A Guide for Sales Leaders

How We're Building an AI-First Sales Team

"January 2026. I stared at a terminal for the first time in my career and genuinely had no idea what I was looking at."

I have been building and leading sales teams for 18 years. Three exits. I have sold to CIOs at Fortune 500 companies and sold a blockchain developer platform to crypto anons via Telegram. I have been uncomfortable before. This was different.

Miles Kane
VP Revenue, DataLane
April 2026
Miles Kane
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If you are a sales leader reading this and feeling like you are behind on AI, I want you to hear this clearly: you are not behind. You are exactly where almost everyone is.

The difference between the people who figure this out and the people who do not is not technical skill. It is willingness to check your ego at the door and adopt a beginner's mind.

Here is exactly how we did it at DataLane. Step by step. So you can take this to your team this afternoon.

1
Step 1
Find Your Nick

You do not need to become a developer. You need to find the tech-curious person who already works at your company. Every org has one. The RevOps person who builds automations for fun. The BizOps analyst who taught themselves SQL. The AE who is always the first to try new tools.

At DataLane that person is Nick. He is our Marketing Lead who operates as a quasi RevOps Lead in his spare time, and the reason any of this works. I did not build our agents. Nick did. What I did was show up with the use cases, the priorities, and the willingness to sit in the tool with him and learn.

Your First Action Item
Your first action item is not to open a terminal. It is to walk over to your Nick and say: "I want to try something this week. Can you help me get set up?" That conversation is the unlock. Everything else follows.
2
Step 2
Get Through the Awkward Part

The setup is real. You are going to connect to GitHub. You are going to open a terminal. You are going to feel like you are back in school learning something for the first time. That feeling lasts about two days.

Your Nick handles the initial wiring. Getting Claude Code installed. Connecting it to your systems. This is not a six month IT project. This is an afternoon. Once the environment is set up, you are going to open Claude Code, type a question in plain English, and get back something that makes your jaw drop.

Your Team's AI Workspace
your-team/
    skills/← reusable agents the whole team runs
    branding/← templates, logos, voice guidelines
    accounts/← shared deal intel, call notes, research
    workspaces/
        miles/← my corner of the workspace
        nick/← Nick's corner
        new-ae/← onboard a new rep in minutes
Think of it like a shared drive, but one that your agents can read and act on. When your CEO posts call notes to the accounts folder, your agents pick that up and start working. When a new AE joins, they get their own workspace and inherit every skill the team has already built.
The Moment It Clicks
Mine was asking Claude to research an account I had a call with the next day. In 30 seconds I had a company snapshot, recent news, key contacts, and suggested discovery questions. I had been spending 30 minutes doing that manually before every call for nearly two decades.

The trick is not to overthink the prompting. Talk to Claude like you would talk to a sharp colleague. Say something like "act like a top tier prompt engineer and help me come up with the best prompt for this — here is what I am trying to achieve." Let Claude help you write the prompt. Then plug that into Claude Code as a repeatable skill. You are not writing code. You are having a conversation that turns into automation.

3
Step 3
Go Claude-First on Everything

This is the real mindset shift. Before you start any task, ask yourself: "Can Claude do this for me?"

Prepping for a call. Drafting a follow-up email. Building an account plan. Researching a prospect. Updating your CRM notes. Writing a business case. The answer is almost always yes.

The Key Insight
Stop thinking about Claude as something you occasionally query and start treating it as your central operating system. It is a fundamental change in how you operate day-to-day. Every email, every account plan, every prep session — Claude should be in the loop.

Instead of slides, build polished microsites for customers — the kind of thing that would cost hundreds of thousands to produce otherwise, built in five minutes. Auto-draft email responses. Generate account plans across 5 accounts simultaneously. Run forecasting so your manager never has to ping for updates. For knowledge workers who find the terminal intimidating, Cowork offers essentially the same power as Claude Code but with a friendlier UI.

4
Step 4
Connect Your Systems

Claude is only as smart as the data you give it. This is where your Nick comes in again. Connect your CRM. Connect your email. Connect your call recordings. Connect your calendar. Once Claude has access to all of your data, it stops being a tool you query and starts being an operating system you run your business on.

HubSpot
Grain
Gmail
Slack
Calendar
Mixpanel

Now when a rep finishes a prospect call, Claude has the transcript, the deal context, the contact history, and the account research all in one place. It drafts the follow-up email before they are off the call. It updates the CRM without anyone asking. It reviews the call, flags what was uncovered and what was missed, and posts a coaching summary to Slack so I have real-time visibility into where my reps need help — without scheduling a debrief. Forecasting rolls up automatically. No more pinging reps for updates.

That is not a productivity hack. That is a fundamentally different way of operating.

5
Step 5
Build Your First Two Agents

Start with these. They are the fastest to build and the easiest to feel. Both solve pain your reps feel every single day. And both build the trust your team needs before you start automating the harder stuff.

1
Meeting Prep Agent
Before every call, it generates a pre-call brief. Company snapshot. Why now. Contact intel. Suggested discovery questions. Your reps stop spending 30 minutes scrambling before calls. They show up sharp every time.
Time Saved
25-30 min per call
Build Time
1 day
Why First
Immediate value. Gets the team bought in.
2
Follow-Up Email Agent
The call ends and a draft is waiting. It pulls from the call transcript and CRM context. References what was actually discussed. Restates next steps. Your rep reviews it, makes a few edits, and sends. What used to take 20 minutes now takes 2.
Time Saved
15-20 min per call
Build Time
1 afternoon
Why Second
Speed to follow-up converts meetings.
What Happens Next
You Won't Go Back
1w

After one week

Someone on your team is going to come to you and say "I built something you did not ask for." That is how you know it is working.

1m

After one month

You are going to look at how your team operated before and it is going to feel like a different era. The same way you look back at selling before Salesforce, before LinkedIn, before Gong.

1y

A year from now

An AE somewhere is going to close a deal they never could have closed alone. Their quota is going to be twice what it is today. And nobody is going to call it AI-assisted selling. They are just going to call it Thursday.

The companies that win in GTM over the next two years are not the ones with the best AI tools. They are the ones where the entire team operates differently because of AI.

Ready to get started?

I'm sharing how we build these agents in real time. Happy to walk you through the setup or just jam on what's possible.

Connect with Miles on LinkedIn Visit datalane.com