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Who you’ll learn from

Today marks Aviv Canaani’s 5-year anniversary at Datarails! When he first joined Datarails 5 years ago, the company was 90% outbound, with analysts emailing inbound leads to SDRs once a week. Today it’s 90% inbound, 30x bigger, and has raised a $70M Series C.

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

Episode highlights

0:00 – Cold open: “90% of marketing is noise, be the 1%”

1:29 – Welcome, and joining DataRails after a founder’s $1.5B unicorn

3:19 – Company size at the start: ~50-60 people, a couple million in ARR

4:10 – “Try marketing”: the original vision, brand and paid media

5:45 – From 90% outbound to 90% inbound, and the 2022 crash pivot

7:15 – Why inbound and outbound are one machine

7:50 – The humorous brand play, and a board member’s pushback

8:47 – Where the brand voice came from

10:50 – Cracking Instagram, X, and TikTok in a finance niche

13:02 – How to articulate brand ROI to a CEO and board

14:30 – The time horizon for brand, and zero-KPI brand

16:13 – The four-signal attribution model

16:38 – Taking over sales with no quota-carrying background

18:01 – Promoting from within, and retention as a success marker

19:20 – Why he always cared about the revenue number

20:48 – Why SaaS is moving toward one CRO owning the funnel

23:33 – The other critical GTM moves: offshoring, speeding the funnel

25:22 – Killing their own category to launch the “Finance OS”

26:57 – How Finance OS changes the go-to-market

27:55 – Advice on category creation: be bold, then go all in

29:25 – Hiring: the “biggest accomplishment” question

31:20 – Screening for ownership over blame

33:00 – The AI unlock: automating everything so reps just sell

34:30 – Hiring now: splitting inbound and outbound AEs, and a “wild card” role

36:35 – Finish the sentence: the loneliness of leadership

37:26 – The most underrated startup advice: “you are not Steve Jobs”

38:46 – The best advice he got: you can only change yourself

39:48 – Where to find Aviv

Key takeaways

1. Follow proven founders, then flip outbound to inbound as the scalable engine.

Aviv took the job largely because a co-founder had already built WalkMe, which sold for $1.5B. When he joined, Datarails was 90% outbound, and an analyst literally emailed inbound leads to SDRs once a week. He invested in two things from day one, branding and paid media, and built a system that showed cost per meeting, per opportunity, and per deal. Five years later, it’s 90% inbound. The nuance: after the 2022 crash, outbound still generated as many leads, but they converted worse than inbound, so they doubled down on what worked. Now they’re rebuilding outbound on top of that inbound base. His framing is that it’s not two funnels, it’s one revenue machine. On a recent outbound call, the prospect said “I see your ads all the time.” So he measures every channel on the total cost to close a deal, not cost per meeting.

2. “98% of marketing is noise. Be the 1% people care about.”

Datarails won a notoriously dry niche (FP&A) with a Gong-style brand play: memes and humor so specific they only land for the 0.1% who live the FP&A-vs-accounting in-jokes. Early on, a board member questioned it through the CEO: “You’re selling to serious people, to CFOs. Why are you doing this?” The CEO trusted him. The LinkedIn page now has 67,000 followers, the Instagram account has 55,000+, and the podcast has 600,000+ downloads. His core belief: at a startup, no one cares if you post a bad ad, so take bold creative risks. You’re not just competing with other B2B brands. You’re competing with people’s friends, family, politicians, and comedians in the feed.

3. Prove revenue first, then you earn the right to invest in brand, and don’t over-measure it.

Paid media came first because it shows hard ROI, and reliably hitting pipeline targets is what earned him the latitude to keep investing in podcasts, memes, and thought leadership. Brand is a long-term investment, like a VP of Sales hiring an AE who won’t pay off until next quarter. So he deliberately gives his VP of Brand zero revenue KPIs and measures engagement instead of demo bookings: thousands of likes and hundreds of comments from the ICP. You’d never greenlight a funny meme if you had to attribute pipeline to it. To satisfy skeptics, he checks attribution four ways: HubSpot, an open-form “how did you hear about us?” on the site, the SDR asking live, and mentions in Gong calls. The four often disagree. Someone tagged as “Google” might tell the AE they see Datarails on TikTok all the time.

