Making Sales a Team Sport with Matt Yalowitz and Ross Rich

“I saw a lot of great salespeople really struggle with understanding the value of cross-functional interactions, both for the customer and for themselves.” — Ross Rich

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The hosts:
Trinity Nguyen
Trinity Nguyen
Co-host
A profile photo of Christian Kletzl
Christian Kletzl
Co-host

Ross Rich, CEO of Accord, and Matt Yalowitz, Head of Corporate Development at Stripe know one of the biggest mistakes you can make as a sales rep is undervaluing collaboration with the rest of your organization.

And when you’re selling a complex product, it’s even more important to lean on your team.

This kind of teamwork is easier said than done. So how do you develop strong internal collaboration while moving quickly and serving your clients?

Listen in to hear Ross and Matt’s answers.

Key Takeaways:

  • How to align individual and organizational goals
  • How to collaborate with partner teams to close deals
  • How to navigate complex sales processes
  • How to address product feedback from sales to drive user value
  • How to efficiently educate and enable sales reps and customers on your product

Things to listen for:

[02:00] Matt: “At a product-led growth company like Stripe, coordination with the product team is key because a lot of our users were self-sign-up and self-serve, and the sales team had unique insights and perspectives that we were hearing from our largest users and our new enterprise customers being able to translate that feedback into actionable items on the roadmap for the product team was really important.”

[03:50] Matt: “When you’re selling complex products, it's much more incumbent on the sales team to be a good partner to cross-functional groups so all the pieces of the broader puzzle pieces can fit together.”

[05:07] Matt: “Nailing the communication cadence with cross-functional teams is key in building the relationships in such a way that people feel comfortable. It creates a baseline layer of trust and understanding about what different teams do and that we’re all trying to do the best thing for the organization.”

[05:45] Ross: “Having a trusted partner on other teams was how I approached collaboration as a top rep. Time kills all deals, and I didn’t want to have extra back and forth because of a miscommunication.”

[07:55] Ross: “Interfacing with other teams is part of your job. It’s not a secondary part of the sale. You should be a value add for each of those pieces to the customer. It should be positioned as taking work off their plate, getting answers quickly, and keeping the process lightweight.”

[15:07] Matt: “Instead of asking, ‘Where are there opportunities to drive more revenue?’ ask, ‘Where's our opportunity to drive more value?’ If you're driving more value for your customers, revenue will follow.”

Reference Links:

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Read Transcript

Trinity Nguyen:

Hey, everyone, and welcome to another episode of The First 100 Days, a show for revenue practitioners, by revenue practitioners, exploring how to build an aligned revenue engine one practical tip at a time. I'm Trinity Nguyen.

Christian Kletzl:

And I'm Christian Kletzl. This season, we are talking about building revenue alignment by asking high performing teams how they got it done.

Trinity Nguyen:

Hi, everyone. Welcome to another episode of The First 100 Days. Joining us today are Ross Rich, CEO and co-founder of Accord, a software for sales and customer success teams to collaborate with buyers on next steps, timeline, and business outcomes. And Matt Yalowitz, who heads up corporate development at Stripe. Companies from Fortune 500 and startups use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Ross and Matt used to work together in sales at Stripe. Welcome to the show, guys.

Matt Yalowitz:

Thanks for having us.

Ross Rich:

Appreciate the invite.

Trinity Nguyen:

So in this season, we discuss all aspects of revenue, alignments, and so far, our guests have come from marketing and sales. But revenue alignment also needs to come from aligning with other business partners outside of the revenue teams. So I'll kick off the first question, easy one, Ross, what were some of the teams that you worked closely with?

Ross Rich:

There is a long laundry list of teams at Stripe who we had to work with to close revenue. Off the top of my head, we partnered with sales engineers, executive sponsors, risk management, compliance, legal. If it was international, it'd be the international local teams on the ground. We worked with the product teams, typically from alternative payment methods, to the CONNECT platform to pay out to businesses, to potential betas that we're trying to get unlocked. So it was a lot of cats to herd internally, not even getting into how many folks on the customer side that we had to partner with. But yeah, on the internal side, a lot of alignment required to get deals done at Stripe, especially in those early days.

