Improving sales efficiency at scale: an enterprise leader’s playbook

Greg Baumann, the Senior Director of Enterprise Sales at Outreach, discusses how the platform enhances sales efficiency through comprehensive data analysis. He emphasizes the importance of real-time information, pipeline summaries, and deal health concepts in helping sales leaders and their teams improve performance. By leveraging Outreach's extensive data collection, Greg can track quotas, win rates, and sales progression, ultimately fostering better collaboration between sales and marketing. The platform's insights allow for a clearer understanding of lost deals and pipeline sources, making it a valuable tool for sales leadership.

Why Sales Leaders Need Better Data to Run Their Teams

Hi there, my name is Greg Baumann. I'm our Senior Director of Enterprise Sales here at Outreach. And today we're gonna walk you through a little Outreach on Outreach. So there's so much goodness here for sales people, for individual contributors.

And we know a lot about that, right? If you talk to any of our happy customers, they'll see how they're being more effective and more efficient. What I wanna talk to you about today is a conversation that I have with a lot of sales leaders, right? I'm talking to first line leaders up to CROs that I'm speaking with on a regular basis.

And one of the things that we're talking about and that we have to realize is Outreach gives you an entirely new data set with which to run your team and your business. So there's a lot that we can do in the platform. I've been told by my marketing team that I can't talk through all of it because it won't fit on our website in a single video. But today I'm gonna walk you through a single page.

The Pipeline Summary Page

This is our pipeline summary, okay? And so as we look at the pipeline summary, it's super easy because this is your homepage in Outreach. This is something that I view as like the front cover of the Wall Street Journal for my business and for how I'm running it. And it's the first place that I point new leaders on our platform.

So at the top here, you'll see that there is a dropdown, right? So if you are a leader of leaders, or if you're a leader of leader of leaders, or if you're an individual leader, individual contributor, you're able to click down and make sure that you're looking at a specific group, right? So if you are a first line leader and you're looking for specific information to help you prepare for your next one-on-one with people on your team, this is a great place to do this is you can go ahead and click directly in and look for information on that specific person. However, today I'm gonna be looking and walking through this as a direction for my business and as the data that my team is running at this time.

Real-Time Pipeline Health and AI-Powered Forecasting

So at the very top here, as I walk you through this page, you're going to see a lot of opportunity for me to quickly come up to speed on real-time information within the platform. So at the very top here, as a sales leader, we're very competitive. We love to be able to look at the scoreboard and this is what it's showing me. So it's showing me the health and progress of my pipeline.

Shows me how much that I've won to date, how much I have left to go to my quota, how much pipeline I have to get me there, and then how many days I have left to make sure that my team and I are gonna sell against that. On the top right, similarly, it's gonna show me two-period quota. It's gonna show me the percentage of my current quota. So for the month or for the quarter, and it's also gonna show me my annual quota as well and how I've attained to that and the specific numbers for it.

Now, as I scroll down a little bit, we have our total projected finish. This is something where Outreach stands alone. We have petabytes of data that we've collected in our 10-year history of being able to understand what shapes a successful deal for your business based on your business requirements. We're collecting billions of data points on an annual basis from those phone calls, from those video recordings, from the emails, from the sentiment, from the responses and the reactions, and we're bringing all of this in to make sure that AI can help you be a forecasting superstar.

So this is something that, as I speak with other sales leaders, they say, "Hey, this total projected finish has helped me work with my leaders to make sure that I'm curing them of their sandbagging ways." Or if you're a little too aspirational, this is gonna bring you right back down to reality to help you understand, based on how these deals are progressing, their health, their stage, where's our projected finish for the quarter? We found this to be incredibly helpful and it's revolutionized our forecasting internally.

Keeping Reps Accountable With Leaderboards and Scorecards

We've got the leaderboard. This is a great place for me to help my reps understand where they are within the stack rank. I've got a very competitive group over here at Outreach. Hopefully you've experienced that if you're watching this video, and it's something that we're able to have a quick thumb on.

Now for myself, I'm less competitive against going up against somebody else, and I'm much more competitive against Greg Bauman from a day, a quarter, or a year ago. And so this is when I look at the revenue attainment dashboard. This is gonna show me where I'm performing in my numbers for this quarter versus last quarter and versus a year ago. This is really helpful for me to understand the linearity and the pacing of my net revenue for the team to make sure that we're going to not just hit, but exceed our goals year after year.

Speaking of being able to hit and exceed our goals, I'm able to have a scorecard here that captures for individual team members, as well as for teams themselves, whether they're hitting their monthly pacing targets.

Understanding Deal Pacing and Coaching to Close

You'll see there's a lot of opportunity for us to create save view here and make sure that makes sense for your business. We have customers on a much more transactional model that are used looking at this on a weekly or monthly basis. And we have customers that are looking at things on a much broader time horizon that are looking at this quarterly. Now, this one is one of the most important things that we've seen in our sales team.

This one is one of my favorites. This is our deal pacing. And so I talked about this earlier. Outreach is providing an entirely new data framework for sales leaders to be able to lead their sales teams. So we released last year our deal health concept. Based on those billions of data points, we're able to understand very easily what makes a good deal. And Outreach is gonna provide you with that score. And then based on that, based on the stage it's in, based on the time to close, we're able to understand, is this pacing appropriately? Now we all know that you can have really excellent deals that are not gonna close this quarter. And they're not gonna close when they're forecasted. So this deal pacing helps me keep my sales leaders and their sales people honest on if we are pacing accordingly.

