How to Perfect the Customer Journey from Marketing to Sales to CS with Pilot's CEO and CRO

All right, I think we are good to go. Thank you so much, everyone, for joining. I'm going to hand it over to Wasim and Chloe, who will get this session started. Thank you again.

Perfect. Thank you, Caitlin, and thank you all for joining. I'm Wasim Dahir, CEO of Pilot, and Pilot specializes in bookkeeping, tax prep, and CFO services for high-growth startups ranging from pre-seed to Series D. And when you work with Pilot, you get the expertise of a finance team that takes all this work off your plate so you can focus on your business. We're the largest provider in the space, working with over 1,000 startups. So if there's ever anything we can do to help out, please reach out. Our contact information is on the slide below. And I'm joined today by Chloe as well.

Hi everyone, I'm Chloe. I run the sales team, SDR, at Pilot, and really excited to get to spend some time with you.

And so we're both here to talk to you about our talk, How to Perfect the Customer Journey from Marketing to Sales to Customer Success. And I'm very, very glad Chloe's joining us for this. She has a wealth and depth of experience, not only at Pilot obviously, but in her previous roles at Eventbrite and a bunch of other places as well. And I think the lesson here is actually quite a simple one, which is I think there's a right way to think about this and there's a wrong way to think about this, which is The right way to think about your customer's journey is to center the customer. It's super easy and super tempting to look at this from our perspective, which is, oh, you know, the journey starts with the customer seeing some marketing and then talking to sales and then giving us money, and then CS helps convince them to keep giving us money. But that's not how your customer sees themselves. And if you really want to make the experience feel high quality and white glove, you need to center that journey on them. And their experience. And from their perspective, they're not there to buy a product or service. They're trying to solve a problem. And the consequence of that is your job is not to just sell them something, it's to help them solve that problem. And just to maybe emphasize this point a little bit more, I promise you that no one has ever said, you know what, I really want to give a company some money today, or I really want to buy some enterprise software, or I would love to spend to spend several hours talking to a sales rep. Like, no, there is a reason that they're embarking on this journey. So let's talk about what this actually looks like. And very naturally, I think this includes the pre-sales process, the sales process itself, and post-sales. Or if you like, that maps pretty cleanly to what your marketing team does, what your sales team does, and what your customer success team does. So let's start at the top. At the beginning is always a great place to begin. So centering the customer really starts all the way back in marketing. And again, this is why you don't just send emails all day that say like, buy our stuff. Like, yes, that's what you want to happen, but it's not helpful to the customer. Instead, ideally, you're trying to engage them with content or events or outreach that is designed to answer questions and actually provide useful information for the problem they're trying to solve. And I want to give you a very concrete example from our own experience here at Pilot. So as kind of I mentioned at the top, you know, Pilot sort of runs your financial back office for you. We effectively act as your accounting team, helping out with bookkeeping, tax, budgeting, forecasting, etc. And if you look at our customer base, a lot of our customers are recent founders who in many cases are extremely talented engineers or product designers or what have you. They don't have a lot of experience running a business overall and specifically kind of managing the back office of the business. So for many of our customers, the problem they're trying to solve is how do you get up to speed on that very quickly? How do you make sure you're meeting all of your financial and tax and compliance requirements without preventing you from focusing on kind of the core business opportunity that you're targeting? And if you go to our website, or if you look at sort of what we do from an email perspective, we offer a lot of content to help founders who are trying to educate themselves on various back office concepts. And importantly, A lot of it doesn't even mention our service at all, because at this stage in our buyer's journey, the customer is not trying to buy something. The customer wants information. And so our events or our content is not 10 reasons why Pilot is great. It's how to get ready to fundraise, or how to set up your budget, or things that founders have actually told us they want help with. And in the course of learning more about this stuff, Of course, we're enhancing the brand, we're building credibility. And in the course of learning more about bookkeeping and taxes and forecasting and everything else that goes into that financial side of running a business, many founders conclude, oh, maybe the highest value use of my time is not DIY these things. Or actually, you know, I have a provider in this space, but maybe they don't have the expertise that these folks have. And they reach out to us about helping them handle those facts of their business. So we're just like in the course of generally learning about how to run a business, fundraising, how to structure a sales team, how to run your board meetings, etc. They become familiar with us, and then we're top of mind when they actually encounter some compelling event that puts them in the market for the services we offer. So broadly, we think about what we do on the marketing side really is about building awareness, building the brand, establishing us as a high-trust player in the space. And not, here's a coupon for 20% off, or buy now. It's very much about kind of laying the groundwork so that when the need is there, we have a relationship with the customer we can act on.

