Shifting the Finish Line of Sales Enablement with Stripe's Marcela Piñeros
Sean Lane: Hey, everyone. Welcome to# Operations, the show where we look under the hood of companies in hypergrowth. My name is Sean Lane. How each of us learns is a pretty fascinating thing. Isn't it? How we retain information or more frequently, how we do don't retain it, the different mediums that are available to us and the variety of different content that we have to choose from. Okay? Chances are, if you clicked on this podcast today, you came because you wanted to learn something. Our guest today is an expert in learning, and it was one of those conversations where as soon as I was done recording, all I wanted to do was share the things that I had learned with my colleagues, so we could start to use them for ourselves. Our guest today is Marcela Piñeros, global Head of Sales Enablement at Stripe. Yes, that Stripe, most recently valued in March, 2021 at$ 95 billion. The online payments provider is the most valuable private fintech company in the world. Marcela and her team enables the sales organization that is most certainly still in hypergrowth and in her year plus, since joining Stripe, Marcela has set out to transform the way that the company enables its reps. In our conversation, we talk about how to avoid the hamster wheel of enablement content. We talk about the way that she has reinvented Stripes new hire program to democratize tribal knowledge and why she thinks the word onboarding is a lie. Let's start though with that transformation that her team has undergone and how she set that in motion when she first arrived at Stripe.
Marcela Piñeros: So I started that Stripe a little bit over a year ago. It seems like it's been an entire lifetime just based off of everything that we've been able to accomplish in a very, very short amount of time. When I joined, I had two key priorities. My first priority was to start with data first. So build a data architecture model that lets us become more data driven from the onset. And then the other key theme was to enable first line managers first, because it's often that audience that gets punted because we have very urgent things that always come up, and so we punt on manager enablement. And I've learned from personal experience that there is a glass ceiling that you hit from a scalability perspective, if you're not enabling your leaders to enable their teams, there's only so much that you can do from a growth perspective. So those were my top two. But in joining the organization, there was just so much opportunity and so many great things to do, including rolling out a new sales methodology and implementing a new tech stack. And so kind of a hit the ground running motion.
Sean Lane: In this hit the ground running motion, Marcela and her team were also faced with the tall task of enabling a sales team that was growing over 100% in size year over year. So let's dig into what that actually means. What are the different motions that Marcela believes to be" enablement," turns out it's not just about launching new stuff. It's much more about what comes after what you launch.
Marcela Piñeros: There's a motion that it's very, very easy to get trapped in because it's probably most natural, both for the organization and for enablement teams and it's to just react to requests with content and to lean on moment and time enablement like live sessions, live delivery. It's what folks associate with enablement, right? But the biggest challenge with that is that, and I wrote an article about this a while back, it's a hamster wheel. You can never get off of it. Once you get on it, it's very, very difficult to transition off of it. And the reality is that you can never have the very latest information if the enablement team is responsible to be subject matter experts. So trying to be the content creators just sets you up for this endless treadmill of demand. And then the moment in time training, that live delivery, there is a misconception, I think that we have just as humans in saying," Well, if I tell you the information, that must mean that you understood it, and you processed it. And now that you're aware, you're going to do something about it." And it's really our assumption that's the case, but in reality, it's not. We might tell you something that doesn't necessarily change anything in your behavior. So my team is significantly focused on what we call shifting the finish line. And it's looking beyond that moment in time to what happens after awards, what happens after someone is aware of something, what is it that you need to do to ensure that then transfers to their day- to- day and the last mile actually results in the changes that you want to see either in behavior or in knowledge and awareness? So it's definitely a shift.
Sean Lane: And I would imagine it's not a only a shift just for your team, but for the teams that you're enabling. Right? I think a lot of what you were saying about what people think of when they think of enablement, that's not just among enablement folks, that's among the reps and those frontline managers.
Marcela Piñeros: Totally. crosstalk.
Sean Lane: And so can you talk a little bit about how you helped not only make that shift within your team, but I would imagine the work that your team produces and the deliverables and all that kind of starts to move that line a little bit, is that right?
