5YF Episode #36: Clari Co-Founder & CEO Andy Byrne

Future Of Selling: AI Revenue Intelligence

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Today we dive into the future of enterprise sales.

AI isn’t just streamlining the sales process — it’s reshaping who sells, how they sell, and when selling even begins.

In this episode of The 5 Year Frontier, I spoke with Andy Byrne, CEO of Clari, a platform managing over $4 trillion in pipeline for the world’s largest companies. We covered the collapse of manual sales ops, the rise of procurement platforms that match buyers and sellers before contact is made, and how the CRO of the future will orchestrate revenue with a predictive, AI-powered command center.

Take a glimpse into how enterprise sales will work in 2030.

The sales rep is going to go from human to superhuman.

My 5 Year Outlook:

• AI Co-Pilots Will Bring the Human Back to Enterprise Sales: Bringing listening, problem solving, and human connection back into the fold.‍
• Procurement As A Matchmaking Layer: From AI agents to private procurement marketplaces, no sale will start cold.‍
• Revenue Will Flow Will Be Holistic Data System: Money flowing like data and orchestrated by the CRO.

Curious? Read on as I unpack each below 👇🏼

AI Co-Pilots Will Bring the Human Back to Enterprise Sales

The stuff that goes away is the administrative burden… That allows me to do my best work, which is this human-to-human problem solving.

In a world of noisy outbound and overloaded CRMs, the best sales reps will stand out not for their admin skills, but their human touch. As selling becomes more complex, the best reps won’t be the ones who master data entry — but those who double down on the human connection. AI co-pilots will quietly handle CRM updates, pipeline tagging, and deal-stage forecasting in the background, freeing sellers to focus entirely on the buyer relationship.

Clari’s early customers have already cut down manual workflows by automating deal inspection and forecast hygiene, letting reps reclaim time to actually sell. One Fortune 500 customer used AI to flag stale deals in real-time, then automatically route coaching to reps — resulting in a 28% increase in pipeline conversion.

Gartner predicts that by 2026, 65% of B2B sales organizations will transition from intuition-based to data-driven selling, powered by sales tech like Clari’s co-pilots. But ironically, that shift will re-humanize the sales motion, not strip it down.

Andy Byrne CEO of Clari

Clari is the #1 Enterprise Revenue Platform trusted by over 1,500 companies managing more than $4 trillion in revenue. From pipeline to close, renewal to expansion, Clari brings end-to-end visibility, control, and predictability to every revenue-critical function in the enterprise. The company has raised $520 million in funding from top-tier investors including Blackstone, Silver Lake, Sequoia Capital, Bain Capital Ventures, and Sapphire Ventures. Recognized as a 2024 Deloitte Technology Fast 500™ winner and growing at 227% over three years, Clari is leading a movement to modernize how businesses run their revenue process — transforming it from siloed and reactive to unified, intelligent, and data-driven.

Andy Byrne is Clari’s co-founder and CEO. He is a defining voice in the future of revenue operations. A serial entrepreneur and two-time CEO, Clari marks the fourth company he’s helped build with backing from Sequoia Capital — a rare feat that speaks to his track record and long-term vision. Known for being thoughtful, resilient, and a true builder, Byrne has helped scale Clari into a global platform used by the world’s most sophisticated sales and finance teams.

Procurement As A Matchmaking Layer

In the near future, sales cycles won’t begin with a cold email — they’ll begin with mutual intent.

Buyers will proactively opt into platforms like Clari Align or vertical-specific marketplaces, privately registering their tech stack, desired capabilities, KPIs, and timelines — not for public broadcast, but to enable intelligent vendor matching. At the same time, vendors tag their solutions with architecture compatibility, core functionality, and pricing thresholds. Should marketplaces be seen as too direct then AI agents can build such understanding in real time and use their predictive matching as a way to pre-qualify conversations.

“We built Clari Align to bring the buyer into the platform… it’s a collaboration paradigm that allows both sides to map out how we’re going to transact.

Basic alignment — such as “Do we integrate with your ERP?” or “Can we help you hit this retention KPI?” — is handled upfront. From there, AI agents surface qualified matches, vet timing, budget fit, and compliance alignment. What emerges isn’t a pipeline of cold leads — it’s a curated stream of ready-to-engage meetings where both sides already agree on the problem space.

Imagine: instead of reps wasting cycles on misaligned accounts, they walk into buyer conversations focused on co-designing solutions and long-term partnerships. This flips the funnel — from chase-and-convince to match-and-collaborate.

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Revenue Will Flow Will Be Holistic Data System

This is about optimizing the entire revenue rubric.

The modern CRO is evolving from pipeline overseer to AI-powered strategist. In the next five years, revenue leadership will move from spreadsheets and dashboards to dynamic, self-optimizing systems that surface risk and opportunity in real time.

Clari’s 1,500 customers are no longer thinking about sales, CS, and marketing in silos. The CRO of the future will command a full-spectrum view of every revenue stream, cadence, and risk point. Today’s CRO might run a forecast meeting with lagging indicators. But tomorrow’s CRO will run a revenue control room — powered by predictive models that synthesize data from emails, calls, pipeline shifts, and buyer behavior. They’ll ask: Which regions are slipping? Which deals are stalling? Where should our top reps focus next week? And the system will answer.

Clari, for example, already processes over 10 million closed opportunities to surface insights about win patterns and conversion triggers. In five years, this kind of data exhaust won’t just inform strategy — it will run the system. The CRO becomes the conductor of an instrumented, AI-powered revenue engine.

The future of enterprise revenue isn’t just faster — it’s smarter, more connected, and built around alignment from the first touch to final close.

Let the money flow!

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