How to make enablement your predictability super power

Marcela Piñeros: I see enablement as a change agent and as a driver of consistency and predictability and efficiency in the business.

Danny Wasserman: This is Reveal: The Revenue Intelligence Podcast, here to help go- to- market leaders do one thing, stop guessing. If you're ready to unlock reality and reach your potential, then this show is for you. I'm Danny Wasserman, coming to you from the Gong Studios. Sales enablement teams look a little different in every organization, but this episode's guest is sure of one thing. Enablement should be the driver of consistency, efficiency, and predictability. Marcela Piñeros is the global head of sales enablement at Stripe, a financial infrastructure platform for businesses, used by millions, yes, you heard me correct, millions of companies worldwide. In this episode, Marcela shares her philosophy on hiring for and building a world- class enablement team. She's also giving us some practical advice on how you can ensure that enablement becomes your predictable superpower. Here's our conversation. It is such a pleasure to have this guest on Reveal, Marcela Piñeros, the head of enablement for none other than Stripe, yes, the highest- valued startup in the history... Oh my God. What a privilege to bring someone of such stature into Reveal. Marcela, thanks so much for being here.

Marcela Piñeros: Oh, it's my pleasure. And with that intro, I don't know that I'll be able to live up to the hype, but I'll try.

Danny Wasserman: Well, I'm excited because as a fellow enablement professional, learning from someone who has walked so many more miles than I have, and certainly, to have experienced what you've gone through, certainly, in your... I mean, how long has it been since you've been at Stripe now, because you have been there for about a year?

Marcela Piñeros: Yeah, a little over a year and a half.

Danny Wasserman: In the time that you've been there, certainly, there's been tremendous change, unprecedented levels of uncertainty. And when we think about the function that is enablement, I'm really excited for you to share with our listeners, for a cross- functional function like enablement, I'm wondering, when the train was leaving the station at the start of calendar year 2022 versus now, what you, I imagine, have been asked to do to pivot, remain agile, rethink how you're going to be successful. Maybe let's just start there. As people are saying," Do more with less," how are you reacting as that's maybe a departure from the original blueprint or playbook for this year?

Marcela Piñeros: Oh, definitely. So I feel like, one, Stripe is a very conservative organization, right, so we're always considering efficiency as leverage, and that's something that we prioritize. And I feel like so many of us out there have already been doing a lot more with less, and when somebody says," We want you to do more with less," it's like, oh, you want me to do even more with even less? And there's this just sense of reactiveness or it's disheartening. And so, I actually reframe that with my team and I encourage them to think of it more in terms of, are you doing the right things with what you have and really think through critically what you are accepting on your plate. And so, instead of being in that reactive position, it's more like you have a reprieve to look at everything that's on the table and identify, are these still the right things for us to be focusing on? Will they give us the biggest impact? Are they aligned to strategic priorities? How do we know what data tells us so? How long until we start seeing ROI? Are they big bets? Are they quick wins? So just really looking through what it is that you have in your portfolio and ruthlessly prioritizing what would be the biggest impact of the business. So it's a bit of a shift. It's going from a scarcity mindset to an empowered mindset.

Danny Wasserman: And talking about ruthlessly prioritizing, this is a topic I want to double, if I could triple- click into, because when what it is that the teams that you serve need is an evolving landscape, in fact, sometimes there are tectonic shifts in what is to be a vital few top three, four, five priorities, well, in the face of economic downturns, geopolitical unrest in Ukraine, any number of things that could eradicate your original 2022 playbook, I'm wondering, how do you play this balancing act so politically as, at times, a cost center with the team that's driving revenue, and say," Hey, but remember, you said that this is what our north star was going to be, or these were going to be our north stars," and those are a vital few, not everything could be a north star. What is your strategy that you could advise our sellers? Whether they're go- to- market leaders or fellow enablement professionals, how do you play that diplomatic role so that you don't disenfranchise the people you serve, but then also, scope creep doesn't make your team a Jack- of- all- trades and a master of none?