Matt Yalowitz:

At a product-led growth company like Stripe, coordination with a product team was key, because a lot of our users were self sign up and self-serve, and sales team had unique insights and perspective that we were hearing from our largest users and our new enterprise customers. And being able to translate that feedback into actionable product items on the roadmap for the product team, I think was really important early on.

Christian Kletzl:

I found the wording interesting when Ross said, we had to work with those teams. I think some of these are very helpful in the sales process, and some of this is more like, I need to involve more people and get the compliance [inaudible 00:02:44], I guess.

Ross Rich:

Yes, so there's a difference, definitely, between partnering with a sales engineer, who's going to partner with the technical stakeholders and help answer questions and drive the deal forward and provide more value, versus what we need to do for our business to make sure that we don't sign up merchants that don't make sense. Credit risk, compliance, these are all great things as a shareholder of Stripe, some with equity, but in terms of trying to get a deal done, obviously, there's more questions and folks that you need to involve. And if time kills all deals, and spending energy on things that aren't necessarily value driving to the conversation, it's really tricky to balance all of those things, especially in the early days without a very clear process.

Christian Kletzl:

And I think that's the interesting thing, because if you talk about compliance, it could mean that a deal that probably, you think, hey, this is going to happen, I close a bunch of business, and then compliance comes and says, hey, we don't do that. So I think it's very interesting how these departments can actually work a little bit competitively, and how to align that.

Matt Yalowitz:

I think it's especially true to a financial services company like Stripe, where we're not just selling traditional software licenses, but we're selling complex money movement products that have implications from both a regulatory and credit risk standpoint, as Ross mentioned, a policy standpoint, as well, on different types of user supportability. It ends up becoming a much more complex sales process as a result, and it's much more incumbent on the sales team to be a good partner to all these cross-functional groups, to work effectively with all these different partner teams, so that all of the different pieces of the broader puzzle can fit together well.

Christian Kletzl:

How do you best do that? I feel like, in a sense, the goal of the individual AE is then very different than the goal of, let's say, the compliance organization. How do you align that so that you actually make both happy?

Matt Yalowitz:

I can give my perspective from a management angle, and then I'd love Ross's thoughts on this, as well. But I think the key thing is communication at the start, so understanding, what are the two different teams' goals, and how those goals ultimately ladder up to the broader organization and company's objectives. And even if there are different ways in which each of those individual teams are pursuing the end company objectives, we're all ultimately on the same teams. So I think communication around how each individual team's goals ladder up to the broader goals, understanding, what are the directives of each of those teams, and education about how those teams function, setting up a regular cadence of communication. I think the worst default is where people are filing tickets or JIRAs or emailing, and there's no face to face contact, there's no communication, no one picks up the phone just to make a call.

Matt Yalowitz:

Maybe I'm old fashioned in that sense, but I think just really nailing the communication cadence with cross functional teams is key in building the relationships in such a way that people feel comfortable. There's a baseline layer of trust and understanding about what these different teams do, and that we're all trying to do the best thing, and using that communication and that trust to then figure out paths forward and communication about specific issues when they do come up. Because when you build that level of trust and communication, when things do pop, when there are issues and tension points, people are all coming at it from the best possible angle, an angle of trust and mutual understanding and respect.

Ross Rich:

Yes, you need that baseline understanding, but what I've found, maybe to be super honest here, having a stakeholder that I knew on the other teams was how I approached it as a top rep. Again, time kills all deals, and I don't want to have extra questions or an extra back and forth with my key stakeholders and champions who are going to bat for me to make a hundreds of thousands or multimillion dollar decision to rip out how they accept all of their revenue from customers, and how they're planning on growing internationally, because of a potential miscommunication with someone new on one of those teams that I'm coordinating with.