Marcela Piñeros: Yeah. And it is, it's an ongoing change management initiative because every day there are new people joining the organization that have that same definition of enablement. And so it's an ongoing process, but you do need to look at it as change management, right? So what I tell my team is, imagine that you are going through a drive- through for a fast food restaurant. And what they give you is a keto bowl with quinoa and super healthy foods. And what you ordered was a burger. You're going to be really disappointed and borderline frustrated and angry because what you're getting is not at all what you were expecting, right? So you start slowly, you start by showing on the menu, some healthier items, and you start by marking, just to raise awareness on calorie count, or whatever the case is. So that folks start to realize," Oh, wait, there are options that I may have." And that's how you kind of slowly start moving the needle. So I can go through the drive- through, and maybe I wanted a burger when I started, but as I started to interact with what was available, I chose something that was potentially healthier for me. So we can't be the drive- through operators that decide for the person coming through what they need and what is better for them, without aligning their expectations first. So that's kind of a step one, is making sure that everybody's aligned on expectations, but as we've rolled out some of these programs, people are seeing the difference and they're seeing the results. And they're seeing that there's less training scrap, that there's less materials that are needing to be built, but then are never used. And that becomes a very compelling reason for them to say," Well, maybe we can order the salad instead."
Sean Lane: This concept of shifting the finish line is really interesting. And I think it's a great north star for any enablement team to take away from this episode. Marcela has been pushing both her team and her internal customers to think beyond the moment in time need and to focus on what comes next. Otherwise that hamster wheel of content that she describes can be overwhelming and never ending. Marcela also said that the change management of shifting the finish line starts to get a little easier when people start to see results, makes sense. So of course I wanted to know what those results?
Marcela Piñeros: Probably the best place to go to look for that change in mentality is with hiring managers, that have people that are going through our reinventive new hire program, right? When they see what they experienced and they see what people experience prior to them, and then how long it took and the amount of just hand and holding that was required after the fact versus the folks that are coming in now, they're noticing a difference, right? And that difference is primarily that rather than just try to fill people's head with information at the onset, we just put them into an experiential mode so that they're witnessing the work being done at the onset. And just that in mindset has led to a tangible difference in the way that people are approaching their work and how quickly they can get there. That's one thing. The other thing I would highlight is also back to change management and mentality. I'm working with my team to make sure that our enablement materials aren't only available in the enablement platforms. They have to be available wherever the rep is or wherever the sales team works. Because when you want to change the oil in your car, you don't go to Coursera or udomi to look for how to change the oil. You just go to Google and you type in, oil change my car, whatever it is that you type in. And the learning materials will appear in the context of a lot of other things. And then you are able to opt in. So I'm trying to get folks to understand that enablement is not something you do outside of your day- to- day. Enablement is part of your day- to- day. It's something that you do in your constant workflow.
Sean Lane: And so what does that look like? Does that mean that if I'm in one particular tool, instead of having to go to an LMS, I've got kind of real time enablement helping me within whatever process or tool I'm working on?
Marcela Piñeros: There's so many different ways that this is done, right? There are tools that will offer guidance for software training in the context of the UI. There's just from a content management and governance perspective, how you structure your materials, the level of granularity that you structure your materials. So I see our learning management system and our sales readiness platform as a place where you can go to get a curated recommended chef's menu, right? Like, this is how, if we were going to do it, we would do it this way and in this order, right? But each of those individual pieces are available through our content management system, which is where you're going to go to look for case study for X industry. Right? And you may also get the case study, but you might also get a recorded webinar of a win story in that industry. Right? So it really helps folks who don't know what they don't know, come across resources that can help elevate their game.
Sean Lane: Two things that I think are important lessons from Marcela here. First, her idea that instead of defaulting to a teaching mode that is just trying to get as much information into new reps out as possible. Her team at Stripe is actually focusing on the experiential learning where reps can witness work being done. Sit tight, we're going to come back to how they witness that work in a minute. Second, she's been pushing her team to make information available wherever the rep might be in their workflow. If all of your enablement content only lives in a learning management system, guess what the consumer of that content thinks when they're going through it? They're being enabled. If you can find creative ways to embed those learnings in the already existing day in the life of your reps or wherever they might be consuming that content, it tends to be much more compelling and useful at the moment that they need it. All right, let's go back to that experiential learning. If you listen carefully, you might have caught Marcela mentioned that they completely overhauled the new hire training at Stripe after she arrived. So I wanted to learn exactly what that overhaul entailed and what we might be able to take away for the new hire onboarding processes at our own companies?
