What the Top 1% of Sellers Do Differently | with Ross Rich (CEO, Accord)

0:00You talk to, again, sellers all day long. You have your own team too, but you're in the trenches. Like, everybody says AI is changing the sales process, is changing sales in general. Like, is it really? What's happening?

0:10Ross Rich: It helps the top performers be more efficient. You can write these amazing skills, you can get more insight into customers, and you already know how to use that stuff. Ross Rich, co-founder and CEO of Accord. Giving your team Claude Code and these insights is going to suddenly change how people are engaging with those different layers of the organization, saying the right things, speaking French, Japanese, sure, mention the right people at the same time. Maybe it tells them how to, but not when. The transition from founder-led sales to a first sales hire, a second sales hire, is one of the most challenging parts to get right.

0:40Like, tell us your learnings, your stories from going that transition.

0:44Ross Rich: Mistakes that I've made is handing it off and working on other parts of the companies too quickly and not staying with it. I call it the curse of knowledge. You know it so well, it seems so obvious to you because you've obsessed over it as a founder, as CEO, that it's so obvious the things to do. What do you think the biggest misconception is around sales right now? No one wants to be a salesperson anymore.

1:18Ross, welcome to DTM Now.

1:20Ross Rich: Thanks for having me here. Excited to kick off. It is a pleasure to have you here. For anyone unfamiliar with Accord, give us a quick one to two liner. Yeah, basically Accord helps operationalize value selling. So all the things that you're as a sales leader, maybe banging your head against the wall being like, why doesn't everyone do this? Everything from quantified business cases, mutual action plans, stakeholder mapping, account planning, all the things that help you win more revenue and have a better customer experience. We help make sure that gets done in a field friendly way. Super cool.

1:50And you were at Stripe for over five years, leading go-to-market in partnerships, sales, different capacities before this. What made you decide to actually jump into the founder seat?

2:00Ross Rich: Basically, I was just excited to build the thing I wish we had that would have been really helpful for doing some of the stuff we were doing. So I joined there pre-CRM, just like, hey, what do we say to customers? We should probably talk to them proactively instead of just responding to support tickets. So I was really lucky to kind of join there at the perfect time of, you know, again, being more proactive around our customer acquisition versus just, you know, engineers and using our our docs and APIs off the website. And as we scaled our CRO and head of RevOps and enablement work in this project around playbooks and process.

2:32Ross Rich: So every rep that's joining doesn't have to relearn what we relearned, you know, for the first couple of years and found that all of the tools and workflows basically just became more homework and inspection than actually doing that stuff with the customer. So I'm sure you're familiar with it. Hey, we're going to change the names of our Salesforce stages. We're going to add a bunch more fields. We're going to do the separate MedPix scorecard on a Google Sheet. We're going to bring in this trainer and they're giving you a 55 page laminate and PDF. how do we actually make that touch the customer versus all of this internal conversation so that's what really led me to to kicking off everything with a cord super cool i love that use case when people felt the pain firsthand i think it creates the greatest passion for a problem itself and i mean to solve that problem now you're talking to hundreds of cro's you serve thousands of reps now like you're on the ground talking to everyone give us a sense like what are you hearing what What's going on?

3:26Ross Rich: Yeah, things are changing insanely fast. I was just talking to one of my co-founders. I'm like, I think I've learned more in the last four to six months than the last four plus years of building Accord just in terms of, yeah, like the experience for sellers, for frontline managers, for leaders, just wildly, wildly different, I think, recently. And we were just joking about this in terms of, you know, I think a lot of people look to the senior leadership at some of the best, the best right now, the company's growing fastest, like in Anthropic, like in OpenAI. but I think the advice and what I'm seeing across, you know, our customer base and most prospects I talk to is their world is very different than that.

4:02Ross Rich: Obviously, it would be great if that was everyone's universe. But I think, again, from my experience at Stripe, a lot of times when you're at those companies, you're helping people buy, you're not selling. And I think there's a really important distinction there. And thinking about the playbook you're building should be very different for when people are, you know, pulling out of your hands and pulling off the shelves. And when you actually have to think about unique value props and your sales motion and being super dialed there. Right. Yeah, that's such an interesting distinction. And now you help people get really dialed with all those different aspects to ultimately help them create the best selling experience and be the best seller.

4:37Like we talk about best all the time. It's a funny word. We love to throw around for different things like the best sales rep. What does best actually mean? Just to level set this. How do you define best?

4:48Ross Rich: Yeah. And I would maybe break that up from best in terms of a seller and how to think about it versus the sales leader. I think the sales leader thinking about it in terms of frameworks and culture and the things that can multiply across a large field with different roles and the seller in a slightly different way. So maybe starting off with the sales side, because that's kind of, you know, the passion that kicked all this off. I think it's all about being as prescriptive, consultative, proactive as possible. I always thought about it when I was, you know, younger in my career at Stripe, I was talking to all these amazing founders and CTOs and like I didn't come from a technical background I'm not an engineer but I knew for Stripe in particular I knew the payments world I knew how to help them go international I knew how to help them set up a marketplace with payments all these cutting-edge things and I always thought about it how can I help teach them something even though I could learn a hundred times more from them but for this tiny narrow universe that you're selling into you can be that expert and they're looking for advice and if you can be I always think about this analogy and I talked to my sellers about it is, you know, when you go to that amazing restaurant and the waiter or waitress is like, you know, maybe you're struggling to order something, you ask what's best.

5:56Ross Rich: They ask you a couple of questions and they give you that amazing recommendation that gives you the confidence that you picked the right thing and you can enjoy it. I think that's a great, really simple analogy for what makes a seller great. You know the space so well, someone comes in, has a problem, has a need, and you can just nail that proactive recommendation to give them that confidence, I think is kind of the core of what I think great salesmanship is. That's kind of what I fall back onto. I love that. I love that. And then, I mean, if we were to take that analogy and almost like distill it down to the individual components, like technology or the ability to adapt technology or anything to do with perhaps more of the actual relationship side of things, like what do you think the unique components actually make that picture?

