What the Top 1% of Sellers Do Differently

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Who you’ll learn from

Ross Rich is the co-founder and CEO of Accord and spent five years leading go-to-market and partnerships at Stripe. He talks to hundreds of CROs and serves thousands of reps, so he has an unusually clear view of what the top performers actually do differently.

His starting point: roughly the top 20%, often closer to 10%, of any sales team drives most of the revenue. Every leader says they want to move the middle 60%, and Ross doesn’t think AI is doing it. Tools like Claude and Codex make the people who already have the taste and judgment far more efficient, and the gap widens from there. What closes it is unglamorous and human: a leader with a point of view, a shared language simple enough to stick, a field-friendly process, and only then the technology to reinforce it.

Ross gets specific on what “best” means for a seller (trust and EQ first, then frameworks learned so cold they run subconsciously), the disconnect between what CROs think they’re buying and what reps actually receive, the “no-ask note” for multithreading into a CRO, why he sells through his own executives instead of around them, and the biggest lesson of his founder journey: market beats product.

What you’ll learn:

What separates the top 10% of reps from everyone else, and why AI is widening that gap instead of closing it
The two ingredients of a great seller: the “give a shit factor” you can’t fake, then plays run so subconsciously you can get creative
The waiter analogy that explains great salesmanship in one sentence
Why the people, process, technology order is the one most teams get backwards in the AI rush
The disconnect between a CRO’s multimillion-dollar investment in the field and what reps actually receive: a 76-page laminate, more Salesforce fields, none of it touching the customer
Why the best methodology is simply the one that gets used, and why debating how many Ps are in MEDDPICC is optimizing the fringes
“Unavoidable excellence”: how to take what your top performers do organically and make it standard across the team
The “no-ask note” for multithreading into a CRO by showing respect instead of asking for time
Why CROs own revenue and not tools, and how to sell through their rev-ops and enablement leaders
“Show, don’t tell”: leading with peer references at stage two when everyone can sound the same and ship a surface-level solution
The founder-led sales handoff mistake Ross has made twice, and the curse of knowledge behind it
Why market beats product, via April Dunford’s positioning and the surfer, surfboard, wave framing

Episode highlights

01:18 – Welcome, and what Accord does

01:49 – Why he left Stripe to build the tool he wished he had

03:26 – What he’s hearing from hundreds of CROs

04:48 – What “best” means for a seller: the waiter analogy

06:40 – Trust, EQ, and learning the plays until they’re instinct

08:48 – The leader-vs-field disconnect on frameworks

11:56 – The best methodology is the one that gets used

13:14 – People, process, technology, in that order

17:01 – Why starting with technology fails

17:44 – “Show, don’t tell”: proof over claims in the AI era

20:03 – Who Accord serves, and why non-famous PE-backed companies win on selling

23:45 – The five-star hotel sales experience

24:54 – The biggest learning: market beats product

26:19 – The surfer, the surfboard, and the wave

27:41 – The isolating side of leadership

29:23 – Is AI really changing sales? Top performers vs. the middle

33:22 – The application layer and “unavoidable excellence”

35:33 – The self-driving car analogy: does it touch the customer?

37:07 – How to sell to a CRO

39:55 – The “no-ask note” explained

41:30 – How to multithread by selling through your own executives

44:38 – The biggest misconception about sales

46:52 – The founder-led-sales handoff mistake he made twice

49:13 – Fill in the blank: leadership, underrated advice, best advice ever

51:19 – Where to find Ross

Key takeaways

1. AI is widening the gap, not closing it.
Reps already at 150 to 200% of quota can write skills and pull sharper customer insight. The middle 60% can’t, because none of these tools were built to be collaborative. Ross: “I don’t think organically it’s moving that middle.”

2. People, then process, then technology. Teams keep running it backwards.
The point of view on how you engage customers comes from the most senior leader, and the process has to be field friendly and built around the customer’s journey, not internal inspection. Only then does technology reinforce a standard that exists.

3. The best methodology is the one that gets used.
Ross credits the line to Russell Sherman. If you’re debating how many P’s belong in MEDDPICC, you’re optimizing the fringes. What’s rare is an entire company, leadership through frontline, asking the same questions in the same language.

4. Leadership thinks it’s investing in the field. The field experiences homework.
One CRO told Ross he’d never spent more time, money and effort supporting his sellers. On the ground that looked like a multi-million dollar consultancy, more Salesforce fields, more quarterly inspection, and a 76 page laminated PDF. None of it touched a customer.