Marcela Piñeros: Onboarding in most organizations, and I have deep respect for people that work in onboarding because it's incredibly challenging with the highest expectations from the business. But in most organizations, onboarding consists of a schedule, a calendar of live delivery, or of," here's some information that we will spoon feed to you." Right? And after one week or two weeks or three weeks or whatever the duration of that onboarding program is, you just kind of spit people out into the wild. They say," Okay, you're done." And then you send them out. And the truth is that in their real world and their day- to- day, they're never going to be spooned information the way that you did during those couple of weeks, right? So you are modeling a behavior that is not really going to be consistent with their success. That's one thing. And then the other part of it is that we know what the forgetting curve is. We know that if you are offering a 100% of the information to someone in a very condensed amount of time, you're lucky if they retain 20% of that after the first week, 8% of that after the second or third week. So really what you're looking at is 92% of the information is lost. Look at that, just from a context of ROI, especially if you flew people in to the location. Right? So granted there is definitely a value in live, people coming together, the networking, the intangible kind of feeling of belonging that happens there is incredibly precious. But if you're trying to also get people informed and capable to do the job, that may not be the best model, right? So what we do is something different. We launched a reinvented program that we don't call it onboarding, precisely because I think that onboarding is a lie. And with our program, what happens is that when you join in our go- to- market organization, you need to do 20 customer ride alongs in your first 30 days. From the onset, you're going to be observing what is happening in the wild what's happening live. We give you the resources so that when you have a question, you have a place to go to get answers, right? But let's say that you've shadowed or you're following one of these ride-alongs. At the end, you have to fill out a form, one to get credit. And two, to be able to give us a little bit of line of sight. And you going to answer what was the most surprising thing I saw? What is the most confusing thing I saw and where will I go to get more information? So the most surprising thing is actually just helping them reflect really quickly on everything that they just witnessed and they have to compare. And in that reflection, it helps also retain the information. The most confusing thing is actually a data point for us, because if we have a lot of new hires highlighting the fact that there's something that's very confusing, common amongst all of them, that's an indicator to us that's a good place for an intervention and where they're going to go to get more information. Sometimes they're going to respond things that we didn't even know existed, repositories that have happened organically across the organization. Right? So it becomes also a great data point for us to be able to source, where is knowledge being shared? And if you have a new hire that just has no answer to that question, like," I don't even know where to start." That's a flag for the ambassador of the cohort to be able to reach out and say," Hey, I heard that you were having trouble with this specific topic. Let's talk it through." Right? So that's one big shift, is that instead of having people sitting, observing, and trying to consume content at a incredibly hectic pace, what we're doing is trying to get them into the field, be exposed to the reality as soon as possible with the premise of giving somebody the answers before they're asking the question, doesn't give you the same results.
Sean Lane: Got it. You said something really interesting, ambassador to the cohort. What's that?
Marcela Piñeros: So we have folks that are in region that meet weekly with the new hires and they have different conversations, we're modeling doing role plays and having guest speakers and different types of things. But this is where folks are going to come together. One, to be held accountable for the work that they're doing. Two, to learn from each other, because it's a mixed cohort. It's not only the people that started on this day. It's everyone that's in that program, in that region in a span of time. So you're going to have folks that are on their 90 day mark, and you're going to have folks that it's their first day. Right? And we want to establish those connections. I don't know about you, but I still remember very vividly the exact people that were in my new hire class in this company and the company before that and in the one before that. Right? But there were people in the class before and the class after, that I have no idea. I really don't know. And if you think about the misconnections that are there, right? Because you can actually learn from somebody that just went through this, they have all the empathy, they know exactly what you're going through and you're able to engage with them. It's so valuable.
Sean Lane: It's so funny how we think like that. I know, just because I remember the dates, I know of people who started three weeks after me, but in my head I've been here way longer than them. Right? And it's weeks, right?
Marcela Piñeros: Yes. Yeah.
