This article is based on a discussion between Matthew Darrow and Jarod Greene. You can watch the full conversation and presentation on Youtube.

AI in Sales is a Mandatory Shift

AI adoption is no longer optional. It’s no longer a “nice to have” experiment or a future-state initiative. It’s here. It’s real. And it’s creating a divide between teams who are successfully adapting and those getting left behind.

At Vivun, we’ve spent years thinking about how to operationalize AI inside revenue organizations. We’re not talking about automating call summaries or adding a chatbot to your website. We’re talking about using AI to actually run your sales process — to eliminate friction, accelerate deal velocity, and make every seller perform like your best rep.

Here’s where most teams go sideways: they treat AI like a band-aid, layering point solutions on top of individual problems. One tool for call summaries. Another for forecasting. Something else for pipeline gen. 

It feels like progress, but it creates a mess: disconnected systems, inconsistent workflows, and compounding complexity instead of compounding value. You don’t get smarter over time — you just get noisier. The real unlock comes when AI is applied holistically, across the full sales motion, where it can act with context and deliver outcomes end-to-end.

Easier said than done, though, and no one knows where to start. You need a strategic, phased approach to implementing AI. One that earns trust, delivers outcomes, and scales with confidence.

Here’s our advice for developing a Crawl, Walk, Run strategy for introducing AI sales tools.

Getting Started: Choosing Where to Apply AI

Where you start matters just as much as how. Too many teams make their first move in the obvious zones — outbound, forecasting, support. That’s fine, but it’s not where most of the real friction lives. And it’s not where the revenue is made.

If you want AI to drive impact, start in the mid-funnel, or "messy middle" as we call it, the stretch from first call through customer implementation. It’s where the majority of selling happens: prepping for meetings, building value cases, aligning with stakeholders, running deal strategy, and coordinating handoffs. It’s also where 60% of a rep’s time is spent — and where the buyer experience is won or lost.

Here’s the truth: pipeline volume without velocity is a dead end. You can keep asking Marketing for more leads. You can keep pushing SDRs to book more meetings. But if your team can’t metaphorically eat what’s already on their plate, more pipeline won’t save you — it’ll bury you.

AI should help your reps do the work, not just generate more of it. That’s why the messy middle is the highest-leverage place to start.

Crawl: Start Where You’re Strong

Every sales org has a team that leans into adopting new tools and processes. Maybe it’s your Strategic West team, your enterprise reps in the East, or that one leader who’s always asking for the new thing. That’s your starting point.

The crawl phase isn’t about proving AI works in theory — it’s about proving it works in your reality. Tools that allow a free trial are helpful for these types of tests and evaluations.

The crawl phase builds believers. It creates the internal momentum you’ll need to scale.

Walk: Scale What Works, Don’t Force What Doesn’t

Once your pilot team has momentum, it’s time to bring the rest of the org along — but with intention.

Not every seller is ready to dive in headfirst on AI tooling. Some have never used an LLM. Others are skeptical, resistant, or just heads-down in their number.

That’s fine. Don’t throw the whole thing at them.

Pick one workflow. In Vivun's case, we recommend starting with one AI accelerator that maps to something every rep is accountable for — like a sales handoff, a value case, or a deal review. Something they can touch, see, feel, and use.

We're not setting sellers loose in the ocean before teaching them how to swim. We're helping reps gradually experience what it’s like to have the best digital teammate they’ve ever had — one who already knows their deals, understands their process, and delivers work done at the moment of need.

This is how you normalize AI inside your team. It becomes just how work gets done — not some side experiment.

Run: AI as the Default, Not the Exception

Now you’re ready to scale. "Run" means your entire sales org is using AI to execute across the messy middle — the 60% of the sales journey where deals are won, lost, or stalled.

Every rep is supported. Every deal moves faster. Every prep doc, value case, handoff, and strategy session is powered by AI — and better because of it.

But scale doesn’t mean stacking more tools. The worst thing you can do is build an army of narrow, disconnected point solutions. That’s just complexity disguised as innovation.

What you need is a single AI agent with the brain of an expert — one that understands your motion, operates with full context, and takes action across every deal. One agent, one teammate, delivering real work, not just insight.

This is the future of selling — and the teams who move first will win.

In the words of Matt Darrow, “It’s not about giving your reps more pipeline. It’s about making sure they convert the pipeline they already have.”

What Makes This Work

This strategy works because it’s grounded in how real teams work: You start with the team that wants it. You give them something that matters. You scale to the rest with intention.

At Vivun, we built Ava to do exactly that — to ride alongside every seller, every deal, and every conversation from first call through go-live. Not as a toy. Not as a plugin. But as the teammate they never knew they needed — and now won’t sell without.

Three Things to Remember

1. Choose Tools Strategically: You win (or lose) deals in the messy middle of the sales process. Don’t only chase more pipeline. Select tools that help reps close what’s already in front of them.
2. Understand the Terminology: True AI agents aren’t widgets, chatbots, or copilots. They act without being prompted. They guide with the expertise of a B2B veteran. They transform how work gets done.
3. Don't Wait: The AI race has already started. The longer you wait to learn about this space and its potential to transform buying and selling, the wider the gap becomes between you and early adopters.

Every company will go through a crawl, walk, run journey with AI. The only question is whether you’re the one leading, or catching up.

If you’re ready to get started, we’re ready to help. Take a tour of AI that works for sellers, not the other way around.