


21 Oct 2026 · 40m · 22 chapters

How DataRails shifted from 90% outbound to 90% inbound, grew 30x in 5 years, and created category leadership by declaring the FP&A category “dead” and relaunching as a “Finance OS” for CFOs. It covers ROI for brand, a four-signal attribution system, marketing-to-sales funnel ownership, and AI/ops automation.
Aviv Canaani, CRO & CMO at DataRails. Joined ~2021 as the first marketing leader (company ~50–60 employees, a few million ARR). Previously led marketing at WalkMe’s founder’s prior startup (WalkMe was sold for $1.5B). Later took over sales, then became CRO; now runs Go-To-Market end-to-end.
“98% of marketing is noise”; focus on the 1% audience. Brand is measured via engagement, not just revenue. One funnel: marketing + sales. Brand investment is enabled only after hitting revenue targets. Bold category creation requires repeating the message everywhere.
LinkedIn memes and a niche FP&A podcast (600k+ downloads); outbound SDR calendar-filling; ROI tracking via cost per meeting/opportunity/deal; AI automates CRM updates and follow-ups; inbound/outbound AE specialization; Finance OS messaging updates and influencer/client/employee amplification.
Written by AI. May contain mistakes.
Learn how DataRails transitioned from 90% outbound to 90% inbound marketing.
“You need to be the 1 % people care about.”
Meet Aviv Canaani, the CRO and CMO of DataRails, as he shares insights on the company's growth.
“Aviv brings down how he proves ROI on brand, the four signal attribution system he swears by, why Data Rails declared its own category dead, and what happened when a marketer took over sales.”
Explore the initial challenges and state of DataRails when Aviv joined.
“We have a lot to dig into because you joined DataRails around five years ago, and the company has since grown 30x.”
Aviv discusses his vision for marketing at DataRails and early strategies.
“in the office, getting on calls all day, barely anything inbound.”
Understand how Aviv gained the CEO's trust to innovate in marketing strategies.
“Okay, so you join the company and you follow somebody that's created a unicorn, which there is some good data to support that actually.”
Discover how humor and creativity became integral to DataRails' branding efforts.
“But it's taken years because you built out such a strong inbound system, which is incredible.”
Learn how DataRails' inbound marketing became crucial for lead generation.
“you've made some really critical go-to-market decisions that have helped your growth.”
Explore how DataRails balances outbound and inbound marketing efforts for success.
“I try to post on LinkedIn as well by myself because back then I used to try to do the memes and the content myself.”
Aviv explains how to articulate the ROI of brand investments to stakeholders.
“or don't understand it or your mom doesn't understand it, it's fine.”
Learn why investing in brand is a long-term strategy vital for growth.
“The way I see it, like after a few years, I mentioned I moved to sales.”
Discover how to measure brand impact and attribution effectively.
“In terms of attribution, we're looking at four different things.”
Explore the challenges Aviv faced while transitioning to CRO from marketing.
“Obviously, for yourself as a leader, but on the revenue function, too, because that retention is so valuable.”
Understand the benefits of having a unified view of marketing and sales.
“It's not that one side can win and the other side could lose.”
Learn about the strategies implemented to create a scalable revenue system.
“I know you have some experience in that as well, right?”
Discover the rationale and strategy behind DataRails' category creation.
“So I think that's a lot of parts like in this funnel that we try to improve every time.”
Learn how to craft impactful messaging to support category creation.
“And how does that change your go-to-market with the new shift?”
Learn the importance of boldness and consistency when creating new market categories.
“or that you would almost give other people advice to who are looking to create new categories?”
Discover how to hire the right people who can take risks and own their responsibilities.
“You mentioned you educated the team on the new messaging.”
Understand how AI can streamline sales processes and increase efficiency.
“I want to understand about, I can give you like all the questions I ask, but usually it's about.”
Explore the necessity of specialization within sales teams for inbound and outbound leads.
“What are some other roles you're hiring for?”
Gain insights on leadership challenges and the importance of taking bold risks in startups.
“And Aviv, I've got some last questions for you here.”
Learn how to focus on personal change to improve relationships and team dynamics.
“You know, if it would get you fired if you worked in a Big Apple, perfect.”

Get the gist, explore an idea or ask about something said.
On The GTMnow Podcast, what are the key points of this episode?
Automatic transcript. May contain errors.
0:0098 % of marketing is just noise. You need to be the 1 % people care about.
