The 3 secrets of selling up-market w/ Fivetran VP Sales, Stripe Head of Sales, and Docusign VP Sales

Hello everyone and welcome to this session for SaaStr 2020. I am— we're speaking on the 3 secrets of selling upmarket today. I'm Kelly Del Curto. I'm the Senior Director of Sales at Lever, and I'm joined by 3 incredible sales leaders, each with their own unique experience selling to the enterprise. So let's jump in. I want to do some introductions. Tammy, we're going to start with you. So give us a little bit of an idea of your role at DocuSign. And then for fun, what was your very first sales job ever?

That's a good one. Thanks, Kelly. My current role at DocuSign is actually overseeing an SMB commercial sales org. Prior to this, I was in a number of enterprise sales leadership roles. My first sales job, I was a bank teller. Selling mortgage accounts to folks that were coming in to deposit or take out cash from their bank accounts.

I love it. I'm sure a lot of people had that as a first sales job too. Amazing. And Kate, what about you?

Hi everyone. I'm Kate Jensen. I lead our platform sales organization at Stripe. So right now, that's the mid-market and the enterprise segment selling to SaaS platforms. That's companies who process payments for their customers using Stripe's infrastructure. My first sales job was actually pretty random. I sold large drills to gold and platinum mines in South Africa. It was very cool technology that I just couldn't pass up selling.

A little different from Stripe, but— A little different. —a couple of the last very sales-oriented—

Infrastructure in a different way. Absolutely.

OK, Lauren, to you.

Hi, I'm Lauren Schwartz. I lead enterprise sales at Fivetran. My first sales job was, I guess it was when I was a Girl Scout. So age 6 or 7. And the reason I think it was a sales job is because we sold Girl Scout cookies. So for me, I think my first lesson in sales tactics or sales strategy was about encouraging long-term investment by pointing out that Girl Scout cookies do really well in the freezer.

That's a good upsell move. I like it. And just for the record, what's the most number of boxes you've ever sold?

Oh, um, 847.

Very precise. I love it. Um, wonderful. So I'm really excited to talk to the three of you about this topic, which is why move upmarket? What are we going to encounter as we start to build, uh, and go into the enterprise? And I think as we were prepping for this, we realized how common this conversation is at so many different companies, uh, regardless of the stage or the size. And we also realize that as salespeople, we are often at the front lines of the feedback we're getting from the market, whether our marketing is resonating, whether our product is meeting a customer need. So I'm really hopeful today that the three of you can share some success tips, things that you figured out and could benefit the audience. And then also maybe we'll have some vulnerable moments of what didn't go well or common pitfalls that we can avoid. So for the audience, we're gonna be doing Q&A at the end of this session. So as questions come up, just drop them in the Q&A and we promise we'll get to as many as we can. So let's jump, jump right in here with the very beginning. Tammy, I'm gonna need you to define what upmarket means and if it's different for different companies.

Yes. And you sort of gave away the punchline already, Kelly, which is upmarket is not a precise definition by any means. It's gonna mean different things to different companies. For some companies, it might be defined as upper mid-market. For some, it's actually true enterprise and Fortune 200 companies. And for some companies, they might even be able to sell into what are so-called strategic companies. And I think really what's important in the beginning as a company is to be able to come together and be able to formulate what your ideal customer profile looks like. And so most recently at Lever, what we did was we gathered a cross-functional leadership team together that consisted not just of sales, but also marketing, customer success, product, and a number of other— SEs even, and a number of other functions within the company. And we decided to align on what our ideal ICP was going to look like. And again, that can also be measured a number of different ways. I think the most common scenario that I hear most companies doing is going to be by number of employees. I've also seen revenue, revenue be defined as the defining factor as well in defining what that means. But Basically what this does is by coming together and defining what your upmarket looks like, is it keeps your marketing team aligned with the sales team. So they're not out building campaigns and targeting the wrong audience. And while the product team is also out building a product that's not intended for who sales is actually selling to. So I think the more, the most important thing here, and the biggest takeaway is to come together to define what that ICP initially looks like.

Yeah, absolutely. And often those companies, the reason you're grouping them, I'm assuming, is because they behave a similar way or they like to be sold to a similar way. Yeah, Kate or Lauren, any other different way that you measure it? Is there a different way that you can segment?

I think, I think Kate can speak to this too, but the decision for me is highly contextual. So employee count is interesting and useful for a number of reasons. One, it's like pretty publicly available, and another is that it can be directionally indicative of the complexity of a buying process. So that said, it might not necessarily correlate with how much a customer spends. So if you as a business are a little bit further on the curve of understanding your customers, employee count may not always work. Revenue also can work, as Tammy mentioned. But when you're still defining it and you're still early on that curve, you just Ultimately want to optimize for simplicity so that people know who they're selling to and when. Absolutely.

Kate, you had said something the other day about how you differentiate at Stripe. You have even two different teams.

