"Aligning Sales, Marketing, and CS to Scale Revenue and Retention" Theresa O'Neil, Showpad CMO

I went from being the marketer that asked sales, "If you could just fill out these 15 additional fields in Salesforce, that would help me out a lot. I'd be able to do much better segmented marketing." I went from being that person to the salesperson whose opportunities were never updated in Salesforce. So, became much more empathetic, and it really drove my passion for being a marketing person that supports the the sales team, and that's what I'm gonna talk to you about today. So we all want that big payoff in the end, but the reality is most tech startups fail to exit. And there are a lot of reasons. My belief is that it is related to how we relate to our customers, not only with our products, but through that buying journey. Are we selling the way that buyers wanna buy? So let's talk a little bit about that gap between our buyers and how we're selling. The market has shifted. As consumers, right, we're all both people who buy software as well as consumers. The market shifted. We buy based on experience. Whether it's Booking.com or Amazon, we go for convenience and experience over price or product. Those same expectations that we have at home of our buyers in the office. Now more than half of B2B buyers are buying based on experience over price or product. Showpad wanted to learn more about this. We surveyed last fall 600 B2B buyers. In Europe and the US who had made a software purchase. The whole study is available. I can share a link with that, but I'm gonna just share a couple of highlights today. So we all know, we hear that most of the journey is done before the buyers get to us. But what we wanted to know is how much time are people taking to research before they get to us? And the answer is on average 1 to 2 full business days before they ever— So that was interesting, but what we then wanted to know was how does that change based on the average deal size? So we looked at— this is a little hard to see from the back, but if you look at the green bar is 0 to 5 hours. The gold bar is more than 40 hours. Right, and what you can see over there when the deal is less than $5,000, they're spending about 5 hours, but when you get over to $100,000, they're spending 40 hours, a full work week researching before they go to sales. So what does that mean for your sales team? It means the buyer is really informed, and so your salesperson has to be really sharp and really skilled. So we— then we looked at deals and what can speed them up. So poor content slows down deals. People feel that the information wasn't relevant, they didn't trust it, and it wasn't— it was confusing. So poor quality content can slow things down. So the answer might seem, "We'll just give them more content." No. Buyers are overwhelmed by the content that you're sharing. Most people are overwhelmed when there's more than 10 pieces, and if you think about a whole buying cycle, it's likely you're sending more than 10 pieces. But almost half were overwhelmed with 5. So they're not getting the information they need, but the answer isn't sending more. Buyers are desperate for relevance. Remember, they're doing a lot of research. They want only the information they need to close the gap between what they already know and what they need to know to make a decision. Information that's relevant to them and their use case. The other thing that came out was that interactive content experiences can really accelerate sales. So one of these are the top 3. First is a personalized content portal. So imagine a place that as a seller you can put all the content and information for all the stakeholders in your organ— in the Buying organization, right? Because as a seller, you might be talking to 3 people. There's probably another 7 that you don't even know about. If you could put all the information there and the buyers could all look at it together, and then as the seller, now you're interested in— ROI calculator. I've been around a long time. This has been top of the list for every sales team I've ever worked with. And then things like augmented reality. So if you're in manufacturing or maybe you're making large medical devices, how great would it be to be able to show your product in the context of your buyer's environment? So buyers want relevant, personalized content and helpful sales teams. They still want to interact with salespeople, right? But they want those salespeople to have great information and skills. So buyer expectations are high. And that means that the pressure on sales and marketing has never been higher. In the end, the best buyer experience wins. So how do you deliver that? How do you transform your organization to scale? So at Showpad, we put together what we call a sales transformation maturity model, and it's based on the experience of, you know, hundreds of clients that we've talked to. And I'm not going to go through the whole thing because that would be a whole session in itself. But I wanted to talk about these 3. Startup selling, we've all been there. There's a small team. Your founder is probably your number 1 salesperson. You might have an informal marketing organization. And then you start to have some success. You start to understand which use cases really resonate, adopt more, all those things that you're learning in those first-time selling. This is the gap that most companies have a really hard time. It's like, how do you take that initial success and scale it? And whether scaling means multiple geographies, or if you're gonna be in multiple regions, multiple languages, are you gonna go to multiple industries? Are you going to expand through product lines? How are you gonna take what you're doing today and scale? And so that's what I'm gonna talk about is how do you get from today's success to scale into a really large SaaS company. The key here is that the marketing and sales transformation challenges are shared. And it's both the reality, and if you don't treat it this way, you're not gonna get to that end. So just starting, so