5. Don’t sell to the CRO. Sell through the people who own the tools.
CROs own revenue strategy and forecast, not the tech stack. Multithread into RevOps and enablement first, then send a no-ask note: a short drip in their own language about what you’re hearing from their team, no meeting request attached. And you don’t send it. Your CEO does.

6. Your buyer sees less than 10% of your product before they sign.
“Even with a POC, it’s probably less than 5 to 10% if you have a mature platform.” The rest of the decision is the sales experience itself. Several of Accord’s largest customers today are ones Ross disqualified at the time, who came back a year later because they remembered the experience.

7. The founder-led sales handoff runs to $20M or $30M, not your first VP.
Ross has made the same mistake twice: hire strong reps, hire a great VP, feel confident, move on, lose momentum. He calls it the curse of knowledge. You’ve obsessed over it so long it feels obvious, so you say it once and assume it landed.

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GTM 202 Full Episode Transcript

00:00 – 00:10

Sophie Buonassisi: You talk to a gun 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?

00:10 – 00:16

Ross 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.

00:16 – 00:19

Sophie Buonassisi: Ross Rich, co-founder and CEO of accord.

00:19 – 00:34

Ross Rich: Giving your team Claude code and these insights going to suddenly change how people are engaging with those different layers of the organization, saying the right things, speaking French, Japanese, German to the right people at the same time, maybe it tells them how to, but not when.

00:34 – 00:44

Sophie Buonassisi: The transition from founder led sales to a first sales hire. A second sales hire is one of the most challenging part to get right. Like, tell us your learnings, your stories from going that that transition.

00:44 – 00:57

Ross Rich: 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. I call like 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.

00:57 – 01:00

Sophie Buonassisi: What do you think the biggest misconception is around sales right now.

01:00 – 01:03

Ross Rich: And no one wants to be a salesperson anymore.

01:18 – 01:20

Sophie Buonassisi: Ross, welcome to GTM now!

01:20 – 01:22

Ross Rich: Thanks for having me here. Excited to kick off.

01:22 – 01:28

Sophie Buonassisi: It is a pleasure to have you here. For anyone unfamiliar with the cord. Give us a quick one, 1 or 2 liner.

01:28 – 01:49

Ross Rich: Yeah, basically a cord helps operationalize value selling. So all the things that you’re as a sales leader may be 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 in more revenue and have a better customer experience. We help make sure that gets done in a field friendly way.

01:49 – 01:51

Sophie Buonassisi: Super cool. And you were at stripe for over.

01:51 – 01:52

Sophie Buonassisi: Five years.

01:52 – 02:00

Sophie Buonassisi: Leading go to market and partnerships, sales, different capacities before this. What made you decide to actually jump into the founder seat?

02:00 – 03:06

Ross Rich: Basically, it 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 join their 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 um, 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 docks and APIs off the website. And as we scaled our CRO and head of rev ops and enablement and work in this project around playbooks and process. 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 gonna change the names of our Salesforce stages. We’re going to add a bunch more fields. We’re going to do the separate metrics 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.

03:06 – 03:26

Sophie Buonassisi: It’s 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 crows. 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’s what’s going on?

03:26 – 04:26

Ross Rich: Yeah. Things are changing insanely fast. I was just talking to, you know, one of my co-founders, and I’m like, I think I’ve learned more in the last 4 to 6 months than the last. You know, four plus years of of building a core just in terms of. Yeah, like the experience for sellers, for frontline managers, for leaders. It’s 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, like the best, the best. Right now the company is growing fastest, like an anthropic, like an OpenAI. But I think the advice and what I’m seeing across our customer base and most prospects that I talked to is their world is very different than that. 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 it 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. So.

04:26 – 04:48

Sophie Buonassisi: Right. Yeah, that’s such an interesting distinction. And now you help people get really dabbled with all those different aspects to ultimately help them create the best selling experience and be the best seller. Like we talk about best all the time. It’s a funny word. We 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?

04:48 – 06:19

Ross 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, you’re 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 100 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 talk to my sellers about it. As 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. They ask you a couple questions, and they give you that amazing recommendation that gives you the confidence that you pick 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, I fall back on to.

06:19 – 06:40

Sophie Buonassisi: 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?

06:40 – 08:23

Ross 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 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, and you can just tell that by talking to someone. 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 is like script. That’s like awful frameworks. Like you need to be a great seller. You need to just like think about that conversation. I thought of those as like, you know, kind of used car salesman tricks. And I think now my thought about this stuff is, you know, maybe a good classic sales analogy around, you know, athletes. It’s learning the plays. Then you can get creative around it. 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, if you 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 learn 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. And then you can deliver when you’re an expert in that space that, you know, believable recommendation that they can follow.