Could you tell us a little bit about that? That's right. We've split the product— or sorry, the platform partnership sales organization and the direct sales organization. And a large reason for why we actually split them is this employee count question. Employee count isn't really indicative of customer size for Stripe when you're thinking about how much payments any company is processing. I'll use an example that everyone's probably heard of, which is Shopify. Shopify only has so many employees, but they process billions of dollars a year. They're a public company, so you can see exactly how much they're processing. And so at Stripe, they may have been slotted into the mid-market, but they should absolutely be treated as an enterprise customer. And so we look at payments volume. Absolutely. Like Lauren said, really specific to our business and our customers' buying behavior. Okay.

So it sounds like it's important that, that if you are going upmarket, that you bring your team together and you really discuss what, what would make the most sense for your company, but definitely define and figure out what that means for you. Tammy, a question that comes up all the time when, when I'm talking about this is, is there an ideal time when I know I'm ready to go upmarket?

Well, I think that's also something that's to be defined for each company, depending on what stage you're at. And I think just overall readiness. And I think some of the ways in which you might evaluate that is whether you're ready to pursue more than one motion at the same time. And that means potentially supporting what may be your existing flywheel motion, whether that's already SMB or mid-market even. And as a company, are you ready to support, an additional function on top of it that your business doesn't necessarily have to depend on. The first few cycles might look pretty experimental and may not contribute just yet in a really meaningful way when it comes to revenue. And so I think as a company, that's an important thing to consider. There's also, again, external factors that might be pushing you. Are your customers asking for this? Are you seeing continued interest and demand from customers and enterprise customers that you may not have been getting attention from before? Do you— are you being asked by your investors or your board to consider a move upmarket. So I think it's going to mean different things. And I think the other thing I'll add before I wrap up on that point too is, is product. If you feel like you're at a point where you can devote additional product and engineering resources to build towards enterprise, that's also a strong consideration as well.

Absolutely. And I imagine that there's never a comfortable time where you absolutely feel ready for this.

Probably not. Probably not. You gotta jump in.

Okay. You brought up a good point, which brings us to our next theme, which is the differences between these different sales motions. So Lauren, you've had experience leading SMB teams and also enterprise teams. Is there a difference in the type of sales rep that you hire when you're looking at those two functions?

Yeah, I think the way to think about this is if you think about the difference between the life of a buyer at an SMB and at an enterprise company, um, there's usually more complexity involved in enterprise buying cycles. So what that means is generally it's more challenging to get an enterprise deal done. Generally, for that reason, it can take longer, although I do think sales cycle length is up for debate. That's why traditionally we see folks with more experience doing enterprise deals, because the at-bats are fewer, they're further in between, and they're higher stakes for both that reason and also because of the larger dollar size associated. So it's truly a different motion. Where SMB is fast-paced. It's for someone who enjoys high-velocity deals, for someone who needs that consistent adrenaline rush or just thrives on it and can build a repeatable formula. And also, a unique strength in an SMB rep is someone who can juggle many deals at once because of the high-velocity nature of the role. Whereas enterprise, you're seeing folks, and you're looking for folks who are more inspired and compelled by the strategic higher stakes move across more stakeholders, both internal and external. I think that's really key is as an enterprise seller, you have to get really comfortable with selling internally, not just selling externally. It's also, it can be feast or famine. So you need to have the type of disposition and temperament and frankly financial situation that can accommodate those ebbs and flows. And where, you know, if your internal reward center is focused on more regular frequent reward, that lag between activity and reward in an enterprise deal can be challenging. So one thing, you know, for me, when I moved from leading an SMB team to an enterprise team, what was challenging for me was the concept of longer sales cycles and figuring out how to celebrate the wins, because you sort of lose that immediate reward. So looking at every move forward as a milestone that you can recognize and hold yourself accountable to and also celebrate is something that we look for and operate on in enterprise specifically. Yeah.

You have to celebrate every, every win because it's not, it's not a payday every day in enterprise. It can be the long haul. That's right. Absolutely. Is there, from either or any of the three of you, a really good enterprise AE interview question that you just love?

One that, one that we ask all the time. And I imagine that this is the same for both you, Lauren, and Tammy as well, is just walk me through one of the most complex deals you've sold recently. How did you build energy in the account? Who was involved on the buying side? Who was involved at your company selling internally as well? What were some of the different stages of the negotiation itself? What were some things that you had to overcome where things could have gone very wrong? Just really, really digging into the process and making sure that they were deliberate and organized throughout the entire process.

Yeah, and you want to see that it's going to mirror a similar sales cycle that you likely are going to have, I imagine. Exactly. Perfect. Well, Kate, I will keep you on the hot seat. Uh, let's talk a little bit about product. So you've worked really closely with the product team at Stripe. Uh, as you're moving upmarket, how does the conversation start to change with product?

Absolutely. Um, we can— I could talk all day about how to actually evolve a product roadmap to suit enterprises, but, but I won't do that. This is a sales session. What I'll talk about is how our relationship as the sales team has changed with product organizations in our own sales cycles. So as you move upmarket, as Lauren mentioned, all of the internal selling you have to do hopefully will be reflected externally as well with your customers. And so one thing we actually do all the time is have our product leaders join our sales calls. As a sales organization, you have to be really prepared to have those calls go well. Um, one thing you absolutely need to do is make sure that you have very robust account plans where you can explain to the product team what you're looking to sell, who you're actually selling to, and what the long-term strategy for this account might look like, so that they can come into the call and build really robust and hopefully long-lasting relationships with the senior folks on your customers' teams as well.

