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Sales Operations Manager: Morgan Rosseel of Pegasystems

Morgan Rosseel jumped onto Sales Operations Demystified to share his knowledge and experience in Sales Operations.
Check out all the other episodes of Sales Operations Demystified here.
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Tom: Episode of Sales Ops Demystified. We’re joined by Morgan Rosseel of Pegasystems. Morgan, welcome to the show.

Morgan Rosseel: Thank you very much for having me, Tom. Great to be here.

Tom: I just said before we started recording that [chuckles] we had Chris Santos of Pluralsight a couple of months back who had Navy experience, and she was incredible. Morgan, interestingly, has army experience. For the last two and a half years has been running or managing the sales operation at Pegasystems. I’m hoping we’re going to get some context from that experience bit also transitioning from that into sales operations. Super interesting interview. Let’s kick off with the first question. How did you initially get into sales operations, Morgan?

Morgan: Yes, that’s a great question. Obviously, a fantastic jumping-off spot. I did Army ROTC in college and originally thought that I’d go active duty, do my four years, and take it from there, so I had a guaranteed job. I did my undergrad in Business Administration, but once I decided to go into the National Guard, which is a more part-time version of the army, I said, “Oh, man, I better get some real-life experience out there.”

I started my career in insurance and then worked as a project manager at Stryker, which is a medical device company here in the States. Really, that was my first taste of working with a sales team and going to sit in the customer meetings, understanding how to walk a potential customer or prospect down the road to a solution that you think would benefit them being able to articulate the R or the benefit that they’ll receive.

After doing that for a little bit, I wanted to make sure that I was setting myself up for success for say the next 30 years, essentially the rest of my career. I was always interested in the back-end-data portion of how a sales organization works. I realized that data is only growing exponentially and is likely to do so for the rest of our careers. At that point, I went back and got my MBA in business analytics and said, “All right, great, how can I start applying this leveraging my experience with sales teams?” Sales operations, it was just a dream come true, was a perfect fit for what I was looking for.

Tom: Called a very strategic move.

Morgan: Yes, [chuckles] it was definitely not by happenstance. This was something that I most certainly thought about. What’s really cool with sales is not only do I love the personalities, you tend to have a lot of really big personalities. I chose software specifically because of its huge upward trajectory. I think a lot of the folks that I’ve seen on your other podcasts have probably speak to this, just the fantastic environment. It’s a really fresh interesting engaging place to be with the opportunity to really have an outsized impact.

Even a place like Pegasystems been around for 35 years over 5000 global employees. I feel like if I have a good idea, it will be listened to, it will be considered, and I have the potential to make a tremendous impact. In some of those, what I’ll call more developed industries or sturdier industries, like in insurance, you just don’t have that kind of creative flexibility.

What’s special about the sales teams and what really drew me into them is that they’re going to listen to pretty much anything that they think is going to make them more effective. They’re all ears and we are all marching towards that one goal here between sales ops and the sales teams.

Tom: Got it. That is a great advertisement for sales ops.

Morgan: [laughs] That’s right.

Tom: You mentioned 5,000 employees. How many sales reps and how many people are in the sales ops department.

Morgan: We’re a global company, off-hand the number escapes me on our global sales force, but I’d say we’re over 200 in the US, with a team of one, two, three, four, five, five sales ops managers. Then we have a separate alliances team for our partners and then the management chain up through there.

What’s really fantastic about Pegasystems specifically is the fact that we as a business have made tremendous investments in sales operations in growing out that team and really ensuring that we have a tighter one to one alignment between ourselves as the sales ops managers and their sales VPs. Really ensuring that we get to know the business very well, we can speak to the business and give them the attention that they need to really take on that trusted advisor role. You’re not going to get anywhere without it.

Tom: Got it. When you joined, was that the point where Pegasystems started investing in sales ops or had they been doing that for X amount of years and you came in and took on a management position?

Morgan: That’s a great question. I actually started my sales ops journey as an aide-de-camp. I was picking up all of the– Anywhere we didn’t have resources to handle certain projects, that would fall to me. It was a great opportunity for me in a sales ops role to meet folks around the business, really understand how the business works and how to get things done at my company.

Once we started to really build out and flush out the sales ops management team, we also span off some of what was sales ops into sales effective business. Really building out a programmatic structure around those folks. At that point, I was able to align myself directly with one of our go-to-market sales teams and really get deep on the day-to-day, the nitty-gritty, the opportunities, the prospects and all the campaigns they were running against our target works.

Tom: Got it. Current sales tech stack at Pegasystems.

Morgan: I don’t know how much you know about Pegasystems, or how much any of the viewers do, but we are a very robust company. Whether you want to say we eat our own dog food or drink our own champagne, a lot of our systems are built on the unified Pega Platform. That’s a platform that essentially allows for no low code app creation in the realms of CRM, digital engagement, and then we can also layer in robotic automation and AI into that.