Ross Rich:

So I would always have my trusted partners. I'd have my sales engineer I'd try to use on every deal and every question. I'd have my person in risk and compliance and legal that, as a fail safe, if these things came up, that I'd be able to get the right answer for my customer to avoid any of those further back and forths. Which is kind of what Matt's saying, is like, hey, the goal is, I think across the board, for anyone who gets that ticket. But let's be real, at high growth companies, if you're just jumping onto the team, and it's your second weekend, and you're on the queue and there's this really key deal, if I'm an enterprise rep, it's going to be really hard for me to trust that interaction that you're going to get back to me quickly, so I'm going to get back to the customer, that it's going to be not to require one to two more questions after that interaction. So that was my experience being on the ground floor there.

Trinity Nguyen:

I was going to ask, because I've only been in SaaS, so the partner teams tend to be a lot less complex, comparing to what you guys see on the financial side. So I'm kind of curious, as a new rep joining the team, kind of thinking about you, Ross, when you first joined Stripe, and Matt's like, go build relationship, here's the deal, go close them. When you have like, 10 different partner teams, I'm just making a number up, how do you figure out ... what's your game plan for someone listening to this podcast right now and trying to figure this out, how to game plan this, how to prioritize, and then find someone in each of those team, and build relationship with?

Ross Rich:

I think this is where someone that might thrive in traditional SaaS might have challenges in a sale like this, a very technical sale. And I don't think it's just true for financial services, I think it's for a lot of infrastructure-based companies, where you're interfacing with a number of teams, whether it's compliance and risk, or other internal stakeholders and external stakeholders is, it's part of your job. It's not a secondary part of the sale. It's not, hey, I need to just get these questions answered. You should be a value add for each of those pieces to the customer.

Ross Rich:

It should be positioned in a way that, hey, anyone you're going to work with is going to have these checks and balances. I'm going to make each of those easier than anyone else that you'd be working with. And I kind of approached it that way, where kind of reframing, oh, yes, we need to get these questions answered, and we need to do this stuff, but I'm going to take it off your plate, and you're going to make sure that we're going to get these back quickly. It's going to be super lightweight for you, and you're going to learn about it, as well, which I think everyone in kind of technology at high growth companies should be excited about.

Ross Rich:

I enjoyed getting to know those people, and I think by treating them as humans, not just like that milestone you need to cross, really helped build those relationships. And I saw a lot of people really struggle, great sales people at other companies, struggle with understanding the value, both for the customer, as well as for themselves and those internal teams, how to cross those things off and skip them, and then the deal's dead. So yeah, Matt, I'm curious to get your take from the more manager perspective, on what you saw across the gamut for how reps approach that.

Matt Yalowitz:

I think the most important thing, especially as you're part of a larger and scaling sales organization, goes back to training and enablement. Because, while it's helpful to learn on the job, like the connections, as you pointed out, Ross, individuals on the cross-functional teams, and develop those relationships, and it's incumbent upon leadership to make sure that there's communication and alignment between the broader goals and escalation paths, a lot of it comes down to, when you're onboarding new AEs and new reps to the company, educating them about the various steps in the sales process. And that includes the cross-functional partners. And if you do have, in the case of a complex infrastructure sale like Stripe that touches on financial services, 10 different teams that you need to bring in as stakeholders, you really need to run a tight onboarding and sales enablement process, where you're educating those sales teams around which teams are most important to bring in as part of the sales process.

Matt Yalowitz:

How do you prioritize among those 10 different stakeholders, which are the most important, which should come first? I think there has to be a clear set of communications to the AEs, and clear set of trainings that helps them understand how to navigate this process, because it's not helpful if you have each AE discovering on their own, and trying to figure it out. They'll eventually get there if you hire smart people, but I think you need to help them out at the beginning, and articulate these cross-functional partnerships and key stakeholders as part of that training process that's educating these AEs on the sales process at your individual company.

Christian Kletzl:

I thought that was ... educating them, and I think it's so smart to educate them on what matters to them. A little bit the way Ross said, it's kind of like, I should probably go in and actually understand, what are the OKRs of each of these stakeholders. We all have ultimately, the same goal of generating good revenue for the company, where we each have our own individual goals. And the more I understand those, the better I can work with them and become their friend.