Now, we are no product leadership team by any stretch of the imagination, but, uh, oftentimes when you sign your first enterprise customer, they will ask you for a lot of things. Can you build them into the product? I'm sure product leaders will have different opinions on this, but Kate, what are some of the pros of actually building the product to meet that first enterprise customer? And then what are some of the pitfalls?

I, I think the pros— we'd like to think about it as, could we build products that we could also sell to other customers? Really where our line is, is if this is just a one-off project for this particular account, it's not worth building. If it's something that we could co-evolve a new line of products over time with our customers, then that's always something that we lean into. And in particular, we talk a lot about roadmaps. When we bring our product teams in. And that's one of the reasons that we do bring product teams into the sales cycle, is so that we can jointly talk about long-term product roadmaps and how we might evolve those to optimize for what our customers are looking for.

Yeah, I think that's so great too, because then you're, you know, product is hearing it directly from the prospect or the customer on what that market needs and, uh, and can often influence the roadmap in a really positive and scalable way. Perfect. So let's move on. We've built the foundation. We've committed that we're going upmarket. Let's talk about where we need to adapt. So Lauren, often when you are adapting and you're making a move from SMB to enterprise, you're going to have to manage some competing priorities. How have you seen this go well, or how do you handle it?

Yeah, I think, you know, when you get together with your friends in sales, a lot of stories and battle wounds are shared. And something that you hear a lot over a glass glass of wine with other sales leaders is the unsettling shift in strategy and what can happen. So, you know, I've heard stories of CEO gets up in front of the company and says, we're going into the enterprise and everyone cheers and it's exciting. And then it's really actually quite hard and takes a long time. And so, you know, 4 to 6 months pass and suddenly it's like, actually, we're going to double down in commercial and SMB because we know that works. And that, you know, so you hear these stories all the time. I think it's it really, what it comes down to is it requires a commitment. If you've decided that it's time to follow your customer pull or to make an investment in enterprise, it's a commitment for the long haul, and you don't necessarily see the payoff right away. The good news is a lot of things that I've seen, you know, invested in, in the enterprise ends up, end up being quite beneficial downstream. So, you know, think about Think about Lexus. Lexus helps Toyota sell a lot of cars because they have great features, they have great design, and it creates a halo effect for the broader brand. So as you're investing in more sort of custom higher-end things for enterprise businesses, a lot of times you'll see that shift downstream. And you have to keep that in mind and keep everyone with a flexible mindset of you're not going to see— I mean, it's kind of back to the SMB versus enterprise salesperson. Where if you're used to the immediate payoff, you have to get comfortable with being uncomfortable with waiting for the longer-term payoff. And you end up being a spokesperson internally as a salesperson a lot, evangelizing the future of enterprise and its benefits to the org, even if you don't see immediate returns.

So that's how I've seen it done. Yeah, and goes back to the point of you have to be patient, but you also have to be looking for these small wins. If you're not seeing any, then, then maybe you need to go find a couple because it's going to be a long road. Exactly. Yeah, that makes sense. And another area that often has to adapt is how you support a larger customer. They have different needs than an SMB customer. So, Kate, how have you seen customer success adapt, or what roles are really necessary for that?

There are so many ways that your org has to change to adapt for enterprise customers. One in particular you mentioned specifically is the customer success organization. I mentioned earlier that Stripe— at Stripe, we've actually split our entire sales organization. That's not just AEs, but also our customer success org between platforms and direct. And that's really to align with what we think it takes to make a customer successful in the long term. The conversations you have between platform customers and direct customers are just really different. And so what we want to do is hire specialized customer success folks who work especially in the enterprise with one or two really strategic accounts to define what success means for them and to make sure that Stripe is lining up the resources that are necessary to make that happen. Hmm.

And with that, I mean, is that— there's new roles that are being created, or are you taking the roles that you already have in a customer success or a sales org and just using those and adapting them?

So in some ways, it's what Lauren called internal selling earlier, making sure that the product teams are aware of the feedback that customers have on our product, making sure that the support organization is answering questions with context for the account. Um, but then in other ways, yes, it is actually new sales teams. And in particular, one that we've built recently at Stripe is the technical sales organization. So we have solutions architects who pair up closely with AEs to really map out the technical scope of what a sale will look like. We have a deployment team who actually makes sure that the deployment goes according to plan. And then over time, we have technical account managers who work with accounts over the long term to make sure that any big strategic technical questions they have are very well supported.

And do they all meet and work together? Are they working pretty independently?

They have to work together. I'm sure it's no surprise to hear that, and you'll hear me say this many times throughout this session, account planning is of the most importance. It's really important to just have one place where everyone in the company can go to look to see what's going on with a particular account, what the number one questions they have are, and where they're probably going to need extra support at any given time.