Most of the tools that we use, for example, our CRM, is Pega Sales Automation, and that’s built on our platform that’s managed by our in-house team. We’ve created it, we sell it, so we know it. It’s proven to be a really unique tool that we’re able to quickly, by virtue of the of the product and by virtue of the talent that we had in-house, create the updates, the new views, et cetera, that we need to be effective as a business.

Outside of all of our Pegasystems, we also find Tableau to be very effective, especially when trying to broadcast a ton of information as you can imagine, data visualization software to a wide audience. One of the things that we do is, for example, a quarterly evaluation of the business, sometimes that’s just better shown through a tool like Tableau or Power BI on the back end. Those are a lot of the tools that we use internally as well and across the teams, as you step out of sales operations.

Tom: Got it. Have you, let’s say in a parallel universe you guys are using salesforce and for every two parallel universes. Do you think that in your parallel universe, you in the sales ops team are able to push more customizations easier the way you all versus through your running of salesforce, or not really much difference?

Morgan: I think that there’s just so much overlap there, and we have the folks that have literally been building our products for the last three decades in-house sitting here. It’s like– We’re not limited to what add-ins we can get from a developer. We have our own developer ecosystem that has that functionality built in, but we’re just– We have such robust capabilities because we own soup to nuts, the entire product, we have the code. I think that in terms of any enhancements or customizations that would be required, we have the resources internally to build that out as needed.

Tom: Got it. Now you may have to help me here, but–

Morgan: Sure.

Tom: With your custom your CRM, how you currently managing data quality?

Morgan: Yes, that’s a great question. I often say when it relates to data quality specifically, that it really takes a village. This is a heavy team lift. I talked about the investments that we’re making as a business and how we spun off that sales effectiveness team from sales apps. We’ve always had a very capable sales data and analytics team that owns the data quality for our sales teams.

There are a few other data teams around the business, but what we’re in the process of doing right now is combining everything, and I’m paraphrasing from that team. Combining everything into that one centralized data warehouse so that all the column headers are the same. We’re all reading from the same sheet of music, but, of course, even outside of all the historical activity-based data and whatnot, we have so many functions that that pitch in for that.

We review our own activity data; emails, meetings, opportunities, et cetera, that’s fed from Outlook directly. As I’m going through, I’m religious about keeping my team’s data quality up to date, whether that’s just organizational hierarchy and the way things are assigned. We use some third-party tools for that, like Dun & Bradstreet, D&B Hoovers is a really popular one, to just making sure that everything that sits within the CRM system when we do have to make updates due to termed AEs, new sales reps coming on board and assigning them their portfolios, that everything lines up, but it’s really an exercise in vigilance because when you’re just dealing with the amount of data that we have with our enterprise sales teams, it really becomes a very by inches exercise. Does that make sense?

Tom: It makes sense. That team that you mentioned though responsible for data quality, they sit outside of sales operations.

Morgan: Yes, that’s correct, but very closely aligned to the sales teams. We, in fact, just this morning we were on a phone call for about an hour just working through some reporting that we’re trying to spin up to make some of that data more available, more accessible to the field in a digestible format.

They, in fact, literally sit right next to me. We are very very tight-knit. I think by virtue of the fact that, where does the rubber really meet the road? When marketing wants to judge the effectiveness of their outreach, they can look at certain metrics, but where really comes down is customer engagement and opportunity creation and dollars booked. That’s what sales is about. That’s what we have an unrelenting focus on. That’s all we can focus on.

Tom: Now shifting the view to your relationship with the sales reps. You mentioned 200 in the US. If you are to roll out something new, maybe a new customer as part of the CRM or process, how are you going about getting them to buy in and actually do that thing?

Morgan: Yes, that’s a great question. I think that’s something that every new sales ops professional is going to really, I don’t want to say struggle with, but have to figure out. What I found really helpful in getting to this is it’s really all about becoming a trusted advisor. When it comes to new tools and processes, what we really need to do is start by including the sales team on any of those decisions. They’ll let you know if you don’t. That may mean running things by your sales VP and the other sales managers all the way down to the AE level.

I am always trying to solicit feedback, no matter how minor or at least put, “Hey, this is what we’re thinking about doing. What do you guys think?” so that the first time they see it isn’t once something goes live. Because when you do that, you’re basically the corporate that’s dictating out to the field. Having spent so much– The first, oh gosh, eight years of my career were in the field working out with customers, and it’s very easy to get disenfranchised or feel like you’re being just told what to do. It’s really important that you bring them into the fold, help them be part of the decision making opportunity. That’s actually something that I quickly picked up in the military is you can be the leader that dictates the orders or you can be the person that gets everyone to want to come along with you.

I think that the latter, from my own personal leadership style, is really essential. When you’re looking at a sales ops role specifically, we don’t have the institutional hierarchy power dynamic. We sit outside of the sales teams often. I know we do it at Pega. We don’t always have the tenure of the sales VP that’s been doing this for 40 years. How do you get that guy or girl to come along and want to listen to what you’re saying? You have to guide them down that process using more of a soft influence, a handholding process.

