Jessica Robertson on this episode
Jessica Robertson is the CRO of Orb and formerly VP of Sales at Accessibly, where she scaled the company from under $10M to $50M. She brings 15 years of enterprise sales leadership to her first CRO role, tasked with building a go-to-market engine from the ground up at an early-stage startup. Robertson's credibility rests on her proven ability to build and scale sales organizations across diverse industries, combined with her deep experience recognizing when traditional outbound playbooks stop working.
Robertson's core insight is that relationships—not cold outreach—represent a real, scalable revenue channel for mid-market and enterprise companies. Most revenue leaders talk about relationship-led selling but never operationalize it. At Accessibly, Robertson watched the 1:1 capacity math that had been predictable fall apart; no amount of headcount fixed the problem. Traditional outbound tactics that once generated predictable ratios stopped working. This realization drove her to join Orb, a relationship mapping platform that helps companies index existing relationships as a systematic funnel.
Orb's product surfaces internal relationships—through customers, advisors, investors, and employees—and maps them to ICP accounts where penetration is possible. Rather than waiting for prospects to enter the market or relying on cold prospecting, Robertson and her team use the product itself to turn one customer into three by leveraging warm introductions. The bigger insight: in a world where every company is running paid ads, AI emails, and cold sequences, human relationships have become a competitive moat.
The episode explores Robertson's first-year learning curve as a CRO responsible for sales, marketing, and customer success; how she uses network mapping to unlock pipeline; why her curated dinner events convert when most events fail; and how she navigates sales-and-CS alignment by building the GTM foundation intentionally from day one.
What we cover in this episode
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6:06
Career arc from SDR to CRO Traditional path through sales operations, sales director, VP of Sales; 15 years in revenue; now first-time CRO.
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7:26
Why she left Accessibly for startup Capacity math broke at scale; cold outbound stopped working; saw market gap and wanted to build the solution.
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12:09
Culture shock of startup ICP basics Went from 2000 transactions per month to zero; had to unlearn predictable scaling and re-center on success metrics.
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17:05
Relationship mapping in practice Map existing relationships across org; identify network density; find warm paths into ICP accounts; multi-thread via trusted connectors.
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23:48
Using own product to build pipeline Orb surfaces connections; use connectors to get intros to target buyers; mission to turn one customer into three.
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29:14
GTM motions driving growth Relationship mapping, curated events/roundtables, cold outbound, trade shows; drinking own champagne; testing and iterating.
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31:19
Why curated events convert Highly selective attendee lists; education and problem-solving focus; no pitch; create space where people want to be together.
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47:41
Sales and CS alignment as CRO Building revenue engine foundation intentionally; ICP-first mindset across sales, marketing, and success; less conflict at early stage.
The lines worth sharing
People really want human connection. They don't want to be sold to. They want somebody who's in their shoes.
Jessica Robertson · 0:00
There is a tipping point for organizations where it's way more effective to go through people you already know than cold outreach.
Jessica Robertson · 2:15
It used to be a 1 to 1 relationship. You want this goal, let's back down capacity. Now the math doesn't work anymore.
Jessica Robertson · 8:08
For the first time in my career, I get to sell to myself. Every day I hear how CEOs and VPs of Sales run their organizations.
Jessica Robertson · 10:14
Common questions from this episode
What is Orb and how does relationship mapping work?
Orb is a relationship mapping platform that identifies existing connections within an organization—through customers, advisors, investors, and employees—and maps them to target ICP accounts. It helps teams find warm paths into prospects and multi-thread opportunities using trusted network connections rather than cold outreach.
Why did Jessica Robertson leave a $50M company to become a first-time CRO at a startup?
Robertson saw the 1:1 capacity math that had worked for years stop working at Accessibly. Cold outbound became inefficient at scale. She recognized this as a market gap and joined Orb to build a solution and prove that relationships could be a scalable revenue channel.
How does Orb use its own product to generate revenue?
Orb's team maps their own network and uses connectors to get warm introductions to target customers. Their mission is to turn one customer into three by leveraging existing relationships. They also surface advisors and deal partners through their own platform.
Why are Orb's curated dinner events more successful than typical SaaS events?
Robertson curates attendee lists tightly, centers events on education and problem-solving, doesn't deliver a pitch, and focuses on creating a space where people want to be together. She asks attendees why they came and uses that feedback to refine curation. People value quality company and real connection over sales pressure.
How does Robertson navigate sales-and-CS misalignment as a CRO?
By building the revenue engine foundation intentionally from day one. Robertson ensures sales, marketing, and CS all own lead quality and customer success, not just their individual metrics. ICP alignment across all three functions prevents the classic finger-pointing that happens in scaled orgs.
What operational changes did advisors Warren Zena and Bridget Winston help guide?
Warren Zena, a CRO coach, pushed Robertson to think bigger and build a durable foundation where marketing, sales, and CS function as one revenue engine. Bridget Winston provides positioning feedback and real-world CRO insights. Both have been advisors and referral partners helping Orb navigate scaling.
SEO meta description
Jessica Robertson, CRO of Orb, on building a relationship-led GTM engine from zero and why human connections outperform cold outreach at scale.
Target keywords
Jessica Robertson CRO
Orb relationship mapping
relationship-led sales
GTM strategy
mid-market sales
warm introductions
network mapping for sales
CRO first-time role
sales and marketing alignment
curated events strategy
multi-threading sales
B2B go-to-market
Read the complete conversation
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Read the full transcript · 57 KB · Jessica Robertson
Jessica0:00people
Jessica0:00really want human connection.
Jessica0:02don't want to be sold to they want
Jessica0:04somebody who's in their shoes, who understands what they're going through, who can
Jessica0:08connect with them in a really real way.
