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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)

GTMnow

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