0:04Aviv Canaani: Aviv Canaani joined DataRails as its first marketing leader when the company was 90 % outbound. Five years later, it's 90 % inbound. It's grown 30x and he runs GoToMarket as both the CRO and the CMO. The CEO comes to me and says, you know, like one of our board members is asking like, what are you guys posting on LinkedIn? And I told him, trust me, it's going to work. You're competing not only with other B2B brands, you're competing with people's friends, family, politicians, comedians, celebrities. It's fine if 99.9 % of people don't care about it or don't understand it or your mom doesn't understand it.
0:43It's fine. The only person that doesn't have any KPIs that are revenue related is my VP of Red.
0:51Aviv Canaani: Aviv brings down how he proves ROI on brand, the four signal attribution system he swears by, why Data Rails declared its own category dead, and what happened when a marketer took over sales. The only problem was then I had no one to claim for not closing my amazing leads. There's only one funnel, it's a marketing sales funnel. You are not Steve Jobs. You have to do crazy things, if not, no one's going to care.
1:29Aviv Canaani: Abhiv, welcome to GTM Now. Thanks for having me, Sophie. Yeah, thank you. I'm super excited for the conversation. We have a lot to dig into because you joined DataRails around five years ago, and the company has since grown 30x. Now, the information has called DataRails the number one startup of the year. You recently announced a CRO C funding around$70 million in January. There is so much momentum around the company. And you are currently running go-to-market as both the CRO and the CMO. But when you joined around five years ago, you joined as VP of marketing. So take us back to that moment. What was the state of the company when you joined at that point?
2:07Everything was so different back then. I actually led the marketing in a different startup. And one of the co-founders reached out to me over LinkedIn called Outreach. said do you want to talk I was actually happy where I was but I looked him up and I saw he already had one unicorn he built Walkme that was sold for 1.5 billion dollars so I thought okay maybe this is the opportunity for a second unicorn for him so I decided to join Data Rails back then the company was really at the very beginning it was 90 % outbound we just had people like in the office, getting on calls all day, barely anything inbound.
2:45And the CEO and other co-founders told me, try marketing, see what happens. Five years later, the company is now 90 % inbound. Like you said, like recently raised a Series C, growing a lot. And yeah, things changed. The whole environment is different. I can even tell you that when I joined, it was 2021, back in the good days where the CEO told me just you know start spending in my money in marketing you know once you run out of it like we'll raise more money very different situation now yeah yeah
3:20Aviv Canaani: definitely and then company size where were you at at that point yeah we were about I think 50 or 60 employees like a couple million or something like in ARR really at the very beginning like it was at the point where I was joining again like leading marketing as the first marketing leader at the company for the first time, we were at a situation where all the inbound leads we used to get, we would have an analyst send them over email to the SDRs once a week and they would call them back. It was that backwards back then. Yeah, crazy. Okay, so you join the company and you follow somebody that's created a unicorn, which there is some good data to support that actually.
4:00Aviv Canaani: Follow the people that have built unicorns before and it sounds like you are very much so on the right track right now. But you join to try marketing. Like when you joined, what did that mean? Like what was the vision for marketing? Yeah, so when I joined, I had some kind of vision of what I wanted to create. I decided to invest in two different things, which is kind of obvious. When you think about one is branding, the other one was paid media. On the branding side, I tried to take the playbook from Gong, try to create fun, engaging content on LinkedIn. and also we started a podcast which was very niche a specific podcast on fbna financial planning and analysis is as niche as it can get and in terms of the brand i could just say that when we started i did like a funny meme on linkedin again based on like what worked for gong back then and after a few weeks the ceo comes to me and says you know like one of our board members is asking like what are you guys posting on linkedin like you know you're selling to serious people to CFOs.
5:03Why are you doing this? And I told them, trust me, it's going to work. And luckily for me, I had a CEO that trusted me. And now, you know, five years later, we have like more than 60, 70 ,000 dollars, sorry, 60, 70 ,000 followers on LinkedIn, a very engaging page with the most engagement like across our industry. So that's like one side. Now the other side, I started doing paid media. From day one, we were doing Google ads, Facebook ads, LinkedIn ads, and because I wanted to show value. And within a few months, we started seeing deals come in and inbound. And five years later, that's 90 % of our channels.