Yeah, I mean, one thing that we talk about at Lever all the time is how much an enterprise sale is a team sale. Uh, sometimes in SMB you can win a deal completely by yourself, it feels really good, but you just, you cannot do that when you're selling to a large company. And And they don't want you to do that either. They want to meet other people at your company.

Exactly. Kelly, I think it's also worth noting that the sale isn't over when a customer signs. So for when you think about renewals and ongoing success, I think when, when you're the salesperson and you have this whole cast of brilliant people who are working in tandem with you as your broader team in post-sales and success, in solutions engineering, it's your— one way of looking at it and how I've seen it done successfully is the salesperson's responsibility is to hold the broader team accountable. While it's not always the salesperson doing every single aspect of making a customer successful in the first year, you do get to be sort of the CEO of your franchise and make sure that you're holding folks accountable throughout, such that when you come up on a renewal, you can't just expect that a customer wants to renew unless you've had critical checkpoints with them along the way. Like Kate's talking about account plans, QBRs, the types of things where you say, hey, sales team and success team, we're aligned on the value that this customer intends to get out of this investment. And customer, you're aligned that you made this investment, and therefore you are also driven to get this value. So let's make sure we're doing that so that there are no surprises when it comes to renewal. So that selling happens throughout the lifetime of a customer. Yeah.

Lauren, do you ask those questions about— do you ask in the sales process what their expectations are, or is that something that the customer success team does? I imagine you do it at both, but—

Well, I think in order to inspire a large enterprise to invest a significant amount in your product, you need to be in lockstep with them about the value that you're driving for them. So be very specific about the value drivers behind an investment, and then also very specific about how your company does it, how you do it better, right? And then proof points behind that of how you've done it before, such that you can truly lay out with a customer when they sign, this is the value we intend to bring to you, this is how we're going to do it. And that's when you're in lockstep with the customer success team in laying out, here is our path to actually enabling this customer and making them successful. And so it needs to happen, and the conversation needs to be very clear and critical in order to earn the investment. But then it needs to— it can get lost in translation when you sort of toss it over the fence, historically, over to success. So there really can't be a fence. It just has to be an ongoing level of communication. And to Kate's point, the account plan can enable that.

It's a bridge, not a fence, right, Lauren?

That's right. No fences here.

One way that we actually solve for the no-fence situation is actually in our compensation for AEs. Because, because, and this is especially true for the business model for Stripe, but I, I know that this works at other companies as well. We actually don't pay AEs on accounts. We don't allow them to retire quota until a company has gone live successfully and actually has, has finished that deployment phase. So there, it's extra important to make sure that you're aligning on expectations with your customers up front and then making sure those actually come true.

Yes. So many— there's sales orgs where they do have, they do have a different role because that is, you know, customer success and account management can be a different skill set. But I have seen organizations where the original account executive is in charge of the renewal and they just, they own that relationship and also some of the customer success that goes along with it. Different models, just depends on what's the right thing for the company. Tammy, I'm going to turn it to you. Let's talk about marketing. How does marketing change and adapt as you move upmarket?

Yeah, well, if you're a company that's been more traditionally focused on SMB, probably what your current state looks like is, you know, you have a lot of roles that are centered around lead generation, creating volume, demand gen type titles and roles, or campaign manager. And a lot of the go-to-market meetings between sales and marketing those agendas are mostly going to be around lead routing, weekly, monthly volume of leads, looking at effectiveness of certain campaigns that have been sent, um, channel effectiveness, whether blogs or emails or ads are working better. And a lot of the top-of-the-funnel metrics that you're likely looking at together are going to be things like hand raisers versus non-hand raisers, MQLs, and how those convert in— MQLs, marketing qualified leads— how they convert into SALs, sales accepted leads or SQL, sales qualified leads. And as you go upmarket, those, those, those agenda items and roles will start to change. Enterprise marketing requires a much higher touch. And so think things like targeted account-based marketing, where you might need to touch and reach out to multiple personas or buyers just within one account. Some companies even choose to invest invest in marketing technology that helps to gauge intent and interest based on what folks are clicking on. And content, field, and product marketing functions are going to be key focus areas. And maybe new, new hires that you might need to make or ask folks internally to be able to adapt and include those functions in well. And product marketing in particular should ideally be able to play some sort of dual role with, with helping to enable your sales teams as well. And what they can really provide is updated product messaging that's more aligned to enterprise or upmarket audience. And that's, that's going to be, that's going to be what's going to help your sales team be able to adapt also as they, as they shift.

