  Making it a priority.

Marc:  Oh, in terms of making it a priority. If we can come back to what the impact of them not making a decision is right now. If you can understand how they’re going to be negatively affected by waiting a few months.

For instance, if your solution is going to provide them with some financial gain, every day, every month, every year that they’re using your solution, you can then make the argument that the sooner that they move forward, the sooner they’re going to be reaping the benefits and the reward of the gain they’re going to be getting.

I don’t know if that really answers the question, but what I would say is, in between that, you should be working to figure out who else in the organization is involved and start building relationships with other people within the organization.

Because too often, you get to a point where you rely on the fact that something is going to happen in three or four months, and change has happened within that organization. Very often, you’ll find four months from then, it’s going to happen four months later or four months later.

Shep:  Andrea, go ahead.

Andrea:  Some of it is, when you know your total addressable market and you’re doing a very active marketing campaign and you get that initial interest, but maybe it’s just not now, create a drum beat. Stay on them, as Marc referenced.

Understand the different personas that are in there, and just tweak your messaging a bit in those drum beat touches to keep the rhythm because at some point, they’re going to be sitting in a meeting, someone’s going to complain about something, they’re going to be like, “Wait a minute, wait a minute. Someone just reminded me of that recently.”

That drum beat is going to help them. It’s even subliminal. If they hear it, and they hear it, and it’s said differently, and it’s said by someone else, and they’re in this meeting, and they heard it together, then they’re going to be like, “Oh, my gosh. We do need to do that.”

It can actually convert that latent interest into more of that pain. I think a drum beat and some of that tailored account based marketing where you’re targeting their pain point, not your solution’s ability to solve a problem, and that drum beat is really, really important.

Shep:  One thing I would add to that, because I think that’s a really profound question.

Andrea:  It is.

Shep:  A couple of quick thoughts. One is, Jill Rowley, who I think many of you are probably familiar with, has a great expression similar that idea of a drum beat. She talks about creating the water cooler conversation.

The way you create the water cooler conversation, that’s when a couple of stakeholders that are involved in that enterprise purchase decision run into each other in the break room, grabbing a cup of coffee, and your company comes up.

Because what you’ve been doing is you’ve been feeding great content marketing, really relevant content to all of those people, so you actually become the topic of conversation around the water cooler. They go, “Why did that project stall? Didn’t we hand that down to procurement?” That water cooler, drum beat thought is really, really powerful.

The other suggestion that I would have is get your enterprise reps used to asking what the other priorities are that can derail your projects. Sales people hate asking the questions they don’t want to hear the answer to.

Nobody wants to ask, “Hey, what could get in the way?” Because they’re afraid somebody could be like, “Well, I got XYZ.” They don’t want to hear that, because they feel like they have a deal. Ask.

You have to know what those other priorities are, what’s on their calendar coming up that could derail your sale. We have a question over here. This gentleman has been waiting for a while.

Audience Member:  Thank you for that. After some starts and stops, my enterprise team came online in a very meaningful way in 2015 with multiple seven figure transactions and the like. One of those deals, one of those million dollar deals happened entirely by the telephone, not one in person visit. Is it a trend or one off?

Shep:  Who wants to take that one?

Andrea:  I think it’s a one off. I think the million dollar deals, a lot of them are based on relationships. You clearly had some awesome momentum on that deal. I’ve not seen it become a trend yet. Our buyers are definitely doing…We’ve all seen the CEB statistics and the Forrester stats there.

Over 50 percent down the buying process before they even come to us. You can capture that momentum if you can keep things moving and they’ve got that pain and you’ve got that painkiller. You can certainly move a deal very fast. I just don’t know that it’s a trend, but I would love to be proven wrong because I’m waiting for that to happen.

Marc:  I think it’s just the level. In the seven figure deals, I don’t think it’s a consistent trend that you close that over the phone but there is a number somewhere that’s in the half a million dollar range, 300, 400 thousand that you can consistently close business over the phone.

Andrea:  There’s one over here.

Shep:  Go ahead.

Audience Member:  Thanks. You both started by mentioning that you had built channels and worked a lot of partners. At what stage did you recommend a lot of these companies that are actually reaching the partners and start building their own channel organization to help them start going into these larger customers in the area that you have relationships with?

Shep:  Andrea, do you want to answer that?