6:40Ross Rich: Yeah, I think to be able to nail that recommendation, there's a lot of pieces that go into it. I think the first foundational one is the trust and the EQ. Great. Let's say you say something. Is it believable? And why? So, you know, all the things like active listening and like connecting with people, which I think is the art of it. I think some people have it. Some people don't. It's are you genuinely curious? Do you care? I think that stuff's impossible to fake. And I think you can do a lot of sales training and obviously technology can help. But at the core, you need someone who call it the give a shit factor.

7:10Ross Rich: And you can just tell that by talking to someone. And so I think that's like the foundation of everything. You need to give a shit about the customer. Genuinely be curious, all that good stuff. I think on top of that is and are these frameworks that you can learn. And I think, again, I thought about it going into sales as like script. That's like awful frameworks. Like you need to be a great seller. You need to just like think about the conversation. I thought of those as like, you know, kind of use car salesman tricks. And I think now my thought about this stuff is, you know, maybe a good, you know, classic sales analogy around, you know, athletes, it's learning the plays, then you can get creative around it.

7:46Ross Rich: If you're thinking about what you need to do consciously, you're already at a disadvantage. You need to have those plays, the scripts, the frameworks down so dialed subconsciously that you can get creative and do that really cool stuff. You know, think about your favorite sport. That's how you do, you know, the off the backboard slam dunk type thing alley-oop to a teammate because you both know it so well. And I think that's where kind of, you know, learned myself of it's not a crutch. It allows you to be super present when you know exactly what you need to do. So yeah, foundation, the EQ, knowing your playbook and process super well.

8:18Ross Rich: And then you can deliver when you're an expert in that space that, you know, believable recommendation that they can follow. I love how your mind went to basketball. Not my favorite sport, but for some reason, mine went to football. But you could pull an analogy for any sport for that. That's fantastic. Okay, great. So we've got these two components that are kind of like the ingredients to a great sales person. Why is there a disconnect on this framework side? Like, why is it challenging for people to actually know the plays like the back of their hand and not have to consciously think about it?

8:48Ross Rich: Yeah, I think there's this huge difference between the mindset of the sellers where we started to build from and the CRO and sales leadership who have been far from the field for a while. And this is one of our biggest learnings going from building the thing for the seller and then having to figure out how to sell it. So the first couple of years, we just went out. We're lucky enough to get a lot of VC funding and actually focus in on the end user experience, actually talking to the sellers, talking to frontline managers and actually their prospects and customers. So we wanted to build something that they could actually use to have more successful buying cycles, onboardings and post sales motions started there.

9:26Ross Rich: Then when we realized we wanted to go from, you know, signing those first hundred innovators, early adopters, get into that million dollar mark, raising our series A, how do we get this to 10, 20 million dollars? We realized we need to start talking to more CROs, heads of rev ops, heads of enablement. And the disconnect was like super obvious from, you know, this one quote comes up to me in a big deal last year. It was like the CRO saying, I've never spent more time, money and effort trying to support the field and being effective. And like, what do you mean? What did that look like? It's like, well, we spent this, you know, multi-million dollar investment in value selling through this consultancy.

10:01Ross Rich: We built all this stuff into Salesforce. We did all this stuff. So from his perspective, he's investing in making the field more effective. From the seller side, what does that look like? A 76-page laminate, you know, PDF. It looks like more fields to fill out in Salesforce. It looks like more inspection work per quarter for the QBRs and account planning. None of it touches the customer. So I think that's kind of the real disconnect in these frameworks of like leadership thinks they're doing the right things. They have that empathy. They're trying to do it they're just so far from doing the thing especially at these bigger companies that there's this just massive disconnect and i think that's kind of one of the exciting things as we started to scale a chord and go past just that kind of buyer seller engagement of like how do you operationalize this across thousands of sellers across different overlay teams how does this work for the ae the se then handoff to post sales implementation csm am overlays all of that kind of stuff, everything ends up being siloed.

10:57Ross Rich: It's like, here's the thing for the AE, totally separate tooling and process to the SC, which makes absolutely no sense. Then it goes to the post sales team, probably maybe even a different C-suite leader. So now you have PS led by some team that maybe even be separate from pre and post sales. And this is the stuff and this is why, you know, kind of at the core, the disconnect is everyone's living in their own universe. Even within those team's leadership's lens is so different than what's actually happening with the seller and managers. So I know it's kind of a windy road there. But yeah, I think it's just like the lack of deep understanding of what those workflows are to absolutely nail that customer experience.

11:34Ross Rich: And that's the barriers we're trying to break down. Yeah, no, I mean, that totally makes sense, especially when you're navigating the org and there's so many different leaders and different processes. And throughout the process, like you said, you're solving that at Accord. You actually work with a lot of different methodologies, sales methodologies, different processes, different frameworks. Curious, like what you see the most and then what you see the most to be effective. Yeah. People always ask this like, hey, you know, new CRO joins. What are you guys seeing as like the best methodology in 2026?

12:03Ross Rich: And how's that differing? I'm like, I love this quote. I don't know if it's a generally known quote, but Russell Sherwin, I think is actually maybe involved with the GTM fund. He was like, trick question. What's the best methodology? It's the one that gets used. I strongly believe that you're optimizing for the fringes of effectiveness. If you're really like, oh, like, should we have the two E's and MedPic and all this stuff? It's like, just doing something consistently across the field in the right way is the best thing. Right. And I think, yeah, you're definitely optimizing for the wrong stuff if you're trying to like nail exactly the right qualification questions.

12:40Ross Rich: It's like, are we actually doing this stuff? And that's, again, the stuff that I think is super rare to find an organization is the whole company across those different roles, up and down leadership all the way down to the field. Are we asking the same questions? Are we thinking about things in the same way? Do we have that common shared language? And you explained why there's that disconnect. Now, if we talk about the solve, obviously, of course, it is a solve. But what are the tactics or the things that you're seeing teams do that helps it be effective? Because, of course, you can implement the technology, but you still need reps to do the thing, I would imagine.