5:45Aviv Canaani: That's incredible. Yeah, that is a huge skew. And when you think about the goal of outbound versus inbound was that the goal to really shift the outbound to inbound and see how that's a reflection of people's brand recognition and value so i think we as especially for me like i knew marketing could work so it wasn't instead of outbound we still had like a great outbound team we decided to invest in inbound i think inbound you can scale much faster and we started seeing like a lot of leads come in so everything was working great both in terms of inbound as well as outbound but then 2022 came and for those who remember we had like a tech crash back then and what we noticed is that the outbound team was still generating as many leads and opportunities as they used to but they weren't converting to one deals as much as inbound so we decided to double down on inbound especially as a small company you need to double down on what works and now we're actually like in the past few years like we're rebuilding like everything an outbound but i think at the end of the day you need to measure like each channel on the total cost of acquisition so it's not the only the cost per meeting the cost per opportunity the end of the day it's like the cost for closing a deal and back then it just made more sense for us to invest in market yeah definitely and it's nice when you can scale the inbound motion and then later on outbound when you want not out of necessity like right now you're hiring this offer outbound and ease.
7:11Aviv Canaani: But it's taken years because you built out such a strong inbound system, which is incredible. Exactly. I think everything really is interconnected. And sometimes people see it as completely different, like inbound or outbound or partnerships. You can see now that after we build a brand, I listen to some of the calls and outbound calls that bring great opportunities or deals in. And one of the last ones I listened to, you can hear like our outbound is there talking with someone and the prospect is saying, oh yeah, I see your ads all the time. So is it outbound? Is it inbound? It doesn't matter.
7:45Like it's, you know, it's working for the company and we need to keep it going.
7:49Aviv Canaani: It's revenue. Yes, it's revenue. The machine, you can actually just parse it apart. Like it all works together. And that's probably a big part of your role as both CRO and CMO, which we're going to dig into. But along the journey, you've made some really critical go-to-market decisions that have helped your growth. And switching from that crazy percentage It was a 90 % outbound and 90 % inbound? Yes. That's a huge one. So let's dig into a couple areas there that you mentioned before we kind of shift over and look at more of the sales side itself. Some of your creative plays. So the marketing side.
8:24Aviv Canaani: When you came up with this like more humorous style and you started posting more memes and stuff and a board member was like, hey, what's up? And your CEO said, trust us. Like, where did that come from? Is that your brainchild of like, let's make a humorous brand? Or how did you know to go with the humorous, not the educational? Because I think a lot of people are always trying to find their brand identity or like voice or tone. Like, how did you land on that? Yeah. So I have to say, like, it has to maybe also do with like my personality and things that I like. But also, I have to say, it's not only like humorous.
8:56It's also like some of them was really interesting thought leadership. But the way I see it, especially like in startup marketing, and I used to teach a class in adversity and startup marketing is 98 % of marketing is just noise. You need to be the 1 % people care about. So you have to create your ads or content in a way that at least strives to capture people's attention. Especially if you want to advertise on Facebook or Instagram or TikTok, you're competing not only with other B2B brands, you're competing with people's friends, family, politicians comedians celebrities you have to make the content really good and you have to take bold decisions and try to be creative and the thing is it's fine if it fails sometimes because no one cares you're a small little startup no one cares if sometimes you create content that is horrible or like a bad ad all that matters is once in a while you find like an ad or a piece of content that really works out and yeah generate revenue i like it i like it usually when you meet
9:56Aviv Canaani: people you can tell like they've helped to incubate a brand before and it's usually a reflection of their personality or so forth and it's an early stage person like yourself you posted a meme recently about your sales tech that you posted or go-to-market tech and i actually laughed out loud because i was like this is genius and it's also so on brand for data rails and then i realized is because the Data Rails brand is simply a reflection also of your personality and how you created it, which is really cool. Yeah, yeah. I try to post on LinkedIn as well by myself because back then I used to try to do the memes and the content myself.
10:31It's me and the VP of brand, but now it's like we are a huge company. Yeah. I don't get to be as involved in the day-to-day creative work, and I miss it. So I tend to go to LinkedIn to post things to myself and create it myself on my own personal page just because I can miss that creativity part.
10:50Aviv Canaani: Totally, totally. Okay, so you got kind of LinkedIn, Instagram, X, TikTok. Your Instagram, for example, has over 55 ,000 followers today, which is hard when it's an accounting space or a finance space in general. How did you get those channels working? Was it like the humorous style? Wow, is there any other takeaways for anyone that's really looking to lean into the specific channels? Yes, you have to take the risk. You have to find the content that really gets people to care about it. So, for example, some of our memes are as niche as you can get. It's about internal jokes between the FB &A person at the office of the CFO to the controller.
11:35Accounting versus FB &A. how cfos view marketing yeah especially when they ask you know to fund podcasts as we're speaking today um so creating that kind of content that really is relevant to that one percent of the population it's actually in our case it's like the 0.1 percent of the population that care about it is i think what gets uh content to work and it's fine if 99.9 percent of people don't care about it or don't understand it or your mom doesn't understand it, it's fine. You have to really focus on your ICP and create that content. In addition to the humorous stuff we did, we also partnered with thought leaders in this space.
