Bola Akinsanya
⚡ GTM Deep Dive

Sales enablement is one of the most important functions in revenue. It's also one of the most manual.

What enablement actually does, why it's clunky today, and how agentic AI can support the parts that slow it down while making the human parts matter even more.

If your salespeople are the revenue engine, sales enablement is the team making sure that engine runs smoothly.

Their job is to help sellers close deals as effectively as possible. That means education, assets, coordination, and removing friction at every turn. In practice, it looks something like this:

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Education Product training, competitive positioning, objection handling, value prop development
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Assets + Content Pitch decks, battle cards, case studies, sell sheets. The right materials at the right stage.
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Coordination Bridging product, marketing, finance. Making sure sellers know what's shipping, what's changing, what matters.
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Reporting + Insights Where are deals stalling? What content converts? Where are the gaps?
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Events + SKO Sales kickoffs, training events, team alignment moments that build culture and competence.
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Champion + Connector Part internal marketing, part cheerleader, part the person who makes sure nothing falls through the cracks.

It's a broad mandate. And when it works, it's transformational. Reps close faster, ramp quicker, and spend their time selling instead of searching. Going forward, the best enablement teams will own two things: managing the context that powers the agents, and driving the human-to-human connection that no agent can replicate.

5-10% revenue growth from enablement + coaching + reporting combined McKinsey
10-20% win rate improvement translates to 4-12% topline growth McKinsey
72% of the average rep's week is spent on non-selling activities Salesforce

The function is critical. The execution is often painfully manual. Two areas stand out.

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The Knowledge Gap

Enablement teams spend enormous time gathering, packaging, and distributing information. Product updates from the product team. Competitive intel from marketing. Pricing changes from finance. New features, new objections, new positioning.

And the pace of change at some companies makes this nearly impossible to keep up with. I'd love to be a fly on the wall at a place like Anthropic right now, watching how their enablement team keeps sellers current when the product is evolving week to week. At that speed, the traditional compile-and-distribute model just can't keep up.

Today
1️⃣ Enablement syncs with product on what's shipping
2️⃣ Builds a training deck or doc
3️⃣ Schedules a session or sends a Slack update
4️⃣ Reps attend (maybe) or skim (maybe)
5️⃣ Three weeks later, same rep asks the same question
With an agent
Agent continuously ingests product, competitive, and pricing updates
Gives the rep hints and context during live calls
Surfaces gaps and shares them with the coaching agent so training stays targeted
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The Knowledge Agent

An always-on agent that ingests every product update, competitive shift, pricing change, and feature release as it happens. Connected to your internal knowledge base, product roadmap, and CRM.

During a live call, it gives the rep hints and context. After the call, it identifies where the rep lacked information and feeds those gaps to the coaching agent so training stays targeted and current.

Enablement's role shifts from content assembly line to agent architect. Your enablement work becomes designing the agent itself. Providing the context. Defining the .md files and system prompts. Encoding the skills, the messaging frameworks, the competitive positioning, the quality bar. Enablement stops packaging information for humans to distribute and starts teaching the agent how the business actually works.

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The Coaching Gap

Most enablement teams use tools like Gong to review calls, spot patterns, and build trainings based on what they find. Rep X struggles with objection handling. Rep Y loses deals at the pricing conversation. The team as a whole is weak on competitive differentiation.

The problem? It's reactive, slow, and generic. Someone has to listen to the calls, identify the patterns, build the training, schedule the session, and hope it lands. By the time the coaching reaches the rep, they've already lost the next three deals with the same issue.

Today
1️⃣ Enablement reviews Gong call summaries manually
2️⃣ Identifies common gaps across the team
3️⃣ Builds a generic training to address them
4️⃣ Delivers it to the whole team
5️⃣ Weeks or months between signal and intervention
With an agent
Agent analyzes every call in real time across the full team
Identifies patterns per rep and per team
Delivers personalized coaching to each rep based on their specific gaps
Feeds trends back to enablement for strategic program design
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The Coaching Agent

An agent that listens to every call, reads every deal note, and watches every pipeline movement across the team. Not to replace the enablement leader's judgment, but to surface the signal they'd never have time to find manually.

Rep struggling with a specific competitor's positioning? The agent flags it and delivers a targeted micro-training. Team-wide pattern of losing deals at the procurement stage? The agent surfaces it with data before anyone has to ask.

And here's what changes the dynamic for reps: they can use it privately, alongside the work, in real time. No waiting for a scheduled training. No admitting a gap in a team setting. The rep gets a timely signal about what to adjust before their next call, not after a quarterly review.

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What agents can't replace

Agents handle data, distribution, and pattern recognition. But deals don't close on information alone. They close on trust, relationships, and the ability to navigate real organizational complexity.

Showing up in person My Clay rep came to visit me. He was personable, warm, and referred support we needed during a complex transition. That visit mattered. No agent replicates the trust built by someone who shows up.
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Navigating the shift Moving an org from a non-AI lead gen source to an AI-first one is a seismic change. It requires patience, persuasion, and someone who can walk a team through the discomfort. That's people work.
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The real enterprise buying process For medium to large tech companies, every integration means security reviews, Zip procurement processes, incremental budget requests, and cross-functional approvals. Reps need to know how to navigate that. Agents can't sit in those rooms.
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Upskilling the client's team Adoption doesn't end at signature. The client's team needs to learn new workflows, build confidence, and feel supported through change management. That takes empathy and presence.
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SKOs + relationship building Sales kickoffs, team offsites, ride-alongs. As the routine knowledge work gets automated, these in-person moments become the highest-leverage investment enablement can make.

Agents handle the information layer. People handle the transformation layer. The best enablement orgs will run both.

Enablement is part educator, part coordinator, part internal marketer, part cheerleader, part connector. It's one of the most important functions in any revenue org. And right now, the people doing it are spending most of their time on assembly and distribution instead of strategy and impact.

A knowledge agent handles the "where do I find the latest X" problem and gives reps real-time support on calls. A coaching agent handles the "how do I get better at Y" problem, privately, in the flow of work.

I know the provocative take. People will say: remove the sales rep. Remove enablement. Agents can do it all. And maybe someday they will. But for where companies actually are today, with enterprise procurement cycles, security reviews, org-wide change management, and the trust that only comes from a human showing up? They still need people.

The enablement team of the future has two jobs: manage the context that powers the agents and drive the human-to-human connection that closes deals. Everything else gets automated.

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If you run enablement: which problem would you solve first?

The knowledge gap or the coaching gap?