And so— thanks, Waseem. And so at some point, your customer moves forward in this journey and they're ready to interact with sales. And keeping the focus again on the customer here, it's this point that they're really trying to figure out if the solution is right for them, whether that's yours or someone else's. And so you're going to get better results if you coach your sales team to take a consultative approach, where they're really trying to help the customer understand all of their options and which choice ultimately is the right one for them to make. So the point here, again, center the customer as opposed to talking about yourself, your service, and your business. And when your customer feels like your salesperson has actual expertise in the area that they're investigating and is truly trying to help them make that decision instead of just saying whatever they have to say to make the sale, you're building credibility and this relationship. That's really, really important to do. And helping again isn't just talking about the feature sets of your solution, but the ways in which you can, and sometimes can't, help them meet their goals and ultimately mitigate the consequences that can come if you don't. Actually mitigate or don't meet those goals, I should say. And when you do that, you might find out that you're not the right fit for them today, but their needs can change. And that means they may want to approach you again in the future. At Pilot, a shocking percent of the time, we tell prospective customers, hey, we're actually not the right fit for you today, which seems like the opposite of what a sales team should be doing. Like, it actually feels quite counterintuitive. But in reality, it's super trust building, right? That's really, really important at the heart of what you're doing when you're thinking about centering the customer. From a tactical perspective, this does mean a lot of listening, right? Like, your sales team should be asking a lot of great questions to understand the problem at hand, as well as the size of that problem. And so you need to make sure that your sales team is equipped with the right tools and training so that they're always able to offer the best response to that prospective customer. It doesn't stop there, though. It's really important that you're capturing this information somewhere within your organization because there's often other folks who are involved in that sales process, and they need to be able to just not just access that information, but read the background there. And the purpose here is that the customer should always feel like they never have to repeat themselves or that they're getting passed to somebody who's less credible. It should feel like a step forward and never like a step backwards. So you make the sale. All right. Some customer journey models end here. They're just comprised of marketing and of sales, but the successful companies know that this isn't the case. There's actually a lot of really important work and hard work that happens after the sale is closed. And so after they become a paying client, the customer is hopefully solving the problem that they initially brought to you to solve, right? But needs evolve. We know this. Things are changing. And it's rarely as simple as just flipping a switch, calling it a day. And this is where customer success comes into play. Here again, you want to put yourselves in the shoes of your customer, asking yourself the question of, how can I make sure that the customer is actually succeeding at their business objectives?

And as a concrete example of that, for example, at Pilot, we do quarterly business reviews with our customers. Where we'll get on the phone with them. And the goal of that call is not retention or renewal or getting you to buy more. It's actually talk to us about how it's been going so far and let us know what's going on in your business so we can help you see around corners. And yes, sometimes that does look like purchasing an additional service from Pilot, but sometimes it looks like let's get you a little complimentary time from our CFO services team, or let me intro you to a partner who might be able to add value. And if the only time you're talking to your customers is when you want them to pay you more, or you're apologizing for something having gone wrong, those are both pretty low NPS moments. And so that contact with your team gets associated with, wow, something bad is happening. And of course you don't want that. And on that note, you really cannot manage what you can't measure. You need to keep a finger on the pulse of your customers, whether that's via some sort of formal survey process, like a Net Promoter Score, or whether it's by actually having your customer success managers check in with them regularly, recording our— recording their conclusions. And at Pilot, we actually have a system where if anyone who interacts with the customer in any capacity has a suspicion that the customer might not be happy about something, they have the ability to go in our system and mark them as, well, we think this is at risk, this, this account may be at risk, which actually triggers the whole process from our customer success team to follow up and understand, well, What might they be unhappy about? How can we potentially make it right, etc., etc.? And ultimately, and it sort of sounds, sounds obvious, you want your customer success team to really be about customer success. If your customers are successful, they will be promoters for you and your brand. They will buy more from you. They will refer you more business. It just really gets the flywheel turning. And look, it gets said a lot because it's true. Empathy for the customer really is the secret weapon in perfecting the customer journey. So at every step of the process, designing it where you're putting yourself in their shoes and asking, is this really helping them move forward on the things they need? Because ultimately, succeeding in that will also help you succeed. So if you— I had to summarize the kind of 3 key learnings, I would say your job is not to sell them something, it's to help them solve their problem. You have to actually listen so you know what their needs are to make sure you can either meet them or if you can't, to tell them that. And the third is, you know, when the sale is concluded, you're not done. Stay in touch with your customers. You really cannot manage what you can't measure. And with that, um, Chloe and I really want to shift gears and leave some time for some open-ended Q&A. A couple notes before I do that: we've got our contact information on this slide, as I mentioned. I also have a Substack, and you can follow me on Twitter. And then we actually have a special promo for SaaStr attendees. If you, you or someone you know is in the market for help with bookkeeping, tax prep, budgeting, forecasting, etc., etc., hit that link and we'll get you a discount. And with that, I'd like to shift gears into the Q&A. It looks like we've got a couple questions submitted here. One, where does account management fall when building the customer journey? Is that a sales function, or maybe is it alongside customer success? Chloe, do you have some thoughts you want to you want to offer there?