Marcela Piñeros: So I think CEO of Microsoft says that it's important to switch from a know- it- all mindset to a learn- it- all mindset, and I love that because I feel that that's what needs to happen right now, especially in organizations where enablement is seen as the people that are supposed to know all the things. And we never really do. We need to be the experts of knowing the people that know all the things, right? There's the saying that the best time to plant a tree was 20 years ago and the second- best time is now. If you think of it as an enablement leader, the best time to align with the strategic priorities of your company and position yourself as a lever that's critical to their success was five years ago, but the next best time is today, right? It's never too late to start, but you absolutely need to get yourself on that path as soon as possible. So there are a couple of things that you can do to help your team be more recession- proof, two that I'll call out specifically. So one is, if you think of your function as a business, it would be great for you to walk the store and go around and talk to the people on your team and ask them," Do you know how our company makes money?" Can they explain to you what the margins are? Are they people that are going to be able to sit down and look at the board deck and understand exactly what it is that's going on in that deck, right? Do they have that language? And the key to investing in your team to think as business people is that then, they can surface areas in their points of interaction where enablement can actually strategically partner to help the business grow, so that's one piece. It's, invest in your people to think as business leaders. And then, the other one is to ruthlessly prioritize, right? When you're being asked to do more with less and when you're looking to make sure that you're doing all the right things with what you have, it's really important to choose what not to do, and it's almost more important to be able to articulate what you're not going to do and be able to back that up with a decision- making framework. So a lot of your job is reasoning and making sure that your decision- making criteria is clear, talking through with all of your stakeholders so that they understand how you are aligned to executive leadership. And depending on the size of your organization, if you're able to actually get into a room with execs and workshop your priorities, all the better. If you don't have that luxury, then being able to go through all of the documentation so that you can say,"Listen, this is why A, B, and C is what I'm going to be focusing on, this is the data that backs it up, and this is the decision- making criteria that I'm going to leverage for the remainder of the year, the next 12, 18 months, to decide what else makes it into our charter." I think just the clarity of it is something that people appreciate, especially in time of uncertainty.

Danny Wasserman: When you talk about positioning the prioritization, that ruthless scrutiny that you apply, because it can't just be, everything's a priority, you're using data. And there is a article in HBR called the great training robbery. And I reference that because there's this stigma that follows you and I with an enablement, oh my God, what other team is granted six, seven, eight figures in budget and aren't holding themselves accountable to the same standards that are black and white, like quota, or even with marketing and the advancements in marketing technology, where now, we can follow campaigns end to end, to determine, was that a fruitful use of resources? With enablement, we get lots of, huh, Marcela, that was an amazing training, that was so fun, I love your trainers, or oh my God, you made me feel all the feels, but we haven't historically been at the forefront of applying data. So thinking about a company like Stripe, I'm wondering, what are the ways in which you map your contributions and your prioritizations to data that you then can take back to sales leadership to continue to rationalize or explain, here's why we're sticking with the pecking order, or here's why we're going to actually swap out priority two for this new flavor of prioritization? Can you talk about that?

Marcela Piñeros: Absolutely, so there's a couple of things that come to mind. On one end, there's A/ B testing. I don't think that people A/ B test enough. So if you're able to get two groups of people and you're able to apply your enablement strategy to one of them, and then compare to the other, and be able to demonstrate an increase in revenue, an increase in productivity, an increase in pipeline, et cetera, then that's one really great data point that you can leverage. That's one thing. But then, the other is, it's really hard to quantify some of these more subjective or qualitative pieces like confidence and empathy, right? It's very, very difficult to quantify those things, and that's where I feel that enablement sometimes gets stuck. It's like, well, it's purely qualitative. There really isn't, right? Enablement today, especially if you think of it as revenue enablement, is more than just like, I want to get information to you. It's, I want for you to apply a specific skill or behavior in your day to day that will yield a specific business result. And if you can define it in that way, then you're tracking that specific business result to see whether or not the things that you're doing over here actually move the needle over there. And it'll come all the way down to, if my team were to save two minutes a day in terms of productivity, and they use those two minutes to then turn around and sell to the business, what does that look like, right? You can take time and money, which are two relatively fixed variables, and you can compare them to one another to be able to demonstrate value. So there's all sorts of different things that you can look at from a productivity perspective, but the most important is, when you are setting yourself up to put an enablement plan in place, what is the finish line and how are you going to measure that finish line? You don't want to have to come back afterwards and say," Oh, well, we launched a program and now we have this data. Let's see if we can make a story out of it." It's like, that's very, very hard to do, so you want to do it from design.