Sean Lane: It's such a small thing. I love that idea of that, that kind of like cross timeframe cohort. Is that ambassador, ultimately the person who's in charge of the success of the people coming out of that program. Right? Something that I think can be a bit of a hot potato of a question is, who owns onboarding, right? Is it the enablement team that might structure that calendar you're talking about? Is it the manager who's going to inherit that person coming out of it? Is there a single owner? I'm not sure the right way to answer that question.
Marcela Piñeros: Yeah. I'd use kind of that parallel metaphor of in education, who's responsible for educating a kid. Is it the school or is it the parents? Right? You can't do it alone. The school could be amazing, fantastic. But that's not going to give a full picture. So I think we own the program. We own the experience from an enablement team perspective. We own tracking, we own reporting, but the manager is incredibly critical in this, in helping to assess progress, helping identify blind spots and really kind of shepherding the person through their unique path. We do have milestones built into our program, right? And each of those milestones require manager involvement. The manager is the one that has to check off and say," Yes, this is an acceptable account plan." Or," Yes, this is a good negotiation strategy." Right. So we've identified key moments that we need for everybody to do. And to that end, you might have a really tenured, experienced salesperson join the organization. If they can knock out those milestones in week one, fantastic, more power to them, right? There really is no, I'm trying to break away from this sense that it's up to me or it to you or to anybody to decide. This information is actually most relevant to you on day four, maybe you're precocious and you really needed to know it on day two, or maybe you are at running at a different pace and you're not ready for that until week two. I need to treat the adult learner as an autonomous being that can make that decision for themselves.
Sean Lane: That last seven minutes or so is just one of those clips you can listen to over and over and over again. Or you can send it off to someone who you might be partnering with on new hire onboarding. Marcela is telling us, look, onboarding is a lie, it's ongoing. And all of us, each of us is on the hook for the success of the people that are emerging from onboarding. That's enablement, that's ops, that's the managers. And yes, that's the new hires themselves. I'll tell you what I'm definitely stealing from Marcela and implementing at Drift as soon as I can, the three questions she asks reps to answer after shadowing a customer call, what was the most surprising thing? What was the most confusing? And where will you go to get more information? As Marcela points out the learnings gleaned from these three questions alone will be so valuable, not just to the new hire, but also for the manager and the teammates of that new hire, who might not remember where some of those most helpful resources live. For Marcela and her team, it all comes back to how do you disseminate information most effectively,
Marcela Piñeros: We're trying to democratize tribal knowledge and figure out a way to make that just much more scalable. For example, the ride along model, it's ultimately shadowing. That's not groundbreaking. It's not the first organization to use shadowing. Here's where it becomes different is that, let's say that you are hired, and as a new hire you're assigned a buddy or someone that's going to be accommodating you. Shadowing typically happens because that buddy lobbies on your behalf to try to get you added to calls. So the experience and the quality of your shadowing is going to be very dependent on the political capital of the person that you were assigned. Right? Who do they know? Can they get you into the right calls? Where as what we're doing is making it very programmatic. So it's much more open, much more available. And the new hire takes the responsibility of adding themselves to calls. They're the ones that own whether or not they're doing it, right? It's not up to somebody else to help open the door for them. How do we remove blocks to access?
Sean Lane: I love that mentality, democratize tribal knowledge, remove blocks to access and give people ownership over their own learning. It seems like Marcela's version of enablement is less about standing in front of people to talk at them. And more about step aside altogether. She mentioned earlier in our conversation that she didn't want her team to be content creators. I could see some people viewing this as a bit of a controversial take from an enablement leader. So who are the subject matter experts? Where does the content come from? Turns out from Marcela and the team at Stripe, they'd much rather be content curators than creators.
Marcela Piñeros: You've got to think of it from a couple of different perspectives. There's the actual populating with valid content, and then there's the governance of that content. One of the pieces that in past lives I struggled with greatly was that there was an expectation that the enablement team would be an expert on all things. Like we need a battle card on X, or we need soft skills training on Y, or we need tool training on this. And the expectation was that the team already had the knowledge and the expertise and could just spin something up very quickly. The reality, as we all know, is that someone from the team would need to be deployed to learn the thing, then create the materials and then get it out. And the lag, the latency between the request and actually putting out the enablement was just so great. But beyond that, you have this backlog of requests that you just can't catch up, can't get there in time.