And for marketing, I know in this, the sales process, often, I think Kate was talking about it when we were talking about the product roadmap. Oftentimes, marketing needs to sell a vision. Can you talk a little bit about that? Or—

Well, marketing will always have to sell a vision, it'll be a different one this time. And, you know, I think the promise of something is always is going to be really important. And if you've sort of made a brand or a name for yourself in the SMB market, you'll be up against a bit of a challenge in order to prove your enterprise credibility and be able to demonstrate that you can and are durable and sturdy within the enterprise space. That's what a lot of companies are going to be wanting to understand, things like roadmaps. Kate alluded to this earlier, and looking at product functionality and whether or not it's going to be able to adapt and scale for a larger company. The other thing I'll also say about my prior comment around lead generation is that, you know, companies also have to be prepared for looking at metrics a really different way. The immense amount of leads that you were hopefully getting before from your SMB audience may not look the same to enterprise. If anything, it might just be a much slower trickle that you see on a week-to-week or even month-to-month basis. And what you're really looking for in those early days is getting quality, quality of leads, things that actually will convert into some sort of buying cycle. They may not end up actually closing, but I think that will give you an early indicator of whether your marketing messaging is working in those early days.

Yeah.

Quality over quantity as you make that shift. Okay. Well, that brings us to our third section. We have built this, we're starting to adapt. Uh, Tammy, you, you actually started talking a little bit about what we do with those leads, how do we build that pipeline. So I'm actually going to skip ahead a little bit and, and ask, how do we build reliable pipeline? Do we go outbound? Kate, maybe you can talk to this a little bit.

Sure. I built Stripe's outbound sales team about 3 years ago and managed it until about a year ago when I focused exclusively on what I'm doing now. And I'll say that building outbound teams, this shouldn't be a surprise for the SMB or mid-market, works— you work really closely with marketing. It's all about building a scaled repeatable motion. And then enterprise, Tammy, exactly to what you said earlier, it's all about account-based marketing or account-based outbound. Um, in actually setting up reliable outbound teams, a lot of companies think about it in terms of SDR to AE ratios. In the mid-market, you're thinking usually 1 SDR to about 3 to 7 AEs. Um, and in the enterprise, it's a lot closer to 1 to 1 ratio. So an enterprise AE will sit down with their SDR and actually map out the accounts that they'd like to develop better relationships with. And not only just the accounts, but the people, and think about like, why would someone want to talk to us? What do we think we could do to help them? And really develop that value sale pitch that Lauren was talking about earlier. If you're going to convince someone to engage in in a full sales process where they're thinking about investing in your product, you need to be really compelling when you reach out. And I'll say that's, that's our number one goal in general at Stripe. I would be shocked if it was not everyone's outbound goal, is to make sure that even if you are doing scaled messaging or if you're doing one-to-one enterprise messaging, anyone who opens one of your emails, watches one of your videos, opens a LinkedIn message, They should think that you wrote that email or message exactly for them. And they should think to themselves, wow, they read my mind. That's exactly what we were just talking about last week in our internal meetings. And so you just, you have to be really, really targeted and make sure, make sure that you're reaching out to the right people at the right time.

Yeah. And to Tammy's point on quality over quantity, is that the same with how much outreach you're having your SDR outbound team do?

Absolutely. Especially in the enterprise, we work off a named account list. We have a list of accounts that we know we would be a great fit for, and we're working in a very targeted way there. And the same is true in the mid-market, but like I said, it's a little bit more scaled.

Yeah, and that comes back to the ICP that we were— that Tammy was talking about earlier. And when you're thinking about, you know, once you've identified within your core competencies, like, what is it that you're trying— what problem are you trying to to solve, who has this problem as their largest business problem that you can then attach to. And then when you're moving from selling to like 100-person companies to end goal aspirational 20,000-person companies, right, you don't necessarily make that immediate jump right away. But you start to look at targeting early adopters or late-stage pre- or post-IPO companies or looking in, you know, tech companies that happen to be early adopters, that type of thing, as you're prioritizing in your outbound, so that you're not just shooting for the stars on day one and lacking the opportunity to build up reference customers along the way.

Or even what small pieces of really big companies could you work with so that you can kind of get your foot into the door with an account and then build a better relationship over time.

So kind of a land and expand. You start with a small group and then you make your way into a bigger part of that account.

Absolutely. Kate, that's been really effective in my last role. That was really effective, especially during COVID as there are parts of large enterprise organizations who are dedicated to digital transformation. For example, when, you know, in retail, when people can't come to your store and you make a pivot in your corporate strategy around how can we grow revenue digitally, then a lot of times you'll identify these sort of digital innovation teams that end up being centralized across multiple business units that then are, are more, much more likely to be early adopters than some of the older, slower-moving aspects of broader enterprises.

Yeah, creativity in COVID is so key. I've got our SDR team right now that's prospecting into enterprise customers, and they're using different video outbound tools. And I will tell you, it's having such a better reception because in the sea of emails that any enterprise leader is getting you know, something where someone's holding their name on a whiteboard, it's pretty revolutionary and they'll actually watch it. Perfect. Tammy, I'm going to ask you, so we built pipeline, we're standardizing this, we've gotten a couple of these enterprise logos. How do I make this repeatable?