Danny Wasserman: I look at Stripe from the outside and I say," You are the apex predators," and I think, man, you must be impervious to these downturns, to these headwinds that we're all confronting, these uncertainties that really leave us in a state of confusion. And I'm wondering if you could elaborate a little bit more, as you guys have taken all this uncertainty in stride, how has that impacted Stripe at a macro level, and in particular, how has that impacted enablement?

Marcela Piñeros: Well, first, I don't think that we're impervious to anything, right? I think that Stripe is in a position just like everybody else. We have a front row seat to the impact of an economic uncertain time. We're able to see it with our customers. I think for us, it's been a matter of doubling our focus down on helping our users grow revenue faster, helping them achieve their goals a little bit more easily with less effort and with less cost. So that's just been all the more at the center. If anybody had any doubts, it's like, nope, this is what is most important, and this is our north star. But from an enablement perspective, the questions that I'm asking are," How do we take care of the people that are here? How do we take care of the people that are part of the company? How do we know that they have the knowledge and the skills that they need to be wildly successful at Stripe and to be able to actually help our users achieve their goals? Do they have all those skills?" I have yet to meet an organization in any of my years of consulting that's like," Oh, yeah, our people know everything they need to know. They've got all the skills they need to do that. We're good. We can walk away." That's never the case, right? There's always more to learn. There's always more to do. So from an enabling perspective, it's really looking at that. It's like, are we setting our people up for success? And acknowledging that during times of uncertainty, what the human brain will do is, it'll hyper focus on what's exactly in front of you, right? And that changes the way that enablement engages with the organization a little bit. Whereas, before, you might broadly broadcast things and hope that some of that sticks, now, it really comes down to one- on- one contact and one-on- one conversations where you can stand in the line of sight where people have hyper- focused to be able to convey the message and make sure that you're getting their feedback when you need it. And the big shift really has been more from, let's do things really, really quickly to, let's make sure we're doing things well. And that might be a little bit slower, but that's okay because we're guaranteeing that the impact that we will have will yield the results that we need. So there's definitely a little bit of a shift, especially when it comes to change management.

Danny Wasserman: Want to shift gears a little bit. On Reveal, we've had sales leaders and go- to- market leaders come on, most recently had a guest who is on a crusade to demystify sales and in a lot of ways, buck this not- so- savory reputation that sales has. And I think it's a interesting segue to my next question, being enablement. When I left college, A, I didn't know anything about sales, but in particular, even when I became a seller, I did not know anything about enablement. And I think there's a lot of misunderstanding out in the market about what does enablement do, what don't they do? And in my experience in the last five, six years, having been an enablement specialist, I have yet to see two enablement teams operate in the exact same or identical fashion. Tell me a little bit more about your understanding of enablement and what constitutes that profession.

Marcela Piñeros: My definition, as you've very well noted, is probably different from 15 other people that might be in the room with me. The way that I see enablement is, I see enablement as a change agent and as a driver of consistency and predictability and efficiency in the business. And the way that we do that is by actually focusing on what happens on the job versus focusing purely on creating and pushing out content as a core function. And you'll see that in many organizations, that's what enablement is. Enablement is, let's get as much content as we can out, let's measure the success of our function based off of throughput, how many people are reading, what the viewership is. That's a fair model. However, as we're moving into a world where it's no longer sales enablement, it's a revenue enablement. You're thinking about not just getting to the close, but what happens afterwards, the full life cycle of the customer? You're being charged with looking at everything from customer success to partners. You're also being charged to look at how are the systems and the standard operating procedures working to make people more efficient? It's so much more than just knowledge. So there's this quadrant that I refer to, knowledge, skills, motivation, and environment. Historically, enablement has fallen just under that knowledge bucket, and that's where people have continually put enablement. I see enablement as being a function of all four, where we're able to support knowledge, we're able to focus on skills, that's really where I spend more of my time, but we can influence the environment, and we can also influence motivation. And with those four pieces locking into place, that's when you get business results. If any of them are missing, then you're going to be walking around lopsided. So I see enablement as the steward of those four boxes, making sure that they're all moving in the right direction.

