Stripe's Top 5 Tips for Managing a Sales Team in an Economic Slowdown with Nicole Arboleda

So today we do have another great session. I'm really excited to share that we have Nicole, Platform Sales Leader at Stripe. We'll be discussing the top 5 tips for managing sales teams in economic slowdown. So really excited to speak with her today. A reminder to get your questions ready. I know this is a really relevant topic at this time. So make sure you get those questions into the chat so we have enough time at the end of this session to answer them. I'll be messaging you to see if you're comfortable to unmute and talk through the answers live. So with that, Nicole, welcome.

Thank you, Caitlin. I'm excited to be here today.

Yeah, excited to see you as well. As we normally do, I am going to start off with a few questions to kick this off. And get to know you a little bit better. So first question, how would you define what you do at Stripe?

I appreciate the softball questions to begin with, but I'm a platform sales leader at Stripe. I've been at Stripe for a little over 4 years now, and platform sales at Stripe simply means we work with digital platforms that embed payments or financial services into their own offering or ecosystem and then distribute them on to their own customers. So think of, say, Shopify, Squarespace, Mindbody. And the like.

Great. Okay, very nice intro. Yeah, what you do for your day-to-day, a good way to get things rolling. What project are you working on today you're most excited about?

I am most— so I have a background in payments. I worked at Visa for a bit, and I'm most excited about getting back to the core attributes and foundation of payments at Stripe. I think there have been a lot of, you know, changes that have happened in the last year and excited to see how we can move that forward, especially in the next 6 to 12 months.

Great. Okay. Exciting stuff ahead. And then the hardest question of our lineup. In the last 12 months, what's been the hardest thing you've worked on?

Ooh, there's so many challenging things, I think, for all of us. I mean, it's both a challenge and it's, you know, it's an exciting opportunity. But we have been thinking a lot about embedded financial services at Stripe. And I work closely with our Stripe Capital team over the last 12 months. And it's been, you know, the concept of lending isn't a new one, but the idea of serving, servicing that through SaaS platforms has been a new approach. And it's been both challenging and incredibly rewarding to think about the go-to-market on that front.

Very cool. Okay, challenging and rewarding. So a good combination there. Thank you for letting us ask some intro questions there. But I will let you take it away with your presentation. Thank you again for joining.