4. The marketer-to-CRO path works because marketers think in systems, and the whole funnel should have one owner.

Less than two years in, Aviv took over sales. The company had gone half a year without a VP of Sales, and with 90% of revenue coming from inbound, it made sense for one person to own everything from lead to close. About a year later he became CRO, despite never carrying a bag. His edge is a “revenue architecture” waterfall model. He works backward from a target (say, $5M) to deals, opportunities, meetings, and cost per meeting for each channel. Datarails even fills AE calendars so reps don’t prospect. He argues the industry is moving toward one CRO who owns both growth and cost of acquisition. Splitting them creates misalignment: a marketing head who generates pipeline that doesn’t close, and a VP of Sales who just demands more budget. He admits he’s biased toward marketers taking the role. His honest caveat: the hard part isn’t the spreadsheet, it’s that sales is humans, not website conversion rates.

5. Kill your own category when the world shifts, and be relentless about it.

In March, Datarails publicly declared “FP&A software is dead” and relaunched as the Finance Operating System. It’s one place where CFOs consolidate and trust all their financial data, connect AI, and build their own apps. The product now includes month-end close, cash management, a ticketing tool, and corporate cards. The logic: building applications is much easier now, so the market is consolidating toward one trusted hub. His category-creation advice is to be bold, then go all in. Rewrite every website, PR statement, sales deck, and message, and enlist influencers, customers, and employees. Then repeat it until, in his words, “you can’t hear yourself saying it again,” because that’s roughly when it starts to stick.

Aviv Canaani

Sophie Buonassisi (Host)

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GTM 210 Full Episode Transcript

00:00 – 00:02

Sophie Buonassisi: Welcome to GTM now.

00:02 – 00:03

Aviv Canaani: Thanks for having me, Sophie.

00:04 – 00:29

Sophie Buonassisi: 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 30 x. Now, the information has called Datarails the number one startup of the year. You recently announced a funding round of 70 million in January. There is so much momentum around the company and you are currently running go to market as both The Crow and the CMO.

00:29 – 00:38

Sophie Buonassisi: But when you joined around five years ago, you joined his VP of marketing. So take us back to that moment. What was the state of the company when you joined at that point?

00:38 – 00:57

Aviv Canaani: Everything was so different back then. I actually led the marketing at a different startup, and one of the co-founders reached out to me over LinkedIn, called the outreach, said, do you want to talk? Was actually happy where I was, but I looked him up and I saw he already had one unicorn and he built walked me. That was sold for $1.5 billion.

00:58 – 01:23

Aviv Canaani: So I thought, okay, maybe this is the opportunity for a second unicorn for him. So I decided to join Datarails. Back then, the company was really at the very beginning and it was 90% outbound. Just had people like in the office getting on calls all day. Apparently anything inbound. And the CEO and the other co-founders told me, try marketing, see what happens.

01:23 – 01:47

Aviv Canaani: Five years later, the company is now 90% inbound. Like you said, like a recently raised a series C, growing a lot. And yeah, things changed. The whole, you know, environment is different. I can even tell you that when I joined it was 2021. Back in the good old days or the CEO of told me just, you know, start spending my money in marketing, you know, you run out of it like raise more money.

01:47 – 01:49

Aviv Canaani: Very different situation though.

01:50 – 01:54

Sophie Buonassisi: Yeah. Yeah definitely. And then company size. Where were you at at that point?

01:54 – 02:21

Aviv Canaani: Yeah, we were about I think 50 or 60 employees like a couple million or something like in a are really at the very beginning, like it was at the point where I was joining again like leading marketing as a 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.

02:21 – 02:22

Aviv Canaani: It was that backwards back then?

02:22 – 02:39

Sophie Buonassisi: Yeah. Crazy. Okay, so you joined the company. You follow somebody that’s created a unicorn, which there is some good data to support that actually follow the people that have built unicorns before. And it sounds like you were very much so on the right track right now, but you joined to try marketing, like when you joined. What did that mean?

