E62: CRO Life: from a $20B Exit, to a Hyper-Growth AI Org (Michelle Donnelly, CRO @ Crescendo)

Michelle Donnelly is the CRO at Crescendo, an AI-native contact center which has exploded from $0 to $100 million ARR in under 2 years. Before that, she spent nearly a decade at Salesforce and served as the CRO of Groq, which was recently acquired by NVIDIA for $20 billion. She's been a part of some big deals.

We came up with this notion of doing the world's largest AI inference center, and ultimately Aramco Digital bought it for $1.5 billion.

Michelle shares the reality of selling AI tools in a market where every single competitor says they do the exact same thing.

It's so noisy, it's so confusing. It's really hard to differentiate.

And Michelle shares how they have differentiated, including banning traditional sales demos and implementing a disruptive pricing model.

We're going to charge you based on outcomes, not based on seats. If you're not happy, we're not going to charge you.

We also dig deep into how she builds high-performing teams that outpace the competition.

Really being able to spot great talent. Everything you should do should be—

Welcome to the Revenue Leadership Podcast. Momentum is a powerful tool for turning sales and customer conversations into go-to-market intelligence. Using GenAI, it extracts, analyzes, and automates customer intelligence across your GTM org. The best part, it's not a new platform for your team to adopt. It integrates seamlessly with your existing stack, or it can straight up replace your conversational intelligence tool. At Owner, we ripped out Gong and went all in on Momentum. It writes back to our Salesforce directly. Captures forecast and churn risk, autofills CRM fields, shares product signals, and tracks sentiment. Companies like Cursor, Zscaler, Ramp, and ElevenLabs use it every day. Check it out with a free trial at momentum.io. Today's guest is Michelle Donnelly, who is the CRO at Crescendo and the former CRO of Groq. Uh, Michelle spent nearly a decade at Salesforce, then jumped to sell AI chips at Groq, which was recently bought for $20 billion by NVIDIA. So not too shabby of an outcome. And now she's running revenue at Crescendo, which is an AI-native contact center, and they've gone $0 to $100 million in ARR in under 2 years, which is obviously incredible. And she's lived through a bunch of contrasts that a bunch of us only read about. So she sold pre-AI and now post-AI. Big public company in Salesforce, plus then to a pre-revenue startup in Groq, hardware versus now services and software. And so we're going to dig into a bunch of like what's different in these places, what has changed over the years, and a bunch of the fundamentals that have changed. Because I, I, I spend so much time talking about what is different today and what people are doing with AI. Um, I think, uh, it would be a lot of fun to talk about like what is not the same, or what is— what has not changed, uh, in terms of how we work deals, work with customers, uh, and, and how to build teams. Uh, so I'm really excited to unpack this one, and thanks for joining.

Sure, thanks for having me. Happy Friday. Let's go.

Happy Friday indeed. So, so important. Yeah, I, I gave people like a little teaser of your background, but what did I miss? What's important for people to know about you?

Oh my gosh. Um, so You know, I think this, the thing that's been consistent throughout my entire career is that I, I love to build and I love sales. Like, I love it. Like the, the craft to me is so much fun for so many reasons. But, you know, I went to college and I was an architect. Hmm. And I was living in Chicago, I was making zero money. I had to work as a hostess at night, you know, because I was literally had a mattress on a floor. An apartment on LaSalle Drive. And I was 2 years in and I was 23 years old and I was doing all the big pitches for these, at the time, 40-year-old old guys, right? And that seems really ancient when you're 23.

Yeah.

And one day this beautiful woman walks into our lobby and her name was Susan O'Connor and she looked like Snow White and she had perfect clothes and perfect hair. And I'm like, where do you work? And, you know, she worked at a company called Knoll, which is a furniture manufacturer. And she was selling to architects and designers in commercial companies. And I'm like, I'm gonna go work there. I wanna, I wanna be like you. And within 3 months I was there. And then my journey began, you know, on doing sales. And I've done everything from global branding to furniture sales, distribution, AI hardware, you know, AI software. And it's been just an incredible journey. And there's some things that are very consistent to your point and some things that are very different.

Yeah. Um, very cool. And so, uh, you went from Salesforce, like one of the greatest sales engines ever built. Uh, and then took this leap into Groq, which was like pre-AI or pre-revenue AI hardware, like extremely speculative. Um, like what, at the time, what, what caused you to make that jump? And like, what did you see? Because I think a lot of people are, are, are going through the same thing where you know, established big company doing really well, but then you see all of this craziness, uh, in the world, but, you know, making the wrong decision is, is catastrophic sometimes. And so what did you see to, to give you confidence in that move?