What do I do? Yeah, that's really the name of the game, right, is making this not a fluke, but something that actually is repeatable every quarter and can contribute every quarter. So I think, I think the important thing here is to expect that your first few enterprise sales cycles are iterations. What you want to do as a team post-cycle is to sit down and basically do a debrief, right? A look back on what went right in the deal, what wasn't so great, both internally and externally. And I think internally, It's a lot of, you know, how did people get involved? Did they get involved at the right time? We used to use a phrase at a previous company where it was like watching a children's soccer game where everybody was running at the ball at the same time. That's what you want to avoid. You want to have a situation where the AE is orchestrating the entire deal cycle. But again, that's what the post-deal review is important to do. Look at where did the lead get sourced? Is that something that we can double down on? What was the qual framework that we used to determine whether or not to even go forward with this deal, other than it was a big logo? Who was on the pre-sales account team? Which SEs, which customer success folks helped out? What did we show during the demo? What worked well? And so I'm giving really specific examples here because that's the level of granularity that you really want to get to and figure out what you want to be able to pull out and continue to use. So first and foremost, again, it's just setting expectations and knowing that the first few cycles may not always always be indicative of what the future should look like, but they can really give you some, some early clues. And hopefully, at some, at some inflection point, when you have built out a more mature selling motion and team, and they're starting to, they're sort of starting to get into a rhythm, and they're closing at a healthy rate, they're bringing in a certain benchmark number of new logos or dollars that you've pre-identified, you'll want to start considering standardizing on how these reps sell. If they have vastly different selling styles or approaches, or even how they and their SDR are working to qualify different deals, it's going to be very hard to keep up quarter after quarter. And it starts, it starts to feel like a grind. And so what that could look like is, is, is consider bringing in even just a simple qual framework like MEDDIC. And if you do a quick Google search, it's M-E-D-D-I-C. And it's just basically a framework that helps you figure out what components of a deal you need in order to move forward with it. And you might even consider investing in a sales methodology. And there's, there's dozens of them out there, all of which can be very effective depending on what your sales cycle looks like. But overall, I think the big takeaway here is to figure out a way in which you can standardize.

Tammy, one of the things that you mentioned was that this post-deal review and learning from the things that went well, I think also equally important is a post-mortem when you lose some those early enterprise deals, or maybe not early, just when you're losing these complex deals. And, you know, you've invested 18 months in a sales cycle and it doesn't go your way. And so what I've seen be really successful is, you know, you give everyone a couple of days to recover emotionally, and then you sit down, and before you get everyone in a room, you have folks in different departments collaborate on one central doc doc that says like basically what happened, and you break it into categories. And why it's important to have that doc is because what you don't want is the legal team coming in and the finance team coming in and the product team coming in and saying, well, we did this and we couldn't, you know, you couldn't do, right? It's better to just have like a unified perspective across the org on where we have areas of improvement and why, what we could have done differently to win that deal. I found that to be really effective in learning so that we can do it better next time.

Because it's not a blame game. It's not, you know, no one person usually loses a deal. It's, you know, a team effort, but that way, you know, everyone can be vulnerable and say what part that they had or what they could have done differently. Do you do that with deals you win too? We do. Yeah.

And I think, oh, Kate, go ahead. No, I just, I think it goes to what Tammy was saying earlier about how important it is to build processes and understand what works really well. So you can double down on those things. So that's why we do postmortems. On deals that we win. They're usually a little bit more fun.

Perfect. Okay, so last point here, Lauren, what are some of the things we should look out for that may not be obvious but are really important to enterprise-proof your business?

Well, I think the, the main theme of this, of enterprise-proofing your business, is listening. Listening to your enterprise customers, listening to how they buy, truly understanding the required capabilities. And honestly, it starts with what is the current state of an enterprise when they're not benefiting from your product? And what are the negative consequences associated with that current state? And then walking through with them, you know, what is the future state, their desired future state, and what are the positive business outcomes that are associated with that? And Understanding how to tie what you are building to the things that matter most to them. And when we're talking about really complex big enterprises, a lot of that comes down to things that you, you just didn't invest a lot in when you were selling to SMBs. Things like professional services, things like an enterprise-ready success team, things like security, right? These enterprises need to be able to rely on uptime and certain levels of security that, you know, is something that you'll want to invest in as you're growing with these companies. But I think what happens when you start to win your first few enterprise logos is you've gotten someone who's an early adopter in, because a big, big enterprise isn't usually going to take a big risk on a startup, for example. But when you get an early adopter, then they have, you know, at least in my experience, I remember the first 7-figure deal that we closed in my last company, we We got the early adopters at the company excited about it, and then once we got into the planning phase, they were like, all right kiddos, this is how grown-up companies need technology to run, and we're gonna need this, you know, your support teams to follow the sun. And we were sort of like, well, they don't follow the sun yet, but okay, you know. And so as you're listening and learning from them, you then evolve as a business and grow up together. So having those early adopters and getting that That feedback is really important. And then being able to communicate— this comes back to the internal selling, right? Even after a deal is signed, being able to communicate those needs internally and help your business prioritize, you know, product roadmap's one thing, but legal and security roadmaps, you know, that's another. And how can you grow up with those businesses as your customers?