I can easily go in here and see, all right, of these deals that are on pace and in the discovery stage, what are those opportunities? Or the ones that are off-paced within working or off-paced within proposal, I'm able to hover through and then click on any one of these. And it's gonna show me those exact deals that are making it up, right? Then again, quickly hop in and do deal inspection alongside my team, because accountability is a team sport.

Planning Ahead With Pipeline Coverage and Win-Loss Insights

Now, as we look further, and speaking of accountability being a team sport, there's a lot of conversations in terms of how sales and marketing partner together to make sure that pipeline is healthy and adequate. The next section of this pipeline summary is gonna show that. So here we're able to see the weighted pipeline. This is something that I truthfully am looking at on a daily basis at the start and at the end of each quarter period.

It's gonna show me, I can look at this by forecast, or I can look at this by sales stage from your CRM. It's gonna pull in all of your relevant CRM staging and make sure that you're forecasting there. But this is when Outreach does its thing and runs its data against it. I can see what my current quarter win rate is on things that are in the discovery stage right now, right?

So if it's 19%, I've got $1.85 million in discovery. It's showing me that I can expect to have 352,000 of that contribute to my closed-won for the period. So this is really helpful for me to understand what are our win rates based on staging and helps me coach my team to how we should be forecasting and calling our deals throughout the quarter.

Now, everything at a demo instance is gonna look like demo data. And I'm afraid to say that this is perfect example of that. Otherwise, we're just not prospecting over here, right? And so if you look here at the next period coverage, this is gonna show us based on my team's win rates for deals like this, what is our win rate?

And so this is showing me how much pipeline I have that I've added to for next quarter, as well as what do I need? So in the interest of the zero interest rate phenomenon and post-ZURP era, a lot of the customers that I speak with are having a hard time really being precise and showing their sales team how much pipeline they need to create each quarter. Outreach removes a lot of that guesswork and can show at an individual and team level based on their win rates, based on their deal size, based on the deals that they're working, based on their pipeline and ability to create conversations, how much pipeline they actually need.

So instead of thinking of like 4x as being a roll of thumb, I can be really specific with my team that we need 2.99x. And that so-and-so on the team might only need 2x and someone else on the team might need 17x. Either way, it's gonna make sure that your team individually and as a group is well prepared to walk into next quarter with the coverage that they need to hit their targets. Similarly, we have our historical coverage.

So going beneath here, it's showing me what my average coverage needed has been. It's showing me how much pipeline I've walked into each quarter with, and then how much I've ended up ending that quarter with as well. So there's a lot of opportunity here for us to be able to show what our pipeline coverage model is and how we're able to work through that. Now finally, we have our win-loss model, right?

So as a sales leader, I'm spending very little time looking in the rear view mirror, but I'm using this as an opportunity to understand quarterly and monthly what my team can be doing to understand where we're winning, where we're losing, and what we can do to break that out more easily. So here, this is showing me by the sales stage, what is our win-loss model? We're breaking it out based on the number of days, the amount of activities that are happening in these deals that we're winning and losing within the accounts. Finally, we have the lost reasons.

This is everyone's least favorite thing to look at, and it's something that I hated going to my business insights analytics team to dig up reports on because it was just so painful. But good news, I don't have to talk to anybody anymore and I can secretly look and understand what are the reasons that we're losing deals and what deals are we attributing this to? So it's very easy for me to understand what are those deals we've lost because this is a great opportunity to have a learning moment to make sure we don't lose it again. Finally, pipeline is a team sport, right?

So understanding pipeline by source is really important for us to make sure that my team is being coached for the place to create that information. We have awesome partners across our sales tech and revenue tech space that are helping to contribute to our pipeline creation, and we have different things from marketing, we have different things from customer SQLs, and we have different things from our sales team as well. This is gonna be able to show up and understand what is the amount of opportunity that's being created for each of these? What is the length of the sales cycle and what is the win rate for each of these two?

This has been invaluable in understanding and planning how my team plans and then executes against our KPIs. We've got a couple more here that I just wanna show you as we end. Finally here, we have our sales cycle over time, right? This is showing me the progression of the sales stages and how they're thinking about them from a linearity perspective, right?

We have day zero here at Outreach, and we have day 365 for each calendar year of selling, and we know that our customers do too. So it's really important for us to be able to understand the seasonality and the motion of our business and what that means for how we're thinking about our sales stages and what our chances are for building and winning those deals. Finally, we have our 12 month rolling funnel. This is able to help me see what's contributing to our pipeline and what's happening there on an annual basis.

So there's so much goodness here. Thank you for watching along in the Outreach on Outreach. I'll say I've really enjoyed our time together and hope we can do this again soon. If you'd like to reach out to somebody from your account team or for myself in particular, we'd love to have the conversation with you and your sales leaders about what you can do with this new data that you've given to your team.

Finally, our product team is even better explaining this than I am, and so you'll see there's a lot of product-led growth opportunities to understand how can I understand these better. So whenever you see an opportunity to learn more in our information button, I highly encourage you to glance over it, to click on it and make sure that you're using this within your context of the tool.