02:39 – 02:41

Sophie Buonassisi: Like, what was the vision for marketing?

02:41 – 03:05

Aviv Canaani: 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 a the playbook from gong, try to create fun, engaging content and on LinkedIn.

03:05 – 03:30

Aviv Canaani: And also we started a podcast which was very niche specific podcast and a financial planning and analysis is as niche as it can get. And in terms of the brand, I can 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?

03:30 – 03:54

Aviv Canaani: Like, you know, you’re selling to serious people to see foes. Why 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. Now, you know, five years later, we have, like, more than 670000, sorry, 67,000 followers on LinkedIn. A very engaging page of with the most engagement like across our industry.

03:54 – 04:15

Aviv Canaani: 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, you know, five years later, that’s 90% of our channels.

04:16 – 04:30

Sophie Buonassisi: That’s incredible. That yeah, that is a huge skew. And when you think about the goal of bound 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 of value.

04:30 – 04:49

Aviv Canaani: So I think we as especially for me like I knew marketing can work. So it wasn’t instead of album. So I had like a great outbound team. We decided to invest in inbound. I think inbound you can scale a 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.

04:49 – 05:09

Aviv Canaani: But then 2022 came. And for those who remember, we had like a tech crash back then and what we noticed 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.

05:09 – 05:31

Aviv Canaani: And now we’re actually like in the past few years, like we’re rebuilding like everything in 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 perpetuity. It’s like the cost for closing a deal. And back then it just made more sense for us to invest in marketing.

05:31 – 05:46

Sophie Buonassisi: Yeah, definitely. And it’s nice when you can scale the inbound motion and then layer on outbound when you want, not out of necessity. Right now you’re hiring this offer Hellbound ease. But it’s taken years because you built on such a strong inbound system, which is incredible.

05:46 – 06:11

Aviv Canaani: Second, I think everything really is interconnected. I think 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, the album calls that bring great opportunities or deals in. And one of the last ones I listen to, you can hear like our outbound is you’re talking to someone and the prospect is saying, oh yeah, I see your ads all the time.

06:11 – 06:19

Aviv Canaani: So you said outbound. Is it inbound? I is it it doesn’t matter. Like it’s, you know, it’s working for the company and we need to keep it going.

06:19 – 06:20

Sophie Buonassisi: It’s revenue.

06:20 – 06:21

Aviv Canaani: Yeah.

06:21 – 06:41

Sophie Buonassisi: 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, good market decisions that have helped your growth. And switching from that crazy percentage was a 90% outbound to 90 inbound.

06:41 – 06:42

Aviv Canaani: Yes.

06:42 – 07:01

Sophie Buonassisi: 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, when you came up with this like more humorous dog, you started posting more memes and stuff. And a board member was like, hey, what’s up?

07:01 – 07:18

Sophie Buonassisi: 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 or tone like, how did you land on that?

07:18 – 07:35

Aviv Canaani: 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, it’s also like some of them was really interesting leadership. But the way I see it, especially like in startup marketing and they used to teach class and and and start marketing is 98% of marketing is just noise.

07:35 – 08:08

Aviv Canaani: 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 trying to be creative.

08:08 – 08:25

Aviv Canaani: And I think it’s 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 that once in a while you find like an ad or a piece of content that really works out and, you know, generate revenue.

08:25 – 08:44

Sophie Buonassisi: I like it, I like it. Usually when you meet 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.

08:44 – 08:54

Sophie Buonassisi: And it’s also so on brand for Datarails. And then I realized it’s because the Datarails brand is simply reflection also of your personality. And now you’ve created it, which is really cool.

08:54 – 09:12

Aviv Canaani: Yeah, I try to push like a LinkedIn as well, like by myself, because back then, like I used to try to do the the memes and the content myself, it’s me. And like, you know, the VP of brand, but now it’s like we are huge company. Yeah, I don’t get to be as involved in the day to day creative work and I miss it.