Jessica0:10So
Jessica0:11just being normal and being a human being and not knowing all the time
Jessica0:15really helps with making those relationships.
Speaker 10:17Welcome to go to Market Science,
Speaker 10:19In this podcast, we share tangible, actionable playbooks from the trenches,
Speaker 10:23working as go to market strategy and DevOps consultants for our clients here at Union Square, Consulting
Speaker 10:27and candid conversations with revenue leaders in the market that have been there.
Speaker 10:31Now let's get into it.
Rachael0:34Welcome back to Crow Stories. I'm your host, Rachel Baker, and with me today is Jessica Robertson, the chief revenue officer of Orb and formerly the VP of Sales at Accessibility. Jessica, thank you so much for joining me today.
Jessica0:47Thanks for having me, Rachel. I appreciate it.
Rachael0:49Yeah. So you're 11 months or probably could be over a year into your first official role at or. But when this podcast episode comes out, what has been your biggest accomplishment so far in this first year?
Jessica1:01Yeah, I think that that's a it's a hard thing to bundle down into 1 or 2 statements, because it's been a crazy year. We are our second year in revenue so early stage startup. And I think the biggest accomplishment, if I had to summarize it would be opening really a new category, right? So we've been in this world of reach.
Jessica1:22How far can you get through 1 to 1 contact through, you know, traditional sales manners, whether it's paid marketing or cold outreach, you know, cold calls, cold emails, all of those things. And we are trying to establish and not that we invented relationships. That's it's an old idea, but that relationships can really be a cornerstone or foundation of your go to market practices.
Jessica1:47And there is, in fact, a tipping point for organizations where it is way more effective, way more efficient to go through people you already know to access your ICP accounts than it is to go in cold. So I think establishing that as us as a real channel and understanding what organizations need, how we can create a SaaS product to help them orchestrate and develop these, this as a true funnel is is been a really fun and a huge accomplishment this year.
Rachael2:15Awesome. And can you explain, to the listeners at home what orb does?
Jessica2:21Yes, sure. We are relationship mapping platform. So we start. If you think six degrees of separation, we start on the innermost circle and we establish who does your company know. We do that through a number of different methods. But think about your investors, your advisors, your customers, champions, vendors, everybody you're talking about or talk about the collective relationships of an organization.
Jessica2:42So we map all of those for you, and then we understand who do they know. And we think about that as a network. So relationships in the innermost circle network in the second circle. And we are identifying the relationships that you really care about and who they know and accounts you really care about. So if you think about ICP penetration like you have this, let's take a thousand organizations that you want to get into.
Jessica3:05Just for easy math, we're helping you understand where you have access points into that already, and then accounts who may come in through a different methodology where you have, relationships or network that can affect your win rates, as we all know, multithreading is really difficult. We all say we want to do it more. We don't often have a lot of answers as to how to do more.
Jessica3:27So we believe for that answer. And this is really what we're talking about, is influencing those to the people you already know and who they know.
Rachael3:36I love that so much. I think like human,
Rachael3:38real human relationships are going to become so, so, so much more important now that everything is just inundated with AI
Rachael3:45and everything feels like kind of like sterile and separated, especially on LinkedIn, which used to be, you know, a platform for creating relationships.
Jessica3:52Yeah, yeah, yeah. Not anymore. It's all like, yeah, everybody's running towards AI, which we should be, right. There's a lot of efficiencies drawn from that. We're all trying to make our, you know, our panels look better. We're supposed to be bringing in more revenue and doing it more efficiently than ever before. And AI is certainly a great tool for that.
Jessica4:11But it's it's taken a few, people in its farther few methodologies in its path. Right. So much AI content is written now AI emails I schools, they're all great things. I don't have a hatred for anything, any of those methods, and they work for some organizations, but we're kind of leaning against that at the moment. We're indexing that, companies have worked so hard over the course of their, you know, years in business to create these relationships.
Jessica4:41And we just want a way to amplify that, bring them to the surface, index them for where they can really be used.
Rachael4:47Yeah, I love that. And it's like I can't remember who I was talking to you another another podcast. But something that stuck with me was like finding the thing that's unscalable in your business that like that tie touch thing that makes you different from everybody else and then try and scale that. And I think human relationships is a huge,
Rachael5:06what's the word?
Rachael5:06I can't think of it. Opportunity. There you go a huge opportunity there.
Jessica5:10So it's been like historically, it's been really hard to map the relationships. Right. Because you think CRM, it has the word relationship in it. But I have some arguments that it may not be the best place for indexing relationships as a whole. And that is because that one source of truth doesn't have everybody in it in the company.
Jessica5:29Right? When you're thinking the collective relationships of your organization, your whole organization is not typically in Salesforce, HubSpot, whatever you're using in your CRM. So we are really working at making sure that, that, that net falls and we're able to take all the data, which is a mountainous, amount of data, working with it, making sure that we're organizing in a way that's prioritized for the business.
Rachael5:54Give us a brief background of your career journey so far. And what led you to the Crow? Crow rule, right. I'm all tongue tied today. And specifically.
Jessica6:04I think I think I am, too. We're we're in the same boat. But, listen, I came up the most normal way you could think of. I started as an SDR earlier in my career. Spent some times and some time in sales operations. So I understood kind of the inner workings, the plannings, the forecasting, all of that. And then just straight up through the normal route eight director of sales.
Jessica6:26So the most traditional path one could ever take. I don't have any, like, amazing stories that might shock you, really just came from the most traditional path, but most recently, as you mentioned, I was the VP of sales at accessibly is a completely different organization, very volume driven, very, easy to manipulate the outcome based on numbers versus today we're much more of a mid-market slash enterprise sale.