13:14Ross Rich: Yeah. I think for most change management things like this, it's always people, process, technology. So people, it starts with the most senior leader. They need to be the one driving this. This is right. You think about like, oh, what's our unique positioning? What's the product we're building for who that needs to come from the CEO and C-suite? We need to be like the product leader needs to be building the right features that are reinforcing what we're marketing. that's reinforcing what we're selling, that's reinforcing how we're actually delivering and expanding and re-assigning those customers for that kind of unique value.

13:45Ross Rich: And then for the CRO, I think needs to be like, how do we deliver something that we have this shared language that's really, really simple. So when I was at Stripe and what got me into the whole world around value selling, there's a way to do this instead of just kind of making it up. Gene DeWitt, who is our sales leader, now leading things at Purcell and has an incredible, incredible career, brought in Skip Miller, an amazing sales leader and trainer who's kind of, you know, a legend in Silicon Valley and elsewhere. And he just had this way of capturing in such a simple way, a few really key features and like memorable phrases that reinforced our value selling methodology and framework.

14:24Ross Rich: And like, it became a meme of like, the dog was talking about your features and functionality. So yes, you can be a sales leader and say, don't talk about features and functionality, talk about differentiated customer value. Well, that's a mouthful and not really memorable. You know, what's memorable to a team that can like joke and laugh about the thing is the dog, you know, don't talk about the dog. That's something, you know, again, it's like playful. It's super simple. And, you know, another phrase that stuck with me too, is like speaking different languages to different levels of stakeholders.

14:50Ross Rich: If you're talking to the technical stakeholder, you might be speaking French. If you're talking to the business, you know, CFO, Italian, whatever you want it to be. And it's like funny, you know, you're smiling about it's playful. And I think having that shared language and really simple way of operationalizing that from sellers, managers, different parts of that organization is where you start. It's important. The CRO is sponsoring it. You have this shared language and we have a way of holding the team accountable. Then I think that goes into the process. Okay, cool. We have this great way of talking to each other about it.

15:20Ross Rich: We understand. We know it's super important. How do you build that into that customer journey? Really, again, in that framework of the client's perspective versus the seller. And I think that's like a really, really common mistake. So first is overcomplicating the methodology, getting super obsessed with how many P's are in MedPic and all that kind of stuff. Second is the process stuff. Again, keeping it simple, keeping it field friendly, not having it all about internal inspection, really focusing on the customer lens of that journey. And then last is the technology. Okay, how are you reinforcing that?

15:51Ross Rich: And I think a lot of people, especially in the world of AI, and we talked a little about this before the show, was people are starting with technology because it's so exciting because it's so powerful and you don't have that simple CRO level driven framework to field friendly processes around the customer experience, then technology to reinforce it. And we're starting with a tech and you're not getting any of the value from the rest of it. So yeah. And so instead of starting with the tech and we're starting to see the shift, hopefully, I kind of see the same pattern across different platform shifts, if you will.

16:26The same thing happened with mobile, with cloud. People get so obsessed and interested in the technology itself. And so they'll take that kind of backwards, like you said, approach of technology first and then back into it. And then it takes time for that to shift, but it always does shift back to the customer first and then the outcome first. What do they need first? And you back into the technology. And that's also why we're seeing, I mean, with AI now and how AI is now aligned to outcomes a lot more, but we're seeing this convergence of software and service because at the end of the day now we are putting the customer more first like it is the customer's outcomes that matter yeah and there's a lot of stuff just

17:02Ross Rich: being built internally it's not touching the customer uh yeah and yeah this is coming from someone who's building the technology right it's in my best interest potentially to start with the technology but what we're seeing is you know when we get into these qbrs and when we get into these you know renewal conversations it's like well great you bought all this tech but you didn't have a strategy around it. You didn't have ownership. Who's the leader that's actually driving this and holding themselves accountable? And then what does that look like to actually touch your customer? It's like more intelligence and insight into your customers.

17:32Ross Rich: You need to think about the action to them. How are you touching them with that new technology? What's in it for them? And I think that's kind of a better place to start. Yeah, that's a super interesting approach. So what does your team use in terms of methodology out of curiosity? I think it comes down to for us is, and we have this theme for our second half that we were just talking about at our company wide offsite is show don't tell. I think again, that's kind of grounded in the how are you being prescriptive? How are you being consultative? How do you show them instead of just talk to them about something?

17:59Ross Rich: I think that bar we were talking about as a team is really raised in the world of AI with what you can build and everyone claiming they can do stuff. I think you really need those proof points and for your sales motion to be driven by ideally your customers. So we try to bring up references like stage two instead of like, hey, before you buy, do you want to validate this. It's like, hey, you're working on this problem. Here's two or three peers that you can talk to. They've solved it with the core, but maybe there's other stuff that you can explore. Here's a great network of people to interact with.

18:26Ross Rich: I think that level of trust and differentiation is super important when everyone can kind of sound the same and really quickly build a surface level solution that isn't necessarily fully delivering, especially upmarket. Yeah, that's incredible. I always think about it as we're in the framework, mental framework of how do you make this person, this human successful? And so maybe that's introducing them to a pure network. Yes. Yeah. As your buyer. Yeah. Yeah. Exactly. The way that you are, or, you know, maybe that's helping them in different regards to that is like out of scope. But if you make that person successful, that is your ultimate goal.

19:00Because ideally, if companies are aligning everything correctly, one would assume if you are making X person successful, like the way that they're measured is done in a very intentional way that ladders up to company growth. And so ideally, if everyone can make each person successful, then they're hitting their goals. You might not be able to account for every single one of their goals. But if you can make that person your ICP successful, then ideally, your end customer should be successful too.