09:12 – 09:20

Aviv Canaani: So I tend to go to LinkedIn to post things to myself and created myself on my own personal page, just because I can miss that. Creativity part.

09:20 – 09:45

Sophie Buonassisi: Totally, totally. Okay, so you got kind of LinkedIn, Instagram x TikTok. Your 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? Was there any other takeaways for anyone that’s really looking to lean into the specific channels?

09:45 – 10:16

Aviv Canaani: Yeah, it’s just 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 is about internal jokes between the A person and office of the CFO to the controller accounting versus how CFOs view marketing, especially when they ask, you know, to fund podcasts as we’re speaking today.

10:17 – 10:39

Aviv Canaani: So creating that kind of content that really is relevant to that 1% of the population, it’s actually in our case, it’s like the 0.1% of the population that care about it is, I think, what gets a content to work. And 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, it’s fine.

10:39 – 11:01

Aviv Canaani: 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 the space I mentioned. Like the podcast. Yeah. 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 air space as, again, very niche.

11:01 – 11:32

Aviv Canaani: 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 FPA directors or VP’s or CFOs to speak about what really matters for them in their day to day.

11:32 – 11:44

Sophie Buonassisi: And for these brand plays that you ran that clearly have our why. How do you articulate ROI around brand. Like how did you talk to the board. Talk to your CEO and prove this out along the journey.

11:44 – 12:03

Aviv Canaani: Yeah. So I mentioned that when I started investing through 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 it later, how I moved from from VP marketing to VP marketing and sales and eventually Crow. But first of all, you need to show value.

12:03 – 12:25

Aviv Canaani: 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. But 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.

12:25 – 12:45

Aviv Canaani: 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, you know, 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.

12:45 – 13:01

Aviv Canaani: They’re not going to help them now in Q3, but it’s going to help them hit their target in Q4. Same thing with brand. You have to invest in it. It’s a long term investment. It’s not something you’re getting. 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 it.

13:01 – 13:05

Sophie Buonassisi: And for companies thinking about investing in brand like what is it time horizon to anticipate or why?

13:06 – 13:38

Aviv Canaani: I think it’s very hard to put like a number to it. And it’s interesting now as a crow. So I have a different direct reports and they all have numbers associated with them. Like I have a VP of sales of course, and a VP of growth, and it’s 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 breath, because I want to allow them to do cool and fun and engaging content that doesn’t need to be measured with revenue.

13:38 – 13:58

Aviv Canaani: Because again, 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 the demo? And the way I measure it is to see the engagement. If we create content that you see thousands of likes, hundreds of comments from people in your ICP, you know it worked, even if it’s harder to measure.

13:58 – 14:14

Aviv Canaani: And I’m sure there is going to be some skeptics, you know, listening to this podcast. So I will say how I measure it in terms of attribution, we’re looking at four different things. One is the regular marketing attribution software okay, comes from HubSpot. Like, you know, okay, someone came from Google or Facebook or whatnot. We ask on our website.

14:14 – 14:33

Aviv Canaani: How did you hear about us? It’s an open form. No dropdowns like so people can really write about how they heard about us. Then the SDR also asks, how do they hear about us? And we also listen to gong calls to see what they actually mentioned. So sometimes the results on these four different things can be very different.

14:33 – 14:44

Aviv Canaani: Like someone might come from Google, they would say they heard about it from social media or LinkedIn, but only during the conversation with that kind of executives. You might hear something like, oh, I see, or as on TikTok all the time, really.

14:44 – 15:03

Sophie Buonassisi: And so you can really triage the data that you have and get an understanding of where they’re coming from, impressions that they made. But that’s a fantastic framework. Appreciate you sharing that. And, you know, you mentioned that you moved into sales. So less than two years later you were asked to take over the sales function. And then I believe just over a year later you actually got promoted to Crowe.

15:03 – 15:09

Sophie Buonassisi: What was it like coming from this position, running marketing to suddenly take over sales also?

15:09 – 15:34

Aviv Canaani: 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, so one of the co-founders took over it. And I think because of the situation we were in, were 90% of our revenue was coming from inbound. It 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.