Andrea: From an InsideView perspective, we definitely went direct first and we had a lot of momentum in our direct business but we realized very quickly if we were going get to $100 million and $100 million really quick, we needed to pivot into the channel space in getting other people speaking for us and on behalf of us.

With market intelligence, we’re woven into the CRMs and the marketing automation solutions, allowing those partners that do those implementations and do the BPO associated with changing a sales organization or doing a BI project or master data management.

Getting them to put the skin in the game, to have better data was critical and so we definitely went pretty aggressively down the channel of the whole sales team that just sells through two or three business partners.

It’s great. Our win rate on the referral business is fantastic. I just want more. Channel is really critical because it casts the bigger shadow for you.

Marc:  For us, at Greenhouse, we’re just starting to go through that process. We haven’t developed a full blown channel program yet. We obviously have some really great partners that we work with to refer each other business but from a channel perspective, we have not gone down that path yet.quote5-austin

Andrea:  When you do go down that path make sure resilience is key for your reps there, because partners can be very frustrating because they have their own agenda and they have their own timeline for scaling and enablement but the resilience is, “Just don’t give up on it,” because if you can get it functioning, it’s really worth it.

Shep:  Great advice. Do you have another question over here? Go ahead.

Audience Member:  What best practices do you have for onboarding enterprise sales reps?

Shep:  Marc, do you want to start with that one? The question was best…

Andrea:  Best practices for onboarding.

Marc:  For onboarding sales reps?

Shep:  Yeah.

Marc:  There’s a couple of them. First, you have to make sure that you have a really good cadence in place for what that sales reps can have to go through and you need to work through that in the beginning and let them know exactly what the expectations are going to be.

You have to be able to bring in the right people within your organization to train them on all the aspects of not only how to sell within the organization, but also the product pricing, all of the things that are important.

Just from a best practices perspective, I think it’s just about making sure that you have a really good coaching culture within the organization. It’s not just the actual onboarding, the specific onboarding but that there’s constantly reminders and work coming from managers or other folks on the team that can work with them and share the best practices and make that a consistent cadence that happens, not ad hoc but actually on at least a weekly basis.

Andrea:  We have a sales enablement resource that really helps because it provides the baseline structure. In Enterprise, it’s a little different because it’s not a transactional business, so learning the quoting tool and futzing around with all the Salesforce levers that we work with learning how to read the Marketo triggers.

I actually created an onboarding partner with another enterprise rep, because I’m also trying to foster a team selling environment. If they have a peer to go to ask the dumb questions that maybe I’ve already coached them or one of my managers has coached them on, they’re not as embarrassed to ask the silly questions and they have a peer that they can go to.

You will also find that that peer wants them to be successful, so they’ll actually go out of their way to take a little bit of the burden off of either one of my sales directors or even myself, if it’s one of my global folks. That onboarding partner really is invaluable.

We do it quite informally. I even set it up with, “You’re not their manager. Just invite them to your calls, maybe let them tag along to a meeting or two,” and just be available to answer the questions that maybe we taught them in that cadence and it that rhythm with those expectations, but they don’t do it enough that it’s inherent until they’ve actually tried it a couple of times.

Shep:  I think that’s great insight. The one thing I might add would be that I would encourage you to think about onboarding especially of an enterprise rep as a whole company thing.

Andrea:  Yes, I agree.quote6-maher

Shep:  It’s not you alone. You need to get your product, your marketing, your finance people involved to help and contribute and they should be willing to help but it is a whole company exercise. This is a very serious investment you’re making in a really highly trained and highly paid, hopefully, assassin. It’s a whole company thing.

I know we have a question over here but I think we have one waiting and we’ll come back to you in a moment. Go ahead.

Audience Member:  Hi, thanks. Two quick questions, for a startup who’s selling into enterprise, what’s the best practice or what’s a way to get attention of the decision maker or a buyer because sometimes just getting to that decision maker is extremely hard because they get bombarded with a lot of messages and emails.

At what point, if you are focusing on this account based marketing and you have top 50 accounts you’re going after. You give up on them saying, “OK, let’s just give up and move on.”

Shep:  Great questions, Andrea, do you want to start that one?

Andrea:  First, don’t go to them with you. Go to them for them and if you can be tailored in the way that you’re approaching them with something that’s personalized to them then you’re not making it about you. You’re making it about them.

