How Outreach uses KAIA to coach smarter and close deals faster

Posted September 3, 2025

Everyone does better with a little coaching, right? Coaching is one of the most important levers for sales performance, but also one of the hardest for busy leaders to scale. Sales managers want to be in every deal, but the reality is that they can’t join every call or catch every detail. 

That’s why at Outreach, we lean on KAIA every day. Kaia makes coaching faster, smarter, and more collaborative across the entire sales cycle: 

  • Before a meeting: Playlists help reps know what “good” looks like, so they show up prepared. 
  • During a meeting: Real-time content cards and live-listen whisper mode support reps in the moment when they are on meetings or calls. 
  • After a meeting: Smart Kaia Coach and Kaia Chat make it easy to deliver formal coaching or quick feedback. 

Want to learn how from someone implementing KAIA’s coaching capabilities first-hand?” Here’s how Paul Rosen, our Director of Enterprise Sales, uses KAIA to coach his team day in and day out. 

Real-time coaching in the flow of work 

When deals move quickly, support in the moment can make the difference between momentum and missed opportunity. That’s where KAIA comes in. 

“It’s a tool or a section of the platform that I’m leveraging consistently on a day-to-day, week-over-week basis with my team… not only to coach effectively, but to ensure that we’re inspecting our pipeline in the most effective way possible.” 

With KAIA capturing calls, flagging challenges, and surfacing insights in real time, reps don’t have to worry about missing key details. That’s because KAIA is capturing more than just the recording. It’s capturing conversation signals, insights like topics and buyer sentiment, how much time the buyer and rep spent talking and more. Ultimately, leaders have a better understanding of the combination of all these signals and interactions impact deal outcomes. And for busy managers, KAIA acts as a second set of eyes and ears, ensuring that reps always have support, even when a leader can’t join live. 

Coaching & collaboration  

Within seconds of a meeting ending, KAIA surfaces summaries, key points, action items, and even challenges discussed in the call. There’s even a chat interface of KAIA that makes communication easy for reps. Plus, leaders can add structured feedback through coaching cards, while reps can request feedback on their own calls. 

“Every single reporting page, whether you’re looking from a prospect point of view, a CI point of view, an opportunity point of view, an account point of view, is completely malleable to how you want to view it, whether you’re a rep, or in my case, as a leader,” Paul notes. 

 This turns coaching from a top-down process into a collaborative feedback loop. 

“We also preach that this is a two-way street. Reps need to want to lean into learning and continuing to grow… they can ultimately go back and select me, what type of feedback they’re looking for, and submit that request.” 

Formal coaching at Scale with Smart KAIA coach 

Beyond informal comments and quick notes, KAIA enables structured coaching at scale. Leaders can use pre-built coaching cards aligned to discovery questions, demo best practices, or methodologies like MEDDPICC, Sandler, or SPICED. 

“At the top of the coaching card, our AI is empowering myself and the rest of the sales team with suggested answers. They populate the specific moments within that call that I always have the ability to go and flip to understand what actually transpired.” 

But don’t forget, AI doesn’t replace human judgment. It surfaces suggestions and context, but managers still make the call. 

“Our AI is built to serve up the information for myself as a leader, but not actually deciding yes or no. It is allowing myself the autonomy as a leader to determine what makes sense and what doesn’t.” 

This blend of AI-powered insight and human expertise ensures coaching is consistent across the team, without losing nuance.

The business impact of better coaching 

With KAIA, coaching is no longer an afterthought or a time-consuming manual process. Leaders get instant visibility, reps receive feedback in context, and the entire team benefits from shared learning. 

And the impact shows up where it matters most, in the numbers (stay tuned for our upcoming Sales 2025 report!): 

  • Deals with Kaia close 11 days faster on average 
  • Kaia delivers measurable impact: on deals above $50K, it boosts win rates by at least 10 percentage points — meaning a 30% win rate becomes 40%+, and a 50% win rate jumps to 60%+. 

"That wraps up how I’m leveraging KAIA on a day-to-day basis, on a week-over-week basis, from a coaching perspective… if you wanted to leverage this as well within your deal overviews, your forecasting, your deal inspection, these are a couple of different ways that you can think through how you’re going to inspect the quality of your deals at any given moment.” 

Coach and close more deals with KAIA 

Sales coaching doesn’t have to be reactive, inconsistent, or slow. With KAIA, leaders like Paul can provide targeted feedback in minutes, while reps take ownership of their growth. The result is stronger sellers, healthier pipelines, and more predictable revenue.

Want to see how KAIA can transform your team?

Learn how KAIA can elevate your coaches and their sellers.


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