15:35 – 15:57

Aviv Canaani: The only problem was then I had no one to blame for not closing my amazing leads. 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.

15:57 – 16:16

Aviv Canaani: I decided to promote one of that. 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.

16:16 – 16:31

Aviv Canaani: I don’t think I’m the best sales person at the company. Very far from it. I never carried a bag myself, but I, I think I was able to find great leaders within the sales department and that were able, you know, to grow with me. And they’re doing a great job now.

16:32 – 16:55

Sophie Buonassisi: That’s amazing. I mean, a lot of leaders will reference at 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 that’s incredible to see that she’s gone on to not lead a team of 25.

16:56 – 17:12

Aviv Canaani: Yeah. Very like we again, we have great people and I think like to to your point, like we have I’m not going to work in a great retention numbers. I think it’s, it’s at the end of the day, it’s all about, you know, the people I can talk here about, like tactics and marketing and sales.

17:12 – 17:30

Aviv Canaani: But, you know, if you hire the right people, everything becomes, easier afterwards. And I think I was lucky enough to find the amazing talent. And, yeah, the most important, roles is just making sure they’re happy and they’re engaged. And, yeah, we have a great team.

17:30 – 17:50

Sophie Buonassisi: 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 Datarails, if you will.

17:50 – 18:06

Aviv Canaani: And so the main thing I always cared about the most was hitting my revenue target. It never made sense to me that in a management meeting, the CEO can ask me, what’s the situation with the pipeline? And I can say, oh, I hit my target and the VP of sales would say, oh, I missed my revenue target.

18:06 – 18:26

Aviv Canaani: I, I always cared about, reaching our revenue target. So it only made sense to me once I took over the crew 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 a building.

18:26 – 18:46

Aviv Canaani: 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 accounting are don’t even prospect.

18:46 – 19:07

Aviv Canaani: We fill their calendar with meetings. So in a way I always had this system in place. It’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.

19:07 – 19:19

Aviv Canaani: And when you really think about it like the first class, you’ve got, like in business school, there’s only one funnel. It’s a marketing sales funnel. It’s not two separate funnels. It’s not that one side can win and the other side could lose.

19:19 – 19:37

Sophie Buonassisi: Very, very, very true. I mean that that’s a huge point. And that’s the benefit of having that role consolidated. I’m sure for yourself, the Crow CMO kind of route, you came up through marketing to run both sales and marketing. Do you think that we’ll see more marketers to give to the role of CRL?

19:37 – 20:01

Aviv Canaani: So in general, I see the world going more towards Coros 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 ahead of sales, one is in charge of the cost of acquisition, the other ones in charge of revenue, it also doesn’t make sense.

20:01 – 20:27

Aviv Canaani: 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 crew in other companies that is in charge of the growth of the company, but also of the cost of acquisition can be separate. You can’t be just a video 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.

20:27 – 20:52

Aviv Canaani: So I think the direction of having more cross, I think makes sense. Someone only marketing and sales management and partnerships. And 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 rev ops. But I am biased. So, the reason I think, you know, marketers can be great at it.

20:52 – 21:11

Aviv Canaani: It’s like I mentioned before because you think in a structural manner, like as a marketer, you’re trying to think about, okay, the cost per lead, what happens with the lead comes in and what form did they need to do, like in the next step of the funnel and the cost per click and then the cost per filling out a form and so forth.

21:11 – 21:28

Aviv Canaani: 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 a more challenging than just, you know, making some changes in a conversion rate on the website. And you have some experience in that as well, right?

21:28 – 21:50

Sophie Buonassisi: 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 one. Very interesting. Now, some recent moves kind of were some early moves that you made in the go to market engine was building out the demand side, through paid odds.

21:50 – 22:03

Sophie Buonassisi: You mentioned building out the brand side through all of 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 warehouse has gone through?

22:03 – 22:29

Aviv Canaani: Yeah. So the main one, like you mentioned, was making marketing the main part of that machine because it’s easy, again, to scale and scale 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 creating even more animations around it, creating like a better experience for clients that enter our funnel less time with us.