Jessica6:54There's a whole lot more salesmanship that goes into what we're doing today, than before. So I've kind of been all over the world, are all over the board when it comes to, you know, organizations that I've been in and running. So the full gamut, but, exposure to all of it. But it's been a really fun journey.
Jessica7:11And 15 years later, here we are.
Rachael7:14Yeah. What's, what prompted the decision for you to, to to leave accessibly, getting up to VP of sales to become a CRO?
Jessica7:24Yeah, it's a good question. You know, accessory was probably one of the more fun times of my life. We did a huge run. I was with them from just under 10 million to almost 50 million, like, 550 million when I left. So it was, it was a big run. And, I got the opportunity. I think the one thing that I can say is leading the sales organization.
Jessica7:48I saw the gap. Right? What we had done five years ago was not working anymore. It wasn't. I was telling somebody this morning like it used to be a 1 to 1 relationship. Okay, you want this goal? Let's back down capacity. Here is what I need. Right. So you want $1 million in revenue if your capacity is that one rep brings $1 million.
Jessica8:08I knew exactly how to map that out. And to say, here's how we're going to meet our goals. Right? So, we would send up outbound teams and we could really predict what they were going to do because outbound still worked like you send, you know, seven emails, you get a lead in these sorts of things there, all these ratios that you could work through.
Jessica8:26And what I saw is it didn't matter how many people we were throwing at the problem. Right? It started to become this really inefficient. And we were on the we were on a downward trajectory for what our tactics were actually able to achieve. And we had to be really creative. So we were we were really creative. But I saw that gap in the market and I thought, what is everybody else going to do?
Jessica8:48Right, like all of these organizations who maybe don't operate as at as high a volume, so they couldn't see the numbers as clearly as I could. How are they going to create new business in a world where all of our old tricks don't work anymore? So, when I was introduced to or it was like, oh, that's how they're going to do it.
Jessica9:10Like it was like the answer to the problem in my job. So for sure, it was a risk. Took the risk. I was coming to an amazing team, already in place, that had the vision for what we were going to do with these relationships, how we were going to organize them, how we're going to help businesses find not only more ICP customers for them to go after, but, execute on them in a more efficient way.
Jessica9:34So, needless to say, I saw how it would work out and I wanted to be a part of it. So I jumped over and we did it.
Rachael9:42Awesome. You're seeing the future. This company, I love that. I love it like being able to really believe in a company that you're working for and what you're doing makes the whole difference.
Jessica9:52Yeah, it does, it does. And for the first time in my career, you know, I've always sold really random things all the way through and ran organizations for really random things, everything from tobacco to security cameras to fine art auction software. Like really the most crazy random things. And for the first time in my career, I get to sell to myself.
Jessica10:14So every day I get to talk to CEOs and to VP of sales, and I get to hear how they're running their organizations. I get to hear their problems. I get to see what they're implementing. His fixes. And it's really fun. I've been able to build an incredible network of these leaders that I both admire and learn from every day.
Jessica10:35And, they get to be my customers. I get to be their provider, their solution provider, but also friends. As if, as it turns out right, we're building these relationships with amazing people. So, yeah, that's really been, an amazing part of it all.
Rachael10:50Yeah. I find people with the most chaotic, like, random backgrounds end up in, like, the best places or the best places for them. I used to be I screamed, yeah, I used to be a salesperson, but, like, not online. I worked at a pawn shop once and I was like, working at electronics store and stuff like that.
Jessica11:09And that's awesome. What was the weirdest thing that you got received at the pawn shop? I feel like the weirdest thing.
Rachael11:14It's in this, oh, we got a lot of. So I'm in Canada, like, so we don't have like, guns. You can't like sent a gun to a pawn shop. But we had a lot of swords, like just a crazy amount of swords. There was one. I don't want to get on too much of a tangent, but there was one aisle in the back warehouse that was just the sword aisle, and like, everything was haphazardly sticking out into the aisles.
Rachael11:36Whenever I had to go down there to get something, I felt like Tomb Raider, like Lara Croft, you know, like having to duck around and stuff and.
Jessica11:42Sounds like OSHA or whatever the Canadian equivalent of oh, should be.
Rachael11:46It was. Yeah, yeah. Oh yeah. No, it was horrible. I almost tripped and fell face first on a, an exposed hacksaw that was just laying on the ground. Oh, no. Oh, man. Yeah. But anyways. So your first 90 days of CRO at orb, what was the first, like, major operational challenge you encountered that you weren't expecting?
Jessica12:07It's interesting because I came from a late stage product market fit, scale up company. Right. So I think while, you know, everybody would tell you your ICP documentation is a living, breathing document that should never change and you should be iterating and evolving on it every 3 to 6 months. I had kind of I had teams that were doing this and focused on these things, and I had fallen out of the practice of doing it myself, of really focusing on not just what you can sell, but what can you make successful.
Jessica12:45And I think that those things like kind of the the culture shock of going from a high transaction, we were doing 2000 transactions a month at the time. Like, you know, you click the CRO dashboard update and it there's always something new to look at to a startup where, things are not moving. They're moving incredibly fast in some ways, right on the product and on the sales side.
Jessica13:08But the numbers don't jump out at you as much. Going back to the basics of sales and remembering like, okay, here's our customer, this is the living, breathing organization. We need to iterate on this. We need to develop not only our our tactics from sales all the way to success marketing. Everything needs to be, really organized and put into a document that we just rehearse and rehearse and live and breathe over.
Jessica13:37So I think getting back into that motion of coming from a highly scaled organization back to zero was culture shock, but also refreshing. Right? Because I'm, I'm one of those I love to sell. I love my customers. I love to make them successful. I love to understand why they wanted to work with us to begin with. What are their big boulders?