Great, thank you. And thank you all for, for your time today. I do hope to keep this conversational, so at the end, think of all the questions and glad to answer anything that I can. As I briefly mentioned at the top with Caitlin, I currently work at Stripe today. I've been there over 4 years working on the platform sales organization, and I've also spent some time launching from the ground up the LATAM sales team too. Prior to this, I started my career selling, or I could say cold calling on a landline into a recession, so that bringing that experience to this conversation, but also a number of different operational roles at startups like Uber and larger enterprises like Visa, et cetera. And regardless of the titles or the logos that I might have worked at in the past, I consider myself a builder. And I think from that perspective, despite the economic times we're in, a downturn, whatever you might call it, I still see a lot of opportunity. And that's largely how I approach this conversation today about how we can continue to see the times that we're in today as a productive and fruitful one at that too. So I want to set the table a little bit. And let's see, let's go to this next slide here. So I'm going to set the scene and articulate what you probably already observe, what you know and experience today. And that is, in the current economic slowdown, deal cycles get longer, new business gets tougher, and cross-selling and upselling into your existing customer base bear increasingly more importance. Deal cycles get longer, more scrutiny, more stakeholders, every penny is measured and overturned. More parties are involved, decision-making gets more opaque. And in general, you're going to see more complexity and more, more complexity and time getting introduced in how we're closing deals. New business gets tougher, there's less general appetite for risk and change and appetite for change as budgets tighten. And then lastly, if you are in the position with the existing customers that you have that are loyal to you and know the value that you already deliver today, ideally you're able then to go into that customer base and think about expansion opportunities, either finding new units or organizations to cross-sell and upsell into, or new products and services that they could benefit from too. So generally, probably things that you're also already seeing in your own organization. And with that all— bearing all of that in mind, there are a couple of things that I think that I keep top of mind or I think to myself in this environment too. And the first thing is that just like in high growth periods, down markets or slowdowns are also temporary. So we're in a cycle. We don't know exactly the length or can't predict the length of this cycle. But we do know— what we do know is that it won't last forever. And when budgets tighten and there is more scrutiny, the cream does rise to the top. And you'll continue to win on value. And this is a really important point. It— our customers are going to continue to ask for discounts and, and have that perspective. But our ability to continue to articulate the problems that we're solving connected to the products and services and solutions that we provide and hold the line on value as much as possible is an important one to, to keep in mind. And the last one here is that opportunity can be born out of trying times. And so as one small anecdote here, Stripe was born out of the last recession. And there are a number of important names or interesting names to add to that list too. So just some general thoughts. OK, but I'm going to jump right into the top 5 tips here for managing a team through an economic downturn, my thoughts, and most importantly, what I'm— what I'm recalling from my most recent or current experience at Stripe. I'll tick through this list and then we'll go through some of them in detail. The first is you can't control uncertainty, but you can create stability for your team. And the way that you communicate that is incredibly important. Same thing when you're thinking externally for the customers and for the market. It's communicating that empathy and value and shift— shifting the messaging you're delivering to your customers. It's like I mentioned, investing in customer relationships. We understand that there is the opportunity to go back where we've already won the one legal and procurement and gone through that process. They trust us, they see the value, we can go back, think about upselling, cross-selling, but really investing in customer relationships and retaining that value that you can continue to build a foundation of your revenue. Forecasting with more agility, it's probably safe to say with high probability that the sellers on your team today are probably selling through a downturn. For the first time and helping them understand how to anticipate the additional risk and anticipate the additional scrutiny, understand how to navigate the additional stakeholders that are now involved in a deal will be increasingly important. And then the last piece is something that I've been personally thinking a lot about, which is, yes, multithreading through an organization, but especially empowering the internal champion that your team is working with and making sure that that internal champion can be a voice to win the hearts and minds and continue to sell through an organization with you when you can't always do this the same one by one, as like I mentioned, different stakeholders coming into a deal, adding more scrutiny, et cetera. So I'll go back here. I'll start from the top, and I'll share a little bit more detail and hopefully get a little bit tactical also, so you can walk away, I don't know, and maybe with hopefully one or two tidbits here at the end of this. So the first piece here is that for your team, you can't control the uncertainty, but you can create that stability. And before I get into the how, this a little bit about how I think about the why. And the why is you want to create an environment where your team still feels like they can take risks, that they can be wrong sometimes, and that they can be in an environment where they're continuing to try new things and be high-performing themselves. And so the two things that more recently we've discussed on our team and doing is one communication structure that's been especially helpful. That structure is creating structure to ambiguity, and it falls into 3 parts. And so those 3 parts are communicating very clearly, very directly what you know, communicating very clearly and very directly what you don't know, but what you will know and when, ideally. And then being really clear and transparent about the third thing here, which is what you don't know. And going back, and as you provide updates to the team, it creates a sense of stability around what is actually kind of in this black hole, or what, what, um, what is in the ambiguity. And it starts to just create a little bit of a framework around that also. Um, for the, the last thing that I'll mention here too is that, um, there are all sorts of ways to, um, and this one actually might be a little bit more simple, but as much as things might change around us, your ultimate goals and your missions will likely hold true. And so keeping your goals and your targets clear and stable, and then in addition to that, repeating that as often as possible is super helpful for the team to create that environment of stability. And so what I do is, and likely what you're doing on your own calls, but on the weekly calls that we have with our team, is reminding, reminding them that that's not changing, the fundamentals aren't changing. And the idea behind that is repetition breeds familiarity and familiarity breeds confidence and trust. And so that's the environment we're trying to create there with stability. Similar thoughts here with how we might approach customers as well. And so when top line revenue and growth becomes more uncertain, they'll be focused on their bottom line, on cost savings and operational efficiency. And it's important to meet them where we, where we imagine their mind's eye to be as well. And so So ideally, you're empathizing with the customer and importantly communicating that directly as well and checking in with them as people and not just as prospects. And so, you know, there's— in an environment where you feel the increased pressure and you feel the increased uncertainty, sometimes folks react in different ways. But reminding the team to respond to customers empathetically is an important one. And in good times, it's, you know, it's in good times, it's a lot about growth. But now customer messaging is let's talk about how other businesses like yours are— I'll say it another way. When everything's going really well, the messaging that we typically deliver at Stripe is let's talk about how other businesses like yours are working with Stripe to grow their top-line revenue. And As soon as we started to feel a shift in the market and how people were feeling and anticipating and starting to, you know, respond to different actions in their own business, that messaging started to shift to, let's talk about how businesses like yours are working with Stripe to save money and become more operationally efficient. So staying close to, again, meeting your customers where they are, reminding them that you understand where they're coming from also. And then, of course, making sure that you have the product and services solution set to deliver on those things, but the communication piece probably being the most important here. The third piece here is investing in your customer relationships. I do hear a lot about expansion, investing in expansion and cross-sell and upsell. But what I mean most by this is instead of focusing the team only on growing revenue, it's about reminding them And ideally having the structure on your team so as you're not losing revenue in the first place from your existing revenue base. So working with your team to retain your customers and their revenue, because it's probably a smart idea to remind yourself that they're probably going to come and knock on your door even if they are happy customers and ask for some discounts in some way or form. And so yes, retaining that customer, retaining the revenue they have today before it becomes a gap in your number. And then ideally above and beyond that, expanding into the install base. The fourth piece here is forecasting with more agility. Like I mentioned, sellers are probably selling into a down market for the, for the first time ever in a career. And it's been a great run that we've had, but helping folks understand how to anticipate that uncertainty in their own pipeline is going to be super important. And so be ready to dive in, be ready to double-click, be ready to help your team see around corners and articulate the risks themselves that may have not existed for them before. And importantly, welcome talking openly about the unforeseen risks on your team so that, you know, ideally we're not creating blinders for your team or for others as to what the reality is of your funnel versus, versus what we, what we hope it is or what it used to be in a better market. And like I mentioned, this last piece here on this, on the last tip is about empowering your internal champion. And so we think a lot about multithreading and so mapping one-to-one ideally the executives and the different day-to-day operators within an organization or a deal that you're working on. And that is exceptionally important and will continue to be important. The other thing that I think about and anticipate is an ideal world, or in a, in, in a deal cycle, usually you can multi-thread in your, in only your top accounts. And even with the best strategy and the best intention, you're— we anticipate getting blocked in certain ways. And so knowing that and being ready for that is super important. That's what I mean by empowering your internal internal champion. And so more specifically, empowering your internal champion means ideally you're already texting with them, you're in a really great relationship, you built, you know, they understand the value and the business case, but it's really about arming them so they can do the same as they go through their own organization that undoubtedly they'll know better than yourself or your team. And so as before, but it's even more important in this environment is ensuring that the internal champion that you have within your partner organization has the assets, has the case studies, has the customer proof points, has the ability to articulate and can speak to almost at heart the value that you're providing that other customers can speak to as well. It's those customer proof points that are especially important in these times that are emotionally helpful to make tough decisions these days. And then the second piece is logically they still need to make a decision. You know, like I mentioned, likely the deal is getting— every dollar spent is getting more scrutinized. So making sure they do have an airtight business case written down that potentially includes an ROI model that helps you to demonstrate the investment that they're making in the partnership or in the motion that you're thinking about today. So yes, it's about multi-threading, assuming that it's not always the ideal case that you get in every deal and every single perfect partnership. It's also about making sure and reminding your team that your internal champion is really going to be a key partner for you in these times. So I'll end with that. So ideally for your team, creating stability, doing the same thing, articulating that with your customers, anticipating a lot of that risk, articulating that with your team, getting them comfortable with it. So you're, despite the uncertainty, also building that into your forecasting and then remembering, remembering your internal champion and making sure that they're extra armed in these times. So looking forward to— let's brainstorm and discuss.