19:27Ross Rich: Totally. Yeah. And then it goes back to like, you know, initial waiter waitress recommendation you're making, hey, maybe the thing that we sell isn't their favorite thing. And how do we recommend that first? A lot of our largest customers today were people that we disqualified at the time, because we weren't the best solution for what they're solving for now. It was another priority was key. And then they came back to us maybe six months, 12 months later, or even a different role. And they remember that experience and that compounding. I think that's what makes companies and cultures wildly successful versus that short-term trying to be everything to everyone.

19:59Yeah, that's incredible. And what kind of logos are you working with today at Accord?

20:03Ross Rich: Yeah, we've been marching up market again. I think we started with the classic innovators and early adopters, people just excited about the technology itself versus I think like the big problem that we can solve. Right. So that's typically startups, early stage people, maybe it's founders or kind of like first VPs of sales and sellers at small companies were using us. And then more recently, we've been moving up market, working with like large public companies like Freshworks and Samsara, two of our larger public companies. But yeah, we were joking about this the other day. Lenny, our VP of marketing is like, honestly, where I think we can drive a lot of value or companies that we probably have never heard of.

20:39Ross Rich: They're companies that maybe they were the stars of the show five, 10, 15 years ago. A lot of them are PE backed and they're really hardcore about operational rigor, value selling. How do they stand out in a market where they're not just, again, the anthropics or open AIs or people are just buying from them. They need to be selling. And that's a competitive advantage for them. Their sales and marketing, not just the product innovation. We've had a lot of success with a ton of those companies you may have not heard about across different PE portfolios where we can help them be a competitive advantage and really what matters for them, helping them really cut through the noise in their market.

21:12Yeah. And that's such an important part because the reality is most companies are not anthropic.

21:17Ross Rich: Yeah, that's the truth. Unfortunately, you know, not everyone can have their product fly off the shelves and have people buy from them and expand organically. And of that 200 plus percent NRR, it's they need to have quantifiable outcomes every month, every quarter to retain and expand with their customer base and to sell versus the competition, they need to show up differently. I always say, how much of your product are you seeing when you're evaluating a tool? Even with a POC, it's probably less than 5 % to 10%. If you have a mature platform, even if they're like using it or building a prototype, which is also less than 75 % of deals.

21:49Ross Rich: So how you sell and how you show up is a reflection of the value you're going to get. So that's kind of, yeah, I think. How you sell and how you show up. Do you mean the salesperson? Sales process, the person. Yeah, 100%. Again, making those recommendations outside of the scope, like you said, making people successful, that's going to have the trust, especially if you're signing multi-year large deals. They're in it for the long haul. They don't want to look like an idiot when they're making this case, the CFO being the champion. And then six months later, it's like this thing's not even deployed.

22:18Ross Rich: They could be betting their career on it, on this decision. Totally. Yeah. It all boils down to humans. We see the same on the founder side, too. How a founder runs a fundraising process is indicative or at least representative to a certain degree of how they'll operate. Because on the investor side, you can't actually see into the operational side. Same thing with the product and demos. You get maybe 5%, 10%. You don't actually know the entirety of it. So you're making an informed decision based on a subset of data that you have accessible. And so the way that you run that process is what people have.

22:53It's the sales experience. It's, for example, on fundraising, it's how you're actually showing up to those calls, like how you're responding to emails, how quickly you're responding, all these different things. Like it's just, it shapes human perception at the end of the day.

23:05Ross Rich: Yeah. It's a favorite quote that now I think is kind of a founder meme of like how you do one thing is how you do everything. It's those signals, right? We talk a lot about this with recruiting at Accord. It's like, okay, cool. You showed up and when you were on, you said the right things for that 45 minute hour long meeting and presentation. What about the internal stuff? What about, yeah, the coordinating? How easy are you to work with and to find a time with? Maybe you introduce a little bit of friction into the recruiting or sales process to see how they're gonna deal with that, right? You don't want a vendor, as soon as you ask for something, you're not going perfectly right, to see how they respond to that, right?

23:39Ross Rich: Do they get creative and try to find an alternative solution and bring in other resources, or do they just say no and leave you hanging, so? Yeah, Chris Lee, he's the head of sales at Deal. He uses this cool framework around a five-star hotel that I loved. He was like, what would the experience be from a sales process, if you were going to a five-star hotel, you'd probably get greeted at your taxi or cab or vehicle, however you're getting there, with like a glass of champagne and a welcome and things like that. And it's like, what is the equivalent on the sales side and experience? Because it's not all on that call itself.

24:09Yeah.

24:09Ross Rich: And that kind of goes back to like why I'm super passionate about sales, the process side, the value selling, and even starting a accord in the first place was as soon as I made that mental shift from sales funnel forecast process to customer experience and thinking through their lens and designing a process. That's why, of course, customer facing versus just this internal tool, I think, really reshapes how you think about everything. And again, going back to like the CRO VP of RevOps perspective of they're designing all these tools and processes for their world, which is around forecasting. What do they need to deliver the board?

24:42Ross Rich: It's pipeline and forecast delivery, whereas the seller on the field is thinking about the client. How do we bridge those two things together? Mm-hmm. And so now you've been building a cord. Tell us, what are your biggest learnings from building? Oh, man, a lot. Yeah, it's definitely a steep slope from early career seller, manager, to building new technology, company, leadership, all that kind of stuff. I would say one of the most interesting learnings, especially since starting a company, kind of in the COVID era and the ups and downs from kind of the unicorn to zombie corns to AI, all this kind of stuff, is the power of the market.

25:17Ross Rich: I always thought about product market fit in terms of what you build and product first. Product market fit, you develop more product, you have a better product market fit versus the idea of positioning and you can pick the market you're in and market actually being far more impactful than just product and features. So that's kind of, I would say, like my biggest, biggest learning as an entrepreneur and leader is the power of the market itself versus just the features you can develop. And you can really pick where in the market you can play. I always thought that was kind of like, oh, we picked this space, we built this product, this is our universe just the organic first one that comes versus how you can kind of do you think we should flip that then to market product market product flip maybe it doesn't have to see him roll off the tongue effect quite yet but i mean i think and you know when you talk to probably investors and other stuff i there's like this i forget how the quote goes exactly but you know it's you can have a killer team in a bad market and not do super well you can have a pretty shitty team in an amazing, amazing market, they can be potentially even more successful than vice versa.