Jessica14:00What are we solving for? And that was a lot of fun. So I think just just that initial shock of getting back into it and going back to the basics was, was shocking, but also refreshing all at the same time.
Rachael14:13Yeah. And what was your initial approach to that? What ended up working or maybe not working in the beginning?
Jessica14:18Yeah, I mean, we've iterated like five times this year from, ICP perspective, like, and I believe that that's healthy. I wish I was doing it more in my more, you know, founded roles and things like that. But, what worked was tracking success, not sales. Right. Like looking at, okay, this person came, they were interested, the marketing worked.
Jessica14:39We got them into the funnel, we sold them. They were able to prioritize. But what could we make successful after that? I think that's the definition of getting to product market fit. Right. And once you're in product market fit, keeping it is also a challenge, right? And making sure that you're scaling to the highest potential. So I think the things that worked was always indexing on the success side of things.
Jessica15:03The things that didn't work or I mean, everybody knows this feeling of getting excited because you're selling and you're growing really fast. And if you let your attention fall for one minute off of success and just on what can sell, you end up in a little bit of a different place. So we always had to remind ourself to get back to that, those success criteria and and making sure we're developing not only the entire go to market process for the customer that will ultimately make most successful.
Jessica15:34But also, you know, giving all of the teams that knowledge around us and updating our ICP and continuing from there.
Rachael15:42And on the ICP front, oh, who do you feel like was maybe who did you think was your ICP in the beginning? And then you realized that it wasn't actually, you know, the most ideal customer persona? And who do you feel now is your best customer persona and why?
Jessica15:56It's a great question. So honestly, when I came in, I was like, everybody needs this, right? Like everybody's struggling with outbound everybody's, you know, paid marketing is getting more expensive. Our cash is going up, our LTV is going, how are we gonna solve this problem? So my initial thought was, oh, man, everybody who's doing what I'm doing. So I thought it was just pretty generic B2B, SAS.
Jessica16:19I knew they needed the sales team of some sort. It couldn't be a solopreneur type of thing. But and I knew we also had to have some sort of network density. Right. So we're scaling and mapping relationships so you can't have a company of two people and expect a lot of relationships because they just don't exist.
Jessica16:36And we're not a company that can fake it. We can't build a network for you. It kind of has to be there because we're indexing really high quality, high value relationships only in your ICP accounts. So the bigger the company, the bigger the customer pool that they have, the better off we are. So we started a little too low on that scale to be honest.
Jessica16:57We needed to go after bigger companies because everybody was interested and we were lucky to have that problem. Can you imagine somebody complaining about a top of funnel problem, which is we had too many people interested that we weren't going to be able to serve in the best way possible. So we've since iterated, we're much more of, a mid-market forward slash enterprise forward kind of, sales outfit now.
Jessica17:24Really going away from the startup world who is looking for a quick, you know, flick of revenue versus, people who have this, I call it the tipping point where you're actually more efficient using your relationships than you are doing cold activities.
Rachael17:43I'd love to dig more into, this relationship side of it. I think,
Rachael17:48this would be super valuable for a lot of our listeners just learning a little bit more about you, like literally learning a little bit more from you about, how they can use relationships in their business. And, you know, what processes need to change in order to, make an impact with that.
Rachael18:03So what kind of, how do your customers or your clients see success in, in using, you know, their relationship building operations?
Jessica18:14Yeah, it's really fun. And also a little bit complicated because relationships can literally affect every stage in the sales cycle. So let's go all the way to the top of, you have, you have a list of ICP accounts you want to go after. And so historically, sales leaders have or marketing leaders even have just said, okay, let's go after them all.
Jessica18:33We're going to spray them all with as much information, as much marketing as we can possibly get. And we're going to hope that, you know, certain amount of people come in. This number is typically 5 to 7% is what we call actively in market for SAS companies today. Right. And within their ICP. So how we affect that is at the right size company, you might have 15 to 30% more access into that ICP than you think.
Jessica18:59It's different for every company. So kind of hard to quantitatively put a bet on it depending on, you know, their customer density and things like that. And so the idea is you don't have to wait for somebody to be in market. You don't have to wait for like go get them. Go make them interested through your trusted network already.
Jessica19:17And it's some you're you're borrowing somebody's social capital right there. So they already have it. You don't have to create it. There's a lot of trust. We've gone to this world of, you know, so much sales and innovation that we really want to trust who are hearing it from. We want to know we're not guinea pigs, these sorts of things.
Jessica19:34So that's kind of the first implication when you think about, kind of in funnel, in pipeline, like I said, multithreading, we always say you need you know, to on average, you close when you have six or more people in this world of community buying multi-threaded on any pipeline account. Okay, great. How do I do it? You want me to go back and do cold to all of these people, which we've just established doesn't really work, and or you want me to overextend my champion to make sure that we have all of these people and the the concept there is that we actually have a solution for that.
Jessica20:10We can get you more highly multithreaded to those key people that you need within your pipeline deals to increase your win rate. Right. So and then we, you know, think about warm intros on the top of funnel customer references in the mid funnel, expansion opportunities later on. You can get the idea, event planning is some of the creative ways we've seen it used to understand where your network density is as a company.
Jessica20:38So how to plan your events across your territories appropriately based on where people, you know, we're based. So all sorts of different applications, all really fun. I think I'm probably putting people to sleep by now though.
Rachael20:51So I think then.
Jessica20:52On the application work.
Rachael20:54I think it's really interesting and I think, you know, I don't think, this kind of work is, is really focused on that much, especially in B2B. I think a lot of, people who sell to B2B forget that they're not selling to a company, they're selling to an individual person at the end of the day.