Great.

Okay.

Well, thank you so much. We can take the slide down while we head to Q&A just to make sure we can see all of you while you're asking questions. If you want to ask questions and come off of mute, feel free to do so, as well as turning on your video so we can make this an interactive discussion. First question, Massimo, if you want to kick us off, it looks like you have a question in the chat that's also getting some plus ones.

Sure. I just got a bad cold, so not sounding too good, but my question was, what are your recommendations on how to handle requests for discounts on existing contracts, especially when they're substantial requests for discounts? And do you draw the line at a certain discount amount at all? Yes, to your last— the latter part of your question. Yeah, I think it's important to be able to make the pre-decision with your team from a leadership level and then communicate that early with it, with them, with your team so that they can anticipate and set expectations. And I think the last thing that you want in a— with a customer that you highly value and that you have a great relationship is to deliver a sense of surprise or something that they can't anticipate. So very much yes to knowing where your line line is. I'm holding that line where possible, and ideally pre-communicating that with your team too, so that, that predetermination. Um, the other thing that I think about too, that we think about, um, is, um, I'll say it this way, uh, slowing down to speed up, which is, um, the more that we can understand about their business and the more that we can understand why they're asking for a discount— are the forecasts changing, is something on What about their business dynamic? What about their P&L is changing? So we can get an understanding of where they're feeling the pain the most and where our solution still fits and also where we can, where we might have an opportunity to, to build a better partnership together if costs, if our costs or if there's room in the pricing that we have today to build a longer-term opportunity. And more specifically, what I think about that is that, you know, if if, if in the short term you're thinking about some sort of discounted pricing, ideally you're also putting together long-term partnerships, um, with, with these customers where you're building commitments that they might continue to invest in other parts of your organization too. Um, so I hope that, um, I hope I've articulated it okay, but essentially framing how you might walk into, you know, understanding the user, where they're coming from, and making sure that you're solving not just the discount but solving the, solving the thing that is most painful for them today, then helping to the gift gets, and ideally we're thinking about the longer-term commitment even if there's a short-term temporary loss on revenue.

Great. And any follow-up on that? All right. We have a question in the chat from Kevin, if you would like to unmute and ask.