26:20A hundred percent. Like it truly is all different factors. Like we think about it in a surfing analogy, and this is probably a little earlier stage. It's much more when somebody's starting a company, but either way, it probably still stands from a market perspective of you've got the surfer, you've got the surfboard, you've got the wave. The surfer is the person building or the team building. The surfboard is the product itself. And then the wave is the actual macro environment, the market. And so all those things have to actually align. And you can have the best surfer, the best team, you can have the best product.

26:48But if the wave isn't right, like you said, you're gonna you're gonna fall off the wave. And so a lot of it is like timing and picking the right way, picking the right market. Yeah.

26:58Ross Rich: And I always thought that was just the cards you were dealt and that you couldn't decide you couldn't think about the positioning and how to tweak those things. And one of my favorite books along the journey was April Dunford's positioning book. And super, super, again, getting down to simplicity and framework, you get to pick that stuff. You can define it against the alternatives. And hey, who's really all alternative? I used to think about technology as only tech. Alternatives were your alternative. Honestly, most of the time it's not. It's services. It's other things tangential to your product and value prop that are the alternative.

27:32Ross Rich: So thinking through that stuff I think is really interesting. Yeah, interesting. Okay, so market has been one of your biggest learnings to date. I love that. Any other kind of big learnings? I mean, we could talk about for hours, the people side of things, right? And leadership. I think, obviously, it's one of the most rewarding pieces, seeing people grow, all that kind of stuff. But I think how, as the CEO, it's very isolating. For sure. I would say, you know, I think one of my favorite things about being at different companies before was being on a team. You're together doing it locked in arms, you know, playing sports.

28:05Ross Rich: When I was younger, even today, you know, soccer teams like you're a team. Yes, obviously, I'm building a team. I'm on a team, but you're kind of like more of that coach. I think that like you're pushing the team forward. And yeah, one of my favorite definitions of leadership is how much friction can you create to drive the team forward while still having it? like a positive experience for everyone and not too much. And that's different than being on the team itself. You're kind of, you know, helping drive it forward and creating some of that, like on purpose, I think friction in a positive way to break down barriers and get people to do more than they thought they could do by themselves.

28:42Ross Rich: And I think that is in a way a little isolating that I don't think a lot of people talk about. Yeah, that's a great call out. And I love the friction analogy. It's an interesting time too with AI because, of course, that kind of bar and barometer of what people think they can do and what they can't do is constantly changing, where it used to be a smaller threshold and delta for change. Now it's all over the place and different companies, depending on what technology they're implementing, which is really interesting. It's an interesting time. And so, you know, you talk to, again, sellers all day long.

29:14You have your own team too, but you're in the trenches. Like, everybody says AI is changing the sales process, is changing sales in general. I'm like, is it really? What's happening? Yeah, I always go back to like why we built the thing in the first place.

29:28Ross Rich: I think the top seller, you know, the core problem I think you could bubble it up to for like any go to market team is typically, if you're selling your top 20%, honestly, maybe even closer to sub 10 % of the team is driving most of the revenue. You know, the rest of people can get lucky sometimes. Sometimes there's opportunities to help people buy versus sell. I think the really drivers, the people at 150, 200 % plus every quarter, regardless of the year, regardless of the market, it's a very small fraction of your team typically that are actually doing that. The key solution that leaders are looking for is how do you solve for that?

30:01Ross Rich: How do you move that middle? Everyone talks about, right? There's going to be a part of the bottom that's like doesn't have the skill, doesn't have the will. Cool is focus on that middle 60-ish percent and move everyone up. I don't know if natively the tools that AI provides, like the Claude Coworks, like Codex, like other tools, really helps with that team-wide dimension. I think initially what I've seen on our team and others is it helps the top performers be more efficient. You can write these amazing skills. You can get more insight into customers. And you already know how to use that stuff.

30:31Ross Rich: I think the challenge is, again, with more intelligence, with more insights about your customer, about your company, all this kind of stuff, how do you use that to drive the customer impact side of things and i don't think those tools are natively collaborative without an application layer right so for example we just did this you know hackathon internally at accord this week and you know building different tools different solutions for our customers for internal workflows and even sharing those and collaborating on those it isn't built like that for that and i think you need to be able to use that technology use that insight across creating the application layer to have it more collaborative both internally and externally.

31:06Ross Rich: So that's kind of our focus. But yeah, I think initially I've seen it make people that know what to do, that have that taste, that have that judgment far more efficient. I don't think organically it's moving that middle. Yeah. If anything, it's probably creating greater silos and a greater delta between that middle and the top performers. And I can imagine in a way, it's like, of course, a gift in terms of the people that adopt it. However, it's almost contrary to, it feels like to what you're building with Accord, which is like helping everything run together. And this is actually creating more disconnects when you don't have some kind of application layer on top that's helping to operationalize in an organization.

31:44Ross Rich: Totally. Yeah. You have your top sellers that maybe previously were sharing with their SE and other team members what they were doing in more collaborative and shared workspaces on the application layer. Now it's more siloed. Again, maybe it's a better outcome for the customer, for them, but it's not organically shared. So we're trying to, how do we take those insights, connect to open ecosystem people talk about headless how do we build that layer that makes it unavoidable to do those things that's kind of what we talk about is like unavoidable excellence how do we take what the top people are doing and spread that across the team but again that's where it goes back to starting with people not technology you need a leader who has a point of view on how we should be engaging with customers and building that process and culture and overlaying the technology and insights to that so for example let's say you know hey maybe deals are slipping because we're not high and wide enough in organizations.