Trinity Nguyen:

The one part that you mentioned earlier of Matt's, about product ... so I kind of segued a little bit, but that's when ... I did not see that coming, initially, but that is so true, because a lot of the time, the product roadmap is not only influenced by the feedback from the customers, but from the sales team hearing from the market. So maybe you can share a little bit on how has your experience in kind of influencing the product's roadmap from the sales standpoint, especially in POG, where there are probably a lot of different feedback all the time, from all types of segments in the market that you're going after?

Matt Yalowitz:

I think it's a really important thing to do to incorporate that feedback with the product roadmap. But what you don't want to do is over index on that feedback, because I think that can also be a very dangerous path, if you have a very single large enterprise user who influences the roadmap in a way that benefits that particular user, but not necessarily even the broader user base, or even other enterprise users. I think in companies like Stripe, what we've seen is most successful is if we build a feature or functionality that is useful for the broadest possible base of users.

Matt Yalowitz:

And that, I think, is where ... again, it's a really careful balance of taking user feedback and inputs from the sales team, but not over indexing on just a couple of large users, or very pushy or loud members of the sales organization where [inaudible 00:12:29] specific product ask. And that's why we started to implement through our product operations function, a very structured process as it related to top user asks. And if there was going to be an ask that came through as a priority, ask from a top user that had to get signed off on by both the product and the sales organization, if it was going to jump the queue and the roadmap.

Matt Yalowitz:

And then, in terms of this biannual process we would run, it would assess for all our different market segments and user segments, what were the top asks, and we'd collate and put together a doc twice a year that looked at, what are the inputs from sales from user ops, from the scaled sales teams, from a number of different stakeholders, from technical decision makers? What are all these various inputs we put together, our top user asks twice a year, and then that helped inform the process. But it wasn't just like a one off thing, where we're throwing a long list at the product team, and it has to be done in a structured way that balances the various inputs and doesn't prioritize any one input too much.

Trinity Nguyen:

And Ross, right now at Accord, I'm sure you're hearing feedback from the reps of new feature requests all the time at this stage, right? Yeah. And how do you guys prioritize?

Ross Rich:

Obviously, it's a mix of an art and a science, right? You have your ethics list, and you have your asks, and you prioritize it based on ... at least the way that we think about it, I'm sure this is probably the vast majority, is who's actually paying us who, and could be paying us more? And more immediately, where can we drive revenue? Mixing that with, does this actually fit with the medium and longer term roadmap? Great. If this is a thing that we've already been thinking about, that is going to help incrementally drive revenue with either new or existing accounts, especially with these existing accounts, great, that goes to the top of the list. I think some of the challenging things are, if, in some businesses, especially early stage startups, might have a mix of different ICPs.

Ross Rich:

You might have a couple larger companies that are driving with larger contracts that are driving 50 or a 100K plus agreements, and then you might have a longer tail list of 5, 10, 20K deals. And how do you balance both of those? Because some features might only fit certain subsets. I think what we think about earlier on is trying to prioritize the largest number of end users. So a lot of the stuff that we end up prioritizing are where rubber meets the road, in our case, where the buyers and sellers that are actually engaging on the platform benefit, versus the decision makers, because what we try to go back to them and say is, this actually drives this impact.

Matt Yalowitz:

I like that framework, Ross, of talking about, instead of just, where are there opportunities to drive more revenue, where's our opportunity to drive more value? Because if you're driving more value for your customers, revenue will 100% follow. I think that's a [inaudible 00:15:07] framework to think about is, where are we driving value? Where are we driving impact with our product? Because increasingly, as you do that, you'll drive more revenue, more adoption, greater stickiness. People will be better at recommending your product to their friends and colleagues through word of mouth.

Ross Rich:

Or when they leave their company and go to a new company.

Christian Kletzl:

I think along those lines, we even talk about ... so there's more value for the existing users, or it could be, can you actually generate more users within a company, so that there are more people that can then talk about you? I think we talked about this, and then obviously, we hope that they change the top and move to a new organization. But yeah, the value could be for the users that you have, or you can think about, how can I have more users within my customers, which also obviously produces more value.

Trinity Nguyen:

I don't know if Matt knows the context of why we keep talking about job changes. That's what [inaudible 00:15:57] does, by the way.