Yeah. Um, so I'm gonna tell you a story again. So, um, 10 years at Salesforce was probably the best experience I ever had. I was known as a builder there, so they always gave me the most difficult team to fix, right? So people will say, oh, you came from Salesforce, like, you know, it's a product and marketing machine. Like, isn't it easy to sell there? No. Like, the pace is extraordinary. The quotas are extraordinary. Every year you change everything. And again, I would always get the broken, you know, the broken, uh, teams to really build. And I had like 80% year-over-year growth. One year I had 400% year-over-year growth because like the baseline was low on that one because it was a, a broken machine. So it's something I love to do. We had done some massive transformational deals. Like, there was this cosmetic company, and we started off, like, doing a million-dollar deal, and it ended up being $54 million over 5 years. And it was because we really focused on, like, the customer pain, the customer journey. And what Salesforce does so well, it's always a connected journey, the integration between sales, service, marketing, commerce, right? And if you can tell that story, and show ROI, you can do these huge transformative deals. So it was amazing. We made our customers happy. They got promotions. It was, again, an amazing experience for me. I'd been there for 10 years. Um, I really needed to do something new. I really didn't know what I wanted to do. And so what I did was I went to 10 of the smartest people I know. And one of my friends is, uh, very high up at Deloitte. She was the right hand to the CEO. And I said, Jessica, you know, what's next? So this was in 2022. We'd gone through COVID, you know, COVID for Salesforce, actually, we killed it.

Mm-hmm.

One of our best years because I was in retail, right? And it was restaurants and it was retailers and everybody was like shopping and eating offline, right? Chipotle was a huge customer as we did some transformational deals with them. So I went to Jessica and I said, you know, what's next? What's happening? And she said, well, come to Deloitte. But if you don't come to Deloitte, you need to go to NVIDIA. NVIDIA was one of their biggest customers. She saw what they were doing with the GPU. And I'm like, hardware? Like, why do I wanna do hardware? Like, I love, I love the cloud. You know, Mark changed the complete landscape with the cloud and subscription pricing. He was one of the biggest innovators of our time. She's like, no, listen to me. You gotta go to NVIDIA. So, this is the power of your network. So then I called this woman named Carla Stratfield. She was the head of global sales at AWS. I'd worked for her at a tiny startup. It was a no-name startup, but I was able to bring like Coca-Cola and Microsoft and Marriott, like some really big brands to this nothing startup. And Carla remembered that. So, I called Carla and I said, hey Carla, you've done extraordinarily well in your career. Like, what's next? And Carla said, well, hey Michelle, I just talked to this guy. Jonathan Ross. He's the CEO and founder of Groq. Groq with a Q, not a K. It's not Elon Musk's company. And they want me to be the CRO, but, you know, I've been doing this thing at AWS for 10 years and I need to go, I need to go take a big rest. So, I'm not, I'm not gonna do another CRO gig right now. You should talk to them. So, I'm talking to Jonathan and he's got this, like, enormous brain, right? So, he created the TPU, which is a tensor processing unit at Google, which is their compute, right? NVIDIA has a graphic processing unit and it's important 'cause it'll, it'll bring the story together. Graphics built for graphics, not actually AI. So I'm talking to Jonathan and every time I would talk to him, I would get the chills. Half the time I had no idea what he was saying. Like the guy is, is a genius, right? And he's thinking, you know, 10 years out, but it was a nothing company. Like, and I remember taking the job and my brother works at Switch, which is one of the largest data centers. Like they're building all the data centers for, OpenAI and Microsoft and Amazon. And be like, why are you gonna do that? Like, none of these startups win. Okay, so I go there, right? Um, and, um, so what got you over the hump?

Like what, what?

Chills. No, listen, I, I would say to you, I'm very strategic in how I grow a business. I have never been strategic about my career. Hmm. It's a really weird thing. And like when I went to Salesforce, a friend of mine's like, hey, come talk to us. Like, you'd be great. You understand marketers. I had no technology experience. I walked into Salesforce. I walked out with a job. Two weeks later, I got a note from the recruiting team at Salesforce saying, hey, thanks for your interest. You don't fit any of the qualifications. I'm like, well, I already have a job, so. But like, I am just not that strategic, but what I am is I, I'm super passionate and I have a lot of energy and I love to build and I'm highly competitive with myself, not with other people.

Mm-hmm.

Um, so, uh, back to your question about the Groq thing. I, I really, for the first time actually in my career, I listened to that, the chills that I would get every time I talked to Jonathan.

Yeah.

It was just like, I'm just gonna jump. I knew nothing. About hardware.

Hmm.

Nothing. But I, but I know how to build. And Jonathan was always looking for transformational leaders, people who thought differently about how they would build something. And that was really important to him. And so, he took a chance on me and he took a chance on a lot of really amazing leaders who were experts in their field of how, or of their craft.

Mm-hmm.

And that's what he wanted to bring to the company. And he did, his whole thing was, talent density. And so, he hired brilliant, brilliant people. It's actually really hard to constrain brilliant people when your whole company is brilliant. It's like a bunch of amazing light bulbs, but it's hard to get all those light bulbs flying in the same direction.

So, what do you think the common thread was between seeing Salesforce when you did it and going to Groq? Is it the vibe? Is it some like specific leader? You know, if You're saying you're not strategic, but there's something there that is maybe intuition that, that you're poking at. Like, what, what do you think that is?

So here, here's what I knew about Salesforce after I took the job. The company was 3,000 employees and $3 billion, and I understood, uh, at an intimate level the value prop that Salesforce was doing at the time in terms of building Marketing Cloud. They were doing everything through M&A, not building it themselves. But the integration story was really, really strong. And Salesforce knows how to, how to do M&A and how to bring cultures together. And I knew that as someone who understood the CMO world and the journey, that I could speak to customers differently and sell them this new world of Marketing Cloud. That's why I started with Salesforce. So to me, I, I got, I got the pitch.