32:32Ross Rich: We're going up market and we're used to talking to one or two different stakeholders who can make decisions for sub 50 or 100K deals. Now we're going up market trying to do, you know, high six figure, seven figure deals. There's a lot more people that need to be involved and kind of a more highly orchestrated sales process to run. Is giving your team Claude Code and these insights going to suddenly change how people are engaging with those different layers of that organization, saying the right thing, speaking in the same languages, speaking French, Japanese, German to the right people at the same time.

33:02Ross Rich: Maybe it tells them how to, but not when. And it doesn't drive that kind of standard and accountability. That's where I think tools like Accord and other application layers can help. Kind of that one plus one equals three equation of taking those insights, applying it at the right time, setting that standard really clearly and holding the team accountable. But that needs to come from the right leader and process then the technology to reinforce it. Right, right. Yeah, that completely makes sense. And I mean, it's actually an area that we're pretty passionate about a GTM fund. And we're currently working on an article.

33:30Paul Irving on our team is going to publish it once he puts pen to paper a little bit on it. But he's been talking about it for a really long time. It's like the application layer is just kind of how everybody's getting it wrong. And we have seen this pattern across other eras, too. And it's a very normal thing to prioritize infrastructure for so above application layer. But then in the grand scheme, it all kind of shifts out. application layer typically drives greater value than the infrastructure it's just the sequencing of time and it's a funny thing because i feel like enabling people to just have their own claws and almost go rogue a little bit with them feels like inevitable necessary step in the process

34:08Ross Rich: to just get people's hands dirty yeah you got to learn it yeah but it's not what drives outcomes and that's okay we did that and now we do this yeah yeah well there's a customer that's what i I always go back to as, you know, an ex-top seller leader, like spending all the time on this stuff. It always goes back to what is interfacing with the customer, the final mile. You know, we were joking about the self-driving car analogy. It's like, OK, you can have all this amazing technology and blah, blah, blah. So mind blowing. Does it deliver the end product result that is going to be the outsized impact, which is, hey, you can get in this car and it can take you to that destination.

34:42Ross Rich: All the cool infrastructure stuff to almost get you there is super exciting. And I think that's where I've seen a lot of teams kind of go off track and hire a huge team of go-to-market engineers, really focus on product, all this cool stuff that now we can do. Is all that work and insight touching the customer? Is it wildly changing the number of stakeholders on deals? Is it having super dialed business cases that customers are going, holy shit, we're going to start with three years instead of one or a POC? Or is there our ACV going up massively because they can actually see the results and kind of better understand what you're selling them?

35:14Ross Rich: I don't think that's, on average, what I'm seeing across our prospects and customers. And that's where I think that kind of final mile gets delivered. Yeah, okay. You got to give us the full analogy because it's fascinating. It feels like the intersection or difference between knowing that we need to execute and actually executing. Yeah. Give us the analogy. Oh, I mean, yeah, I think that self-driving car one's good. But yeah, just a recent conversation that I had with CRO and SVP of RevOps and their super talented go-to-market engineer. year. We're on the phone talking to them. They're telling me why X number of deals slipped from last quarter, which I think they nailed the reasons why.

35:49Ross Rich: And I'm trying to think about, okay, to me, it's all about how do you operationalize those best practices to combat those reasons why they slipped. Epic diagram of how they're connecting all of their intelligence and all their previous conversations and emails and using Claude and other interfaces to show this to the rep. I'm like, that sounds super helpful to them, right? That's a great carrot for the seller. How do we set the standards and expectations of what they need to do with that. And if they don't, what happens? To me, that's just like 101. Okay, great. What's really hard to get reps to do and the field to do is consistent value-based process.

36:23Ross Rich: How do we move that middle 60 % your top people are doing organically? So what happens? Like, well, I'm not a sales expert. I'm like, all good. Well, you know, let's pick a specific example. So you feed them the insights and the customer and blah, blah, blah, and the different stakeholders. How do you make sure that they're translating those insights to the client to make those recommendations and get to the right people? He's like, well, we'll serve it up in cloud. I'm like, great. Let's say they don't do that. What then next? And to me, that's the hard part. That's like the eating your vegetables is like the culture of we're going to do this stuff.

36:52Ross Rich: We're going to go out. We're going to say the right things to more people to increase our win rates, all that kind of stuff. And I just don't think without that kind of cultural push from leadership down to use those insights. And that's, again, why you need to have like a super dialed process to that final mile. Yeah, that's fascinating. Okay, Ross, I've got a couple very hyper-tactical questions for you here. The biggest question we hear across our network overall is, how do you sell into CROs effectively? And you, of course, do this and do this very well. And you also empower people to do this well.

37:24So love your sense and take on how do you sell to a CRO well.

37:28Ross Rich: Yeah, it's a fun stakeholder, I think, compared to what I've done in the past, which is like much more technical. CTOs, product leaders, wildly different. What I loved about the technical leaders, super blunt, black and white. They don't love talking to salespeople. So, you know, if they're talking to you, they're interested and yeah, they'll give it to you straight. I think CROs in a certain way are direct, but I would say they like to delegate. I would say when you come to the CRO, it better be at the very end of the deal. And especially if you're technology, they're going to look to the people that own the technology.

38:03Ross Rich: They don't own the technology. They own the revenue strategy. energy they own the forecast they don't think about i think tools as a primary thing and i think they lean on their other leaders their revenue operations leader i think that's why they're such a key stakeholder even if they're not the final eb in a deal economic buyer it could be the cro they're still leading that function i think about cro setting the culture and the high level strategy aligned to the ceo and the board and the people that get that shit done yeah is rev ops their vps and enablement. So when we think about coming to a CRO, we want to make sure we're in lockstep with those stakeholders.

38:41Ross Rich: And then don't go back and say, hey, Sarah, leading RevOps, what do you think about this? I don't know. I don't feel so. Okay. DQ'd immediately. So we have kind of, you know, shifted to that stakeholder coming later in terms of that pitch, but giving them the heads up they like to be read in. So like to get super tactical, we want to make sure we're multi-threading super early with like a no ask note, if you're familiar with that concept. So really early on, we'll have a killer conversation with a VP on their team, a RevOps leader, enablement someone, and have the right person reach out to that CRO and say, hey, it sounds like you're working on XYZ the rest of the year.