Rachael21:10Right. It's not you're not like sitting on zoom talking to a building, you're talking to another person. So I think, like knowing how to use, the relationships that you already have is super important and valuable. I wanted to ask, you talked about some applications for this, but what's, like, have you ever seen, like, a kind of, a weird application that you never thought of using it in that way, or building a relationship in that way?
Jessica21:35I like it's not that we didn't think of it. I just think it's difficult for most organizations to think this way. But a couple of our customers actually identify who has network density that they don't know yet, or that they don't have a super strong relationship. So we always think about, oh, who can Rachel introduce me to? So we actually look at it the other way around as well.
Jessica21:58So you have a whole collective organization of people that you've had relationships with in the past, and maybe they're not fresh. Maybe you wouldn't go ask them for, you know, that introduction or whatever application you're using, but to identify where your relationships with your first degree are not as strong, but they have really big network density on the other side.
Jessica22:21So kind of flipping the script and identifying like, hey, these people could be really important for my organization, but our relationship with them is not strong enough. So kind of flipping that back on the connector and saying, okay, that connector is really, really, really well connected within our organization and this is what we need to, you know, we need to renew that or, relationship with that connector.
Jessica22:44So, it's like, how many times can you say relationship and one sentence, that's it. But anyway, you get you get the point. Yeah.
Rachael22:51So really podcast can be full of it. So.
Jessica22:54Yeah. Exactly. Really identifying those people who have critical relationships that you need to make closer to you.
Rachael23:01Okay, cool. And I read on your LinkedIn that you mentioned, you guys at all have been using your own products to, you know, build the company, eating your own dog food as, CEO Eddie would say,
Jessica23:15I was just wondering. Statement to drinking your own champagne.
Rachael23:18Just more drinking your own. Hey, I like that. That's nice. Yeah, I like that. Yeah. Drinky on champagne. Very good. All right. You heard it here for first of all. So I wanted to ask, like what? What specific strategies would you recommend? Or maybe ones that you guys have actually used to develop these relationships, like once you can see like, oh, I should I should really get a relationship with this person, what do you do next?
Rachael23:46Like what do you do. You just like email them like, hey, do you want to get on zoom? Call and just chat? Like what? What's the play there?
Jessica23:52We legitimately use our own tool. So if I wanted to connect with Eddie, let's say from here, I haven't met Eddie yet. I have a profound respect for the work that he does. I read his newsletter every Saturday like I'm I'm one of these fans. But now I know you, Rachel, and our tool surface that you and Eddie know each other.
Jessica24:10Why? Because you have career overlap. Or because you've interacted with each other on LinkedIn or have a social strong social engagement. I should now use you to get that introduction to Eddie. Right? So I am constantly mapping my network and how they can help me get to the people that I ultimately want to get to. I've found advisors this way.
Jessica24:30I have found all sorts of people, customers. We obviously this is one of our biggest revenue generation tactics is drink, air and champagne. Using our connectors to help us get in touch with other customers. We have a mission here at orb to turn one customer into three, so to use every single one of our customers to get three more new customers, because that's a great thing about knowing cruises.
Jessica24:54They typically know a lot of other people in the sales and CSS and marketing world. So, yeah, this is what we're doing and really just understanding who knows who. I think also people like just a little bit more personally,
Jessica25:09people are really want human connection. They don't want to be sold to they want somebody who's in their shoes, who understands what they're going through, who can connect with them in a really real way.
Jessica25:22So not to not put that aside, like just being normal and being a human being and not knowing all the time and really helps with making those relationships.
Jessica25:33And, I've tried to personally spend this year investing in my own network and building, you know, offering people my time and being there for people when they need help and, you know, really investing in it intentionally because relationships isn't something that comes overnight.
Jessica25:52They're built over years and years and years, especially for, you know, those of you out there listening who haven't intentionally done this, it'll pay itself back in dividends. It always does. Like I'm seeing people. One of my customers today is somebody that I met 15 years ago through an intro. So it's like all of these things just come back.
Jessica26:10So I've been more intentional this year personally, investing in my own network. And, and doing the same for.
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Rachael26:37So do you guys have any like specific messaging strategies or guidelines on how to approach these conversations?
Jessica26:45It's a good question. We call it burning the ask. So making sure your data is correct. Right. Like not going on to the far limb and saying hey can do you know that person over there instead saying, hey, I, I'm pretty sure you know this person. This is what I'm indexing off of. They're always impressed when you come with not only I know you know this person, but here's how I know you know them.
Jessica27:08And then keeping it short and to the point and also providing incentive where possible, for people to make these introductions, certainly if you have a business benefit for doing so, that should be considered. But really keeping it short and sweet, taking all of the work off of the connector, they don't need to do any work. All they need to do is just place one simple message connecting.
Jessica27:31You know, if Rachel, if you are introducing me to Eddie, I would want to take all the work. Hey, Rachel. Here's why I think you should introduce me to Eddie. Here's the benefit that I could bring to Eddie. And then connecting, like, just allowing that message to be forward or whatever. Making sure you get the ask, right.
Jessica27:46The messaging is simple, and the connector doesn't have to do a lot of work.
Rachael27:50Awesome. And so you said before, you know, you have one client that was relationship or person you've known for 15 years. Is that is that like 15 years of consistent following up with them or like checking in with their life? Or is it just that 15 years ago?
Jessica28:04Well, it wasn't like a by chat. Like it certainly wasn't like a one time meeting. We used to be in the same industry. We were introduced to each other, had kind of fallen out of touch and then randomly just picked back up and started chatting again. Again, like I say, it's it came from investing in my network.
Jessica28:21All, you know, over this past year, reinvigorating all of those people that I've known over the years. And I put time out of my week. I prioritize it. It is something that needs to be prioritized. So from a business perspective, you already have these relationships, right? Because the business itself inherently has invested in it through delivering your product or service.