Matt Yalowitz:

It's a very important factor. And that's why, again, your company is such a cool idea, because it is a key inflection point in the sales process, because it is a way for you to communicate when someone changes jobs. The value add that you provided at one organization, you can have an advocate who will make that same value proposition quite well, because they've understood the value in the past, and they'll make it in the future. The other thing I'm curious for your thoughts on, sorry to turn a question to you all [inaudible 00:16:28], but as it relates to education, I think that's a big piece because I think some companies invest a lot in new user acquisition and expanding the user base, but not educating. And I was talking to a friend of mine who's the head of sales at an early stage startup called mmhmm, M-M-H-M-M, founded by [inaudible 00:16:47].

Matt Yalowitz:

And we were talking about how he's been hiring teachers recently onto his sales organization. And I was like, oh, that's an interesting idea. And it's a tough time for teachers, especially coming out of the pandemic. A lot of teachers are looking for different opportunities, but he's like, yeah, I've hired a lot of teachers because they're really patient and great at working with customers and articulating complex ideas in more digestible, easier to understand ways. And when you have a teacher who's in this role at a product led growth organization, they can be quite impactful in getting greater adoption for the product, and stickier adoption, in a way, that helps the users better utilize the product and understand what's actually happening. And then, when they move to the next organization, they're an even stronger advocate. So I think it feeds into this broader cycle, but I'm curious how you view education and training of users about how to use the product as part of that stickiness of a customer lifetime value.

Christian Kletzl:

I think my initial thought was immediately like, it's not only sales where you should have the teachers, but as you say, it should be customer success. And I think as you ... this comes down to the value. The more you educate the people, the more value they get. It's hard to measure, but if the one metric that I'm going for is total value generated, then it's about, how many users can I make happy, or can I provide value, and then increase the value per user?

Trinity Nguyen:

I think everyone keeps saying ... in the sales side, like from ADR to AE, everyone's already been talking about how teachers make really great sales people, for the same quality that you just mentioned, Matt. For customer success, I think that makes sense, too, because they're more patient in guiding through implementation. But also, just to kind of be devil's advocate, for the PLG side, as well, I think it's great to rely on great CSMO implementation specialists to get more adoption, but shouldn't the technology also need to be so intuitive to the point that the users can see value without having someone handhold them, if it's like a PLG product?

Matt Yalowitz:

Yeah, I think it's a great point. I think there are two categories, some of these products that might be more consumer-focused, absolutely, that should be the case. I think when you start working with complex infrastructure products, whether that's AWS or Stripe, even Accord, which is like a [inaudible 00:18:56] product for sales teams, there's enough complexity of the product, because you want a product to be powerful enough to do a lot of different things, that it passes that threshold of being something I think can be totally discoverable by an individual.

Matt Yalowitz:

There's also the element of, they might better utilize the product with more training on how to utilize it. And even how strapped everybody is for time, that's something where, if you can get someone from point A to B, and they can do it themselves in maybe two hours, but you can do it in 15 minutes. People don't have two hours anymore, so that's where I'd say, there's that joy of discovering something on your own and figuring it out, and a product should be intuitive. But if you can short circuit the process and save someone a couple hours by creating great education paths, I think that's really valuable from a time saving perspective. But still agree with you, it should be intuitive.

Trinity Nguyen:

It's a very timely ... because right now, that's something that we're discussing on the [inaudible 00:19:48] side, as well. Because initially, we're like, well, should we get more customer success implementation specialists to try to help our clients [inaudible 00:19:57] implement our tools faster? But then, we also challenge our product team [inaudible 00:20:02], well, we can't just keep throwing body at the problem, when the beauty of SaaS is this technology, and you can get a lot of these done without having an army of people to implement and see the value. So that's kind of like a push and pull right now we're having, and now the product team's trying to figure out how they can do with the product to the max, and then that's when we can kind of figure out the human aspects.

Matt Yalowitz:

And that's where you should also figure out programs at scale, whether it's webinars or trainings or scaled education systems and programs, more complex organizations. I remember at Google, we had a Google AdWord certification program, and Stripe is doing that now, too. You can have these training programs that actually certify practitioners of the product in such a way that shows that they've invested the time to learn about it. But I think that's key, because it doesn't scale where you have a trainer for every team, then you just become a professional services organization, and the cost to serve becomes very expensive.

