Diagnose and Fix Deals With Pipeline Health Metrics

SetSail CMO Peter Mollins recently welcomed Preeya Voss, SVP of Sales at Ellucian, for an illuminating conversation on pipeline health metrics. Drawing on her extensive sales background, Preeya emphasizes the need for quality over quantity in the sales pipeline, and she introduces innovative metrics to identify stalled deals.

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The following transcript has been roughly edited for clarity. Please excuse any errors.

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Peter: Hi everybody, this is Peter Mollins with SetSail. Very excited to have another great conversation about metrics and go-to-market metrics, particularly sales metrics, and which ones you would want on your Desert Island dashboard. So very excited to have Preeya Voss, who's the SVP of sales at Ellucian here. Preeya, welcome to the show.

Preeya: Thank you. It's wonderful to meet you, Peter. Thanks for having me today.

Peter: Absolutely. Yeah. I'd love to hear a little bit more about your background. So do you mind just giving us a quick tour of how you've gotten to where you are today? You know, the SVP sales at Ellucian.

Preeya: Yeah, happy to. So I am a lifelong seller, career seller. I started my first role out of school. I was a SDR, cold calling sales leaders for a solution that I think many of us know as the Challenger Solution today. So I work for the corporate executive board. So very familiar with living in the world of what matters to sales leaders and how do you drive the business forward. I spent eight years there across a number of different practices and disciplines. And then I broke into SaaS in 2013. My first role was an account executive at SuccessFactors. And so I've been in SaaS since then. So HCM, Post Integration into a large company like SAP, was in a number of different roles there, leading teams in an industry vertical, actually had access to our customer experience vertical, which included CRM, commissions, commerce, and then went back to my roots in HCM. I went to a startup. So I went from SAP to a company that was 23 million in ARR when I joined. That was Company BetterUp. My last role there had the good fortune of leading our North American New Business Organization, growing the company from series B to series E. And that led me to Ellucian coming back to some of my ERP roots from SAP, leading a number of different sales teams here, both in our platform technology, our cross -sell, that includes CRM, as well as some financial aid solutions, as well as our services sales team. So I've got three different varied sales teams that work across our customer base.

Peter: That's terrific. Now, because of that breadth of experience that you had, you must have a very interesting perspective on metrics. And I think maybe one thing I'd love to start with is starting out in sales development, how did that influence your perspective on measuring things since it's so activity driven?

Preeya: I think what's so interesting is also that, you know, when I started it as an SDR almost 20 years ago, the world of just pipeline generation was fundamentally different. And so there's nothing I've learned about using data to run the business is that what you measure today isn't necessarily an indicator of your business in the future. You need to recognize the constants as well as what is changing about. your customers, your sales process, how competitive things are, the maturity of your solution, the maturity of your sales force. And so I think if there's anything, it's that you have to assess the moment that you're in and what you're trying to accomplish, but be open as a sales leader to evolve. I think the playbooks from five years ago are stale. I think the leaders that are really succeeding today are creating that new playbook for sales in today's age and modern selling.

Peter: Right. So now that's really interesting that you're getting ahead of that, right? You're getting ahead of that staleness. So are there things that you were looking at, like leading indicators that are helping you to stay ahead, to make sure that your sales processes are adapting? What are those signals that you're looking at that help you to stay in front of these kinds of shifts?

Preeya: Yeah. So, I mean, I think like any other sales leader, of course, I care about ARR growth or I care about our conversion rate. But I'm a lead with why kind of person. And so when I'm assessing either, why are we overperforming or why are we underperforming? I like to start at the top, which is pipeline health. I think a lot of leaders look at pipeline generation. How much did we add? Right. Usually that's when you start digging into activity. Okay. Our teams didn't generate any pipeline. Are we not making enough calls? Are we not traveling enough? Right. But I really like to look into the why behind our pipeline state. And kind of that gets into what I would call like an overarching headline of pipeline health as an indicator of what is in my control to drive better revenue outcomes.

Peter: Right, okay, that's great. And so when you're looking at health, like how do you determine, like what is a healthy pipeline look like? It sounds like it's more than just like a coverage number is what you're looking at.

Preeya: Yeah. And my team hears me say this all the time. I would rather one X of highly qualified coverage than five X of garbage any day of the week. So I think pipeline coverage is sometimes can be really misleading if all pipeline isn't created equal. And so I'm looking at pipeline mix, but I think the big thing is like, what are the attributes that we know about, a high converting deal, right? We know in today's buying environment, high converting deals are where we have a buying team, right? We're not single threaded where we've got multiple stakeholders or champions at an account, right? Where we have milestones where the deals are progressing. So stage aggression. I also look at, you know, my favorite thing to look at is push count. How many times has a closed date? in Salesforce, which is we use today. How many times has that close date moved? That's if you went and looked at your deals that have great velocity and acceleration. We're anchoring to a close date. There's a compelling event. We're aligned with the buyer and we're marching towards that date. But if you look at the deals probably that are mucking up your pipe, it's where you've moved the close date the last 17 quarters in a row and the deal is 500 days old. That's probably not a deal I'm gonna bet on this quarter.

Peter: That's probably not a deal I'm gonna bet on this quarter. That is a fascinating metric. I've never heard anyone express it like that, but it's absolutely true because if you have a plan in place with your prospect or your potential customer and they're not bought into that timeline, yeah, things are going to move. That's a fantastic way to look at it.