22:29 – 22:51

Aviv Canaani: There are more time with that kind of executives. Our sales process is very fast. I think it’s trying to understand, like, everything again, from the first interaction you have with us as a company, when you see our ad to closing the deal and trying to make that as efficient as possible and as fast as possible because people don’t have time, you don’t just see like a meeting on you’re counting with.

22:51 – 23:08

Aviv Canaani: And that’s a week from now, then another meeting with an account executives and so forth. Yeah. So I think there’s a lot of parts like in this, funnel that we try to improve every time. It’s like, you know, 2% here, 5% there. And that’s I think, how, you know, we became more and more efficient, throughout the past few years.

23:08 – 23:33

Sophie Buonassisi: Super interesting. Yeah. You’re treating it, from a highly incremental data driven experimental experiment perspective. It sounds like we’re really tweaking and fine tuning the system that you built, and you have created this kind of revenue system where it is very predictable in the sense you’ve you’ve got the inbound system and then you’ve got the outbound or part of me not outbound, but you’ve got the, the sales team.

23:33 – 23:45

Sophie Buonassisi: Do you think that system, like the predictable revenue system you’ve built, is something other teams can replicate when other companies can replicate? Or is it a little bit unique to your sales cycle, your product?

23:45 – 24:23

Aviv Canaani: Definitely. I think that’s the most important job of a CRO. As a crow, your job is to get a number from the CEO or the board. For example, I’m kind of making up a number, let’s say $5 million, and you can say, okay, this is how I’m going to achieve it. This is the amount of budget I need, which again, doesn’t matter if it goes through paid ads or account executives or stars or, you know, whatever you need, like, to build the funnel and deliver that too, because it’s not just about creating revenues, creating that kind of predictable revenue because it creates trust, again, with the CEO and the board.

24:23 – 24:38

Aviv Canaani: And eventually, once you go to another like investment round, you want to be able to show that, for example, if you’re going to get an investment of another like $100 million, you know what you’re going to do with it. It’s not random. It’s not like we’ll just put a lot of money in the system and hope for the best.

24:38 – 25:07

Sophie Buonassisi: Yeah, yeah, definitely. That makes sense. So switching gears a little bit, in March, your company, your CEO, you published a press release that actually announced your own category that a category as as dead and relaunched finance OS pretty pretty big. It sounds so interesting to come from a company itself denouncing their own category. What happened here and what is finance OS, what was the move and kind of the intention behind that?

25:07 – 25:39

Aviv Canaani: I think it goes back to something I mentioned at the beginning, that 99% of marketing is there’s no 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, as we came to the understanding of everything now happening with AI and the rate of development and what’s possible is that yes, we started as an F and a company, a company that provides a point solution for financial planning and analysis.

25:39 – 26:03

Aviv Canaani: But today. What 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, governance data, and be able to go wild with it and do whatever they want. They can connect it to cloud, ask whatever questions they want, and be able to do more than one thing on it.

26:03 – 26:32

Aviv Canaani: So like last year, we launched a month in Closed solution, a cash management. We just recently launched a a ticketing system called desk and even a 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.

26:32 – 26:42

Aviv Canaani: They can create their own apps on our system. So yeah, we’ve created like this kind of new category that we call the financial operating system.

26:42 – 26:51

Sophie Buonassisi: The financial operating system. Incredible. And how does that change your go to market with the the new shift? What do you have kind of up your sleeve.

26:51 – 27:23

Aviv Canaani: Around that? Yeah. So it’s first of all, updating all of our messaging took a lot of time and a lot of work with the marketing team and the sales team telling them, okay, we’re not a software anymore or something much larger than that. It’s a lot of education and it’s a lot of changing. Old habits. And I think it took some time at 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 or the sales side.

27:23 – 27:40

Aviv Canaani: People are looking for this, full solution for suite for our operating system. But I have to say, it’s hard, like creating a new category and changing mindset. Like, I can’t say it’s an easy feat, but, whether you like it or not, that’s where the world is going.