39:16Ross Rich: It's a big focus. Maybe it's going to market. Maybe it's a new product launch, whatever. Maybe it's going international. Really excited to continue to explore with your team. Is there anyone, maybe it's a light ask, is there anyone else that we should be talking to that's helping lead this? Excited to stay in touch, happy to keep you updated. That's it. And just having those sound bites throughout the process, if it's a big deal, maybe it's multiple months, almost a year, when you meet with them, they're really going to appreciate that. You need to sell in an excellent way so the CRO respects how you're selling to them.

39:44Ross Rich: But when you come to them, you better have all the key answers and stakeholders and everything figured out for the okay. So that's maybe getting really into the weeds, a good example of how we think about selling to CROs. And help us define the no ask no part. Yeah, this is one of my kind of favorite ahas. And again, came back to Skip Miller, Gene brought in at Stripe. It's really showing your respect. And again, that show not tell thing of like, you're giving them a drip of it's in their language, what you're hearing they care about in the team and the feedback from the different stakeholders and personas at their organization and what they're thinking about.

40:18Ross Rich: But you're not asking for anything. And I think everyone starts with, hey, can I get 15 minutes? Hey, can I get this? And when you really think about from the customer's perspective, they're not ready to make a decision. You should know roughly how long the process is and think about from their lens, what do I need to see? Who needs to say yes? Go out and do that work for them and show the work. And I think a lot of people might go out and do that heavy lifting and not get credit for it. And we talk a lot about this for pre and post sales at Accord is how are we getting credit and communicating in a way to the stakeholders that they understand in their own language?

40:49Ross Rich: So post sales, for example, hey, maybe it's every month, every quarter. We're not pulling them in for hours, the senior leaders, but we're saying, here's some of the results we're delivering in your language. Here's this deal that closed, and they had 10 stakeholders. Previous average deal was four or five. That was partly due to a cord. And then when you talk to them once a year or every half year, they have that stuff instead of coming to them and trying to perfectly nail that 30 minutes. I think async is how a lot of people consume information. So doing that really well with the right level person at your company is great play.

41:20Super interesting and bright person and level at your company. So these larger deals you mentioned might take six, 12 months. So you're multi-threading them. Help us understand how do you multi-thread effectively?

41:30Ross Rich: Yeah, I think a lot of reps, what they get wrong, and they might be doing that tactic. I think a lot of people know about that. No ass note. CROs don't give a shit about the seller. It's just the reality. Like I learned this from selling. You need to get the right people at your company to sell. And part of selling, I think part of great mid-market enterprise selling is your internal, how you're seen, how you can get the time from the right people to quickly action that and put it in the right words. So for example, when I was at Stripe, I would probably do most of the deal through the right stakeholders internally as I worked on key partnerships and upmarket deals.

42:03Ross Rich: So how do I get the right C-suite? How do I get the right VP in product and sales and other organizations to send notes to the right people and engage them and get on calls or onsites? So a lot of my selling was internally of here's the right qualified deal for you to spend time on. And honestly, they loved it. And like people, especially at higher levels, don't touch the customer that often. So this is like a great pathway for them to get that feedback. You need to arm them as effectively as you're thinking about arming your champion. So making sure, again, that CRO note, if I was a seller, I'm not sending that.

42:33Ross Rich: I'm selling my CEO, CRO, CMO, whoever the right person is that they want to hear with and they want to network with to get with them. And same thing for their direct report. their SVP of RevOps, again, doesn't want to hear from me. They don't want to be sold. Maybe they want to hear from my RevOps leader, or maybe they want to hear from a peer, or maybe they want to hear from our VP of product, something like that. So yeah, I think you need to get really strategic and creative and kind of play that like 3D chess game when it comes to this stuff. And that's what I love about it. It's, you know, super fun, but I think you can get stuck with like trying to do it yourself in these deals.

43:04Ross Rich: And unfortunately, I just don't feel like this stuff is, people are getting training on it for years and you're just hoping to get, you know, it's kind of like it's like this craftsmanship thing and you need to happen to get into the right like xptc mongodd whatever leadership team that has learned this that has this as their culture and you're just like through osmosis learning it versus like i don't think this is as everyday like best practices in engineering or design is right right that totally makes sense so kind of match the seniority level is that after you've made contact like what does a first touch point look like a good first touch point look like when you're targeting a cro yeah i think having the grain of making sure that you have the grain of the idea of what they care most about.

43:43Ross Rich: So that could be a killer first discovery, second discovery call where you talk to the right person who is plugged in and they're like, hey, they're willing to share with you the strategy. You would do a great job showing your authority in the space. They open up and yeah, you could quickly hit up your whoever the right person is SVP of sales, CEO, blah, blah, blah, and say, hey, this is what they really care about. They're super invested in it. I think we can help in this way. Draft them that note. Hopefully your company has a template for that and a way to figure that out in the process. Maybe use a tool like Accord to do that.