Preeya: Yeah, I think it's one of these, it allows, I think the reps to also take ownership of their own pipeline and qualify out of deals, not muck up your pipeline view. Right. So it's okay. Listen, if, if a deal, if your customer has missed the last three meaningful touch points and they won't agree to the mutual action plan and the deal hasn't progressed to that next step. those should be signals that maybe this deal isn't as qualified as we think it is. And so is it really part of our pipeline coverage or is it misleading us to think we're safer than we are? And that's why I love just pipeline health as an overall indicator, because I might have a conversation with my boss, our chief revenue officer around, hey, we've got 5X coverage. We could still miss our number if that pipeline's not qualified. Or, hey, listen, I've got 1.5X coverage. But here's why I feel great about it. These deals have all progressed in the last two weeks. We're seeing meaningful anchors to those closed dates, which means maybe I can increase our conversion rate. But to me, increasing conversion rate only as good as the health of your pipeline.

Peter: Yeah, that's a great perspective. It's interesting because one of the people that I spoke to, they were looking at pipeline health through the lens of trust. Now for them, trust kind of went both ways, but in this discussion, there was a lot that was focused on, does the prospect trust me enough to allow me to multi -thread? Does the prospect trust me enough to have a text-based relationship? And I love that you're... also including sort of that other direction where me as a seller, do I trust that my buyer has the same energy to keep the timeline going, to keep the next meeting happening? So trust is a two-way street, it sounds like.

Preeya: 100 percent because I mean, I don't like the old adage of buyers are liars. I think our buyers are overwhelmed. They are working through living in a post pandemic environment. Right. Like I'm not going to blame everything on our buyers are just stringing us along. Right. I think it's making sure that like, are we both in it together? Right. Is this this is a mutual investment in time and it may not lead to a buying decision. It may lead to... the board shutting down the spend, it may lead to somebody may quit in the middle of a sales process, right? Like the turnover happens, but it's like, are we getting, we know what a good deal feels like, right? You know when your deal is, you're over your skis and you're like, I have a lot of hope that needs to be part of this. And so this is where I think it's really important that it's like, hey, let's just both assess the objective facts about the deal.

Peter: So when you're having meetings with the various teams that report up to you, how do you use that pipeline health in a practical sense? What are you communicating? What are you asking them for? What are you asking them to do based on that pipeline health?

Preeya: Yeah. So I think a lot of times, right, if I think about some of them, when pipeline coverage became a metric I started looking at, it's kind of like, oh, you've got three X coverage. Great. You check the box, move on. And so I think it's the one, it's my responsibility as a sales leader to understand, right, what's the overall health of the business. But it's to me, it's again, it's a mutual trust around like, Hey, 45 % of your pipelines been stalled in the same stage for the last two weeks. What are you most concerned about? Right? I have a brand new leader. So like this is a great example of I've just hired a new leader, their first time sales leader. So it's also modeling what great looks like. It's like, hey, when you look at your pipeline, here are the things that I want you to look for. Look for all the outliers, right? If our average sales cycle is 67 days, let's look for all the deals that have a sales cycle time right now above 70 days. Right. figure out why are these longer than our traditional sales cycle. So helping some of the pattern matching. And so it's not a gotcha, it's not stump to chump, it's really just being clear on, let's look at pipeline progression, let's look at pipeline age and look at push count. And if you have multiple pushes, the deal is stalled and the sales cycle is longer, that's probably not a deal that should be in your forecast.

Peter: Right, right. Exactly. Yeah. Yeah, that's great. Well, the last question for you is, you know, then managing up, you know, to your board, to the CEO, you know, to other colleagues and the C-suite. What, how do you use pipeline health to have constructive conversations with them about what the quarter, what the year is going to look like?

Preeya: Yeah. And so I think for, I mean, great example. So, you know, a lot of leaders are just looking at the next quarter. Um, I just had my leaders do, did a full audit of the year. So let's look at those deals that are parked in Q4. My hunch is that a lot of those deals were just kicked, the can got kicked down the road and somebody just parked them out there. And so, for example, as we're looking at how's our second half coverage, right? It's like, Hey, You know, you're at three X, you got a lot of pipeline and like, Hey, stop the presses. I'm actually concerned about my pipeline health. And here's why 45 % of my pipeline has been open for more than 300 days. Right? So my guess is that we're going to disqualify this pipeline, but here's what we're doing to replace it. So I'm a big believer in like, don't run away from the reality of your business. Just have a plan to correct it. So. where now each of our sellers has a target for the second half of the year around, like, hey, this is what we want to be able to build because our hypothesis is this is the percentage of pipeline that's likely going to move out. I would rather know that today in February than finding that out in September when it's already too late to correct it.

Peter: Right, right. I love that perspective, you know, just being able to correct ahead of time. I mean, that's any conversation I've ever had with any of my boards or CEOs, it's the same perspective. It's like, thanks for raising the problem. Do you have a plan to fix it? And that's what you want to do and you want to equip your sales team to do.

Preeya: And I think that idea of like running to the risk, I think that's just a solid approach, whether you're a leader or you're an individual contributor, right? When you're an AE, you know, a lot of people don't want to ask that question because they're afraid they're going to hear the answer they don't hear. So if I don't ask it, I didn't hear the bad news. I think sometimes it's the same thing with sales leaders, right? We all don't want to, we're all, I'm competitive. I like winning. I like hitting my, you know, my comp plan. but I'm not gonna hit it if I avoid the realities of what could impact my success. And so I, you know, that's where it's like, let's all run to the risk because the quicker we identify it, the quicker we can remedy it and we can course correct it. Don't let the risk hit you in the face. That is a one-way ticket to underperformance.

Peter: That is great advice. Well, Preeya, it's been a real treat to talk to you about the metrics that matter to you, talk to you about pipeline health. So thanks very much for joining me.

Preeya: Yeah, it was a pleasure to meet you. Thanks so much.

Peter: Absolutely, thank you.