Jessica28:43But personally, it does take time to invest in it. So those of you who are, you know, out there building your own networks, I would say prioritize it, put time into it. Businesses just needed the technology to leverage it. At the end of the day.
Rachael28:56Awesome. And so I wanted to ask you a little bit as well about some of the go to market strategies that you've headed at warp in the last year that you've seen the most impact from whether they're, you know, regarding relationships, the stuff that you guys are doing within your own platform or something else.
Rachael29:13Yeah, we.
Jessica29:14Actually have 4 or 5 go to market functions. I mean, we aren't immune, just like everybody else. We're trying everything. We're experimenting all the time. Of course we drink our own champagne. I would say the vast majority of our revenue comes from that information. We also run a trade show or an events model, but we do it in a very different way.
Jessica29:35We are actually highly, highly, highly qualifying the people that we want to get in touch with at any specific event. We know a lot about them. We're pulling their relationship network, maps. Before we go, we're going in with something to offer them so highly personalized messaging. At those larger events, a way to get attention from the people that we would otherwise not have the ability to catch via cold call or fold emails, something like that.
Jessica30:01We also ran, a dinner series in the past, year that was really, really successful. I was shocked at how it was difficult to get people to come to events. I think people are getting now especially inundated with events. There's a lot of events out there these days, but it was really, really successful. People want to be and we hosted all of ours as roundtables or discussions, more or less like, that we want to bring people together who have something in common and solve problems together.
Jessica30:32So it's a lot less about or. But we did some fun things, like telling each other kind of where their networks overlapped or where they could help each other with their own ICP introductions. So that was kind of fun. We also did, some work with Cold Outbound. We did it in a little bit different way. It wasn't a brand press approach.
Jessica30:52It was again approaching people through social channels, mainly in cold calls. Like everybody else. It was, struggled to make that work and lots of testing with messaging and etc. but, I think we're, we're all over the board just like everybody else.
Rachael31:09We are.
Jessica31:11Trying to grow fast, having a lot of success, but, still trying and testing all of the normal things out there.
Rachael31:19Yeah. Why do you think you guys's events have been so successful where, you know, people are being so inundated with invitations?
Jessica31:27I think it's because we centered it around relationships and investing in education and, you know, solving real problems together. And we didn't do a pitch. We didn't structure it as like, hey, come to learn more about. Or instead we showed them what orb was power like, how powerful it was while while we were there. So nobody came and got a sales pitch.
Jessica31:50Nobody was, you know, required to take a 30 minute meeting afterwards. Really, a lot of people that came to those events became friends, even if they weren't customers. They've introduced me to other people because we really wanted to create a space for our community that was going to benefit them, not just in the way of benefiting us.
Jessica32:12Right? Not just us providing our solution to them, but giving them a real space to connect with others. That were really like minded. We held really tight to a specific type of person. We didn't allow just everybody in, so we curated the list, even if it meant having a smaller event of, you know, ten, 15 people. It was a highly curated list of people that actually wanted to be in the same room together.
Rachael32:38Awesome. Yeah, I can imagine like that having the the company that you do all focused around centered around relationships and networking, it'd be probably easier than other companies to like, create a networking event. What kind of advice would you give? You know, companies who maybe don't have that kind of, they don't have that kind of business model or, product to sell that slot so easily into a networking event,
Jessica33:06Specifically for events. I'll back out of that for a second and I'll speak more about go create the network. Go look at your network, map it because anybody just because our product is like it's easy to like, sell it without selling it. That's kind of the cheat code, the underlying cheat code. But I think it's all about list curation, building the network, being intentional and then providing a really good space for people to come to.
Jessica33:36I actually looked at it a lot and asked all of the people that showed up, why did you show up? And the reason was because we created a space where people wanted to be together, and that was the that was the big thing, right? Is making a space where people want to be together. So, this is this is why we were successful.
Jessica33:56I don't think it matters what your product is. I think it's about how intentional you are with the attendees and what they get from being there. People's time is their most valuable commodity. They're taking time out of their day, away from their kids, away from their work, away from their normal, you know, habits and behaviors to come spend time with you.
Jessica34:17So why? And I think once you get really intentional about that, why it'll be really easy to get people to come to your event.
Rachael34:24Yeah, I love that. So how are you guys planning on, fine tuning and developing these strategies as you go into 2026? And what are you really excited about?
Jessica34:34Yeah, it's funny, I put the challenge to my team, let's half our spending on everything and keep the same results. Like I said from a customer acquisition because we paid our tuition now. Right. We've learned kind of the way of work and how we're going to do it. And it's all about intentionality. Is that a word? I don't know if not to.
Rachael34:53I think it is. I'm pretty.
Jessica34:54Sure. Okay. It's about being intentional, being prepared in every place that we show up. Why are we in that conversation? We know what our customers needs. We know what their pain points are, and we know how we're going to solve them. And we're being or we're researching and we're restricting ourself from the kind of, you know, spreading the fertilizer to really watering the plants and saying, like, here is how we help that company.
Jessica35:22Here's what we're going to prepare our messaging with our our people, with both prior to going in. And then we're going to show up really intentionally and convey that message. And I think I'm I going to brag for just a minute. I think my team at orb is probably one of the best. They are the most intentional about the things that they're doing, while also not sacrificing volume and not sacrificing the things that we need as a company to survive.
Jessica35:48Right? Like, I'm sure people are rolling their eyes on the other side of that as well. That is nice. But I still have a goal that I need to meet. And these are the you know, this is the math that gets me to that goal. So there's always a line there. You have to weigh between how do we be intentional and still get the results that we need.