12:17I mentioned like the podcast. So we started investing in a podcast. What was it like almost five years ago? We partnered with one of the leading influencers in the FB &A space. Again, very niche. and we were able to create like a weekly podcast in the space the only one in our industry and again five years later we have more than 600 ,000 downloads of the podcast some people listen to it regularly so that's like high quality thought leadership stuff not memes or humor or anything like that but giving the opportunity for our target audience which are FB &A directors or VPs or CFOs to speak about what really matters for them and their day-to-day.
13:01Aviv Canaani: And for these brand plays that you ran that clearly have ROI, how do you articulate ROI around brand? Like, how did you talk to the board, talk to your CEO, and bring this out along the journey? Yeah. So I mentioned that when I started, I invested in two things, in brand and paid media. It's important to mention that the most important thing is, first of all, to focus on generating revenue. That's, I think, and we can talk about later how I moved from VP marketing to VP marketing and sales and eventually CRO. But first of all, you need to show value. So I started with paid media. I was able to build a system where you could see based on our budget, what's the cost per meeting, cost per opportunity, revenue, and so forth.
13:44But once you are able to hit those numbers on a regular basis with your CEO, then you get the opportunity to invest in brand. You get the opportunity to do some of these cool things because first of all, you're hitting your target. But if you're not hitting your target in terms of generating pipeline, you're never going to be able to do it. The way I see it, like after a few years, I mentioned I moved to sales. The same thing like a VP sales has to hit their target for this quarter. That said, they are still going to focus some of their time in hiring another account executive, training them. They're not going to help them now in Q3, but it's going to help them hit their target in Q4.
14:19Same thing with brand. You have to invest in it. It's a long-term investment. It's not something you're going to necessarily, you're going to see results now, but you just have to do it and you need to decide how much time you want to invest in.
14:30Aviv Canaani: And for companies thinking about investing a brand, like what is the time horizon to anticipate or why? I think it's very hard to put like a number to it. It's interesting now as a CRO, so I have different direct reports and they all have numbers associated with them. Like I have a VP of sales, of course, a VP of growth, and to generate pipeline or head of partnerships and so on. The only person that doesn't have any KPIs that are revenue related is my VP of brand because I want to allow them to do cool and fun and engaging content that doesn't need to be measured with revenue because again, example, again, you would never be able to do a podcast or funny memes or anything like that if you have to check later how many people have booked a demo.
15:15and the way I measure it is to see the engagement. If you create content that you see thousands of likes, hundreds of comments for people in your IACP, you know it worked even if it's harder to measure and I'm sure there's going to be some skeptics listening to this podcast so I will see how I measure it. In terms of attribution, we're looking at four different things. One is the regular marketing attribution software. It comes from HubSpot, like someone came from Google or Facebook or whatnot. we ask on our website how did you hear about us it's an open forum no drop downs like so people can really write about how they heard about us then the sdr also asks how did they hear about us and we also listen to gone calls to see what they actually mentioned so sometimes the results on these four different things can be very different like someone might come from google they would say they heard about it from social media or linkedin but only during the conversation with account And executives, you might hear something like, oh, I see your ads on TikTok all the time.
16:13Aviv Canaani: Brilliant. So you can really triage the data that you have and get an understanding of where they're coming from. What impressions are they made? Well, that's a fantastic framework. I appreciate you sharing that. And, you know, you mentioned that you moved into sales. So less than two years later, you were asked to actually take over the sales function. And then I believe just over a year later, you actually got promoted to CRO. What was it like coming from this position running marketing to suddenly take over sales also? Yeah, I have to admit it was a challenge. We had a situation where for about half a year we didn't have a VP of sales.
16:45So one of the co-founders took over it. And I think because of the situation we were in where 90 % of our revenue was coming from inbound and just made more sense for them to ask me to take over sales. To have one person that sees everything from the lead at the beginning of the funnel to a closed one deal at the end. the only problem wasn't then i had no one to claim for not closing my amazing leads yeah and but then as i had a sales i can't blame marketing for all these crappy leads they send us and it took time to learn it and gain the trust of the team when i took over i was very quickly like managing a team of six account executives myself i decided to promote one of the account executives to be a team lead was her first management role ever and now a few years later now she's our VP of sales managing more than 25 people also promoted a few other people like as team leads and I think at the end of the day it's as a leader you're not going to know everything I don't think I'm the best salesperson at the company very far from it I never carried a bag myself but I think I was able to find great leaders within the sales department and that were able you know to grow with me and And they're doing a great job now.