I always look, you know, marketing is about revenue and return on investment. Sales is more focused on revenue. So from a basic function here. So let's ask, how many people in here are marketing-focused? Marketing leaders? Great. Sales? And just other, others? Probably. All right, great. I see, I think I saw some multiple hat people too, so I get that. So for, you know, a bane of a marketer is sales presenting off-brand content. And sometimes it's just annoying because it's ugly clip art and you've created all this beautiful stuff and then sales creates their own content? Two things. One, if you're in a highly regulated industry, if you're selling to financial services or life sciences, you need to be really careful about the content that's presented. But the other thing is sales does not— salespeople here enjoy spending their time creating content instead of selling. Oh, I get a little— all right, one honest guy. That's good. They're doing it because marketing's not giving them what they need, right? And as marketers, we cannot be creating custom content for every opportunity, but we need to get better about delivering what sales needs. As marketers, we have a lot of insight at the top of the funnel, right? I can tell you all day long about my AdWords performance and my email performance, but if I ask you what content at the bottom of the funnel is tied to close one revenue. We don't have those insights. On the sales side, they don't spend enough time selling. Like, Forbes says 35% of a salesperson's day is actually spent selling. 'Cause they're filling out all those 10 extra Salesforce fields for me so I can do great segmentation. They're doing forecast reports. They're doing all those things they have to do. They're creating content. They're looking for content rather than selling. Selling. So how can we improve how much time they have selling? Um, it takes new reps a long time to onboard. Now especially if you're a fast-growing SaaS company, you're gonna be adding reps at a pretty high clip. How do you take that initial success, find out what works, and give them the skills they need? Not just on your product, but on selling methodology and negotiation, basic sales skills. How do you do that in a scalable, repeatable way? Then it's tough to turn mid-performers to high performers. This is where I'm going to be challenged having a mic and a clicker. If you think about a bell curve, on this end we've got your low performers. You're probably never going to help them. You just need to move them out of the business. Then you've got the majority, these mid-performers, solid performers, and then at the other end you've got your top performers. There's always a couple. Learning to tell the difference between just the first 2 salespeople who've cherry-picked all the accounts with, or as you grow with the real skilled ones. But if you can take that bell curve and move it just a little bit so that more of your mid-performers are at that high performance rate, think about how that could impact your revenue. And then finally, struggling to articulate unique value. Oftentimes a salesperson, when they get faced with competitive FUD, fear, uncertainty, doubt, They have a hard time responding. They don't know how to take control back of the situation. In fact, Serious Decisions for many years has said the number one reason that salespeople don't make quota is their inability to articulate unique value. To tell the story about why someone should choose you over your comp— nothing. We spend a lot of time on value propositions and messaging. A lot of time. There's a lot of discussion. And then it goes to sales and who knows what salespeople are saying out there. Like when you sit, if you're a marketer, when you sit on sales calls, 99% of the time they are not articulating the value proposition that you spent so much time working on. So how do you help both improve marketing, developing the value prop, but then sales needs to be empowered and enabled to articulate that unique value. So I'm gonna outline 6 strategies to align marketing and sales to drive revenue. Number 1, align on your ideal customer persona priorities. Priorities is the key word. So let me give you an example. Say you've decided your top ICP is technology. You wanna sell to other SaaS vendors. And then the sales leader goes and hires someone whose background is financial services and they've got a great book of business. They wanna go out to those accounts. Marketing has no content. We have no expertise to sell to financial services. So you need to align on industries, on roles, on use cases, on geographies because it impacts where you're going to invest in demand generation, messaging, enablement, and even product. So priorities is the keyword. You might have 6 ICPs you're selling to. What's number 1, 2, 3, 4? That order. Number 2, map content to the buyer journey. So marketers are really good at this because especially when you start, you're thinking about demand gen. So why change? Why change from doing nothing? Why change from a competitor? We're okay at middle of the funnel, why now, right? Because that's what we're trying to push to an opportunity with sales, give them enough reason to do why now so that sales can engage in an active opportunity. Most marketers, most organizations are not great at this because once it goes into sales, it's typically the skill of that salesperson being able to articulate this and marketing has no data to show What content is being used? What sales collateral is being used by sales, viewed by prospects, and what's tied to close one revenue? Once you map content to all of those stages, now you want to align on sales stages methodology. So, you know, what is an MQL? I have been in an organization when I joined, every lead that came in was an MQL, and if they were going to give 6 6,000 raw leads to a sales team of like 10. Not helpful, right? So that the leads that are going to sales have a high propensity to convert into a meeting and then an opportunity and then a deal. So align on those stages and the roles of