How Outreach uses KAIA to coach smarter and close deals faster

September 3, 2025

How Outreach uses KAIA to coach smarter and close deals faster
Paul Rosen O on O

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.

How's everyone doing today? My name's Paul Rosen, Director of Enterprise Sales here at Outreach. And today we're gonna talk a little bit about how do we coach effectively leveraging KAIA within Outreach? 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. And I'll show you a couple of tips and tricks on how I get the insights that I need to not only coach effectively, but if you wanna take it a step further to ensure that we're inspecting our pipeline in the most effective way possible. And deals are on track to close whenever that may be. So taking a look at where I am within the Outreach panel, you'll see on the left side, I have drilled down to the KAIA tab. Ultimately, that will pull up the library of recordings that we have housed within Outreach. Now, a couple of key items to highlight at the jump. At the top, you have the ability to filter down by a number of different filters that we have preset, whether it's account name, the date range, even furthermore, the meeting type, which ultimately, this comes back to really the data integrity that we have within Outreach, a number of different topics, if you'd like to drill down by competition, by budgeting, by discovery, by procurement, you name it, you have the ability to drill down on any of these type of filters. Ultimately, what I've decided to drill down is by our meeting type, and the ability for us to do that is leveraged through our Outreach calendar sync, whether you're on the Microsoft suite or the G suite, excuse me, ultimately, we're mapping over those meeting types, which filter down and push back to your reporting suite here in Outreach, which allows me as a leader to drill down to the specific meeting types that I wanna understand. And today, we've actually filtered down to the initial meetings that you'll see here at the top of the screen. Now, in addition to that, you also have the ability to adjust any columns as you see fit. This is a common theme that you'll see within Outreach. 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. Now, once we've drilled down to the specific meeting types, ultimately, I wanna understand what's going on within these said deals. When I am drilling into a specific conversation, I will populate a new tab that pulls up the full call within Outreach. What I am able to see at that point in time is your traditional overview of that call. What does the actual call entail? What was the outcome of it? A brief summary with a few key points discussed, not to mention some next steps outlining the overall call. In addition to that, if there are any action items, we're highlighting that here below as well. Now, as a leader, if I wanna investigate, did this rep talk about XYZ topic, or what were the challenges discussed in the call? I have the ability to interact with that specific call, and within just a few seconds, KAIA will ultimately highlight what those specific challenges are in a very digestible manner. So if I'm going to look at a specific call to coach a rep on whether it's a methodology, whether it's a specific discovery question, whether it's certain strategies that we enacted as a sales team, I have the ability to easily understand that at any point in time if I want to engage with the KAIA call. Not to mention, if I wanted to dive into a specific coaching element of KAIA, we also have, you'll see at the top of the page, a coaching tab that I can simply flip over to that tab. If I want to add a coaching card to a call, I'll be able to determine who is this coaching card specifically for, meaning who do I wanna send the feedback to, what specific coaching card that we have annotated in a pre-built out way that I have the ability to build out, excuse me, based on whatever criteria I wanna denote within that call. You'll see we have built out coaching cards based on demos, based on discovery questions, based on specific methodologies, whether that's MedPicc, Sandler, Spiced, proposal call coaching cards. For the sake of this specific example, we're looking at an introduction call here with AKG Health Group. So I'm gonna select the MedPicc coaching card based around the discovery call. What you'll be able to see here is at the top of the coaching card, our AI is empowering myself and the rest of the sales team with suggested answers. So ultimately, we wanna understand at the beginning of the coaching card, how well did the seller build rapport at that beginning of the meeting? Our AI will populate a suggested answer, not to mention they will populate the specific moments within that call that I always have the ability to go and flip to to understand what actually transpired at minute 109 to see if that seller did build that rapport in an effective way. Did we actually capture the metrics? Yes or no, our AI is suggesting that we did not capture any metrics here. And again, what our AI is built around is to serve up the information for myself as a leader, but not actually deciding yes or no. It is allowing myself, still the autonomy as a leader, to determine what makes sense and what doesn't. In this case, I agree with our AI, I'm gonna select no and move on to the next question. Now, ultimately, if I wanna save that feedback, at that point in time, I can click save card, where I provide any feedback that is at the top of the card. And I can deliver that directly back to, in this case, the seller who has Declan and provide any type of notes around that call. That'll directly be pushed to Declan's inbox, which ultimately will provide them instant feedback at any given time. Now, on the flip side, as leaders, yes, I can continuously go in there and coach my reps on a consistent basis, but we also preach that this is a two-way street. Reps need to want to lean into learning and continuing to grow in their career. You have this nifty little feature as a rep. If you wanna request specific feedback on a call, I'll push my team to go in there and request that feedback of myself. And they can ultimately go back and select Paul Rosen and what type of feedback they're looking for and submit any notes and submit that request to me, which will populate in my inbox. Now, that wraps up how I'm leveraging KAIA on a day-to-day basis, on a week-over-week basis, from a coaching perspective. And ultimately, 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 gonna inspect the quality of your deals at any given moment. Thank you all for watching. I hope this was helpful. A brief little overview of KAIA coaching cards. If we can be of more help, please feel free to reach out. Looking forward to chat with you all soon.

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
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  • 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%+.
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"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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