08:23 – 08:48

Sophie Buonassisi: I love how your mind went to basketball. Not my favorite sport, but for some reason mine went to football. Um, but you could pull an analogy for any sport for that. That’s 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.

08:48 – 11:35

Ross 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, you know, a lot of VC funding and actually focus in on the end user experience, actually talking to the sellers, talking to the front line managers and actually their prospects and customers. So we wanted to build something that they could actually use to have more successful buying cycles. Onboarding and post sales motions started there. Then when we realized we wanted to go from, you know, signing those first 100 innovators, early adopters, getting to that million dollar mark, raising our series A, how do we get this to ten, $20 million? We realized we need to start talking to more crows, 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 Crow saying, I’ve never spent more time, money and effort trying to support the feel 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. 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 QBs 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 cord 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 AOE? The SC then hand off to post sales implementation, CSM, AMM overlays, all of that kind of stuff. Everything ends up being siloed. It’s like, here’s the thing for the AI 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 may 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 teams 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 that customer experience. And that’s the barriers we’re trying to break down.

11:35 – 11:56

Sophie Buonassisi: 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 a chord. 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.

11:56 – 12:55

Ross Rich: Yeah, people always ask, this is like, hey, you know, new CRO joins. What are you guys seeing as like the best methodology in 2026. And how’s that different? I’m like I love this quote. I don’t know if it’s a generally known quote, but Russell Sherman 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 med Bic 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 you’re definitely optimizing for the wrong stuff if you’re trying to like, nail exactly the right qualification questions, 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? Mhm.

12:56 – 13:13

Sophie Buonassisi: And you explain why there’s that disconnect. Now if we talk about the solve obviously a chord is to solve. But like what are the tactics or like 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.

13:14 – 16:17

Ross 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 reassigning those customers for that kind of unique value. And then for The Crow, 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. Yeah. Um, we, uh, Jeanne DeWitt, who is our sales leader now leading, you know, things up for sale 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, uh, 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 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, it’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’s stuck with me too is like speaking different languages to different levels of stakeholders. 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 like 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. We understand. We know it’s super important. How do you build that into that customer journey really. Again, in that framework of the clients 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 peas are in med pick and all that kind of stuff. Second is the process stuff. Again, keeping it simple, keeping it feels 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? 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 c o 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.

16:17 – 17:01

Sophie Buonassisi: 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. The 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 customers outcomes that matter.

17:01 – 17:39

Ross Rich: Yeah. And there’s a lot of stuff just being built internally. It’s not touching the customer. 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 cubes 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 what does that look like to actually touch your customer? It’s like more intelligence and insight into your customers. 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.

17:39 – 17:44

Sophie Buonassisi: Yeah, that’s a super interesting approach. So what does your team use in terms of methodology out of curiosity.

17:44 – 19:28

Ross Rich: Later stage companies? I’ve seen them be really successful like force management. If you know of them from the ex, you know PTC legends. I think they have like a really, really great reputation. And we have a lot of joint customers who’ve been wildly successful with them. But yeah, another one too is we work with a lot of like PE backed companies who really care about operational rigor and value selling. And I think Vista has this framework called Vista value selling that basically allows you to customize it to your own company. But they have this really great framework that’s simple, that is kind of pre baked that you can again just translate that to your own company and your customer base, which I think is like a great place to to start with. But again, I think the simpler the better. Yeah. And the ones that are really about the customer and your differentiated value. And I think there’s a lot that just obsess over like your internal process that again, I don’t think drives the outcomes that that clients want. So 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, a 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? 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 2 or 3 peers that you can talk to. They’ve solved it with a core, but maybe there’s other stuff that you can explore. Here’s a great network of people to interact with. 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 at market.

19:28 – 19:39

Sophie Buonassisi: 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 peer network.

19:39 – 19:40

Ross Rich: Yes. Yeah. As your buyer. Yeah. Yeah.

19:40 – 20:18

Sophie Buonassisi: 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 like that is your ultimate goal. Yeah. Because 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.

20:18 – 20:50

Ross 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 remembered that experience in that compounding. I think that’s what makes companies and cultures wildly successful versus that short term trying to, you know, be everything to everyone.

20:50 – 20:54

Sophie Buonassisi: Yeah. That’s incredible. And what kind of logos are you working with today at Acord?