I think that’s a tactical mistake that a lot of startups make, is that they think their product is so awesome that, of course, people are just going to line up to buy it. You have to make sure that you’re using an insight that’s specific to their business pain point.

Frankly, we’re networked. We’re all selling. We’re all building products. Tap into your network. Use your personal connections. If you can get a person who is closer to them than you are to actually reference you in…

We all know that references are better than just data and something that’s specific about them, a personal connection is really important. I think when you’re in startup mode that is just vital.

Shep:  Marc, anything?

Marc:  What Andrea said, there’s one point that she hit on that I thought was really valuable, and that’s especially when you actually get to the person having a really good understanding of what your value prop is to that particular person.

If you start to speak to people about the different features and things that make you a little bit different, that’s not something that’s important to a decision maker. They’re looking to understand exactly what your value proposition is, what you are bringing to the table as an organization.

What is value? Obviously, it’s benefits minus the cost, so figuring out not only why or how you’re going to help them with specific features, but what is the value for them that you’re going to bring and what is that actual quantifiable number.

Or what is that quantifiable thing and what is the opportunity cost for them not to be moving forward or something like your solution.quote7-maher

Shep:  Marc, those are some powerful answers. One thought I might add and not to quibble with your question, but I think the way you phrase the question was, “How do you get the attention of the decision maker?”

Personally, I hate the word “decision maker” and I hate the word “gatekeeper,” because if you think about it, and I actually tried this exercise with my team just yesterday, I asked the members of my team, “Am I decision maker or a gatekeeper?”

They all said, “You’re a decision maker.” I said, “What if I’m calling from Silicon Valley Bank and I want to present some funding options to Keith and Chris, our CEO and CFO? Am I decision maker or a gatekeeper?” They’re so polite so they’re like, [stammers] “A decision maker?”

I’m a gatekeeper at that point. Those words make me cringe and I cringe when somebody says, “Oh, well, who’s the decision maker on this?” The point that Andrea and Marc made early on, the way the world has changed. There isn’t really a decision maker anymore. We are doing in a consensus sale world.

Andrea:  Yeah, especially enterprise.

Shep:  Especially enterprise. The gang that wrote “The Challenger Sale” put out an article recently in “Harvard Business Review” called “The Consensus Sale”. It’s a really good read, really worthwhile. It might help you rethink that approach. There might not just be one person whose attention you need to get.

We had a question over here and then we’ll come back this way.

Audience Member:  Hello. Thank you. Can you hear me? OK.

Shep:  Quite clearly.

Andrea:  Yes, we can.

Audience Member:  Two quick questions, one is clearly learned and it’s clear that the closing activities for an enterprise and for the mid- market are very, very different but what about the lead generation activities in terms of do you see the typically outbound campaigns working on the enterprise customers as well, or would you go a different route?

My second question is regarding the enterprise sales people, it’s a very long sales cycle and obviously, it’s difficult. You can’t know whether the deal will close or not, but especially for the early startups, at what point do you know how to evaluate your enterprise sales rep?

Based on the deals are moving but they’re not closing yet and how long do you give them and how do you decide at which point to make the decision? Thank you.

Shep:  Just to recap, two part question. One is, how do you handle lead gen in the enterprise? Is it different from SMB or general business? The other is if it’s a long sales cycle and then you have an enterprise rep who seems to be doing well in building pipeline but hasn’t closed anything yet, when do you know when it’s time to cut bait or let them keep fishing?

I’ll turn it to you all. I have one of you answer one part and one answer the other.

Marc:  Your choice.

Andrea:  I’ll take the last one first. Going back to the question that was earlier on, do you start top down and how do you start for the first couple of deals? If your leadership team has participated in some of those early deals, getting them back engaged, because remember you can’t win it all by yourself.

You’re going to probably need the help of your leadership and product organizations and what not. If you’re nervous about that, and you’re not getting those closes, participate in those cycles again. Get engaged. Ask to be invited.

Again, I don’t know how many of you have seen this in your sales careers, but I certainly have. Executives want to get involved the last week of the quarter. Get them involved earlier in the quarter so it doesn’t look at desperate as it actually feels and there’s a justification of, “I want to prove myself.”

If you get involved sooner, you’re going to start to realize that they’re afraid of asking about the buying process, or they’re not proud of their craft and they’re trying to hide the fact that they’re selling. I’m very proud that I’m in sales. I love my craft.