Jessica36:04And there, you know, this is where I think AI is super easy to dive into, is those efficiency? How do you do those tedious, boring tasks a little bit easier than you did, you know before? So these are we're heavily leaning into that and we're doing everything from like much heavier enrichments, working with a lot of, tool providers to really enhance the people that we're focused on, to make sure they're within our very narrow ICP constricted, you know, swim lane, if you will.
Jessica36:41All the way to the back end of Let's Invest and you know what we look like when we go publicly. What what are we going to take? And we're spending development hours to make sure that what we're showing the customer is the best thing that we can deliver.
Rachael36:56Yeah. That's a pretty big goal. Other than just stuff. Yeah. Other than the stuff you just listed. Like what are the other maybe process or efficiency changes that you're planning to make to try and achieve that.
Jessica37:08think from a process perspective, we've been looking at a couple of different tools to really help, narrow down our ICP bucket. I spoke briefly on this a little bit, but I'll go into the process a little bit more. So when we go to a trade show, we need to enrich everybody that's going to be there.
Jessica37:24We need to understand that that company is the exact company that we want to fall in love with. I tell my team, like, go fall in love with these accounts, know them inside and out. So how are we going to do that? This is where we're really diving into the process. We're going in to get better enrichment tools to make sure that the company is in our profile.
Jessica37:45Then we're doing some genetic workflows and making sure that we're hitting their website and understanding everything that there is to know about them, not just, you know, your classic, you know, where's the company address and are they in software sales and things like this? We're really diving one one layer deeper, and we're using some tools and genetic workflows to help make that possible.
Jessica38:07All the way to kind of let's go into pipeline really digesting all that we can. And making sure to track every stage that we're in. Do we have everything that we need there? So, we actually built a custom agent through, who's now turned into a dear friend, but another company that develops custom agents for companies.
Jessica38:29And that agent is solely analyzing our pipeline and all of the calls that happen with a customer and how they benchmark against our company knowledge base and things like this. So we're diving into the nitty gritty of the sales process and understanding how we can be more efficient, how we can give our team what they need at the right time when we don't have collateral and things that we need, that once it pops up to a certain amount that we are creating it.
Jessica38:56Like everything involved in those workflows, from knowing the customer to making sure we have everything when we need it, is under review for this year, so, it's intense, but it's, as well.
Rachael39:08And that work is like it's absolutely going to pay off, because even if it pays off by just a point of percentage, like that could be hundreds of thousands of millions of dollars.
Jessica39:20Exactly, exactly. It's you never you never know what the effect like. It could be massive. Right. And you're you're shooting, as you said, for those, you know, percentage points that you can tack on to every conversion rate, to every win rate, to every single part of the sales process. And there's so many break points. And it's our job as the zero to solve those problems.
Rachael39:41So yeah.
Jessica39:42We better be studying.
Rachael39:44I reminds me of, a piece of content Eddie put out recently called the quote that the ROI of go to market ops, because he gets those questions all the time on sales calls where they're like, okay, well, you want to do this, you want to help, like change the process, but what's the ROI on that? And and he's just like, your processes are broken and you're asking me what the ROI is to fit because it's like it's it's obvious.
Rachael40:03It should be obvious. Like just making a little some tweaks, like whatever investment you're putting in to that work, like the man hours budget and stuff, it's going to pay off for itself many times over because it's a it's like a domino effect as well. It affects one thing, affects your your sales process. You're getting better customers into your pipeline.
Rachael40:22You're you're closing deals, with customers that are going to get more out of your product, your product. And it goes all the way to customer success. So now you have fewer tickets because your clients are like having a great time with your product and you know, you're getting better. Case study stories and you're getting, more retention and less churn.
Rachael40:41So.
Jessica40:42Yeah, all the way through, it's like, yeah, it's funny, because I was speaking with, a head of an engineering CTO, recently, and he was like, Jessica, I wish I could measure my team in the same way that sales teams and CSS and marketing, we're so lucky, right? Compared to other functional organizations within a company, because from literally the first marketing dollars spent to the lifetime of the customer, we have numbers and we can fall back on those numbers to make sure that we're handling everything in the best way possible.
Jessica41:16It's no doubt a mission to keep all of those numbers in check all the time, but we're certainly the lucky ones as far as measuring our business goes.
Rachael41:25Yeah, and you got to use it. I mean, I feel like it's not an exact science behind by any means, but I feel like every single department, even if they're kind of far away from revenue, if revenue is going up, then they're probably doing something right. I know I.
Jessica41:40Have interdependence, the interdependence on other departments as a, as a podcast for a different day. Like. Yeah, because there's as you said, it's not an exact science, but, you know, there is a lot of thought process around, okay, if sales isn't able to meet their goals, all of those numbers are suffering for one reason or another.
Jessica41:59What is the dependency that you have internally on other organizations? And it for sure exists. Like why are we not hiring the amount of people that we need to have, the capacity that we need, that's an HR dependency. Do we not have or do we have it all a plug motion, and how is that worth? It's a product dependency or a, engineering dependency or it's our tech debt in the CSS department.
Jessica42:22And are we able to retain our customers due to performance, like all of those interdependencies, a lot harder to measure. We have numbers on our side to say, you know, what the end result is, but it can end up in a lot of finger pointing. If you, if you, if you treat those conversations incorrectly. So.
Rachael42:40Yeah. So I wanted to change gears a little bit here. I saw online that in the last year, or brought on two advisors, Bridget Winston and Warren Zina. And these are two very, very awesome people who I've had the pleasure of having some great conversations with in the past right here on this podcast. So what kind of operational changes have they helped guide the company so far?
Jessica43:01I'll take Warren first. Warren is, he's like the Hall of Fame crew coach, right? Like, this is what he does for the job. This year. Well, collective. So, I got so lucky with Warren. I actually met Warren at a roundtable, and I literally. I mean, you're asking how early I just went up to him, and I was like, hey, I love you.