20:54 – 22:03

Ross Rich: Yeah, we’ve been marching up market again. I think we started with, you know, 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 a startup’s early stage people. Maybe it’s founders or kind of like first VP of sales and sellers at small companies. We’re using us. And then more recently we’re moving up market working with like large public companies like Fresh Works and Samsara, two of our, you know, 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. There are companies that maybe they were the stars of the show five, ten, 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 anthropic or OpenAI’s 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 maybe 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.

22:03 – 22:08

Sophie Buonassisi: Yeah, and that’s such an important part because the reality is most companies are not anthropic.

22:08 – 22:46

Ross 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 have that 200 plus percent LRR. 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. 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.

22:46 – 22:49

Sophie Buonassisi: How you sell and how you show up. Do you mean the sales person.

22:49 – 23:09

Ross Rich: The sales process, the person 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, you know, look like an idiot when they’re, you know, making this case, the CFO being the champion. And then six months later, it’s like, this thing’s not even deployed.

23:09 – 23:12

Sophie Buonassisi: They can be betting their career on it. Yeah. On this decision.

23:12 – 23:12

Ross Rich: Totally.

23:12 – 23:57

Sophie Buonassisi: Yeah. It all boils down to humans. Like we see the same on the founder side too. Like how a founder runs a fundraising process is indicative or at least representative to a certain degree of how they’ll operate, because I’m going on the investor side, you can actually see into the operational side. Same thing with the product and demos. You get maybe 510%. You don’t actually know the entirety of it. So you’re making a 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. Like it’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.

23:57 – 24:37

Ross 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 100 or so signals, right? We talk a lot about this with recruiting at a court. 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 going to deal with that. Right. You don’t want a vendor. As soon as you ask for something, you’re not going perfectly right. See how they respond to that, right? 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.

24:37 – 25:00

Sophie Buonassisi: Yeah. Chris Lee, he’s the head of sales a 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 experience? Because it’s not all on that call itself.

25:00 – 25:40

Ross Rich: Yeah. 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 chord in the first place was as soon as I made that mental shift from a sales funnel forecast process to customer experience and thinking it 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 Rev ops perspective of their designing all these tools and processes for their world, which is around forecasting, what do they need to deliver the board, its pipeline and forecast delivery, whereas the seller on the field is thinking about the client and how do we bridge those two things together? Mhm.

25:40 – 25:45

Sophie Buonassisi: And so now you’ve been building a chord. Tell us what are your biggest learnings from building.

25:45 – 25:47

Ross Rich: Oh man a lot. Yeah it’s definitely.

25:47 – 25:48

Sophie Buonassisi: A big question.

25:48 – 26:43

Ross Rich: Yeah. Steep slope from you know early career cellar 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. 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 markets 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.

26:43 – 26:46

Sophie Buonassisi: Do you think we should flip that then to market product.

26:46 – 26:47

Ross Rich: In product flip.

26:47 – 26:50

Sophie Buonassisi: It doesn’t have the same roll off the tongue effect quite yet.

26:50 – 27:11

Ross Rich: But I mean, I think and you know, when you talk to probably investors and other stuff, 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.

27:11 – 27:49

Sophie Buonassisi: 100% 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 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 line. Yeah, I love that. And you can have the best surfer, the best team, you can have the best product. But 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.

27:49 – 28:25

Ross Rich: Yeah. 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 positioning. Yeah. Book great 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 is only tech alternatives where your alternative? Honestly, most of the time it’s not it’s services. It’s other things to tangential to your product and value prop that are the alternative. So thinking through that stuff I think is really interesting.

28:26 – 28:32

Sophie Buonassisi: Yeah. Interesting. Okay. So market has been one of your biggest learnings to date. I love that. Any other kind of big learnings.

28:33 – 29:38

Ross Rich: 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 at arms, you know, playing sports 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 a 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. And I think that is, in a way, a little isolating that I don’t think a lot of people talk about.

29:38 – 30:14

Sophie Buonassisi: Yeah, that’s a great call out. And I love the friction analogy. It’s an interesting time to with AI because of course, that kind of bar and barometer of what people think they can do and what they can 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. 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?