Danny Wasserman: And when go- to- market leaders mistakenly consider enablement to just be sales, and I love your distinction, it is not just sales, it is revenue, and there's more than one quadrant... Therefore, I guess, examining perhaps a legacy pattern of go- to- market constituents who misunderstand the complexity that is enablement, what has been a winning formula, in your experience, when you have found, ah, we've broken through that misunderstanding and now we're moving and grooving, go- to- market is doing the tango with enablement, could you... For the leaders out there that are thinking, how do I best partner with my enablement peers, or how do I get all the dividends that I know exist in enablement, but for whatever reason, we just can't quite squeeze all that juice out of that, maybe explain a little bit more why you've been so successful with your peers at Stripe or even at other companies you worked at.

Marcela Piñeros: I think it comes down to being savvy about the business. So you know the saying, when you're selling, you will always be referred to the person you sound most like, so if you are coming in and you're doing a very technical sale and you sound like product, they're going to send you to an engineer, and if you come in and you're doing a very high- level business sale, they're going to send you to the business side of the house, right? When you're coming in and all you're talking about are clicks and views and consumption, then they are going to imagine that you belong in that bucket of knowledge and that's it. When you come in and you're talking about pipeline, and you're talking about throughput, and you're talking about churn, and you're talking about all of these measures that actually move the needle in the business, then they'll take a step back and they'll be like," Oh, wait, okay, so this is a business conversation," that's what it needs to be. If you keep it at a business conversation and you're able to connect the dots and express your vision in the context of the business, then you're helping them see what enablement can potentially be and how it can be a competitive advantage for them. That's, I think, the big shift.

Danny Wasserman: Thanks to incredible enablement leaders like Marcela, the market is finally starting to see the value in enablement. According to G2, sales enablement has experienced an explosive growth with, you ready for this, 343% increase in adoption over the last five years. Not only that, organizations with sales enablement report some impressive secondary effects because of this team's impact. Organizations with enablement report, on average, 31% improvement in supporting changes in sales messaging and 15% improvement in low- performing salespeople. Now, let's hear more from Marcela about how to build an effective sales enablement team in your organization. So you think about growing your team and sourcing talent, what are some pearls of wisdom that you would offer for prospective candidates out there that are kicking the tires on a career in enablement, whether it's on your team at Stripe or just at the industry at large, some things that you would want that younger generation of up- and- coming trailblazers in enablement to hear from you?

Marcela Piñeros: The first thing that comes to mind is grit. So I tend to hire for grit and for kindness and for growth mindset. Those are three things that I look for. Kindness, to me, is really important because I believe that the highest- performing teams operate under an umbrella of psychological safety, and when people that are around you, their first instinct is to be kind, that it's more likely that you can achieve that and get superstar productivity, which I've been really, really fortunate to have brilliant people that are working with me, that are able to hit those goals because they are kind, they're kind humans. So that's one thing that I would say. The other thing that I would say with grit is that enablement is redefining itself every day. If we go back in a time machine, you and I, Danny, to two years ago, the way we defined enablement was different. Five years ago, the way that we defined enablement was different. It is constantly evolving to meet the needs of the business, and candidly, its charter keeps growing and growing and growing because the potential of what we can do and we can change is greater and greater. So you need to be agile and have grit to be able to go out with something, oh, wait, that's not it, you're going to get knocked down, you have to get back up, and figure out, what is the next iteration, what is the next iteration? So that's really important, to have that flexibility and mindset, and then the growth mindset. When I get folks in an interview and I ask them," What is the last book you read," or," What is the most interesting thing that you've recently learned, that shifted your thinking about how people learn, or that shifted your thinking about anything in the world," and folks just stare at me blankly, that, to me, is an indicator, well, maybe they're not really dedicated to nurturing their brain into coming up with new ideas and new perspectives, because I can say, when I think of creativity, which is also really important to enablement, creativity, in my mind, is your ability to connect the dots between disparate things. And the way you learn to do that is by exposing yourself to as much knowledge and different thoughts and different frameworks and a lot of diversity. Then, you are able to suddenly be able to connect the dots so much better and faster, and I feel that's a really important skill in enablement.