I do. I think that it really depends on the type of sales process that you have and what your unique customer journey looks like in terms of your business. I often see account management as part of the CS function. It's really as a way to ensure that we are providing the right types of support and partnership to the, to the customer. If you have a more complicated service or solution that you're selling, there's often different types of roles in CS, and account management tends to be one of those that I see.

Nice. Another question, and this is a very interesting and anonymous question. My org is extremely sales-centric. As a CSM, I get a lot of new customers where there really aren't enough notes from the sales team. They're just trying to get in as many deals as possible. How can I encourage sales to provide more information while still staying in my lane? Chloe, I'm gonna have to ask you this one again as well.

Oh, I have so many thoughts on this. And anonymous, I feel you. I've been there on both sides. I run sales right now, but I have a background in CS as well. It's really about that cultural shift that has to happen within your organization. So sometimes easier said than done. One thing that I have found to have worked is— and this is the empathy building that Waseem was talking about with customers, but also with your internal stakeholders— working together to build that handoff process, I think, can be one way that you'll get buy-in from sales. They'll understand why that information is so important to you and ultimately how it's really important to the customer. It really goes back to the theme of this talk, which is centering the customer. Providing the right level of information to you means that you can actually help them do what they came to your company to do in the first place. But I think tactically speaking, if you can build that process internally with somebody on sales, you might just get more buy-in there.

Another question from our audience: How can you check in with every customer quarterly? Like, how big is your team that does this? It's a great question. I think maybe the more general answer is this will depend on the nature of your business and your customer count and the size of your sale, etc., etc. With Pilot, because what folks are buying from us is not a piece of software, what they're buying is we run your financial back office. There is already a very kind of high-touch, white-glove human relationship that's there. And so the act of actually checking in from time to time on, hey, how's it going, is very consistent with the way the business is staffed. Because again, We're not selling you a piece of software. We actually do all the work for you on QuickBooks and using all the industry standard tools. What we're really giving you is that white glove relationship. Now, if your business is a much more consumer-focused business, or you have hundreds of thousands or millions of customers, no, realistically, you're not going to be able to, you know, hop on the phone with all of them and say, hey, how's it going every quarter? The question then I think would be, can you surface in a more scalable or programmatic way Which of your customers do you think require intervention? Did they do something to suggest that they were unhappy? If so, maybe we should try to check in there. Or maybe did they do something that suggests they're really excited? Maybe we go and try to get a case study from them, or we try to get them to refer people. So I think being more surgical in where you devote the, the time of your team, if that's a scarce resource, is probably one place, um, one place I would kind of take a look at. Let's see what else we got here. We've got a question. Articles on how to run a board meeting or how to build marketing, a marketing team are not really core experience of a CFO. How did you build up this content? With an agency, with your on-site staff, with freelancers? So we actually developed a lot of this in-house leaning on expertise that our team had. So if you kind of look at the how to run a board meeting article, This actually came from my co-founders and our CFO, who was previously VP of Finance at Dropbox. It very much is drawing on the experience of the customer base. And the reason that we do that is, again, I think what our customers are looking for is to hear that and to see that Pilot has expertise in businesses like mine. And it's less about, oh, I want Pilot to explain to me how to read a balance sheet. It's more, I want to make sure that when I have tricky questions about how to run my startup, I'm talking to a team who's done it before and who will know what to do in the future, which is why we've kind of oriented it that way. Okay, let's see. I think we've got time maybe for one more. Chloe, is there anything here that calls out to you that you're particularly excited about?

I don't know, Waseem, they're all really good.

It's true. There's a lot of good stuff here. Let's see. Okay. I just joined my company about 2 months ago, and it's just me on the CS team. I'm trying to add structure to the support piece and make sure there are owners at each stage of solving a problem. Previously, product owned this. Are there any tips on first steps to build out that initial structure in customer success? Chloe, any suggestions there?

Yeah, I think again, it comes down to what is it that you're solving? Like, what are the problems that you solve? And then what are some of the sort of like key milestones that you're seeing in your customer journey post-sale, thinking about what the customers are, you know, asking about, where they have the, you know, they need the most handholding to start, what are some of those important milestones within the journey that will help them become stronger adopters of the different services that you might have. I think mapping the roles to that customer journey at that point is one way to help you prioritize who you might need and what the scope of their role should actually include.

Perfect. And with that, unfortunately, we're out of time. Thank you everyone for joining a really great session. We have a lot more great content for you today, so see you in the next sessions. I've also dropped a couple links in the Zoom chat to, again, the kind of pilot page, Chloe's contact information, my contact information, and a blog where we kind of talk about all things startups. So thank you again for the time.

Thank you so