I got it.

It resonated with me. I knew it was something I could sell. With Groq, it was, I knew that AI, this is before ChatGPT.

Yeah.

This is before Meta launched Llama. Groq was built for AI. They created a category called the LPU, which is language processing unit, which was, it's built for AI. It's built for those large language models. And I just felt like NVIDIA was already big. It was doing amazing stuff. but there was something really special about the speed at which this chip could compile open source models. And I, I, I felt like I go, I could go there and do something special.

Hmm. So, so it's almost like an intuition of the future of that market and, and you are following your nose on sort of that commercial fit. That, is that fair to say?

I would say that, um, like I'm a big collaborator. I trust Jessica implicitly. Jessica had said to me, this is where it's at. NVIDIA is where it's at. And Groq wanted to compete against NVIDIA. So, I knew that, I knew that AI was what was next. So, Salesforce was about digital transformation. Groq, NVIDIA were about the AI transformation. And I wanted to be on the next wave. And you don't always get your bets right. But it felt right. Yeah. It was an intuitive call and the people were incredible. You know, the board was incredible. The leaders were incredible. I mean, every time I talk to someone, I'm like, there's something really special here.

Yeah. So, so the takeaways for other leaders that are thinking about transitions, like one is the power, power of your network and the smartest people in your network. Yeah.

And having them, innovators, the future thinkers, the ones who really have a tap on what's next. Like, that's what Deloitte does. They're all about the future. What's next?

Yeah.

And so, I really, you know, put a lot of— and, and, and Carla was incredible, right? Like, she worked for Larry Ellison, you know, she grew AWS from like a billion to— I don't even know what's AWS at right now.

Tens of billions. Yeah.

Right. These, these were, these were growth hackers. These are people who are sort of seeing the next phase of the marketplace. And my brother too, at Switch, like, the volume that they were getting around AI was astronomical. So, I already knew there wasn't even, there, there was so much demand for, you know, the data center, like, like all the signals and signs were saying like, this AI thing is gonna explode. If you make the right decision here, your bet will pay off.

Right. Very interesting. I would, I would definitely not say that is not strategic. I'll push back on you. That's, I think it's, it's strategic in a different way and potentially like intuition-led. But, uh, I see this all— I see this all the time, people making like sort of odd career changes that don't match with the future, and like, you know, folks not leveraging the insight they have around them. I especially, you know, point people back to like, who do you know in venture? Like, who are the smartest friends you have that are, you know, actual investors that are doing deals and, and are thinking nonstop about What's next? Like tapping into that I think is so critical because I've said this a bunch now, but company picking has never been more important because the divergence in outcomes between good and not good and good and really great is bigger than it's ever been. There's been, you know, now going zero to $100 million, like, you know, it's common. It's crazy.

I mean, it is crazy. I mean, like I think about, we purchased, you know, PartnerHero, which is a BPO, which is part of our AI plus human play. PartnerHero had no sales team.

Mm-hmm.

But like, that is not a luxury that I have with Crescendo.

Yeah. At all.

We, I literally just got off like a board meeting and they're like, show me the money. I have a big, big picture next to me of Tom Cruise. Like, literally I can show it to you. Oh, show me the money.

That's awesome. I love that.

Yeah, yeah, yeah, yeah. Yeah.

So, so you went from selling into tr like traditional CPGs, like a, um, you know, a type of buyer that many of us are extremely familiar with. And now like an, it, it's an AI buyer. Everybody's got like AI in the brain, obviously.

Yeah.

And so what, what is most different about the two selling environments as, as you've seen it the last couple years?

Yeah, I, I think I have to answer this, explain this question first, which is to say Groq was really different because I was selling AI hardware versus AI software, right? That's, that's, that's obvious. It was a company of engineers. I came from a company of really sales and product professionals, right? Completely different environment. We had no product-market fit at the time. That's really hard. We knew we had an amazing piece of technology. We didn't know if we were gonna sell hardware, if we were gonna go to the cloud. We didn't know if we were gonna do cybersecurity or we were gonna do work with the federal government. Um, so, you know, it was, uh, to go from a company that is world-renowned as having great product and marketing fit to one that doesn't know who they are was really, really, it was the hardest thing I've ever done in my entire career. And tried many different go-to-market motions every month, actually. We created a new category. That was one of the reasons why I think the company started to take off. The LPU was a whole new category. But the market wasn't ready for us. When the market was ready for us, Groq found product-market fit. And that happened when Meta released Llama, which is an open-source model, so we could run those open-source models super quick. It happened when ChatGPT came out, and we could literally show side by side the demo of how much faster Groq was than ChatGPT. I had built this incredible enterprise organization, public sector and, you know, commercial in finance and telecom. We knew CX was a huge problem back in '22. We thought they would be the first adopters and that Groq could do that because of the real-time voice that we could deliver. So we knew CX needed to be transformed, but we didn't know how to get there. And it wasn't until we literally were doing like I mean, it was insane, like 100 demos a day where we were showing side by side, anybody who would listen to us, look at how fast we are, look at how fast we are. And then we were in Dubai and we were in a pizza parlor and we came up with this notion of doing the world's largest AI inference center. And ultimately Aramco Digital bought it for $1.5 billion. But when all these things started to converge, the demand started happening and we didn't have enough capacity. And so we shifted from a public sector team and an enterprise team to all developers because we can get the dev— that was sort of what Microsoft did a long time ago.