Sean Lane: Impossible, yeah.
Marcela Piñeros: The reality is that in the organization, there are people that are much more knowledgeable than we are about specific topics. We are the experts in learning, they're the experts in competitive intel. They're the experts in competitive tooling, whatever the resources are. So our job, instead of creating all the content is to be really savvy about who's who in the organization, who can we go to, to do a 30 minute interview, to get a recording that we then chop up into a masterclass that people can consume, that is very quick to be able to go to market. So that's one approach. And then the other part is how do we use tech and tooling to help us govern and create a publishing pipeline so that people see, for example, you have someone that just came off of a conversation where they presented a specific sort of value proposition that was really successful in this article. And they want to share it with the rest of the world. They're like," This might help other people." Normally they'll tell their manager, maybe they'll share it with their friends and their peers. And that's as far as it goes. And this is like something that could be game changing for a person that's on the other side of the world. So if people have that ability to publish these aha moments and to publish their learnings, and when they're publishing it, they have to assign an expiration date to the information that they're posting, such that when that expiration date is coming along, the system emails them to let them know," Hey, is this still valid?" And if they don't respond, the information comes down. If they do respond, then they're vetting," That, yes. And this is a new expiration date. This is something that, it's going to stand behind. So that helps kind of in immediately weed out content that may or may not be accurate or relevant. And then there's the additional governance for this team.
Sean Lane: And that's the original poster that it's going back to?
Marcela Piñeros: Go ahead.
Sean Lane: That's the original poster that it's going back to ask if it's still valid?
Marcela Piñeros: Yes. Yeah. It's the author.
Sean Lane: Got it.
Marcela Piñeros: It's the author.
Sean Lane: Got it.
Marcela Piñeros: Now, we are still on that journey of how do we for create a publishing pipeline that is as efficient as what I have in my mind, but that's where we're headed.
Sean Lane: That's awesome. I think the really important point that you called out in your process, that I think is I think the extra mile step that it sounds like you and your team go is that moment of you do that interview with the subject matter expert. And then you all use your expertise in how people learn to actually piece that information together in a way that's going to be digestible and retainable for the audience. So what I've seen sometimes in the past is you do lean on those subject matter experts. And then it's like," Okay, subject matter expert, go record a video, put together a deck on this topic, and then you present it." And I think you miss that expertise that a team like yours might have on how that content can be delivered in the best way. Is that an explicit, extra step that you've added in to solve for that?
Marcela Piñeros: Yes, definitely. And we're not going to be able to do it for all the things, right?
Sean Lane: Sure.
Marcela Piñeros: When you think about an organization of our size and that keeps growing, there's going to be more, again, demand than there is a possibility or the bandwidth to support with consultation and instructional design resources. For those cases, the team is actually working on something that they're calling project Ikea because it's like," Here are all the pieces we're going to give to you so that you can build the table yourself." And the intention is to be able to create that building block set for the inaudible to be able to use so that they can then create content that already has certain guardrails from an instructional design perspective. Right? And that's going to, again, help them scale. But one of the key challenges that I think probably a lot of the people that are listening face is just prioritization when there's so much demand and so many things you could do, what do you do? What do you choose? What request do you actually go out and talk to the crosstalk, and record them, and then come back and edit and create a masterclass, when do you do that versus giving them templates and saying," Here you go." And there is a need for any enablement executive or any enablement team to be so closely aligned with the key objectives from the business all the way up. We roll up under revenue, the specific business leaders, what are the changes and the results they want to see? What are the top three things and do those three things really, really well. Right? And be able to offer resources for everybody else.
Sean Lane: The other thing I would imagine that comes up in that conversation is let's say you do a great job of picking those top three things. Let's say you do a great job of your prioritization, the content itself, and the point of view itself, when you have so many potential opinions, subject matter experts, potential authors in that publishing funnel that you're describing, how do you think about making sure that whatever it is, you are enabling people on is actually the company's point of view, right? Is it the point of view that you want people to be learning, as opposed to that one person's point of view that might be based on, of a totally different experience than what everybody else on the team might be facing with their customers.