The fact that I sometimes have people on my team that are soft footing around asking for the business. If you’re not comfortable asking the customer, “What it’s going to take to make this deal happen?” then you’re just dancing around the topic all the time.

You’ll know a little bit of that. If you get back engaged, I think you’ll start to figure out if they’re cutting the mustard or not.

Marc:  I’m just going to add to that part of the question that you asked. For me, it’s also it’s not necessarily whether how long the deal’s been in the pipeline. If you actually can look at a buying process and align your sales process to what the buyer’s needs are and have verifiable exit criteria.

Aaron Mohamed, one of the directors on my team, worked with me to come up with some really great exit criteria to make sure that our reps, as we go through the sales process, we know that the deal is moving as we expected to.

I would measure it based off of the velocity that it’s actually going through the process as opposed to whether you actually close the business. I know that’s hard to do but at least if you have those verifiable exit criteria, you’ll have the ability to measure how that rep is taking the enterprise deal through the process. I think we missed the first part.

Shep:  Lead gen.

Andrea:  The lead gen. I have very strong opinions about sales development or lead generation. It’s just not a transactional effort, a transactional businesses and more of a small business, faster paced deal, these are long plays. If you’re going to round robin the leads that come in, and your reps…

Let’s be honest. Enterprise sales reps are control freaks, and you want them to be. They’re impatient, and you want them to be. If you’re bouncing SDRs into that relationship, and there’s not a continuity point where they can trust and hand off, how many deals get deeper into the sales cycle and then stall?

Do you want your enterprise rep taking their time away to be calling, and stalking, and checking in and John Barrows has that famous, “Did I lose you?” tagline on an email?quote8-austin

Do you want them doing that or would you rather your SDR to do that? Handing it back into their SDR or their handful of SDRs, is really important. I believe that separating small business from enterprise sales development is vital.

I think the continuity and the long term relationships, when you land the deal, and a lot of enterprise is a land and expand approach, when you land a deal, why not put your SDR back into that deal because they had developed the relationship, get referred into another line of business?

They’ve developed that rapport, they understand the account, they know the rep. It just creates a selling team versus an SDR that’s going after creating an opportunity. But that’s my opinion. [laughs]

Shep:  Right, that’s well put. We’ve got a question in the back. This gentleman here then we’ll come back to you.

Audience Member:  What do you think about RFPs coming out of the blue? What should startups do to things like that? There’s a lot of effort involved in answering to them and the chances may be pretty low. Rule of the thumb, we heard this RFP, which you don’t have contributed to it previously is a lost to RFP more or less?

Shep:  The question was RFPs. When an RFP comes in out of the blue, should you respond or not? Marc, do you want to start with that one?

Marc:  It depends at what stage you’re talking about. Obviously, if you don’t have a ton to do then yeah, that’s a great, great thing to try to bring on a customer. Right now, the way we look at it, if an RFP has come on but we haven’t done a good enough job yet of qualifying that customer, we’re going to respond to the RFP but it’s going to be a very generic response done by a sales engineer in our organization.

If they’ve taken the time to qualify, if they’ll get on the phone with us and speak to us about their needs and their challenges, and we see that as someone that is potential fit for us, yeah we’re going to out the time and make sure that we respond the right way to be able to give thoughtful answers and be able to put ourselves in the best positions to potentially win the business.quote9-austin

Andrea:  For us, it does depend, Marc. We’ve stratified our organization with named accounts and then general territory. If it’s in general territory, I sense that we’re column fodder , I don’t waste my reps time on that. I don’t want to be column fodder. Our team is too proud for that, our time is too valuable.

If it’s a named account, yeah. I’m definitely more inclined to participate but I definitely ask for that meeting, as Marc referenced, to help re-qualify some of the buying decisions, some of the priorities.

You can get that discussion in a named account or a targeted account and change at least a portion of the criteria to make it tied to your differentiators. It’s worth it. It’s cold and then it’s a general territory, I feel you’re just column fodder. I really believe that. I’ve not really regretted it, because it’s coming late and we’re a bit of an afterthought.

Shep:  Great answers. If you’re looking for a book that covers that subject and some depth, there’s a great one out there called, “Let’s Get Real or Let’s Not Play” and it talks about handling that exact question. I think we had a question over here. Go ahead.