marketing and sales. And that leads us to number 3: Define your metrics for SaaS success. So one is the definitions. Again, what is a marketing qualified lead? Get agreement with sales. Sales stages we talked about. And then the waterfall. So as a marketer, like we're not just the creative, right? We're more math. I don't know when marketing became math for that originally, but there you go. So you want to start out, how many raw leads do I need to get a marketing qualified lead? How many MQLs to get a meeting? How many meetings to get a deal or an opportunity? How many opportunities to a win? So you agree on that with sales using— if you have historical data, great, but when you're starting out, sometimes you don't. So you have to make it up and then just test and see, test your hypothesis. Take your revenue target, your average sales price, and that will tell you how many raw leads you need, but you have to align on this with sales. Once you align on the model, then it's pipeline and revenue contribution. Now depending on how much you're selling directly or through channel or even online, marketing contribution expectations will differ. So are you expecting marketing to contribute 20% of your pipeline? 50? 80? Agree on that with sales 'cause that's gonna drive marketing investment, right? So if you're gonna drive 80% through marketing, you're gonna invest more in marketing than you are in sales. And then attribution. Ah, this is the conversation that never gets old. What is marketing sourced? And it's something you just have to keep agreeing on. If you move toward multi-touch attribution, then you can have a different conversation, right? There's marketing sourced and then there's all the things that marketing does to influence, but just agree on it with sales. And you'll have to repeat it over and over again. If you— and then gross and net. We'll talk a little bit more about this later, but like I am compensated on net. Right? And we'll talk about why it's important. It changes behavior, right, when you compensate on net versus gross for revenue and churn. Data and reports. This might seem simple, but as you grow, you might have a sales operations person and maybe you get a marketing operations person later. If they're different people reporting into different orgs, they're probably gonna have different reports and sales will never believe marketing's numbers. One report, one set of data. It sounds simple. I see a lot. It's true, right? I mean, Say, like when marketing, when sales, if sales has a difficult quarter and marketing is all green, sales calls, you know, baloney on that. So I'm gonna keep it polite. So same data and reports. Keep going back to them. And then finally KPIs. What are your key KPIs? Revenue. For a marketer, for everyone, revenue is the number one metric. You know, leads are nice. I had a colleague who said, "You can't buy a beer with an MQL." In the end, it's about deals and revenue. For SaaS, go a step further and say you want to look at net. Net revenue, net— whoops— net bookings. So not just new logo acquisitions, but what are your upsell and cross-sell targets? How do you look at churn? Because it changes behavior. Think about for your agents so that they're responsible not only for new bookings, but for the net for that account. If they're responsible for churn because if they say they're— say they're— I'm gonna use, again, the math thing. Say they're responsible for €100,000. If they churn 30, that means they have to go sell 130. It's harder for them, right? So, by being responsible for churn, they're gonna do what they can to sell into the right ICP that's not gonna churn and keep that customer whole so that they have to sell less new bookings. So consider that. It really does drive behavior. Chief revenue officers drive sales and customer success for the very same reason, right? A revenue leader who is measured on net and owns customer success just drives that idea of customer success over time. Okay, 4. Whoop. Giving away. So 4 is plan together. So some key elements, and this can be done at the global level, but really at your regional levels depending on how, whether it's region or sub-region, but getting the sales and marketers aligned first on the numbers, that waterfall model so they all agree on who's generating what. And then marketing commitments for DemandGen. Again, what is the percentage? How many? And not just leads. How many marketing-sourced meetings? How many marketing-sourced opportunities? In the end, what is the revenue that I as a marketer am committed to? Seems simple, a calendar of events and campaigns. And by the way, sales will— it doesn't matter how many links, they're not gonna go look at it. So just keep putting that in front of them and getting feedback and staying in front. And if you have inside sales or SDRs who are booking meetings for sales, as your marketing team, team with them to think about outbound campaigns. Whether you're giving them content or messaging or value props, what tools can you give the SDRs so that their outbound efforts can be more successful? Content and experiences, like we talked about those interactive content experiences, what can you develop for your sales team? And then finally, enablement, and we'll talk about that a little bit later. One, we're gonna spend, 2 minutes on account-based marketing. First of all, the name is stupid because it's not marketing alone. ABM is partnering with sales and marketing. It's account-based engagement, right? And it's an orchestration of account planning and execution between sales and marketing. So some key things. Now, if your model is you've only got, you know, 500 target accounts, this might be your whole marketing and sales strategy. If you have a broader base to go after, a broader market, this might be a partial one that you work toward over time. So some cornerstones you have to have. Sales has to be good account planners because in the end, this is what this is. It's joint account planning and execution. So make sure they have those skills. You're going to have to have