So yeah, no better way to get that startup reputation off your back than to become compliant, to get all these certifications. Lay the groundwork of all the things that seemingly feel boring but are so crucial for those larger companies. Exactly. Perfect. Well, thank you for answering all these questions. As I'm getting ready to open up some of the Q&A, and for the audience, if you have any questions, please drop those in the Q&A and we'll get to as many as we can. Let's, let's take it away with what, what should you remember from this session? Tammy, can you kick us off?

Yes, absolutely. So I think takeaway number 1, this should actually say define and differentiate why and who. Figure out why it is that you're going upmarket. There's no wrong reason, but be able to understand what that is so that you can set a target accordingly and be able to align your teams around that. And same thing goes for who. Again, your upmarket audience is going to look different from the company across the street. So make sure that you take the time to align on that early. And if it needs to adapt, that's fine. But having at least some sort of predefined goal of who that looks like is going to help you.

And then once you've defined that, the predefined goal of who it is, the, the second takeaway from today, I think, is ruthlessly prioritizing and coordinating. So prioritizing can mean anything from your product roadmap to how you invest in your sales and support teams You're not just thinking about selling to the enterprise. You're thinking about building for the enterprise and what that means and what features they need in order to be successful at scale, which is really what you need to be able to prioritize. And that requires coordination across every department at your company, because unless the entire business is running in the same direction, it's going to be challenging to, to commit to something that, especially when you're first starting to do it, you don't see payoffs necessarily right away.

And the third is to develop consistent and reliable practices. I think you've heard us again and again say things like develop account plans, coordinate and communicate, and it's really important to, to use Lauren's analogy, to teach people how to run and teach them what direction to run in so that you don't just win a few enterprise logos and then your business drops off, so that you can continue to do it again and again. Build a really robust business over time. Perfect.

These are 3 excellent takeaways for anyone that's, that's making the move. Uh, thank you. And I'm gonna stop sharing my screen here and we're gonna move to some live Q&A. Uh, so first question from the audience, uh, what kind of rules have you established to cut loose an enterprise prospect that just can't seem to get to a decision? How long of a sales conversation is too long with a Fortune 500 prospect? Tammy, you're laughing.

I'm going to just put you on the spot. Sure. Yes, I had an immediate reaction because I think this is a good question to ask. It is very, very tempting when you have Walmart on the line to— just using them as an example— to have to even want to push back or even consider pushing back, especially if you are a very early-stage company that wasn't in conversations with a company like Walmart a year ago. I hate to be ambiguous and give you a, it depends conversation, but in a way it does. Are they your only prospect and pipeline at the time? Or if you have a number of similar size opportunities and pipeline awaiting in the wings, then it might not be something that you need for your quarter or for your year. I think the other thing to consider too is whatever demands or asks asks or requests this company is making, is it something that you could productize and use to sell into other companies, right? And so it may be arduous and it may seem a difficult, like a difficult task to be able to accomplish those. But if it's something that you feel like can be used in other situations, it might be worth considering. And if not, I think it's also fair just to have a really open dialogue with your prospect about it too, which is, hey, Hey, you know, we've been engaged with you for the last 18 months, and we're very motivated to earn your business. But for whatever reason, we're finding more and more that we're getting all of these new requests that keep trickling in. You know, how can we come to a resolution here? And I think it's perfectly okay, especially if you've had that long of a sales cycle and you've built that trust and credibility between each other to have that conversation.

Yeah, Tammy, I agree with that. And also, when it's, you know, product roadmap or asking for things to be built, that's one thing. I think another way of looking at this comes back to something you said earlier, which was MEDDIC, or MEDPIC, as some of us use, in terms of opportunity qualification. So I think two things that stand out within MEDPIC for me, the I and the C. I means identified pain, and C for champion. If there is truly an identified pain, and you're tying to a real pain that the business feels, it should not be dragging its feet. So if there are, if the deal is stalling, you should go back and ask yourself, have I attached to the largest business problem? Is there a true identified pain? And then the C standing for champion, do I have a true champion? Meaning, you know, a champion is defined in 3 ways. A champion is someone who's willing to sell on your behalf when you're not there, someone who is incentivized by your success, your success is their success. And lastly, but not least, someone who has influence and power within an organization so that someone can actually make a decision, an economic buyer to make an investment and then maybe move discretionary funds your way. So if you're seeing, and this is to the person who asked, if you're seeing deals stall and take longer than you anticipated, those are important questions to ask because they shouldn't be stalling if there is true pain and you have a true champion.

The definition is so important on that because it's so easy for, especially for a sales rep that's very emotionally involved in a deal, to think that the person that they like, that they talk to every day is a champion. They need those three things. Really good point. Okay. Next question here. I really liked this one. At what granularity do you communicate product roadmaps to enterprises? How deep do you go versus painting a vision that maybe you don't know about yet?

I think it depends on the product. If you've really mapped out your product and you know exactly what you're going to be building and you know that your company has committed resources to actually building those things, go into as much detail as you possibly can. I talked earlier about bringing our product folks into sales conversations. We did this last year with a company called Lightspeed. They're a commerce platform for small retailers. They do POS systems. And early, early in the sale, just to talk about payments, we talked about the rails that we were going to be building to help them set up a lending platform. And so they launched their Lightspeed payment solution with Stripe, but then only a couple of months later, re-launched and launched Lightspeed Capital as well. And that was purely a function of the fact that our product team got very engaged and shared high-level details about exactly what we were planning to build, and they built it alongside us.