27:40 – 27:52

Sophie Buonassisi: 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?

27:52 – 28:15

Aviv Canaani: I would say it’s be bold about it. And once you make the statement, go all in. I mentioned that like we had to update all of, you know, 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, you know, of the salespeople, once you go in, you have to fully believe in it.

28:15 – 28:35

Aviv Canaani: You have to create a lot of content to support it. We worked with a lot of influencers in the space and clients so far, 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.

28:35 – 28:47

Aviv Canaani: You have to say it over and over again. I think the saying goes that like once you maybe heard it for the 1000 time and you can’t hear yourself saying it again, maybe then it starts to stick.

28:47 – 29:05

Sophie Buonassisi: Yeah, there we go. Well, we will be hearing a lot more of that from Datarails than until we heard about 1001 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.

29:06 – 29:10

Sophie Buonassisi: How do you identify like the best in breed people to hire?

29:10 – 29:34

Aviv Canaani: 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. For example, like last year, we hired a head of management, was the first account management person in the company.

29:34 – 30:01

Aviv Canaani: And we just have 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 how 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 a manager is maybe remove some blockers, let them go wild.

30:01 – 30:26

Aviv Canaani: And I’m lucky enough to have like a great team of departments at VP’s 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.

30:26 – 30:49

Aviv Canaani: I can’t review now every blog post we do or every sales deck or let’s say every upsell paternity 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 it over more things. I can even get back to like, the part where I led marketing and let me, take over sales.

30:49 – 31:05

Aviv Canaani: Exactly. Because of that, they had great leaders. Reporting to me as a director is another VP’s 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 capacity to now take over something else.

31:05 – 31:11

Sophie Buonassisi: What do you do tangibly like? What is one thing that you do in the hiring process to identify one of those traits?

31:11 – 31:26

Aviv Canaani: So I, I do like a few different things. I want to understand about giving like all the, all the questions I asked, but usually it’s about, I want to understand what’s your biggest accomplishment?

31:27 – 31:27

Sophie Buonassisi: Okay.

31:27 – 31:44

Aviv Canaani: And it’s but I, I always tell them we 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 initiate or someone else just told them to do it, or if something more unique or something obvious that anyone in their role would do it. I want to understand what they like doing.

31:44 – 32:08

Aviv Canaani: They don’t like doing. I want to get a sense of really this kind of ownership mentality they have. And as I mentioned before, I want to see that they can challenge me. And, also, you know, if I ask the 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?

32:08 – 32:32

Aviv Canaani: And it’s interesting that some people would blame the environment. You know, 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. And you can see that they also thought about it. They self-reflect. They always think about, like, how they could have handled something better rather than, like, put the blame on.

32:32 – 32:46

Sophie Buonassisi: Someone else. They’re taking ownership for it too. They’re not pointing to blame. Yeah, that makes sense. That’s fantastic. And now you’re equipping them with AI internally across all your operations. Like what has been one unlock for you on AI internally?

32:46 – 33:09

Aviv Canaani: I think the way we work in the sales team, coming from marketing, I’m used to having everything laid out in 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 him, like update the CRM at this, at that.

33:09 – 33:33

Aviv Canaani: Now, 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 system and 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 demo room called align.

33:33 – 33:58

Aviv Canaani: For all the content, I want to maximize the amount of time that salespeople can be in front of clients, and everything else is automated and updated by I. 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 their clients.

33:58 – 34:07

Aviv Canaani: Also ideas for things they can send them, like everything is trying to support them. AI is trying to support them as much as possible so they can focus just on the southern.

34:07 – 34:15

Sophie Buonassisi: Part that is seller’s dream and you’re hiring. I mentioned earlier on outbound AI. What are some other roles you’re hiring for?

34:15 – 34:34

Aviv Canaani: Yeah, so I’m hiring like several like, 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 album leads, just because the way to sell is so different.

34:34 – 34:56

Aviv Canaani: 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, like we are filling their calendars with meetings. So in many cases it’s back to back to back meetings. It’s hard for executive to try to do something completely different from one meeting to another. And of course, you know the inbound lead that raised their hand.