44:10Ross Rich: And yeah, they send that note really quickly and you just build it into your process. So it's not something special. And it's like, how do you create going back to, I think you showed that example, the sales leader at deal, like how do you build in that five-star experience to every deal? And it's not just like, oh, we have this killer late stage deal. It's a million dollar opportunity for us this quarter. This is how you're doing everything. So you're creating that opportunity to get lucky across your entire pipeline. Yeah. Yeah. That totally makes sense. What do you think the biggest misconception is around sales right now then the biggest misconception around sales there's a lot of them yeah and no one wants to be a salesperson anymore obviously you're seeing gtm or you know whatever the the thing is i think it gets a bad rap i think especially in technology i think sales people don't have the same level of cachet as an engineer or product leader and i think that is just because at companies like the bar is so low like the things we're talking about that should be standard i think this is seen as like a rep who can do that stuff is like oh my god they're the top top rep unfortunately that's the case unfortunately i don't think there's a lot of teams that hold that standard high standard for execution to me any team that a rep is on at our company or would be on my team like that's just how you do the job and i think there's this very low bar for it a lot of companies because there aren't enough leaders i think that that have that standard that are driving that tops down totally no that makes sense i mean it's just easier to measure i think it's harder to measure sales output in a way where sales methodology traditionally now it's becoming easier but i think also the shift towards go-to-market titles is is also an indication of more of a consultative approach to sometimes yeah but i think sales could be seen as that and i think because of the way it's been done for so long i think people want to move away from it and kind of rebrand it which i get like i get that i've seen the standard of sales across most of our prospects and customers.

46:03Ross Rich: And unfortunately, it is a very low bar. There's very few leaders, I would say, even of our qualified prospects who have that high level of standard and culture to show up in that five star way. Right, right. And so I get why people would want to rebrand if they're used to that. Say you're a COO at a company and you're like, I don't want our sales team to be like these other sales teams. I totally get that because that's what most experiences look like? People are DQing people through email being like, here's our minimum. Well, if they don't know your value and they think about you like a tool, yeah, they might not be willing to spend 40K in their mind and you're DQing them.

46:40Ross Rich: Well, if you have a great conversation with them and it's tied to one of your board level initiatives, maybe they're willing to spend 400K on you, but you don't know. And again, I think that's just kind of unfortunately the standards and sales and what we're really excited about raising the bar for. Yeah, definitely. And I mean, now you've got a team of sales rep and you've built out an incredible team at Accord overall, but once upon a time you had to do the the traditional kind of baton path to a sales rep the transition from founder-led sales to a first sales hire a second sales hire is one of the most challenging parts super hard to get right like tell us your learnings your stories from going that that transition yeah i think you're still you know one of our board advisors said this and it's it's still super true it's like you kind of need to be driving it it's not that first couple million dollars it's not that first few sellers and a sales leader it's really to your first 20 30 plus million dollars i think depends how fast you're growing and your market and all that kind of stuff but i think you need to stay close to it and the mistakes that i've made is handing it off and working on other parts of the companies too quickly and not staying with it it should be a slow transition and there's so many parts of it that if you just jump to the next big problem because you're like oh i've solved this i have a couple killer reps and i have this amazing vp blah blah blah, I can work on other parts, you know, that I'm excited to figure out at the business, you can drop that ball and lose that lose that momentum really quickly.

48:01Ross Rich: And I've had to relearn this a few times. And it's the right things to pass off over time and make sure onboarding those people to how you've been doing it, and still staying involved in like a scalable way. So that would be my biggest piece of advice is that these are your reaction, I've done it twice is, you have the right people, you have the ultra confidence in it. And I think it's this, what I call like, you know the curse of knowledge you know it so well it seems so obvious to you because you've obsessed over it as a founder as ceo that it's so obvious the things to do if you just say it once you need to do it with them first for a few quarters make sure that they're doing it and slowly move away from that that's kind of maybe helpful to share my mistakes of the past and why it's so hard i think you take for granted what you've learned over obsessing over it and also So a lot of people will buy from you because of who you are, again, going back to like the role matching.

48:52Ross Rich: And so how do you stay involved in a scalable way instead of doing everything or a lot of things where you're still driving that passion and insight and they're taking the bet on you and your company, but not just because you're talking to them every single day for hours. Yeah, that makes sense. I've got a couple just quick fill in the rest of the sentence questions for us. Yes, let's do it. Okay. The part that nobody tells you about leadership is? I would say the emotional energy versus the time. Yeah, I think I've thought a lot about one of my intentions this year is how do I make sure the energy going into leadership and people is always positive?

49:32Ross Rich: And if I'm ever noticing the drain there, then having to really proactively solve for that. Super interesting insight. And what about the most underrated piece of go-to-market advice? The most underrated piece of go-to-market advice, getting on site with customers, classic, people talk about it. You can always be doing five times more, and that's going to be the number one way of moving pipeline, moving revenue, customer expansion, lowering churn, get out them, see them, talk to them. Super easy when you do that. Super underrated advice. Incredible. Now, if we zoom out, and this could be in any sense, take it any direction you want, But what is the best piece of advice that you have gotten and who gave it to you?

50:13Ross Rich: The best piece of advice. One thing that I always go back to, and maybe it's best because it's simple and memorable and going back to the frameworks, the things that you remember and use are always the most impactful is your greatest strength is your greatest weakness. And that was super memorable. I was wrapping up my time at Stripe and going back, Gene was giving me some advice. And I was like, I knew when you came in, you're going to start your own thing. You shared that. And I was like, I don't even remember sharing that. But it was a great way to give feedback because it's kind of that shit sandwich of like, here's what you're really good at.

50:43Ross Rich: And it's so true where people spike. There's an other side to every coin. And I think remembering that it's such an easy way, I think, to internalize feedback without getting defensive. Because what are you great at? There's going to be another side to that, that other people are going to take as a potential negative. Right. The duality. Yes. And which is just a truism in life, in people and everything. So that's something that really sticks with me. And when I'm giving feedback to people, I always look on myself and like, hey, I'll give you an example. This is what I think I'm really good at.

51:10Ross Rich: This is what makes me really bad in other areas from that. Hey, this is where you're thriving. You're doing amazing in these areas. That's causing this. And be more conscious of it can help. Duality to everything in life. Yes. It's part of life. And where can people find you if they want to follow along with your journey? LinkedIn. Definitely spend a lot of time there. That's where our customers are. Prospects. So they're for myself. And yeah, it's fun to share the journey. both you know how we're building a cord what we're building all that good stuff and yeah it's always fun to connect with people passionate about this stuff so always happy to have a chat amazing well ross has been amazing thank you so much really appreciate you coming on yeah it was super fun thanks