Yeah.

And the company went through like the roof as a rocket ship. But it, at that point, you know, everything I built was like gone. So that was actually an interesting thing to go through. And I actually left 'cause I'm like, you guys don't need me. Like, you need an inside sales leader to do this developer stuff. Fine. Was, I think I probably learned more there than I've learned at any other company I've been to. I learned what I love to do and I learned what not to do and I learned what I wanted next.

Hmm. And, and so maybe let's contrast the buyer today you're selling to at Crescendo versus the buyer you were selling to at Salesforce. Are those actually that different? Like, are, do they have different appetites, needs, buying patterns, or, or are the fundamentals sort of the same and it's just, you know, one was a cloud paradigm shift and now it's an AI paradigm shift.

Yeah. Let's talk about like Crescendo versus Salesforce, 'cause I think they're more similar.

Mm-hmm.

Um, you know, Crescendo has this really, um, you know, was that NRF? And it's the biggest retail show. And I was walking around and everybody's talking about their AI agents. Right? I'm a customer. I mean, it's so noisy, it's so confusing, it's really hard to differentiate, right? And I sort of started to feel how hard it is for this, these CX customers to figure out like, what do I buy and why do I buy it and what matters, right? It's a really, it's an important space and there's important innovations, but it's really hard to understand like, who should I buy and why? And the one thing I noticed as I walked around, you know, NRF was that nobody was talking about the, the value and the importance of humanizing AI and how important that handoff is between the sort of the front-end AI, like the AI agents, and the integration to like the actual human agents who can really solve those more complex problems, right? And we power that, that whole journey. So to me, that was a real differentiator. And I was thinking about customers, right? Because a lot of my customers at Crescendo are very similar to Salesforce.

Mm-hmm.

Some inherent differences, when you're selling, and we really do own the mid-market, and we're gonna start to move upmarket 'cause our customers are dragging us upmarket, which is great 'cause I come from the, the big deal world.

Mm-hmm.

But living in sort of this mid-market space, what ends up happening is that, you know, we're selling to CX leaders who are in a lot of pain around like, how do I solve my problem? How do I get better CSAT? You know, how do I drive my costs down? Um, How do I get insights about what my customers care about and don't? But what we're finding is that there's a disconnect between the CX leaders and like the CIO and like the CTO and the CFO. And we just had a shoe company that has like had wild success with us. And the CIO made a decision to, you know, buy Salesforce, who has their AI agents, and took some of that money from the CX budget without telling the CX leader. I was saying to the team, like, we have to go up, we have to go up in our customers. You know, we have to own the C-suite. These decisions, these are more than just, you know, cost centers. Like, we can actually increase the basket of their shopping cart by how good our shopping assistant is. And if you go to Salesforce, Yeah, I was there in like 2013 to like 2022. Um, you know, Salesforce does own the executive suite.

Big time. Yeah.

So, when you're coming in from the top down, those conversations are more transformational. So, that's the challenge that I'm seeing now with like this company that, that is really a unicorn that's moving very, very quickly, is that we have a lot of trust with the, the BPO that we bought and those customers, but we're not at, a high enough level to really do those transformative deals, and we're gonna have to get there.

Yeah. And so that would be probably in the basket of what's not changed, you know, multi-threaded, multi-threaded relationships, executive stakeholder management. Yeah. And so would you say the biggest contrast between sort of the move to cloud and what you did with marketers at Salesforce versus today is just like the noise and intensity?

I would say it's the noise, it's the intensity, and it's the speed. I mean, the speed is unbelievable. And it's speed for our customers, like how quickly can you get them up and running, right? Like this is not the world of Salesforce where you buy a large instance, it's based on numbers of seats.

Yeah.

Then you have to get a systems implementer and then it takes you 3, 6, 12, 18 months to implement.

Yeah.

People don't have time. I mean, Kyle, you know this from all of your customers, right? Like we had this great conversation, Kyle, where you were telling me about how you leverage AI to target all of your restaurants in the same neighborhood. Yeah. And you share with them what their competitors are doing and it creates this sense of, oh my God, like doing this and I'm not doing this. So we're seeing a lot of that in our space right now, which is, there are people who are moving at much greater speed with how they integrate AI and how they're having these transformational experiences with our customers. And the ones that aren't doing it are actually getting really freaked out that they're behind.

Yeah. That competitive FOMO is so true.

And then there, and then there's all these, um, uh, implementations that aren't actually working, right? There's people who are investing a lot of money into AI and it's sitting on the shelf.

Yeah. Yeah, yeah, yeah.

So it's like they all have this mandate, you must get AI, you must transform this, but then they don't know how to use it.

Yeah.

Like once it's implemented, it's not being tuned. So we, we, we have an answer for all of that with what we do, but I mean, it's like to be a customer right now, I think is actually really, really difficult because of the pressure to save money, the notion that AI is gonna help you save money, and not really having the expertise to really know how to do it once it's up and running.