Christian Kletzl:

Especially for PLG, I think that could be even more difficult there.

Trinity Nguyen:

But Superhuman does it well, though. I mean, they're the one that have someone meeting-

Ross Rich:

I wonder what that model really looks like at the end of the day. I never ended up using it. I wonder what percentage of people actually end up doing it, and what the difference would be, and should it be able to use ... they've been successful, but they've never really kind of crossed over to be that slack type, Gmail type popularity. And I've always had a question in the back of my mind being like, we always talk about it as their examples of the product market fit calculator and the handheld onboarding. I'm like, maybe it was really well- marketed, and I don't know if it ever really got to be at the same level effectiveness of other examples that we've seen. But just maybe a hot take, and I don't know the answer to it, but I've always had that thought in the back of my head.

Trinity Nguyen:

Yeah, no, I'm curious, too. When I first heard about it and saw it ... our AE team loves Superhuman. They don't even touch Gmail anymore. And I'm curious, how does that work from the operational side of the business? The burn multiples of the [inaudible 00:21:58], all that stuff, especially right now, just thinking about it gives me heartburn a little bit. So I don't know how they do it. And is it scalable in the next two years with the market condition that we're seeing right now? So when we publish this [inaudible 00:22:11] podcast, if anyone hasn't answered, I hope they tag Superhuman's CEO or something for some comment, because I'm really, really curious. So we at the bottom of the hour, Christian, do you have any last questions?

Christian Kletzl:

I think what I would love to know is, as the final question there, so when you join a new organization, who's the first person you make your best friend to help you with the sales process?

Ross Rich:

And this example at Stripe, that's a really good question. I think first, your manager, because they're going to help you most navigate the ... actually, I'm going to change my answer, not your manager, the top rep on the team. I want to make the top rep on the team my best friend, because they are doing what I want to do. They have successfully done this, and that's really what matters at the end of the day. You're in a revenue generating role, the person that's done it before consistently, that's where I want to learn from.

Ross Rich:

That's where I learned a lot of my best sales skills from is listening to ... Matt's an incredible salesperson, and listening to his talk tracks and emails. There was a guy Daniel [inaudible 00:23:07] Smith, who I listened to, and learned a ton of my talk tracks from, and other folks. I think it's seeing how they sell and integrate into our internal selling team, and how they coordinated with compliance and risk and deal desk, and stuff. That's what I want to replicate. Obviously, managers are great, but at the end of the day, you want to do your job really well.

Matt Yalowitz:

I'll plus one Ross there, but I'll also say, it's really, really important to hire strategic sales people who are critical thinkers, because the best sales people will take the cue from the best sales rep on the team, and learn from them and make them their best friend, but then improve and take it to the next level. And then, in turn, up level that person who they were learning from, and then you get this great feedback loop. So you always need to hire people who are willing to break down the sales process, be strategic thinkers, be critical thinkers around, how can we improve. Even if it's, these are our three or four stakeholder teams, maybe there's a way to consolidate two of those teams into one decision making body to streamline the sales process and reduce time to live, or whatever it may be.

Matt Yalowitz:

So we need those critical thinkers, smart people who can come in and assess, this is the best, I'm going to learn from them. I'm going to see where their process is, and I'm going to take it one level higher, and then continue to up level the [inaudible 00:24:20]. Because if you're not constantly up leveling it, you're going to be in trouble. The other thing I'll say is, if you're the first salesperson, and there's not someone to learn from, then you got to talk to the founder, and understand how they've been pitching it directly, because it's likely to have a founder led sale at that point. And you have to be open to experimentation and launching and iterating, and just constantly improving and developing your sales process.

Trinity Nguyen:

Well, thank you so much, guys, for making the time and joining the podcast, but thank you for joining and sharing all your experience and feedback, and just tips for the audience. Thanks for joining us on this episode of The First 100 Days. Be sure to hit that follow button as we get more revenue teams to share their stories.