Sure. Thanks, Nicole, for doing this. This is great. My question would be, how do you suggest getting multi-threaded with more of the senior-level decision makers and getting access there without running the risk of, you know, frustrating your main POC or champion or having them feel like you're just going above their head? Yeah, it's always case by case, but that's probably not— that's not a sufficient answer here, it feels like. I think like the real answer I have for that is Similar to my previous response is helping them anticipate that that's normalizing that process. And so very early on in any deal that we have, we kind of explain the process that will take them through. And one of those includes likely we'll get leadership involved, likely they'll reach out directly to, you know, X person that you want to get connected to just to set the expectation that, you know, we do this all the time. It's completely normal. It's not because of anything that you're doing incorrectly or not, right? And it's more just to make sure that we have the partnership in a great place.

Great. Any follow-up questions on that?

No, that's helpful. Thank you.

Great. Okay. So question about percent of sales team promoting and firing during rough financial times. Do you have a go-to statistic you use? Do you believe in promoting during those times? Do you believe in firing during those times? And if so, what guidelines do you use?

Ooh, that feels like a question for a much larger conversation. I mean, I'd say it really depends on the revenue goals in the short term for your organization, how you've structured your organization, what your variable and your fixed comp and cost look like. And then I think you also have to think about— it's one way to think about it is the cost savings and also the revenue that each rep is generating, but also the engagement and the expertise that you're losing when you go through those tough cycles. So on the promotion piece, I don't have a specific stat, but I do believe very strongly that you're strong, that the environment might change around all of us. But I'd say this the same thing about ourselves and that it doesn't change change the skills or the expertise that we have today. The same seller that, you know, sold and, you know, as part of the President's Club last year could have a very different year based on a very different environment. And that doesn't necessarily always speak to their skills changing, so to speak. So I'd say probably emphatically there's always, you know, different edge cases here that we should continue to reward high performers. And then I think I'd consider product market fit as much as what we're putting on the sales team in earlier stage companies. And probably with Stripe, that means for earlier stage products, right? In trying to parse out when you're missing revenue numbers or when you have revenue targets that you're trying to get to, what is a function of the sales process or individual sales reps versus, you know, how the product or the service is resonating in the market too.

Great. Okay, thank you for that feedback. And if there's any follow-up on that, please let us know. What is your perspective on hiring a VP of demand gen? That's something we talk about a lot at Sastr and would love to hear your thought process on?

My two quick thoughts here are ideally salespeople aren't on the hook, and they're the main primary focus with some of the best reps that you have are building relationships and closing deals. And in an ideal world, they're not also creating demand or necessarily prospecting because that But depending on your product and service, again, that can feel like an inefficient time for what you're— what you're— what your rep is there for. And so I'd say probably in very general terms, I'm bullish on DemandGen serving as that function, especially cutting through the chase or cutting through the noise when it comes to just creating demand in general. So yeah, I'll end with that because I see it as a time and I see a lot of value in that specific function.

Great. What are some ways you retain and grow your top customers? Do you have any programs in place for retention, anything along those lines?

Yeah, I think some of the things that we're excited about— I'll mention one program at Stripe specifically, but we have a customer advisory board, or we've had different variations of that. It might be called something different these days, but certainly, I mean, you probably want it too within your product or your solution organization, getting feedback from your top customers and what what they're looking for also. And so making sure that they have a seat at the table and making sure that they're connected to your organization and leadership and, and feel like it's a, it's a two-way partnership and a two-way street on having that relationship, I think is super important. So that the idea of some form of customer advisory board has been, I think, very helpful.

Do you have any— follow-up question— do you have any tips and tricks to making that customer advisory board useful for those customers? I feel like some people or some companies struggle to make that a useful, useful asset to those joining.

Yeah, that's a great question. I think it's, you know, asking for feedback is an important thing. And certainly I think people value being asked for feedback. But at the same time, it's like I mentioned, a two-way street. So making sure that when you're creating intentional time for a customer advisory board, you're also ideally providing some leadership perspectives in your own particular field of expertise that they can learn from also. And so ideally they're helping you learn about your organization and how, you know, they as a customer are seeing that. And you're also able to add some thought leadership about, about how they should run their business too.

Great. All right. If we don't have any more questions, I know we are at time. I guess one final question. What are like a prediction or two you have for sales in 2023?

Ooh, I actually stopped predicting the future in 2020. I'm really bad at it. But I will say I think I'm just watching really closely. I think what we all are, which is I never had no expectations for ChatGPT to be where it is today. And I'm very excited to see what that does across many industries, including our own in sales.

Great. Okay. Well, thank you so much, Nicole. I know this was really timely content, um, and we really appreciate you coming today and speaking to us. Thank you all for joining as well. Um, love to have you here and hear all of your insights, comments, questions, etc.