34:56 – 35:18

Aviv Canaani: That is interesting. That is in the market. It’s a different sales process than an outbound lead. So now we created different teams that only deal with different teams that only deal with inbound. We also created based on like SMB and mid-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.

35:18 – 35:45

Aviv Canaani: So that’s why we’re hiring like different account executives for a different roles, trying to think either than that, like what I’m hiring for. We’re always interested, you know, and and hiring creative, unique talent. So for example, now we’re hiring like a different type of 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.

35:45 – 35:46

Aviv Canaani: I can call it like a wild card.

35:47 – 35:48

Sophie Buonassisi: Yeah. What a fun role.

35:48 – 36:06

Aviv Canaani: Exactly. Yeah. We’re looking for people that know how to take things from 0 to 1. Yeah. And, I think you always need to be open for it. Like, now you actually have a role posted for it. But, you know, if people outreach to me like online and have a creative idea or something that I haven’t thought of and always make like a new role happen.

36:06 – 36:20

Sophie Buonassisi: Oh, brilliant. Well, the careers page will be in the show notes for anyone interested. And if you have got some last questions for you here, help me finish these sentences. The thing nobody tells you about leadership is.

36:20 – 36:37

Aviv Canaani: Is how lonely it can be at times. There is 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 don’t share the same accomplishment or frustrations and you do your own thing. It’s a leader, like, have to own your number.

36:37 – 36:56

Aviv Canaani: You have to get there. It’s not that the you share the same challenges as other sea level executives. It’s not that you can share. Like all the challenges. You know, the CEO 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 mole or a crow.

36:56 – 37:01

Aviv Canaani: And, it’s not easy. But again, I’m not complaining. I love my role.

37:01 – 37:11

Sophie Buonassisi: Yeah. Oh that’s fantastic. That is fantastic. And what is the most underrated piece of startup advice? Underrated.

37:11 – 37:35

Aviv Canaani: You are not Steve Jobs. That’s what I tell every marketer that starts in a startup. Everyone’s looking at the best examples of Apple. But you know, if if you were working in the marketing team at Apple today, not 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.

37:35 – 37:57

Aviv Canaani: People are going to stand in line to buy the new iPhone. Doesn’t matter. Like what changed or what didn’t. But when you start up, no one cares. You spoke about it a bit earlier. It’s you have to be bold. You have to take your risk. You have to do things that are out of the box and risky. And that might have been reasons to fire you.

37:57 – 38:09

Aviv Canaani: 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 things. If not, no one’s gonna care.

38:09 – 38:27

Sophie Buonassisi: I love that rule of thumb that you mentioned. You know, if it would get you fired if you worked at 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.

38:27 – 38:31

Sophie Buonassisi: But what is the best piece of advice that you have gotten and who gave it to you?

38:31 – 38:55

Aviv Canaani: So there is something I got from my executive coach. He was telling me that I can’t change anyone. I can only change myself. I think for everyone listening to this, you know, you might be hearing this interview, listening to other podcasts and you’re saying, okay, what you can or can’t do something and you blame and usually like, you know, your manager, the CEO or other people in your team or colleagues.

38:55 – 39:17

Aviv Canaani: 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, like a game. It’s like, okay, people are who they are. How do I maximize each relationship? How do I create the best situation for me to thrive in and be successful?

39:18 – 39:33

Aviv Canaani: Because again, for everyone listening, you are not going to change other people, especially people, once they get 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.

39:33 – 39:39

Sophie Buonassisi: That is excellent advice. And if you. Where can people follow you and find you if they want to follow along your journey?

39:39 – 39:46

Aviv Canaani: Most active on LinkedIn so you can find me on LinkedIn only and LinkedIn. So would love to connect with you.

39:46 – 39:53

Sophie Buonassisi: That is a very fun fact. It will also be in the show notes for anyone looking at me. Thank you. This has been absolutely fantastic. Appreciate the time and conversation.

39:53 – 39:55

Aviv Canaani: Thank you so much Sophia. I really enjoyed this.