18:01Aviv Canaani: That's amazing. I mean, a lot of leaders will reference retention, number one, of employees, but then also the ability for employees and teammates to be promoted within a company is like a true marker of success. Obviously, for yourself as a leader, but on the revenue function, too, because that retention is so valuable. So it's incredible to see that she's gone on to now lead a team of 25. Yeah. Very. Yeah, like we, again, we have great people. And I think like to your point, like we have, I'm not going to work with great retention numbers. I think it's, at the end of the day, it's all about, you know, the people I can talk to you about, like tactics and marketing and sales.
18:42But, you know, if you hire the right people, everything becomes easier afterwards. And I think I was lucky enough to find amazing talent. and yeah, the most important role is just making sure they're happy and they're engaged and yeah, we have great team.
19:00Aviv Canaani: That is awesome. You know, you mentioned there were some challenges at first when you started taking over sales naturally and just any transition in general plus adjusting to the sales function but how did you adapt throughout taking over sales to then CRO having never kind of carried a quota before Data Rails, if you will? And so the main thing I always cared about the most was hitting my revenue target. It never made sense to me that in the management meeting, the CEO could ask me, what's the situation with the pipeline? I could say, oh, I hit my target. And the VP of sales would say, oh, I missed my revenue target.
19:36I always cared about reaching our revenue target. So it only made sense to me once I took over the CRO role. But also beforehand, when I was leading marketing and the way I built it was a waterfall model where we were able to understand, especially in paid media, the cost and the cost of acquisition of building this kind of framework, understanding, for example, if you have a specific number you need to hit, let's say$5 million, I understood, okay, how many deals I need to bring based on that, how many opportunities, how many meetings, what's the cost per meeting for each one of the channels. We have also a very unique model where our account executives don't even prospect.
20:15We fill their calendar with meetings so in a way i always had this system in place that's kind of revenue architecture so now it was just about like stepping into sales working with the team seeing how we can improve the conversion rates but at the end of the day i always was thinking about everything as a revenue machine and when you really think about it like the first class you get like in business school there's only one funnel it's a marketing sales funnel it's not two separate files. It's not that one side can win and the other side could lose.
20:48Aviv Canaani: Very, very, very true. I mean, that's a huge point and that's the benefit of having that role consolidated, I'm sure, for yourself. The CRO-CMO kind of route, you came up through marketing to run both sales and marketing. Do you think that we'll see more marketers taking over the role of CRO? So in general, I see the SaaS world going more towards CROs to have one person that owns the whole funnel, like I mentioned before. And I would add to the point I made earlier that if in the past you had like a head of marketing, a head of sales, one is in charge of the cost of acquisition, the other one's in charge of revenue.
21:29it also doesn't make sense it's more challenging i think for the ceo because you want to be able to speak with one person in that case it's me and my company or every ceo and other companies that is in charge of both the growth of the company but also of the cost of acquisition can't be separate you can't be just a vp of sales just demanding more and more and more budget or ahead of marketing just creating a lot of pipeline that doesn't necessarily generate revenue. So I think the direction of having more CROs, I think, makes sense. Someone owning marketing and sales, and I guess also account management and partnerships.
22:06And I think there can be people that come from it from different backgrounds, from sales, marketing. Even I heard of some people coming to that role from RevOps. But I am biased. So the reason I think marketers can be great at it is like I mentioned before, because you think in a structural manner like as a marketer you're trained to think about okay the cost per lead what happens with the lead comes in uh what form do they need to do like in the next step of the funnel and the cost per like click and then the cost for filling out a form and so forth and you understand that even the sales part at the end of the funnel is another part of that machine the only problem is it's actually human beings that you work with it's uh more challenging than just making some changes and a conversion rate on the website.
22:56I know you have some experience in that as well, right?
22:58Aviv Canaani: Yeah, definitely. It certainly becomes a lot more complicated when you stitch it together. But to your point, that's probably why it is the most paramount to actually have that consolidated in one. Very interesting. Now, some recent moves kind of, or some early moves that you made in the go-to-market engine was building out the demand side through paid ads you mentioned, building out the brand side throughout your social work, podcast work. What were some other critical go-to-market moves that you've made in the past five years that have really accounted for this incredible growth that Data Rails has gone through?
23:33Yeah, so the main one, like you mentioned, was making marketing the main part of that machine because it's easy, again, to scale and descale as needed. Also, one of the things we did was move all of our inbound SDR team to the Philippines to make everything more efficient. and now we're starting creating even more automation around it, creating a better experience for clients that enter our funnel. Less time with the SDRs, more time with the account executives. Our sales process is very fast. I think it's trying to understand everything, again, from the first interaction you have with us as a company when you see our ad to closing a deal and trying to make that as efficient as possible and as fast as possible because people today don't have time.