Jessica43:23Can you be my advisor? Like, in a non weird way, like, but yeah, and he agreed to do it and he's a force and he always forces me to think a little bit bigger than, than we are right now. Right. Because it's not very common to have a CRO at this early stage of a company. But it is such an advantage if you can build the foundation in a way that is long lasting, right?
Jessica43:53Making marketing sales and see us all play together as a revenue engine, not as singular, siloed machines that all produce different outcomes. So I think, building the infrastructure from the very bottom or from the very foundation. When I came in and built the first go to market team has been invaluable. And, kind of to your point before, I don't think we've seen all the ROI that will come in in the future years of our collaboration with Warren.
Jessica44:27Also, he's the most incredible referral partner ever. So, if any of you guys ever get introduced to me through Warren, take my goal. But he is the absolute best. Just a treasure trove of information. And he's seen a lot of organizations when he's seen a lot of organizations fail. And he really understands why, from the leadership perspective of the CRO, that that's the case.
Jessica44:52Switching gears a little bit to our beauty queen, Bridget. Like, what can't she do? I really don't know. She is an absolute maniac of a brain to watch it function and to pitch ideas and to understand. She is like my use case for if I'm selling to a CRO. She's the dream CRO to sell to, so I bounce literally every positioning and product market fit.
Jessica45:21Question around her. I watch how she builds and scales organizations. And she's really good at providing just straight up honest feedback. She doesn't cut many corners when it comes to telling you the truth. And, she's absolutely incredible. I've been super blessed. And for those of you out there, I called outreached her. So it's not that it's not completely dead, but, she is incredible.
Jessica45:50And I can't say I mean, thank you to my CEO enough that allows these people to come and advise us because we don't all know everything. And I love having the opportunity for these people to be so invested in our company and want us to win and understand what we're doing and really, like, fall behind the narrative of what we're doing.
Jessica46:16And having them beside us is incredible.
Rachael46:19As awesome as my next question was like, was the impact? And like the value seen from having these guys on board? But I feel like you've answered that perfectly already.
Jessica46:26Like immeasurable. Yeah. And there's so many, many more people that are not officially, our advisors but have advised me along the way and like, really, everybody start building these paths of people who know your job, who know. I mean, I'm lucky because having a CRO as an advisor in our company makes a lot of sense. But maybe if that's not true, like build your network of people that are doing the same thing as you and you can learn from them.
Jessica46:54Like, we we've done a lot of positioning changes and both of those, people in many, many more have been involved in those, you know, advisory capacity and helping us make those shifts as we grow. So, yeah, it's been a lot of fun and also very rewarding.
Rachael47:12Yeah. I don't want to like, pitch our services that much here, but like who? My for people who are just listening our audio. My little hand is up. I'm like yeah, we're advisors too. Yeah yeah.
Rachael47:23So, Jessica, as a first time CRO, you know, responsible for the entire revenue, engine sales, marketing mix. Tell us about a time where in your first year you had to navigate misalignment between departments or like, a breakdown of that connective tissue?
Jessica47:41Yeah, it's funny because I'm sure every, person or sales background person is just giggling in the background saying, when wasn't there a misalignment between marketing sales? And yes, right. Like these are just, it's crazy to think about because almost every organization where I've come in and a little bit later of stages has seen this, right. Like, I'm bringing you warm leads and you're not closing them.
Jessica48:06These leads are crap. Like, that's the you know, he said she said against between marketing and sales. Never more present than in some of my high volume jobs. Right. Like these. It's really, really difficult when you're dealing with leads in sales at scale. I would say the component between sales increase is what did sales sell? And that's not what we have.
Jessica48:31So how did this even get in our laps? It shouldn't have been sold. And I think one of the unique things as being an early stage CRO in charge of all three of those components is I really get to start building the foundation of this is how we work together. Everybody's in charge of the leads. Everybody's in charge of making sure they close.
Jessica48:50Everybody's in charge of making sure that the that customer is successful. It comes back to what we've talked about a lot in this podcast so far, which is ICP, ICP, ICP, ICP. Do we have the right customer coming through all of those things? And then on the other side, what is our messaging and what are we selling, and can we make them successful with what we're selling.
Jessica49:14So those two things together, I actually think I've seen less of it in this job as I have ever before, because we're building it from the foundation. And one person who has seen all of those, you know, and not to say we're perfect, like, for sure, we've favored sales and that has hurt us in success, this year because we needed to show momentum and we need to grow fast.
Jessica49:40But I think we're seeing a lot less of it. And, you know, I've pulled my hair out at certain points in my career dealing with those, friction points before. And I think, you know, Warren's and I previously spoke about he's one of the biggest proponents of this ever, this kind of culmination of, those three positions being held by one person.
Jessica50:03I think we're starting to see the benefits of structuring things that way. Right. And it's not, it's not in every company that this is possible because of various things, but, one we're trying to make possible here to work. But I would say the dissonance between sales and success is probably the most brutal one to face, just because it's you're dealing with a third party involved, right?
Jessica50:28That you have to make that person successful, and you have to make sure you're delivering the right product for what has been sold. So, that that's my take on it. Like, I think it exists everywhere. We're certainly not perfect, but, we're trying to build that foundation really firmly.
Rachael50:48Awesome. Well, we're coming up on time here. Jessica, this has been amazing. And thank you so much. I feel like I learned a lot, some stuff that we'll probably take into our business as well. Also. Well, thank you.
Jessica50:59For having me. I really appreciate it. Yeah.
Rachael51:02All right. And thank you everyone at home for listening.
Jessica51:04Yeah. Thank you guys. Have a great day.
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