Right. And so what, what changes do you make in terms of how you work deals? And then we'll get into how you, how you think about managing the team in a world that is noisy, hyper-competitive, like higher intensity. What, what have you done different in terms of your go-to-market approach?

So the way that we're doing it is making sure that there's strong product-market fit, which we've got, making sure we've got customers and we're helping them upsell. The thing that is most challenging for me as I scale over 30 new salespeople is messaging, clarity, and that's something that, that I am struggling with. My forte has always been taking the complex and making it simple. People are moving fast. They need simplicity in messaging. If you can't understand who we are in 30 seconds, we have hashtag failed. So I think taking complex in making it simple, not making your customers do a lot of homework. Literally draft, seeking to understand the pain, because that hasn't changed, Kyle. Nothing's changed. Your customer will tell you how to sell to them. If you ask the right questions, they will tell you their pain. Uh, our chairman of the board never sells. All he does is ask questions. So understand the pain and then come back with like, here's our plan for you. Here's phase 1, phase 2, phase 3. Here's what it looks like through the sales process. Here's what it looks like once we get you implemented, and here's what it looks like long-term. Here's what's gonna cost you. We're gonna charge you based on outcomes, not based on seats. If you're not happy, we're not gonna charge you, and we're gonna do everything humanly possible for you to expand beyond those use cases. We're going for market share grab. This is not about like, like profitability right now, even though we are profitable. This is about making sure we get the best customers who wanna grow with us.

Hmm.

And so how do you eliminate the noise? You really create simplicity out of what's really complex for many, many of these leaders.

Okay. I love this. So, uh, let's double-click on the messaging then. Like in your space, there's all of these competitors that are very well funded and seemingly have, uh, strong products. All sort of saying the same thing, but like, no, we're better. It's like, no, we're the best. And so how do you, how have you been able to bring simplicity to the messaging so that the customer can like clearly make those decisions?

Okay. So we say that our value prop is the human agent that intersects with the people powered by AI, and we will get you up and running quickly and we'll make sure we take care of you throughout the entire process and we'll make sure that the quality is there. So how do you do that? How do you prove it? Because everybody's saying it. So I'll call you.

Hold, let's just, how did you get to this messaging? So you come to the company, you're like, we need simple. And they probably wasn't simple before because, oh, we want to say this and this and actually our accuracy's better. Or like, these are good proof points. And so like, walk, just walk me through first the process of like distilling down and how do you like to, to—

You want me to tell you how hard it is? Yeah. It's been really hard. Like, honestly, like, it's been bloody hard. So what did we do? We tried out our messaging. Like, I have an amazing BDR team, so they're literally doing 400 calls a day per person. So they're doing the messaging in real time. So I can, I have an office with our BDRs so I can go and listen. I wanna hear how it's landing. We took our pitch deck to existing customers and asked them what didn't work. They told us our pricing was too complex. They told us our messaging was too complex. It took 20 minutes for them to get the aha moment. That's way too long. They would say, wait, oh, oh, you mean like you guys do the people too? You've got like a whole team of 3,500 call center agents. Oh, I didn't get that. You know, like, so we tested it and we had different people testing. We had our founders testing it. I was testing it. Our BDRs were testing it. Our AEs were testing it and it didn't work. At all. So, we redid our pitch deck. I mean, I think I've been there for 6 months and we're on our 5th pitch deck. We hired outside consultants to give us feedback. Some worked, some didn't. And right now, we are on another iteration, literally, and we're doing a whole workshop internally and externally because when you have to ramp 30 AEs and hit a huge number and reduce their overall, like get their productivity to 80% in like less than 4 months, which is incredible. The one thing you need is clear and consistent messaging. Otherwise, but we keep testing and testing and testing and we rip ourselves apart and we do it in real time and we have a culture where clarity is kindness. And so we all rip each other up. We're doing a workshop next week, a day workshop to see if it works. And then we're going to bring existing customers and new customers and have them look at it again.

Very cool. Would you say this is the single biggest area of focus that you've had?

It's one of them.

Where does messaging stack rank and your priorities in your first few quarters as the CRO? Seems like you're spending a lot of time here.

My first priority was scale because of the numbers we had to hit, right? And 9 out of 10 companies don't hire enough capacity. And then I had to look at, do I hire in a traditional way or do I, like, so I, I did all the numbers for like, what do I need to hit this number, right? And then I thought about, well, how much can I reduce that headcount based on what we're doing with AI, right? Like, can I say I need 20% less because of AI? You know, I didn't do that, just so you know. Because I want— I didn't. What I, what I'm gonna use AI for is to take my 5-month ramp down to 3 months.

Yeah.

So that's what I'm gonna do. 'Cause I would rather over, you know, overreach on the number of heads I need and overachieve versus fail, right? 'Cause there's no path for failure here. So I think scale is my number one thing in building out an organization that could own the mid-market while still going upmarket. So I had to hire different players. I also had two different teams. One was focused on install base and one was focused on direct new logo business only. And I decided that having two separate teams wasn't gonna work if I wanted to drive productivity. Mm-hmm. Because people learn from existing customers, 'cause it's, you're 67% more likely to convert a, an existing customer than you will a new customer. So, I needed my AEs to learn more quickly.