messaging and content for each ICP and persona because that's the starting point and you personalize it further for that account. You need data. You need the contacts in the organization, right? In different regions, that's more or less difficult. So have a plan for that. Technology can help with that. You might get those contacts through retargeting or content syndication. And then technology can help with personalization, gifting. But technology is just going to help speed things. It's not a requirement. It's mostly about process, sales and marketing alignment, and enablement. So having that, if you're going to have PRs and marketing all reaching out to the same account, you need to orchestrate that so you look like one company and you're making meaningful connections with the prospect. So 5, enable the revenue team. Now often you hear about sales enablement and I will talk about sales enablement and that's generally where companies start is enabling your account executives. But everything I talk about applies to your SDRs, customer success, professional services, anyone who is customer-facing. It's just the biggest bang is gonna start with the AEs, and that's why it's often called sales enablement rather than revenue enablement. So you have technology. There's some core technologies that you— whoops— that you have. So content management or a DAM to store all your files. You've got your CRM. Really, that's just a data collection for executives to do analysis. It doesn't help the sales team, right? It doesn't help a seller at all. And then marketing automation for scalability. So these are all super important, but they don't help the seller in their day-to-day work. And that's what sales enablement comes in. So sales enablement, it's not once and done, right? You might think about onboarding, right? So if you're bringing all those new reps in and you want to onboard them, that's— really important, but again, not once and done because as SaaS companies, you're probably releasing new products and new features all the time and you need to enable your teams on them. Enabling them to deliver competitive messaging, differentiating messaging, new presentations, company overviews. How are you empowering them to do that? And then finally, hopefully you'll get to a size, right, where you're doing sales kickoffs and bringing everyone together to both educate and inspire them. So sales enablement is a continuous process. What does it look like underneath? So the first one is training. So this can be a combination. It can be face-to-face. And maybe when you start, you're in one location and that works. But as you scale and you have more and more remote sellers in different countries, you need a way to combine face-to-face with online learning. Assess. Information, but actually assessing them whether it's through quizzes or however you want to assess that. Including having them actually present back. One of the things that we found with our client base has to record a pitch for their manager to review. They recorded on average 6.6 times. It's a lot. Just think about, we'll talk, actually I'll go forward. When you hear something, at the end of today after you've heard all these great sessions, you might remember 20%. Of what you've heard all day. But if you were to practice or your salesperson is gonna practice, they're gonna retain 75%. So just the act of having them practice their pitch and submit it to their manager is going to increase retention. And then giving tools to the sales manager to coach. So giving them the opportunity to review all of those presentations at scale at their leisure rather than trying to set up meetings. But think about your sales manager. They are what really can make a difference in the performance of your— And then on the content side, right, you want to centralize all the content so it's easy to find. And not just asking the salesperson to find things, but surfacing the right content at the right time, ideally right in your CRM. You know, based on this sales stage in this industry, here's the collateral you should use. Making it easy to personalize and stay on brand, so finding ways for them to, you know, Give your company presentation, pulling in the slides that are important for them and then doing some customization to talk to that client. And then finally optimize, measure the stuff. Just like you do at the top of the funnel, measure the bottom of the funnel for effectiveness. So all of this comes into a platform for enablement, right? The most important thing is that buyer engagement, but it's supported with content solutions that make it easy to discover and share and measure content that is impacting your buyer. It's about that ongoing training and coaching for not only new sellers but sellers that are evolving over time with your portfolio. All of this feeding data and AI to make recommendations and improvements. And then finally, measure, iterate, and improve. So with all of this, you're gonna do the same processes that you would do in marketing and sales but coming together to understand what's working so that you can continuously improve. So align on ICP persona priorities, map content and messaging to the buyer journey, define and measure success together, plan together, enable the entire revenue team starting with your AEs, and then measure, iterate, and improve. You know, all of this requires alignment at the top. So this is me, our president Jason M. Lemkin, and our CRO Dom Matejko. Don and I, we talk every day. We are aligned on everything. Mostly it's him complaining to me about what marketing's not doing, but that's what marketing here is. But we are aligned, and because we're aligned, our teams are aligned. We've set that expectation that their job is to work together to solve the problems. So if you do that, you'll win because you're gonna deliver the best buyer experience. There's more. There's some— There's a bunch of— including the buyer report and everything else— some good resources here. I'm happy to talk to all of you, but thank you so much for your time.