24:17You don't want to just see like a meeting on your account with an SDR a week from now, then another meeting with an account executives and so forth. Yeah. So I think that's a lot of parts like in this funnel that we try to improve every time. It's like 2 % a year, 5 % there. And that's, I think, how, you know, we became more and more efficient throughout the past few years.
24:38Aviv Canaani: Super interesting. You're treating it from a highly incremental data-driven experimental perspective, it sounds like, where you're really tweaking and fine-tuning the system that you've built. And you have created this kind of revenue system where it is very predictable, in a sense. So switching gears a little bit, in March, your company, your CEO, you published a press release that actually announced your own category, the FP &A category, as dead and relaunched Finance OS. Pretty big. It sounds so interesting to come from a company itself denouncing their own category. What happened here and what is Finance OS?
25:19Aviv Canaani: What was the move and kind of the intention behind that? I think it goes back to something I mentioned at the beginning, that 99 % of marketing is this noise, and you need to make bold statements. And that's something the CEO of DataRails and I worked on, together, of course, with our amazing marketing team. We came to the understanding, with everything now happening with AI and the rate of development and what's possible, is that yes we started as an fbna company a company that provides a point solution for financial planning and analysis but today what cfos are looking for is one operating system where they can trust the data at one place where they can consolidate all the data have all the financial data in one place govern data and be able to go wild with it and do whatever they want They can connect it to Claude, ask whatever questions they want, and be able to do more than one thing on it.
26:18So like last year, we launched a month-in-close solution, cash management. We just recently launched a ticketing system called Desk, and even corporate cards and so forth. And I think the world is going towards more consolidation because creating applications is much easier than it used to be. So we want to be the one place where CFOs go to to work with their data and do whatever they want with it. They can even create their own apps on our system. So, yeah, we create this kind of new category that we call the financial operating system.
26:57Aviv Canaani: The financial operating system. Incredible. And how does that change your go-to-market with the new shift? What do you have kind of up your sleeve around? Yeah, so it's, first of all, updating all of our messaging. It took a lot of time and a lot of work with the marketing team and the sales team telling them, okay, we're not an FP &A software anymore. We're something much larger than that. It's a lot of education. It's a lot of changing old habits. And I think it took some time in the beginning, but I think we recently really got to a point where it's really sticking and it's working and we're seeing better numbers in terms of our conversion rates, whether it's in the marketing side.
27:36or the sales side. People are looking for this full solution, full suite for an operating system. But I have to say it's hard. Like creating a new category and changing mindset, like I can say it's an easy feat, but whether you like it or not, that's where the world is going.
27:55Aviv Canaani: Is there a playbook or any advice that you've picked up from other companies that have really leaned into category creation that you're trying to emulate or that you would almost give other people advice to who are looking to create new categories? I would say just be bold about it. And once you make the statement, go all in. I mentioned that we had to update all of the messages across all the different websites and what kind of company we are and all of our PR statements and all of our messaging and slides of salespeople. Once you go in, you have to fully believe in it. You have to create a lot of content to support it.
28:32We worked with a lot of influencers in the space and clients of ours and employees to really share that message across. Because especially I think in marketing, it's not something you can just do one time and hope that all of a sudden, you know, you create like a new category and everyone's going to start searching for it. You have to say it over and over again. I think the saying goes that like once you maybe heard it for the 1000th time and you can hear yourself saying it again, maybe then it started to stick.
29:02Aviv Canaani: Yeah, there we go. Well, we will be hearing a lot more of that from DataRails then until we hear it about a thousand and one plus times. Let's talk about the team a little bit. You mentioned you educated the team on the new messaging. Prior to that, earlier in the conversation that you mentioned, it really comes down to hiring phenomenal humans. How do you identify like the best in breed people to hire? So I don't think there's like one way to do it. There's not one kind of persona that works. I'm looking for people that are smart, that are hungry, that are not afraid to take risks, people who have great ownership mentality.
