Michael Rivo
Every Sales Team Has Chat, So the Advantage Moves to Proactive Agents
Table of Contents
Every sales team has chat now. Reps open it to research an account, draft an email, or prep for a call. Then they close it, and it waits.
Chat Only Works When a Rep Remembers to Ask
Usage is not the problem. Sellers prompt AI tools every day, and AI spend keeps rising. Pipeline coverage, win rates, and expansion have not moved with it.
A revenue leader at a public SaaS company put it plainly: "We have great AI tools. They save a few minutes a day. I'm not getting more revenue."
The reason is structural. Chat answers a question, then waits. Its output is capped by how many questions a rep thinks to ask, about the accounts they already remember.
Picture an AE with 60 named accounts. On Monday she asks chat about the three deals on her forecast. The other 57 get no work, including the one where a new VP of Operations started last week.
What changes is who starts the work. When the account is the starting point instead of the prompt, coverage stops depending on a rep's memory and a free hour.
Every Rep Prompting Alone Means Every Handoff Starts Over
It takes a village to close a deal. SDRs, AEs, SEs, managers, and account managers all touch the same account. With chat, each of them works alone, in a separate window, with separate context.
Single-player AI keeps nothing between people. The SDR's research lives in one conversation, and the call notes live in another tool. The AE rebuilds both before discovery.
A breakout group of revenue leaders described the result: "Too many signals across too many tools. None of them wrong. None of them synthesized."
Take the handoff from SDR to AE. The SDR knows the champion wants to consolidate vendors and that procurement slowed the last renewal. Unless that lands in a CRM field someone reads, the AE learns it again, or never does.
The fix is one shared understanding of every account. Shared Account Context pulls CRM, calls, email, and product usage together with news, people changes, and market activity, and keeps it current. Reps, leaders, and agents work from the same picture, so work does not restart with every prompt or handoff.
That is what multiplayer means in practice. The whole team works one deal from one context.
Leaders Cannot Enforce a Playbook They Cannot See
Most revenue leaders have a playbook. Multi-thread every deal above a certain size. Confirm the economic buyer before stage four, and send a mutual action plan after the demo.
Chat does not know the playbook exists. Each rep decides what to ask, so execution varies by rep. Leaders usually find the gaps on the forecast call, when there is little time left to act.
Consider a VP Sales reviewing the commit list two weeks before quarter end. A $400K deal sits at stage four with one contact and no meeting with finance. Nobody ignored it on purpose, but nothing was watching for it.
The shift is from insights to enforcement and action. A leader sets one playbook rule, every deal is checked against it, and agents start closing the gaps. In that deal, an agent would have found the finance contacts and drafted outreach for the AE to approve weeks earlier.
Manager visibility changes too. Managers stop chasing which actions reps took and spend their time coaching the judgment calls that decide the deal.
Proactive Agents Start the Work Before Anyone Asks
Most sales teams sit at the first two stages of AI maturity. The full model has four:
Chat: ask, answer, then it waits.
Skills: repeatable tasks, on request.
Multiplayer: collaboration and enforcement between reps, leaders, and agents.
Autonomous: acts continuously within your permissions.
Getting past skills is hard. It takes shared account context, a shared place to collaborate, and agents that start without a prompt. Each one depends on the others.
Here is what that looks like for an SDR on a Tuesday. Overnight, a target account opened a new office and hired a head of security. By 8 a.m., an agent has researched the account, found three contacts, and drafted outreach for review.
The SDR reviews, edits, and approves. Then she spends the morning on calls. The work was already underway before she logged in.
This is how Actively's proactive agents work. They research accounts, find contacts, engage, and book pipeline. They identify deal risks and work to mitigate them, and they watch the customer base for expansion signals.
Each morning, reps review the decisions teed up for them. Agents do the work within the permissions leaders set. People own the relationships, the judgment, and the close.
Teams running Actively see it in the number. Verkada's reps once spent 15+ hours a week choosing accounts, reading prior interactions, researching, and writing emails. Rep productivity has more than doubled.
Dithi Ganjam, Growth Lead at Verkada, described the goal: "Time should not be spent deciding which accounts to focus on and how to activate them, because machines do that better."
At Greenhouse, pipeline per rep is up 54%, and ramp time was cut in half within six months. Samir Joglekar, Chief Revenue Officer at Greenhouse, named the difference: "Most AI tools we evaluated were just assistants; our reps still had to connect the dots." At Ramp, win rate is up 23%.
Chat will keep improving, and every team will keep using it. That is exactly why it no longer separates one team from another. The difference now shows up in the accounts that got worked before anyone asked.
You are already paying for AI. Look at your territory this morning and count the accounts that got real work before a rep opened a prompt. That number is your gap.