Mm-hmm.

Just, you know, took all those walls down and created one team. So, Creating the organizational structure, making sure we're hiring the right talent, making sure I was aligned on the vision was really, really important. So it was, you know, own the mid-market, move upmarket, you know, make sure we're always selling AI with our people. And then in order to scale, the messaging has been my pain point.

Hmm.

Very cool. And I started listening to all the Gong reports about, you know, like what people were saying and I go, my God, like, what are you saying? But when you have that many new people, and I have like an enablement team and they do everything through AI, and we literally like have win-loss reports that go out every week. We know by name who makes a deal better and stronger.

Yeah.

But the messaging is not consistent. And I came from Salesforce. The messaging was amazing.

Yeah.

But it's complex, right?

Yeah.

Simplicity is actually really hard to get to.

Of course. Yeah. And so what, like once you get the messaging dialed and you feel like it's something you like, how do you think about reinforcement? Like what, what, what's the path to getting everybody like beating that same drum?

Well, I think you, you get more wins, right? And you'd ask your customers, why did you buy from us? Like, what was it? When was your aha moment? I think speed is a big differentiator for us. Speed and scale, right? Um, So, I think, you know, people listen to the Gong reports. We're actually using Gong to do our forecasting now. So, we'll literally sit on a forecast call, and I'm on the forecast call at an AE level, 'cause I want to hear, 'cause I'm still learning what works and what doesn't. And we'll click in, we'll read emails, we'll see what customers are saying. We spend a lot of time figuring out why we lost. So, we're constantly reinforcing like the messaging and what really works. And then we're doing a lot of show me, 'cause I don't believe, like, I, I mean, we're talking a lot today, but I'm a big believer in pictures and show me why you're different. Like, I don't believe what you say.

Mm-hmm.

And so, you know, people talk a lot about demos. We're not doing demos. We're basically saying, okay, like I had this gaming company that called on Monday and they're doing this thing for the Super Bowl. They're like, our volume this month is exactly the same as it was all of last year. I need to get something up and running, you know, in a week for Super Bowl.

Hmm.

We're like, okay. So our head of product built an AI expert agent right off of their publicly available knowledge base. And within less than 24 hours, we could show them how it worked for them. And it was voice, it was text, and then we show them how we're gonna deploy, and we show them who's who's gonna help them deploy, 'cause it adds credibility and trust. Like, this is the person who's gonna deploy for you, and it's gonna take you, it's gonna take us under 30 days to do the whole thing and integrate into your ticketing system, but we can get you up and running on your website, you know, in 3 days, and here's how we're gonna do it.

Hmm.

A lot of show me.

And so you're calling that not a demo, that's really like a solution. You're, you're just building a—

Yeah. I mean, like, 'cause some of our stuff is, because of the power of our AI, and it's not rules-based, it's autonomous. So it scrapes and it learns and it knows how to answer questions really well. You know, if we had access to the tickets, we could actually go into all our tickets and scrape all of that and then, you know, continue to build on the knowledge base. So I think it's really important that, I mean, think about it. Like, wouldn't you rather see an experience customized to how I'm gonna solve your pain at Owner versus seeing, a demo, like, you know, for the restaurant industry, you kind of want to see how it works for you.

Yeah. So, so I, this was another topic I wanted to double-click into, which is, which is proving value and building trust. And so, uh, obviously it, you know, Salesforce, you've got like this, uh, you know, tons of evidence and case studies and G2 reviews and Gartner quadrants, all this stuff. And in AI, so much ambiguity, like everybody says they do everything else. And, and so clearly this is a piece of it. So don't just demo and promise, but like show a thing and, and go build. And that's probably uniquely possible because you can actually build the thing with AI to actually, to, to bring to that scenario. What, what else are you doing to build trust in this, in this new world?

So, one of the things I learned at Salesforce is become a customer of your customer. You know, a big piece of our ICP at Crescendo is retail. Like, we do insurance, we do healthcare, we do SaaS as well, but a big piece of what we do is retail. And so, we tell our prospects, like, go check it out. Go to Lovepop, which is this card company, and go check it out. Go buy a card. See how they upsell you to buy more cards for Mother's Day and Father's Day. See how they answer your questions. Or go check out, you know, a clothing brand that we're— go check out Doc Martens and see how they actually create a larger shopping basket because you're looking at a pair of boots and they think you might like something else. And they actually pop that into the window for you. Like, go look at it and see how it works. And it's interesting, like, people actually— and I'll send them the link and I'll tell them, like, what they should be looking for and how it relates. And they come back and, you know, sometimes they're like, one, we had this company, Rachio, and it's a sprinkling system. So, like, use your app to, like, tell it when to water and based on your location and your soil. And one of the customers had Rachio, so she goes and she checks it out and she's like, Well, I hated the experience. Like, they didn't know who I was and I'm like, you know, like a gold member and it didn't authenticate me. And it's like, you can't do that, you can't work with us. But like, it engaged the customer and the answer was, well, they didn't wanna do that. They didn't wanna authenticate you. If you wanna be authenticated in, like, let us show you how you can do it. So, it really engages prospects, again, to show me.