29:43For example, at Classy, we hired a head of account management. He was the first account management person in the company. We just had customer success beforehand. And with little guidance, he was able to completely change our track in terms of upsells and generating more value to our clients. And now he manages a team of seven people. and it's you want to hire the type of people that run fast that all you need to do as their manager is maybe remove some blockers let them go wild and i'm lucky enough to have like a great team of departments at vps that are able to do it and i think that it sounds easy or obvious for you know the listeners but i think as a leader it's the ability to step away at times and understand you're not going to make all the decisions and you're not going to be in all the details i can't review now every blog post we do or every sales deck or let's say every upsell opportunity we have you have to allow them to do it because once you have the team that can do it then you get the opportunity to take over more things i can even get back to like the part where i led marketing and let me and take over sales exactly because of that i had great leaders reported to me as the directors and their vps that were able to really run the marketing department and it was able to convince you know the ceo and the co-founders i have the
31:18Aviv Canaani: capacity to now take over something else what do you do tangibly like what is one thing that you do in the hiring process to identify one of those traits? So I do like a few different things. I want to understand about, I can give you like all the questions I ask, but usually it's about. Please. I want to understand what's your biggest accomplishment. Okay. But I always tell them they have to pick one thing and it's interesting to see what they pick and then I try to dissect and understand if it's something they initiated or someone else just told them to do it. or it's something more unique or something obvious that anyone in their role would do it.
31:57I want to understand what they like doing, what they don't like doing. I want to get a sense of really this kind of ownership mentality they have. As I mentioned before, I want to see that they can challenge me. And also, you know, if I ask a question about something that didn't work for them, I always try to push back a bit and ask them, what would you do differently? And it's interesting that some people would blame the environment. They would blame the client, the manager, the colleagues that something didn't work. I think the best candidates are the people that say that they know what they would do differently.
32:40And you can see that they also thought about it. They self-reflect. They always think about how they could have handled something better rather than to put the blame on something else.
32:48Aviv Canaani: Yeah, and they're taking ownership for it too. They're not going to be the blame. Yeah. That makes sense. That's fantastic. And now you're equipping them with AI internally across all your operations. What has been one unlock for you on AI internally? I think the way we work in the sales team, coming from marketing, I'm used to having everything laid out in an operational way. like I mentioned before, you know exactly how much revenue came from each campaign and what worked and what didn't. And it was very hard for me at the beginning of sales that I had to convince them, like update the CRM, add this, add that.
33:24Now, a few years later, rather than just, you know, pushing on them and trying to convince them to do stuff, my decision was to try to get them to do as little as possible. I try to automate everything, like we use different systems, like Momentum and Chili Pepper and others to make sure that all they have to do is just show up for meetings follow up of course you know with clients we even use a demo room called a line for all the content i want to maximize the amount of time that sales people can be in front of clients and everything else is automated and updated by ai it's the follow-up emails it's like i mentioned the demo rooms we create we also create like all these insights for them and like after meetings like what worked what didn't like what are the different challenges you know they're facing with clients, also ideas for things they can send them.
34:16Everything is trying to support them. AI is trying to support them as much as possible so they can focus just on the selling part.
34:22Aviv Canaani: That is a seller's dream. And you're hiring, I mentioned earlier, an outbound AE. What are some other roles you're hiring for? Yeah, so I'm hiring several outbound account executives. It's actually interesting. You're talking about the playbook and what changed earlier. So one of the things we came to the understanding only this year is that I want to separate between the A's that take on inbound leads and outbound leads, just because the way to sell it is so different. And again, I see it as a machine, so they might have like different quotas and targets, but it has to work in different systems.
34:56Like I mentioned, we are filling their calendars with meetings. So in many cases, it's back to back to back meetings. It's hard for a different from one meeting to another and of course you know the inbound lead that raised their hand that is interesting that is in market it's a different sales process than an outbound lead so now we create different teams that only deal with outbound different teams that only deal with inbound we also create based on like smp admin market and up market like different teams there but i think it's creating that kind of specialization for each one of those team members so that's why we're hiring like different account executives for uh different roles trying to think other than that like what i'm hiring for we're always interested you know on hiring creative unique talent so for example now we're hiring like a different type of like growth director that's gonna try to just do unique and different things that are not obvious out of the regular you know day-to-day stuff you could call it like a wild card yeah what a fun
36:03Aviv Canaani: Exactly. We're looking for people to know how to take things from zero to one. Yeah. And I think you always need to be open for it. Like now we actually have a role posted for it. But, you know, if people have reached me like online and have a creative idea or something I haven't thought of, you know, let's make like a new role happen. Oh, brilliant. Well, the careers page will be in the show notes for anyone interested. And Aviv, I've got some last questions for you here. Help me finish these sentences. this the thing nobody tells you about leadership is that's how lonely it can be at times there's so much going on so many things you have to solve and it's not like you know when i was a team of like many different marketers like you all share the same accomplishment or frustrations and you do your own thing as a leader like you have to only remember you have to get there it's not that you share the same challenges as the other c-level executives it's not that you can share like all the challenges you know the ceo i always try to be like as open as possible with my colleagues my team my ceo but there is a lot of pressure associated with being like a cmo or a cro and it's not easy but again i'm not complaining i love my role yeah oh that's fantastic that is fantastic and what is the most underrated piece of startup advice underrated you are not steve jobs That's what I tell every marketer that starts in a startup.