30:14 – 32:07

Ross Rich: Yeah, I always go back to like why we built the thing in the first place. 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 the people can get lucky sometimes. Sometimes there’s opportunities to help people buy versus sell. I think the really drivers, the people at 150 to 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? How do you move that middle? Everyone talks about, right. There’s gonna be a part of the bottom that’s like doesn’t have the skill, doesn’t have the will. Coolest 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 Co works like codecs, like other tools, really helps with that team wide dimension. I think initially what I’ve seen on our team and others as it helps the top performers be more efficient. Right? You can write these amazing skills, you can get more insight into customers and you already know how to use that stuff. I think the challenges again, with more intelligence, with more insights about your customer, about your company, all that 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 hackathon internally at a cord 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. 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.

32:07 – 32:35

Sophie Buonassisi: Yeah. If anything’s probably creating greater silos and yeah, a greater delta between that middle and the top performers 100%. 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 if feels like to what you’re building with a cord, 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.

32:35 – 34:14

Ross 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. We’re going to market, and we’re used to talking to 1 or 2 different stakeholders that can make decisions for sub 50 or 100 K deals. Now we’re going to 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 cloud 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. 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.

34:14 – 35:01

Sophie Buonassisi: 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, Paul Irving, on our team’s 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. And 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 ourselves 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 to just get people’s hands dirty.

35:01 – 35:02

Ross Rich: Yeah, you gotta learn it.

35:02 – 35:09

Sophie Buonassisi: Yeah, but it’s not what drives outcomes and that’s okay. We did that, and now we do this. Yeah, yeah.

35:09 – 36:13

Ross Rich: And now comes the customer. That’s what 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, okay, 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. 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. 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.

36:13 – 36:24

Sophie Buonassisi: Yeah. Okay. You got to give us the full analogy because it’s fascinating. It feels like the intersection, the difference between knowing that we need to execute and actually executing. Yeah. Give us the analogy.

36:24 – 37:58

Ross Rich: Well, I mean, yeah, I think that self-driving car one is good, but yeah, just a recent conversation that I had with the CRO and SVP of DevOps and they’re, you know, super talented go to market engineer. 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. And you know, I’m trying to think about okay. Like 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 like using Claude and other interfaces to show this to the rep. And 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. 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 in 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. And 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 the stuff, 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 nail that final mile.

37:58 – 38:19

Sophie Buonassisi: 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. So love your sense and take on how do you sell to a CRO?

38:19 – 40:44

Ross Rich: Well, yeah, it’s a fun stakeholder I think compared to what I’ve done in the past, which is like much more technical, uh, 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, I’ll give it to you straight. I think Ciro’s 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 your technology, they’re going to look to the people that own the technology. They don’t own the technology, they own the revenue strategy, 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 there’s such a key stakeholder, even if they’re not the final EB and a deal economic buyer 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. They’re VP’s and enablement. So when we think about coming to a CRO. We want to make sure we’re in lockstep with those stakeholders and then go back and say, hey Sarah, leading DevOps, what do you think about this? I don’t know, I don’t feel okay, dude. 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 multithreading super early with like a know ask note if you’re familiar with that concept. So really early on we might have a killer conversation with a VP on their team, a rev ops leader, enablement someone and have the right person reach out to that crow and say, hey, it sounds like you’re working on XYZ the rest of the year. It’s a big focus. Maybe it’s going to market, maybe it’s a new product launch, whatever it may be, 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 to the Sierra respects how you’re selling to them, 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 to crows.

40:44 – 40:47

Sophie Buonassisi: And help us to find the no ask no part.

40:47 – 42:10

Ross Rich: 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, and the team and the feedback from the different stakeholders and personas at their organization and what they’re thinking about. 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 it 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 a core it is how are we getting credit and communicating in a way to the stakeholders that they understand in their own language. 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 ten stakeholders. Previous average deal was 4 or 5. That was partly due to a chord. And then when you talk to them once a year or every half year, they have that stuff instead of coming to them and like 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 a great play.

42:11 – 42:21

Sophie Buonassisi: It’s super interesting and right person and level your company. So these larger deals you mentioned might take 612 months. You’re multithreading them. Help us understand how do you multi thread effectively.

42:21 – 44:19

Ross 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 no crows 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 seeing 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 up market deals. 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 on sites. 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. I’m selling my CEO, CRO, CMO, whoever the right person is that they want to hear, whether they want to network with to get with them. And same thing for their direct report. Their SVP of Rev Ops again doesn’t want to hear from me. They don’t want to be sold. Maybe they want to hear from my rev ops leader, or maybe they want to hear from a peer. Or maybe they want to hear from our VP of product or 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 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 a it’s like this craftsmanship thing and you need to happen to get into the right like Exp, TC or MongoDB, 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 and engineering or design is.