Audience Member:  Yeah, I got a question coming back to the consensus sale, and the importance of the enterprise to have an internal sponsor or champion. Interested to understand from Andrea or Marc, any methods or tools that you’ve used to enable a champion to sell internally to other stakeholders?

Shep:  Marc, go ahead.

Marc:  I’ll take it. First of all, I’d mentioned earlier that one of the big mistakes that reps make in the process or anybody makes in the process is relying on the wrong person and thinking that they’re your champion, when in fact they’re not. They might be your coach.

There’s a big difference between a coach and a champion. There’s a lot of similarities, a lot of qualities that are the same. They’re going to help you to navigate through the process. They’re going to an advocate for you but the big difference is whether they have access to authority.

Whether they can either get you in front of the decision maker or they have the political clout within the organization to be able to influence that decision with the decision maker. Once you know that that is the right person and the champion, then it’s just building that relationship working with that person constantly.

Making sure they’re armed with all the things that are necessary for them to sell internally, and anything that you would be selling, you want them to be able to talk about your value proposition as well as you could if they’re going to be successful.

Also, making sure that when you’re looking at that champion that they have something that they’re going to gain from moving forward with your solution, personally.

Andrea:  We’re a challenger shop, so we definitely look for that mobilizer. If any of you follow “The Challenger.” That we will actually become that mobilizer’s assistant, and we will help them build their internal materials to go and do the presentations.

Again, that whole, a little servant leadership type of thing and the philosophy of making them be the hero. We’ve got some nice technical prowess when it comes to PowerPoint and presentations and proposals. Why not leverage to that to their advantage because it’s to our advantage?

We definitely try to make the mobilizer, the successful entity and even if they’re not the decision maker, they’re definitely pushing things within the company, and they’re being heard because they are the mobilizer and so that’s our approach.

Shep:  Great. Good insight. I think we have time for two more questions. Let’s take these two right here.

Audience Member:  [off mic question] .

Shep:  We can hear you. I’ll repeat it.

Audience Member:  Sounds great. I’m VP Sales of a startup, I came from IBM, Cisco and the enterprise world and I’m working with a first time CEO working in enterprise sales. What are you’re onboarding tips for working really well with that CEO?

Shep:  Just to clarify, you are a VP of enterprise sales. You came from IBM, Cisco, that big company world. You’re working with the CEO…

Andrea:  First time CEO.

Shep:  …who is new to enterprise sales and has never done enterprise sales before?

Audience Member:  Right. Our company is enterprise solutions.

Shep:  Enterprise solutions.

Audience Member:  How do you make that dynamic work well?

Shep:  Good luck. Next question.


Shep:  Just kidding. Andrea, do you want to start with that one?

Andrea:  Yeah. Especially, first time CEO, there’s probably a little optimism and definitely happy ears that goes on. I think a lot of coaching, especially with your enterprise background. In the bigger companies, having worked at IBM many years of my career, it’s a miracle anything got done.

I was told many times, “You’re exactly what we need at IBM. But man, you scare the crap out of me,” because I like to break glass. You cannot be afraid to break glass with your CEO. Every leader and I have this conversation with my reps all the time, don’t assume that they know what they’re doing.

Audience Member:  I don’t.

Andrea:  We can’t, right? Help coach and guide them so that, again, so they can look like they know what they’re doing and then they’ll start learning. It’s harder for you and you’re going to have to do a lot of their work, but give them a role, don’t just hand the presentation to them.

I’ve seen it done over and over again. “I’m going to bring my CEO in. I’m going to bring my CFO in, and they’re just going to do what they do.” They don’t know what you want them to do. Be prescriptive.

Tell them what you want their role to be and even coach them, “If the conversation goes this way, pivot this way.” Lay out the roadmap for them. I think, then that first time CEO will appreciate, and want to be more involved, and will actually learn how to shut up. Because that’s very important. Sometimes we got to get people to just shut up.

Shep:  Marc, I know your CEO’s in the room somewhere, so does that mean you want to answer the question or…?

Marc:  He just left. He didn’t want to hear the answer.


Shep:  Do you want to weigh in?

Marc:  No, that was exactly what I wanted to say as well.

Shep:  OK, perfect.