Danny Wasserman: One thing that I'm noodling on, that you just said, you're looking for grit and you're looking for kindness, at first, blush, I hear grit, and I think tenacious, fierce, almost competitive, and kindness, there's a tenderness, a warmth, something gentle about it. And I'm wondering, how do we reconcile what could be mistakenly understood to be paradoxical, because as an enablement specialist now, I think about, if I'm going in front of, especially upmarket segments, I need to be buttoned up, because they're conditioned to being cynical, they want to just poke holes and spar almost for sport, so if I'm not gritty, I'm going to get blown out of the sky. So whether it's advice that you have for fellow enablement personnel or for sellers, how do you make sense of being both gritty and kind, because we are in service of sales, but we also can't necessarily be just spineless?

Marcela Piñeros: Yeah, I think, as you're describing it, one way, potentially, to think about it is, you need to be kind with your peers and enablement. You need to be able to always assume positive intent when you're getting feedback. You need to be able to seek out the greater good of the people that are working around you and genuinely, genuinely want to see other people succeed. Those are some of the manifestations of kindness that I would expect to see. Grit, a hundred percent. You're going to be talking with people that are going to want to knock you down, and they're going to be poking holes in what you're doing, and that's part of the job, and that's absolutely fine. The confidence level that you have and the way that you present to others has nothing to do with the fact that you are also genuinely thinking, what is going to be best for them, how can I best help them, right? So I actually don't think that they are... I think they're very complimentary. If you have somebody that only has grit and is ruthless, they're going to go far, but they're going to go alone, right? If you have somebody that has kindness and a service mindset and is really interested in seeing other people succeed, then that's the secret sauce, right? You get somebody that can both be fierce, but also be sensitive and kind and empathetic.

Danny Wasserman: Are there any pre- determinants prior to hiring an enablement individual or even launching a career in enablement? Are there pre- determinants that, for you, signal or insinuate success? As an example, some enablement leaders or even go- to- market leaders say," I only want to put people in enablement who have carried the bag," because they viscerally have felt the challenges, the emotional strain of knowing that anywhere from a fraction to 50% of your income is variable, so enablement personnel who have lived that uncertainty are more effective. Is that something, as an example, that's a non- starter for you, or do you have different criterion that you would share with enablement leaders and go- to- market leaders?

Marcela Piñeros: I do have different criteria based on the different teams that I have, right? So enablement isn't a one- size role. Within enablement, you'll have program managers, you'll have instructional designers, you have what I call enablement business partners. Enablement business partners, I do require to have a sales background because these are people that are going to be speaking to the field and they're going to be speaking to the sales leaders, and I need for them to be speaking from a space of empathy because they've gone through it themselves, so that, I, a hundred percent, agree with. But then, you've got other folks in the strategy organization managing systems, managing tooling. I don't necessarily need for them to have carried the baton, but I do need for them to think like business leaders. I do need for them to understand how the business works, because again, they are going to have line of sight into conversations and meetings that I'm not going to be in the room, and they'll be able to pick up on the fact, like," Oh, wow, this is going to be changing in the next 12 months, and that's going to have this downstream impact," and they're able to connect the dots for me, and we can come back and come up with a vision together.

Danny Wasserman: Well, Marcela, as it's abundantly clear to me, you could write the book end to end on structuring and strategizing the most world- class enablement team that also happens to harmoniously partner with go- to- market. You've generously indulged me with my barrage of questions. We have one question left, and if you've listened to Reveal, it's the same question we ask all of our guests. I know we've largely focused on enablement, but we're going to pivot back to sales now. Marcela, if you could describe sales in one word, what would it be?

Marcela Piñeros: Outcomes. I think of sales not only as your business outcomes and your revenue outcomes, but also, the outcomes of your customers. When you have a really well- functioning sales organization, these are people that have the skills, they have the knowledge, they have the tools, they have everything they need to help their customers achieve their desired outcomes. And then, that, in turn, achieves the business' desired outcomes, so I think that's a both end-to-end description.

Danny Wasserman: I love that. Marcela, I can't thank you enough for sharing all of your knowledge and your gifts with Reveal and our listeners' networks. It's been so much fun. I really appreciate all of the candor.

Marcela Piñeros: Thank you so much, Daniel.

Danny Wasserman: Thanks so much for listening to this episode of Reveal. If you want more resources on how revenue intelligence can help your team win, head on over to gong. io. If you like what you heard, give us a five- star review on Apple Podcasts, Spotify, or wherever you may listen.