Marcela Piñeros: Right. So it's actually the content that is crowdsourced. The content that's produced across your organization becomes this really rich repository that we can pull from. And to your point, if we pull something, let's say, regional differences are probably the easiest to think through, right? Like perhaps something in Australia would not resonate in Canada. Although those are probably two audiences where it would resonate.
Sean Lane: Sure.
Marcela Piñeros: Something in Japan would not work in Brazil. Right?
Sean Lane: Got it.
Marcela Piñeros: So when you are putting together an enablement function, a curated path, you do need to have subject matter experts that are going to sanity check it both from an accuracy and from a relevance perspective. And it's that relevance piece that you're talking to where it might be relevant for this team in this segment, but is it really relevant globally? So the type of environment that we're trying to create is right now, we're at a scale where my team is building the global enablement materials. And I have dedicated people on the ground that then take those materials and add the regional sort of lens or the regional flavor to try to account for those things. The other part is we use the masterclass model frequently. And what is great at the about the masterclass model is that Stripe is a very complex organization that has multiple segments. So if you have someone that is in a specific segment selling to a specific vertical and a specific part of the world, they can submit a masterclass that this is how we do X here. And that becomes an asset that's available to all the people and that team, versus something that comes out from my organization where it's like," This is how we do this generally, broadly." Because you end up having to water it down so much so it becomes relevant to everybody. Let's just embrace the uniqueness of the specific need to audiences and give them the resources and the tools so that they can speak to that.
Sean Lane: Before we go, at the end of each episode, we're going to ask each guest the same lightning round of questions. Ready? Here we go. Best book you've read in the last six months?
Marcela Piñeros: The Culture Code. It's fantastic. It's fantastic. I highly recommend it. Actually, I just launched a culture club within the organization to help apply some of the principles from that book. So it's a very good book.
Sean Lane: Amazing. I'll add it to the list. Your favorite part about working in enablement?
Marcela Piñeros: The impact. That you can have really tangible impact, not just on people's lives, the satisfaction with their job, but on the business itself. You can be that competitive differentiator for the organization when you do things in a certain way.
Sean Lane: Flip side, least favorite part about working in enablement?
Marcela Piñeros: I think it's the challenges that come with prioritization. I think there's definitely, always more to do. And it becomes really difficult to narrow it down to the top three things. And it's painful because you don't want to say no. Right? You don't. So it's not a pleasant experience.
Sean Lane: Yeah. I think ops is very much the same.
Marcela Piñeros: Yeah.
Sean Lane: Someone who impacted you getting the job you have today?
Marcela Piñeros: Someone who impacted me get... My recruiter. My recruiter was amazing. I think you can never underplay how valuable the recruiting team is. They are the first line of defense. Yeah. I would say that she sold me on it before anybody else did.
Sean Lane: That's awesome. That's amazing. Shut up to her. All right. Last one, one piece of advice for people who want to have your job someday?
Marcela Piñeros: Learn how to do what I call altitude switching, learn how to go from strategic view to really tactical in the weeds, back to strategic view and learn how to do that really quickly. And that's going to set you up for success. It's one of those things that is hard do early on, and then you have to sort of build the muscle. So you can go from one meeting to another meeting where you're just in completely different altitudes and you just kind of have to.
Sean Lane: Thank you so much to Marcela for joining us on this week's episode of# Operations. And thank you to Ariana Spina for making the introduction. Really appreciate it. If you'd like what you heard, make sure you're subscribed up to our show, so you get a new episode into your feed every other Friday. And if you learn something from Marcela today, like I did leave us a review, let us know, leave us a six star review on Apple Podcasts or wherever you get your podcasts. Six star reviews only. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.
How each of us learns is a pretty fascinating thing, isn't it? How we retain information, or more frequently, how we don’t retain it.
Our guest on this episode, Marcela Piñeros is an expert in learning. Marcela is the Global Head of Sales Enablement at Stripe, the online payments provider most recently valued at $95 billion.
Marcela and her team enable a rapidly growing sales organization and in her time since joining Stripe, Marcela has set out to transform the way the company enables its reps. In our conversation, we talk about how to avoid the hamster wheel of enablement content, the way she reinvented Stripe’s new hire program to democratize tribal knowledge, and why she thinks the word "onboarding" is a lie.
Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️ review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz and @DriftPodcasts.