So critical to a potential upsell and really deepening your partnership is sharing and being comfortable sharing if you, if you're sure that you're going to build that.

If you're sure that you're going to build that. And you have to make sure that you know you know that you actually are. Because that is the worst-case scenario, is you say you're going to build something and then change your mind.

Kate, what about sharing dates? Is your product team comfortable with you committing to dates on the roadmap?

Of course. It's always an internal debate, and exactly what we were talking about with the importance of, like, really deep communication internally. And oftentimes, our AEs feel like they have to sell internally to push the product team to agree to dates. And there's a difference between agreeing to a date in principle and agreeing to a date in a contract. And that's all very, you know, something you have to really agree on as an internal team before you present anything to a customer.

Yeah. And building on a question that just came into the chat too, do you commit to those things in a contract, or when do you commit to something and putting it in writing?

That's a question that impacts a lot of the different departments that are responsible for making that you have a business that can go public, frankly. So from a finance perspective, when you're thinking about revenue recognition, it can be very difficult to put into a contract that we will deliver X deliverable at this point in the contract and be able to recognize that revenue. So that's probably the first red flag that I would note. I think that there are ways of doing it where you can agree to using commercially reasonable best efforts to build something and agree to keeping an open dialogue about it, but I would be very be very careful with putting future commitments into a written contract.

And one, one way I've seen workaround— well, ways to accommodate that too is instead of full commit on if it's a product request or so, even building in milestones to get to that. And there could be revenue tied to those specific milestones as you get there too. It's doable, but to Lauren's point, there's got to be full company alignment and also the legal team to help wrap that up nicely in language that feels protective for the company.

Perfect. Pivoting gears here a little bit. We talked about sales engineers or the pre-sales. What's a good ratio? How many SEs do you need to an AE team?

Again, this— Oh, go ahead, Lauren.

We're going to say the same thing after you.

I think we are. Go for it. It depends. Shocker answer, I think it depends on how technical your product is and how technical the buyers are. I'll just leave it at that and let Kate add to it.

And what exactly you're building, so which part of your product they're buying.

Yep, that makes sense. At Lever, we often do like a 1-to-1 ratio, but sometimes, you know, you have to separate it. So it's got to be based on Some sales engineers are going to be experts on enterprise sales and they want to get into the weeds and go technical. And then you've got some that can handle many different AEs on an SMB team and you can have a one-to-many.

I will say, if you are a leader wondering whether you should overinvest in sales engineering, my answer is yes. So many of our most successful customers had extremely strong sales engineers involved in the sales cycle throughout. I think it, that is an invaluable resource, and I would not overlook it.

I couldn't agree more, and, and that goes back to the question of what should the ideal ratio be. If you're looking to decide if you should invest in this function, don't, don't wait to invest until you're able to invest to a 1-to-1 ratio. Start building the team now and try your best to build a scaled model, prioritize certain accounts, and then build that function out over time to get to maybe eventually a 1:1 ratio.

Sales engineers for sure build the dream and, uh, you need them. Uh, perfect. I think we have time for one more question, and I like this question because it's, how do we work well with our cross-functional peers? So how can sales best work with other departments? Do you— I'll pass it to each of you. What's your one piece of advice when you need to collaborate with your other department peers on enterprise deals? I can start.

I can say it's not optional. You've got to have full alignment. Going upmarket is not hiring a sales team and wishing them the best of luck and seeing what happens once the quarter's over. Going upmarket requires full company visibility, dedication, and buy-in from the leadership. And so it means that you've got to be closely tied in with marketing to figure out how you're going to target, your prospects. It means that you've got to have product and engineering involved to understand what you're building for and for who. And we've talked a lot about this today too, is customer success, being able to catch and receive and service and renew those customers so that you can set up a repeatable sales motion and sales function.

Agreed with everything Tammy said. I'll just give one example. I think You can't make any assumptions. When you're thinking about cross-functional collaboration, there are so many opportunities to step on each other's toes and to have misaligned incentives. And the only way to make sure that you don't do that is to ask a lot of questions and be curious and don't make any assumptions. Because at the end of the day, while you— while sales and legal might be speaking different languages, you're trying to accomplish the same thing, which is make your company and your customers wildly successful. Until you let go of assumptions and seek to listen and learn, you won't be able to do that effectively.

I'll just say one last thing to build on all of that. I couldn't agree with what you're saying more. Our strategy is always to bring it back to the customer. Speak in terms of their language. This customer wants to use us in this way to solve this problem, and usually that helps rally teams around a singular idea and helps us to work better together.

Leaving on the warm and fuzzies, I like it. It was wonderful speaking to the three of you. Thank you so much for all of this insight, and thank you for everyone who joined. We really enjoyed it. Thanks everyone. Thank you, Kelly.

Thank you, Kelly. Bye everyone.