37:32Everyone's looking at the best examples of Apple. But if you're working in the marketing team at Apple today, like when Apple started, you have a team of hundreds of people working on every ad, every line of messaging, whatever they announce. It doesn't matter. People are going to stand in line to buy the new iPhone. It doesn't matter what changed or what didn't. but when you're a startup no one cares we spoke about it a bit earlier it's you have to be bold you have to take huge risks you have to do things that are out of the box and risky and that might have been reasons to fire you if you were working for an apple or like a samsung or any company like that so you will have to be bold like you have to do crazy uh things if not no one's gonna care
38:24Aviv Canaani: I love that rule of thumb that you mentioned. You know, if it would get you fired if you worked in a Big Apple, perfect. It's a good thing because at the end of the day, they are such an outlier statistically. You're right. It's hard to emulate that. Brilliant. And any context doesn't have to be go-to-market, could be go-to-market. But what is the best piece of advice that you have gotten and who gave it to you? So there is something I got from my executive coach. He was telling me that I can't change anyone. can only change myself i think for everyone listening to this you know you might be hearing this interview or listening to other podcasts and you're saying okay well you can or can't do something and you blame usually like you know your manager the ceo or other people on your team or colleagues and i think the better way to look at everything and position it is in a way it's like okay everyone is as they are how do i get the most out of it like thinking about it like a game it's Like, oh, if people are who they are, how do I maximize each relationship?
39:26How do I create the best situation for me to thrive in and be successful? Because I guess for everyone listening, you're not going to change other people, especially people once they get in a certain age. Like, people don't change. Like, from my experience, people don't change at all. So embrace it. Just think about how you can change yourself and adapt to the different situations you face.
39:48Aviv Canaani: That is excellent advice. and Aviv, where can people follow you and find you if they want to follow them on your journey? Most active on LinkedIn. So you can find me on LinkedIn. I'm the only Aviv Karani on LinkedIn. So I would love to connect with you. That is a very fun fact. It will also be in the show notes for anyone looking. Aviv, thank you. This has been absolutely fantastic. Appreciate the time and conversation. Thank you so much, Sophie. I really enjoyed this.
Today marks Aviv Canaani’s 5-year anniversary at Datarails! When he first joined Datarails five years ago, the company was 90% outbound, with analysts emailing inbound leads to SDRs once a week. Today it’s 90% inbound, 30x bigger, $70M Series C, and The Information named it the #1 startup of the year.
Transcript:
Full interview transcripts can be found by episode at https://gtmnow.com/tag/podcast/
What you’ll learn:
- How Datarails flipped from 90% outbound to 90% inbound, and why they doubled down on inbound after the 2022 crash
- The Gong-inspired brand playbook: why “98% of marketing is noise” and how to be the 1% people care about
- Why niche memes for 0.1% of the market work (FP&A vs. accounting in-jokes)
- How to prove brand ROI: the four-way attribution model (HubSpot, open-form website question, SDR ask, Gong calls)
- Why his VP of Brand is the only report with no revenue KPIs, and how he measures brand instead (engagement from the ICP)
- The marketer-to-CRO path, and why he thinks one person owning the whole funnel is the future
- The “revenue architecture” waterfall model: working backward from a number to channels, meetings, and cost
- Why they killed their own category and relaunched as a “Finance OS,” and how to pull off category creation
- How he hires: the “biggest accomplishment” question, and screening for ownership over blame
- Why he automates everything in sales so reps only show up, follow up, and sell
Aviv Canaani, CRO, Datarails
LinkedIn: https://www.linkedin.com/in/avivcanaani
Datarails' website: https://www.datarails.com/
Datarails' career page: https://www.datarails.com/company/careers/
Sophie Buonassisi, Partner at GTMfund
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona
About the guest: Aviv Canaani is the CRO and CMO of Datarails, an FP&A platform the company now positions as a “Finance OS.” He joined roughly five years ago as its first marketing leader (VP of Marketing), later took over sales, and was promoted to CRO, overseeing the full revenue funnel across marketing, sales, growth, and partnerships. Under his tenure Datarails grew about 30x and was named a top startup of the year by The Information.
About GTMnow: The media brand, GTMnow, shares how the best companies get built, told from every perspective: founders, operators and investors, at every stage of company building. GTMnow is owned and operated by VC firm, GTMfund.
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The GTMnow Podcast
The GTMnow Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
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