The 4 Skills That Accelerate AI Adoption

Most companies have one. You need all four.

Jason Lemkin has done something rare in B2B: he's documented his entire AI transformation in public.

In blog posts, podcasts, and events, he's shared what it took to go from 10 salespeople to one AE plus 20 AI agents, same revenue. The wins. The failures. The 15-20 hours of weekly oversight. The 90 days of daily training. For anyone trying to figure out AI in sales, it's been a masterclass.

So when he says:

"The agencies don't know how to do this. You've got to do it yourself."

It's worth taking seriously.(That quote, and most of what follows, comes from his conversation with Lenny Rachitsky.)

But Lemkin is actually a rare case. He had the time, the inclination, and the capability to go deep. He has a Chief AI Officer spending 20-30% of her time on agent orchestration. He personally invested hundreds of hours learning the technology.

Most sales leaders don't have that runway. And if they take his advice at face value, they won't become Jason Lemkin. They'll stall, because the skills required by AI transformation barely exist in the market.

AI sales transformation isn't one skill. It's four capabilities that rarely exist in one person, or even one team.

1. Sales Expertise Methodologies like SPICED and MEDDPICC. Sales messaging and objection handling. Process design and optimization. Metrics analysis and interpretation.

This is what agencies and fractional leaders do all day. It's literally the job. The best ones have seen dozens of sales orgs, know what good looks like across industries, and can pattern-match faster than someone seeing it for the first time.

2. Company Context Your ICP. Your internal processes. Your competitive positioning. The institutional knowledge that lives in the heads of your product marketers, your customer success team, your top reps.

I'll grant this one. Internal teams should know themselves better than any outsider.

But here's what I've found: that knowledge is fragmented. Product marketing has one view. CS has another. Sales has a third. Someone has to synthesize it. And sometimes an outsider asking dumb questions gets to the real answer faster than insiders who've been too close to it for too long.

3. AI & Technology The technology itself. Prompting. Workflow design. Automation tools like Clay, n8n, Make. Integration architecture. Knowing what's possible and what's a waste of time.

Where is this person in your org? Maybe you have a GTM engineer. Maybe an automation specialist. Maybe a RevOps person who taught themselves.

More likely, you don't. More on this in a minute.

4. Change Management Training. Coaching. Designing the rollout. Governance. The people side of making technology actually stick.

This is a mix of internal knowledge and best-practice expertise. You need buy-in from your team (that's internal). But knowing how to drive adoption? That's learned through reps across multiple transformations.

How many internal trainers does your sales org have on staff? How much change management expertise is sitting around waiting to be deployed?

Lemkin's implicit argument is: build all four internally.

If you can do that, congratulations. You're the exception.

Here's the market reality.

AI transformation leadership is hard to find. Chief AI Officer searches now take 7-9 months on average, up from 4-5 months in 2023. About 70% of companies report senior AI roles stay unfilled for more than 90 days.

GTM engineers are even harder. Average time-to-hire is 120-150 days. Only 1-2% of candidates have both the technical depth and business acumen required. One founder reported receiving 200+ applications over six weeks with zero qualified candidates.

The compensation cost is steep. GTM engineers at top companies command $175K-$250K+. Vercel pays $252K. OpenAI pays $250K. If you're offering $120K, you're not in the conversation.

So yes, if you can find a unicorn who understands sales methodology, knows your business, can build AI workflows, and can drive adoption... hire them immediately and pay whatever they ask.

But while you're searching, your competitors aren't.

Here's what's interesting. Lemkin didn't actually do it alone. When he explained how he picked vendors, he said:

"Training is more important than picking the perfect vendor. There are very few agentic products where you want to do something like interact with customers, speak with authority, close deals—it wouldn't have happened if we put zero minutes of training into it."

Artisan and Qualified won because they "did the work with us." Forward-deployed engineers. Dedicated support. Partners who showed up.

That's the real lesson buried in his "do it yourself" advice. The distinction isn't agency vs. internal. It's "do it for you" vs. "do it with you."

Here's a warning for leaders feeling pressure to show AI progress:

"The failure that I see especially CMOs make is they're looking for a hero purchase. They want to go to their boss and say 'I bought AI.'... That hero purchase is probably going to be aligned with something you're decent at. The bar is so high and you're not going to know how to train it because it's your first agent."

The layup roles are where nothing is happening at all: support that takes a week to respond, outbound SDRs who won't send emails, qualification that relies on "fill out this form and hope someone gets back."

Start where the work isn't getting done. That's where the ROI is obvious and the risk is lowest.

I've spent the past year doing this work with clients. One example shows how these skills intersect.

A client (global simulation training software, $50M+ revenue) had a four-person BDR team across four market segments. 90+ unconverted leads sitting in their CRM. The BDR manager was coaching on intuition, not data.

We analyzed 78 call recordings and found the patterns: BDRs were engaging influencers instead of economic buyers. Timeline discovery was weak. One top performer was scoring 2x higher on timeline questions by linking to specific project milestones. Nobody else knew that. (Sales expertise.)

We built industry-specific BANT frameworks for each segment. Different qualification criteria for construction versus education versus ports versus utilities.

For another client (national legal services firm), we built an AI-powered automation system: PDF processing pipeline, GPT-4 extraction handling 33 distinct fields, qualification engine with state-specific logic for all 50 states. Processing time dropped from 8 minutes to under 1 minute per case. 620% first-year ROI. (AI & Technology.)

But the technology is the easy part. Getting people to use it is hard.

With the simulation training client, we didn't just deliver frameworks. We did 10 hours of skills training targeted at specific gaps we'd identified. We built AI-powered coaching reports. We created Slack integrations so insights surfaced where people already worked. (Change management.)

Six months later, the BDR manager is generating his own AI reports. The BDRs started requesting more practice sessions. That's adoption, not compliance.

Lemkin was honest about what this actually takes:

"It's just going to take a month of your time and it might take you 50 or 60 hours plus qualifying the vendor."

This isn't set-and-forget. It's set-and-manage-forever.

SaaStr's Chief AI Officer, Amelia Lerutte, spends an hour every morning going agent to agent, checking outputs, catching errors, improving prompts, managing escalations. That's a real job, and most companies don't have someone doing it.

Research shows 70-85% of AI deployments don't hit their expected ROI. The gap isn't the technology. It's the ongoing care and feeding that nobody budgeted for.

Ask yourself: which of these four do we actually have in-house? Sales methodology expertise. Synthesized company context. AI/automation capability. Change management capacity.

If you answered yes to all four, build internally. If you answered no to two or more, you have a decision to make: wait and hire (120-150 days, $175K+ minimum), or find external partners who can fill the gaps while you build.

A note for GTM leaders feeling pressure: Lemkin shared a story about a CMO looking for her next role. His response was blunt:

"I got nothing for you. You don't know this stuff yet. Go out and deploy an agent. Tell me how it worked. Tell me how the training went. You come back to me, I'll get you two jobs. But I got nothing for you now."

The same applies to sales leadership. The VP of Sales who's deployed agents, trained a team on them, and can point to pipeline impact has a fundamentally different conversation with the board than the one still running the same playbook from two years ago.

The market wants people who've done the work. Not people who've read about it or "encourage their team to experiment." Hands-on experience deploying, training, and managing AI agents is becoming table stakes for senior GTM roles.

The window is open. The question is whether you'll move before it closes.

I help B2B sales teams fill the skill gaps that stall AI transformation: methodology, technology, and change management. If you're not sure which ones you're missing, reply and let's figure it out.