44:19 – 44:30

Sophie Buonassisi: Right. Right. That totally makes sense. So kind of match the seniority level is that after you’ve made contact, like what is the first touchpoint look like a good first touchpoint look like when you’re targeting a CRO?

44:30 – 45:24

Ross Rich: Yeah, I think having the grain of making sure that you have the grain of the idea of what they care most about, 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. Drop them that note. Hopefully your company has a template for that in a way to figure that out in the process. Maybe you use a tool like a cord to do that. 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 $1 million 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.

45:24 – 45:29

Sophie Buonassisi: Yeah. Yeah, that totally makes sense. What do you think the biggest misconception is around sales right now then.

45:29 – 46:20

Ross Rich: The biggest misconception around sales? I think there’s a lot of them 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 salespeople don’t have the same level of cachet as an engineer or a 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 wrap. 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 at a lot of companies because there aren’t enough leaders. I think that that have that standard that are driving, that tops down totally.

46:20 – 46:39

Sophie Buonassisi: 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 you know.

46:40 – 47:06

Ross Rich: 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 see the standard of sales across most of our prospects and customers, 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.

47:07 – 47:07

Sophie Buonassisi: Right, right.

47:08 – 47:43

Ross Rich: I see. So I get why people would want to rebrand if they’re used to that. Say you’re a CEO 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 queuing 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 40 K in their mind and you’re doing them 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 400 K on you, but you don’t know. And again, I think that’s just kind of unfortunately the standards in in sales and what we’re really excited about raising the bar for.

47:43 – 48:06

Sophie Buonassisi: Yeah, definitely. And I mean now you’ve got a team of sales rep and you’ve built out an incredible team at a chord overall. But once upon a time you had to do the traditional kind of baton pass 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 to get right. Like tell us your learnings, your stories from going that that transition.

48:06 – 49:58

Ross Rich: 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 in a sales leader. It’s really to your first 20, 30 plus million dollars, I think depends on faster 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, blah. I can work on other parts, you know, that. I’m excited to to figure out a business. You can drop that ball and lose that, lose that momentum really quickly. And I’ve had to relearn this a few times, and it’s the right things to pass off over time and make sure you’re onboarding those people to how you’ve been doing it and still staying involved in a scalable way. So that would be my biggest piece of advice is the knee jerk 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 a lot of people will buy from you because of who you are. Again, going back to like the the role matching. 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 for hours.

49:58 – 50:04

Sophie Buonassisi: Yeah, that makes sense. I’ve got a couple just quick fill in the rest of the sentence questions for you.

50:04 – 50:04

Ross Rich: Let’s do.

50:04 – 50:09

Sophie Buonassisi: It. Okay. The part that nobody tells you about leadership is.

50:10 – 50:28

Ross Rich: 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? And if I’m ever noticing the drain, they’re then having to really proactively solve for that.

50:28 – 50:35

Sophie Buonassisi: Mhm. Super super interesting insight. And what about the most the most underrated piece of go to market advice.

50:35 – 50:55

Ross Rich: 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.

50:55 – 51:05

Sophie Buonassisi: 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?

51:05 – 51:49

Ross 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 to. Jean was giving me some advice and I was like, I knew when you came in you were going to start your own thing, and you shared that. And I was like, I don’t even remember sharing that. But, um, 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. And it’s so true where people spike. There’s another 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.

51:50 – 51:51

Sophie Buonassisi: Right. The duality.

51:51 – 52:10

Ross Rich: Yes. Which is just a truism in life and 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 I’m like, hey, I’ll give you an example. This is what I think I’m really good at. 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.

52:10 – 52:16

Sophie Buonassisi: So 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?

52:16 – 52:32

Ross Rich: LinkedIn definitely spend a lot of time there. That’s where our customers are. Prospects. So therefore myself and yeah, it’s fun to share the journey both. You know how we’re building a chord, 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.

52:32 – 52:36

Sophie Buonassisi: Amazing. Well Ross has been amazing. Thank you so much. Really appreciate you coming on.

52:36 – 52:38

Ross Rich: Yeah, it was super fun. Thanks.

Sophie Buonassisi

Sophie Buonassisi is the SVP of Marketing at media company GTMnow and its venture firm, GTMfund. She oversees all aspects of media, marketing, and community engagement. Sophie leads the GTMnow editorial team, producing content exploring the behind the scenes on the go-to-market strategies responsible for companies’ growth. GTMnow highlights the strategies, along with the stories from the top 1% of GTM executives, VCs, and founders behind the strategies and companies.