Shep:  One other thought that I’ll give you in that scenario, I was in a sort of similar scenario, it was a second time CEO, transparency and visibility is critical. This is probably a pretty smart analytical guy. Give him visibility.

For us, we co-located, so we were all sitting in one room and he could see the activity. We gave him access to Salesforce right away. Don’t try to hide or operate over here and say, “Stay out of my way.” Bring him in and let him see all those things that are happening. I think that will help as well. We have time for one last question. Right here.

Audience Member:  Hi, I just have a quick question regarding the tools and strategies you guys have implemented to help shorten that enterprise sales cycle. We all know, depending on…I think you mentioned enterprise, for Andrea, is 400 to 2,500 employees.

Shep:  And up.

Audience Member:  And up. What have you guys used with your sales teams to help reduce that very long sales cycle?

Shep:  Tools and strategies to reduce the sales cycle.

Andrea:  Yes, of course…

Shep:  Oh, Andrea, go ahead.

Andrea:  No, sorry, go ahead

Marc:  No, go ahead. You were talking. Please.

Andrea:  We use InsideView, of course we do, because it’s our own technology and we sell to sales and marketing. That allows us to be very precision-oriented on focusing on the data, the insights and the connections.

The connections is really vital. We’re a Salesforce, Marketo shop. A lot of it is how you enforce the usage of those things. I even had a conversation with my leadership team, because we’re implementing an executive sponsorship program right now.

It’s all on the enterprise side and our executives are the worst at putting their activity in Salesforce. I’m going to do a little coaching session for them. A lot of it is the tools that you choose. It’s how you create a cadence around the use of those and best practices.

You can spend a whole lot of money on technology, but if you’re not actually helping people understand how to use it and the purpose of using it, it’s not just for me to look at activity from my reps, it’s for hand offs and transitioning from sales into the customer success organization and bringing other people in.

The same thing with Marketo, interesting moments. That’s awesome. We didn’t used to expose that to our Salesforce. We now do those types of things. The tools, it’s a lot about how you implement them and enforce that.

Shep:  Marc, anything to add?

Marc:  We use a bunch of different tools. We’re using InsightSquared a lot to help us to work with the reps to make sure that we’re getting through the process in an efficient manner but, also, making sure that they’re hitting all of the things that they need to hit in each of those steps.

I would say the biggest tool, and it’s not a solution, it’s what I said before. It’s a reverse timeline. It’s making sure that document is used properly, coaching reps on how to use it, understanding all the steps that need to go from now through even the next step, to the next step, until they want to be up and running.

Like I said earlier, it’s making sure that the buyer, the customer, is on board with what you think those things are. Confirm that stuff. Make sure that they agree with all the things, and keep it as a living document.

Work with them every time you’re speaking to them to see where you are in the process. That way, you’ll have a much better chance in navigating with them more quickly through the process.

Shep:  Sounds like we have time for one more question. Is there one more question out there? You, go ahead. If you didn’t get your question answered, we will be hanging out. Come find us. Please feel free. Track us down. Go ahead.

Audience Member:  This goes back to the tools you were talking about. Presentations are critical to the sales cycle. Is there any tools or secrets that you use to keep everyone singing off the same sheet of music or ensuring that your slides and what you’re using are all up to date?

If you have 80 people, they’re not making disparate messages out there based off some presentation six months ago. Any tools, any presentation management?

Andrea:  We store things in Box. We reference it through Chatter and Salesforce. We don’t store documents in Salesforce, because that becomes heavy. We link them within the Chatter with the documents into Box.

It helps navigate. Sales people are impatient and a little ADD. By having them source through Box is, sometimes, overwhelming for them. We’re, right now, considering content management. It’s another mechanism to make it tied into our sales process and allowing it to link into the source document.

We’re big advocates of Box. Sharing, pushing PowerPoints around, version control, logos that should and shouldn’t be used, it can get you in a little bit of hot water.

Marc:  We do a similar thing.

Shep:  One thing I might add is for us, some deviation from the norm is OK. For us, we want to have core messages the same. We want to have some version control over the PowerPoints that are out there. An enterprise rep putting their own spin on it and adapting it for the particular situation they’re facing is just fine.

With that, we’ll wrap the session up. Thank you all very much for your time. Andrea, Marc, thank you so much.

Marc:  Thank you.

Andrea:  Great questions, guys. That was awesome.

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