And making, it sounds like the two things there is just making it really tangible. In a low-trust environment, doing everything you can to make it real.

I mean, yeah. I mean, like, isn't that how you buy? I mean, that's how I buy.

Yeah. Yeah. It's, I'm sure more challenging in other environments that don't have that same, like, B2C component that you can touch. But I think the through line here is figuring out for your unique scenario how you can make the thing like much more tangible because the, the trust, the level of trust in AI is very low because there's so much vaporware. It's such a, it's such a competitive environment that, that needing to go above and beyond is so essential. And, and when are you doing this in the sales cycle? Like how early are you?

We won.

Yeah.

Yeah.

I figured.

Like, like real I'm like, go check it, go check out our customers. Don't take our word for it. I mean, I think the other thing that we're doing that is very successful is because we, you know, have this operational side, you know, with all the people, we bring in operational folks who are not there to sell. They're there to say, look, like, we get it. We've been in your shoes. Like, here's what to look for. Here's how we can help you. Here's what to watch out for. Like, even if you don't use us, like, Here's what we've learned. And because we have so many, you know, we have this big, think of it as a pipeline of these BPO customers, we learn all about what's working and not working for them because we're with them every day. Some of them are using our competitors because they started working with our competitors before Crescendo bought PartnerHero. So we learn a lot about our competitors too. So we know when things aren't being implemented and we know when things are failing. So we've learned a ton. So it's been kind of nice little, you know, extra added benefit.

Well, have you always been this in the weeds, like this close to the front lines?

All right. So look, yes. I mean, I will go into the gutter to understand. I will. I will go into the gutter. And it's interesting that you asked me this because I have, um, my, my, my org is quite large. I just took on marketing.

Yeah.

Um, and so I have like 13 or 14 direct reports, which is a lot. And it's intentional right now because I need to see and I need to understand. So I will go as deep as I need to go to seek to understand, but I can also fly really high to ensure that I simplify for everyone in my org what are the 3 things we have to do. I don't want to give them 4. I don't want to give them 5. They know— everybody in my org can repeat to you on call, what are the 3 things we're doing this quarter? Driving focus and clarity of message internally, not just about to our customers, but what do we have to do? How are we gonna get there? Where do you go for help? What happens when you get stuck? And then tell us everything that doesn't work for you in real time and we'll fix it.

Okay. Do you think the diving into the weeds is any different than it has ever been, or that's the thing that like great leaders have always sort of done?

I don't know any other way of doing it. I mean, I always had a problem, you know, when leaders come in and they tell you what to do, but they haven't been on a customer call in a while, right? Like, I just, I think for us to win, it has to be grounded in reality. And I always want to hear from the people who are on the front line. Because they're the ones who are experiencing all the pushback and challenges. And you have to listen to your people because they will also tell you how to sell. I think it's hugely important. But, but, but, but the also, like, you know, Matt, Matt Price is, he came from Zendesk for 20 years. He's our CEO. And the guy is like, he has 1,000 ideas a minute and he uses Whisper to like track all of his ideas, you know? So like, he can like, You know, and he gives me like, oh, Michelle, I got all these great ideas. And it's a lot, right? And so I think we're really good partners because I'll say to him, great, how many are we gonna do this quarter?

Yeah.

I'm doing 1 or 2. So, so I'm able to take his vision, understand how it's gonna get us to our number, and then simplify it for my team to like reduce the noise internally. That's my job.

Yeah.

You have to understand what they're dealing with. To be able to simplify the message.

Yeah. To quote another longtime Salesforce person that I worked with at Shopify, Dan Ross would always say, he's like, we've got way more good ideas than bandwidth. And I think that is certainly true at high-growth companies and companies where you have good product-market fit. There are so many things. I constantly battle this myself because I'm similar. Like I'm an ideas person. I see something, I'm like constantly reading and I get to do the podcast and I have 1,000 new things that are now really cool ideas to chase. And then you, but bringing it back to the simplicity of like, all right, like that's backlog, that's backlog. Like what are the top things? It is a challenge. Certainly not one that I've like perfected.

No, it's very hard. I mean, I think like I would just say to you, for me, it's always 3 things. Nothing more.

Yeah.

Only to do 3 things.

Where do you put those 3 things? Like, how do you keep yourself accountable to, to those 3 things and not let yourself drift?

There's no path I'm gonna drift. Like, I, I literally just went through my 3 things with the entire executive leadership team right before this call. That's what I was doing.

Yeah.

Have, you know, every 2 weeks I do the CRO Connect. I remind everybody, you know, what we're focused on and what we're doing. My enablement team is doing the exact same thing. Everything we do is around those 3 things. So, reinforcement, reinforcement. We have channels like Slack channels where I remind everybody where we're at. I show metrics.

Yeah.

Like, like, I am, I, my instincts are very, very good because I've done this for a long time, but I've also learned that I have to run a data-driven business. You know, so I, I brought on a really awesome team of revenue ops leaders who are helping us really drive that data-driven business so that I can turn the dial.

Yeah.

You know, make decisions not always based on gut. So, that's been, that's hugely important to us.

Yeah. I wanna hit on one more topic before we move into sort of the quickfire. You mentioned onboarding, you're trying to compress it from 5 months to 3 months. And like, that's the big application of AI. What are you doing there?

