I spoke with the manager of a Global 500 IT consulting company about how they use AI. His response: Excel. Not AI Copilot, Monday, or even Jira. This despite the company having spent millions on infrastructure, deterministic models, and on-prem data. Unironically, most startups today have also near-zero long-term adoption. Very few products survive the 1-year mark, and it's because we've become too obsessed with top-down motions (i.e., executives wanting AI) and too disconnected from the end users. We forgot what building for the real customer looks like, not just the financier. Founders, don't gloss over adoption metrics. They're the real thing that tells you whether you have any real success down the line, or get acquired for pennies.

Most people assume the hardest part of enterprise tech sales is the get-rid-of-incumbents part. But that blocker has now been largely solved by AI. Implementations that used to take months now take weeks, if not days. Agents now proactively address technical issues before it ever gets to a solutions engineer. Most of the enterprise SaaS industry recognized this. However, they forgot to look at the other side of the coin: because if buyers are now less concerned about migration, they’ve become increasingly concerned about durability. These are the three main concerns I've heard most frequently: • Will my data remain secure over time (not just today)? • Is the product always going to work as per the demo? • Will the company still be around in 3-5 years? The fact barriers-to-shipping got lower doesn’t take away from the fact businesses want as few problems as they can have. They don’t want to think about the guardrails their vendor's software should already have, or go through another platform migration process a year from now. Speed and ease of migration are not deal-breakers anymore. Certainty (and lack thereof) is.

2025: question the agent. 2026: the agent questions itself. 2027: the agent questions you.

Only two types of tech companies make it into enterprise: 1. Early-stage vendors: those who help define objectives and lead the strategic side of things (i.e., end-to-end implementation partners, consulting companies) 2. Late-stage vendors: those who facilitate execution once strategy has been set (most SaaS platforms are here) The mistake most early AI founders make is trying to be both under a generic, lazy title like "your first digital employee". That worked in 2024, when enterprise was still largely skeptical of AI. That part of the equation has been solved, but the rest of the picture still remains unclear: how do we implement it, build guardrails around it, and have it continuously improve? Founders should aim to solve one piece of the problem, not 13 at once. A great feature will always beat an all-in-1 platform nobody uses fully.

1. you'd never guess my favourite color 2. any advice on how to avoid linkedIn slop is highly appreciated

The thing that puzzles me the most about enterprise AI is how detached most founders are from how organizations work. Everyone is rushing to sell agents, but the average CTO (the one outside the Bay Area) still needs to wrap their head around how to prepare their org for AI. Companies that are clearly winning the AI race (Cognition, Linear, etc) don't just have superior technology, but have embraced the boring work of taking a company through the whole implementation process (and not just the last bit): defining AI use cases worth going after, establishing roles, cadences, guardrails, who touches what, who gets blamed, who doesn't, etc. No wonder founders are not selling shovels. The buyers they're selling to don't even have a place where to store the gold.

Prediction: by 2030, the most contrarian thing a 20-year-old founder can do is actually finish their degree at stanford.

Most B2B SaaS founders treat governance as a sales/marketing buzzword until it shows up as - an intern merging a PR with no auth that breaks other features - marketing getting access to restricted data from finance - an ex-employee jailbreaking into the company’s knowledge base - a customer seeing exposing data from another customer - CRO asking what data the agent used to calculate this quarter’s revenue These are the risks your CIO worries about but the demo doesn’t show, which (later) prevents your pilot from turning into a real contract. Less feature talk, more addressing the elephant in the room.

Don’t see enough tech companies talk about education as a crucial part of selling into enterprise or regulated industries. CIOs / CISOs and other decision-makers know their little box very well, but when it comes to sourcing and selecting vendors, many are being pitched before they have a clear sense of where AI fits into the picture. They hold the strings when it comes to translating business needs into the existing architecture, but they can’t reasonably have eyes everywhere. And as a founder, you're the expert in the room, so you take many things for granted. For someone who’s directly or indirectly managing billions of dollars, having someone who can help bring clarity to the landscape is more valuable than dozens of use cases pasted together. That said, founders don’t really struggle with education. They're natural sellers of their product. Where I see the major roadblock for early-stage tech cos is visibility. That's also something we, at Venatrix, help with. More importantly, the more you hang out in the prospect's industry, the more familiar you become, and the more likely they are to buy. Invest in visibility early. Don't hire a PR agency. Share your own unfiltered thoughts on LinkedIn, email, events, whatever. Your point of view is priceless. It only becomes valuable when it’s out there.

founder: our tool saves your team 10 hours a week CIO: okay. But how do I prove 10 hours saved across 10.000 employees to my CFO? That doesn't reduce headcount and it doesn't show up on P&L. every enterprise buyer is sitting through 5 of these calls each week while CFO asks which licenses to cancel.

Something extremely underrated in today’s tech world: Palantir spent years building custom solutions before turning what they’d learned into a SaaS product. You barely see that today. The prevailing mindset is ship an MVP in a few weeks, find product-market fit, or perish.

founder on a demo: "let's do a 30-day proof of concept to test the tech" CIO / CISO: runs in a sandbox for 4 weeks, pulls the plug because nobody tied it to a line in their P&L.

Watched a founder lose an enterprise deal because nobody inside the company had a personal reason to push it through. Jumped into mid-market after he had strong SMB revenue and retention. Employees made intros, managers were excited, but suddenly everything "fell out of priority". Turns out that when the manager pitched, nobody in the upper ranks was really willing to give up their long-time implementation partner for a newlywed B2B SaaS. "Why would I do it? They deliver on time (most of the time). They're fine" Tech stack wasn't the problem; politics were. This happens in more cos than you think.

I've helped 40+ companies build their GTM since 2023. Almost every time a founder tells me they're "scaling to multiple channels," it's because their first channel isn't converting. Channels don't fix a conversion problem. They just make it harder to find.

I've run the same find-out-what's-wrong playbook across 40 companies' GTM teams. Think of a horror movie: Payback spikes to 24 months, conversion rates stay 0.5-1%, each hire adds a tiny little profit on top before breaking even. And customers churn in less than 3 months. But what surprises me the most isn't how they run GTM. It's that they looked at the numbers and thought "let's just hire more people" instead of doing a hard pivot.

Most founders are selling at less than what they hoped for and only get to grab their piece of the pie after early-investor dilution + co-founder split + taxes. They'll have a 'celebratory dinner' at a Michelin restaurant if they feel like it, then get back to work because the pie only allows for a few years of financial freedom inside major tech hub cities (NYC, SF).

I was on a call with a founding eng of a $3b company that got acquired. 8 months into his new company, and he's talking with investors about raising $5m at a $50m valuation. High multiples. Product & GTM carry 99% of it. - customers coming from 5-6 GTM channels - 2-3 channels are partnership-based - all organic, ramping up on ads soon This is what happens when you build around failure modes early. They didn't bet everything on one channel, and that's the part most founders skip. Speed gets you an angel check. Speed + built-in longevity gets you a real fundraise.

The core logic behind every message that gets replied to always boils down to one thing: relevance. Two ways of becoming relevant asap 1. Stand out (work on something cool, work with big names, work on what they're working on, etc) 2. Get intro'd (proximity still wins, even in the digital age) I can't recall how many times I cold emailed someone and intro'd them to customers or friends. Warm or cold doesn't matter. If it gets you there, it's worth doing.