Yeah. Okay. So, you know, we are going to drink our own champagne. We have to like, live and use our own AI. So, we have a, we call it our sales launchpad and her name is Harmony. And so, Harmony is something that the BDRs and the AEs use and actually our agents use it for their customers. And we literally dump all of our knowledge base into, you know, this assistant who can very quickly give us information. So, for example, I might be talking to you, Kyle, and I would say, hey, tell me like who owner.com's competitors are, tell me what their revenue is. And I want to know 3 lookalike customers because I want to share with them everything we're doing for the customers that work with us today that are similar to them. Right. Kind of to your point of like FOMO that we talked about. So everybody uses that. And I think that's been really effective. We have all of our competitive information in there. I'm trying to think of what else we have in there. It's tons. So we use that AI assistant. Again, we use all the win-loss reports from Gong. We actually just, I think we're buying Salesforce today because—

Good day to buy for Salesforce, end of the fiscal.

Oh my God, it was so interesting to be on the other side of the table and like knowing all the plays. It was really fun. I loved it. And actually, you know, I was gonna say, we should all become customers more often. It's amazing what you learn when you're being sold to.

Yeah.

Have, have you been like buying lately? 'Cause I was actually surprised at how not great some of the sales cycles were. I'm like, oh my God, like we're killing it at Crescendo. I actually felt the need to send a note to one of the sales reps saying like, you have such an amazing story, but you didn't even ask anyone who joined the call like what we cared about.

Yeah, I buy quite a bit of stuff. I, I tend to— I've— we've bought a lot of early stage tools, so it's, it's usually working with founders. And so I always go out of my way to, to like give them some feedback on the positioning and, and, and the sales cycle. Uh, but certainly agree, it is, it is really informative to be on the other side. Uh, we also like signed a bunch of Salesforce stuff yesterday, and, and, uh, shout out to our rep Zach. It's, it's, uh, I've had a great experience working with them in this iteration. You know, it's hit and miss. I've had like not so great reps and really good ones, but you can tell the world is changing so much because as a buyer, you just have so much understanding and knowledge and leverage. And certainly where I'm at career-wise with my network, I know exactly who's paying what for what. And so the, the, like the tables are so much more even today as, as a buyer than, than maybe it once was.

Yeah, I agree. And that's why I think like we're really transparent in pricing because we don't want to be that company that's like, we're super transparent. I think it makes a difference.

Yeah. Okay, let's get into quickfire because I know we got to wrap. What do you, what do you think separates a good CRO from a truly great one?

I think collaboration and really surrounding yourself with the very best talent you can possibly find that are experts in their line of business, but also are, have a willingness to roll up their sleeves and do whatever you need to do to get the job done. I hire gritty people. All of my BDRs are athletes, every single one of 'em. We go after people that have done crew because crew's a brutal sport and like, they're grinders, literally.

Crew, swimming. Yeah. All the sports that just suck.

Yep. So, we look for grinders in, at this type of company. So, I think really being able to spot great talent and then giving that talent the opportunity to win and be seen and do their very best work and feel like they're super valuable. I think the people part to me will never change as a CRO. Get the best people, enable them, empower them, and let them fly.

That's definitely a will never change thing. If anything, the best people are worth even more today than they were in the past, and that's like a, A lesson to double down on. What's the most common advice you give to new sales leaders to avoid the bad first-year mistakes? Your first-time VP of sales, for example.

Yeah. Be really clear on what your goals are. Stay focused on your goal. Everything you should do should be about meeting your goal. Make sure your customers are really happy. Listen to your customers. Make sure you've got the right talent and don't be afraid to make changes. Make changes quickly. The hardest thing to do as a leader, I think, is to hire and fire.

Yeah. What's the hardest lesson you've had to learn in your career?

Uh, product market fit.

Hmm. Um, last question. What's the best thing you've read in the last 12 months?

Hmm. Okay. So I have it right here, actually. I bought this, I got this book from our head of HR, Stories That Sell, you know, because my big issue has been about messaging. So I wanted to understand the art of storytelling, which I think I learned at Salesforce, but I wanted to understand like how people still, people are still people. We buy based on emotion and then we rationalize with analytics and data and pricing and everything else.

For sure.

The human connection, the trust, the stories that sell. So I, I read that 'cause I wanted to seek to understand like what stories resonate with people and how do we continue to tell stories in this world where people are moving fast and they do everything online and everything's on Zoom and we're not sitting around, you know, a table having dinner together.

Yeah, that's a great one. A book I love in that category is, uh, Made to Stick by the Heath brothers. And it's like Why, why do they get that one? Well, Michelle, this was awesome. I, I think we hit exactly what I wanted from this episode. We got into a ton of things that are like timeless and won't change all the way from choosing the right things and leveraging your network to positioning and, and establishing trust. So this was a ton of fun. Appreciate you coming on.

Thank you so much. So fun. You're the best.

Yeah, thanks. Thank you for listening to the Revenue Leadership podcast. If you enjoyed it, don't forget to subscribe, and you can find a link in the show notes. And be sure to leave a 5-star review, share it with your network, and please join me next Wednesday for another great conversation.