The last thing that I want to point out on this because I think it’s a really important point is that it’s not all about saying, “Hey, here’s what we sales ops think that you need to be doing now.” It’s a two-way dialogue. My sales VP and the sales team that I support will often come to us with tools and say, “We’re really interested in this or we put down the budget to do a sample of this and see how it’s going and we really like this.” Well, we’re going to take that. We’re going to investigate it. We’re going to have the conversations with other sales leaders and say, “Maybe what’s good for the goose is good for the gander, and we want to roll this out widely but we’re going to listen to what you have to say.”

Everyone wants to be heard. Even the sales folks will tell you that the customers want to be heard. We really want to make sure that we are considering the end-users or the recipients of all these tools as we’re going through the process of developing and rolling them out.

Tom: Got it. You touched on something I wanted to ask you about is, your experience in the National Guard, and you mentioned your leadership style, do you think it has impacted you or like– Maybe a better question is, how has that impacted the way you lead and interact with sales reps?

Morgan: Yes, absolutely. As I mentioned before, working with any sales team, you’re going to have a lot of big personalities, and a lot of folks that have been doing this for a long time. I remember when I first came in as a brand new officer, I was 22 years old. I had folks under me that range from 18 to 45 in the guarded. You can really run into those circumstances, and that continued throughout my career. You can’t go in there guns blazing. You can’t act like everything. You have to be willing to just provide an unbiased view and make your best recommendation but also you don’t need to operate in a vacuum.

I always solicit feedback before I make a decision because chances are very good that there’s folks whether on my sales operations team and in my management chain, or within the sales teams themselves, that had been through this at some other company, have run into a similar issue, and they have great feedback.

I think what I learned during my time as an officer in the Army National Guard is that I’m not too proud to seek out guidance from others because, again, looking back to that idea of trying to facilitate cooperation amongst the team and not have that dictatorial type of environment. I think it’s really important that we all agree, this is what we’re going for, we’re in this together, like it or not.

Now, I may ultimately have to be the decision-maker, and you can’t please everyone all the time, but it’s really important for me to make sure that I understand all of the perspectives, so I’m always thinking. Even if it’s just a format to an email. Okay, I know that this person is traveling this week, so they’re going to be looking at this on their iPhone, so I’ve got to make this in a format that’s digestible for them. Always considering the person that you’re supporting, your end customer, which for us is that sales team.

Tom: Got it. We’ll talk about the sales team. What are you guys currently doing to make individual reps more productive?Morgan: [sighs] That’s the million-dollar question. I think that that’s something that most organizations are never completely done working towards as a goal. One of the things that I think is really important again is that impartiality. We’re not confined to the day-to-day chasing of deals. We’re not looking at, “Hey, do we get the offer? No doubt.” I mean, we look at all of these metrics in aggregate or as a one-off, but our day is not consumed with that, like it is for the AE or the frontline sales manager.

We are able to have a wider aperture. One of our big initiatives this year, well, for the last couple of years, but something that we’ve done in fits and spurts and are trying to institutionalize across the organization is the sense of a cadence. We are going to proactively put the information in front of you that’s going to allow you to start looking up to 2020. Let’s look at mid-2020. Where do we stand? Building out some of the common sense metrics that are going to go along with that.

If you’re an AE and your quota is $1 million, and you have $1 million in pipeline for next year, you better be an all-star AE or you’re going to miss your number. We start looking at how many times, what’s your multiple of your quota that you have going into next year? Great, what’s the quarterization of that? Are you looking to book something every quarter? We’re facilitating those conversations, all the way up from the CEO level down to the AE and their FLSM. Establishing, not only the data-driven conversations because we will present the unbiased data. That is the is only the jumping off point.

The sales managers up and down the line will inject their knowledge, their awareness of their teams to further drive those insights. We as a sales ops organization are presenting that data proactively, systematically, programmatically, and really not letting anyone take their eye off the ball. I know that we have– You can talk to multiple folks around here who can say, “Yes, yeah, towards the end of 2018, I was so focused on closing business,” which I understand you have to do that, but if you start to take your eye off the ball for 2019, which various folks will say maybe they had done, then they pay the price for it in that first half of the of the new year because it’s all-hands-on deck feast or famine kind of boom and bust cycle. That’s something that is just not sustainable.

Again, not to harp on the fact that it’s just so great at Pega specifically that we are investing the resources, that we have the bandwidth to develop these reports, to attend the meetings, to provide our insights, and to ultimately ensure that we are inspecting the right tools, the right metrics so that that cadence is effective in setting both our AEs and our wider sales teams up for long term success.

Tom: Got it. Moving on to forecasting. How are the sales ops team involved in the sales forecasting process at the moment?

Morgan: Sure. Our sales ops teams run the forecast calls. We are the facilitators of those calls, which I think is really great because it gives us all the most in-depth understanding of where the specific businesses that we support are, and we do those every week. Within our CRM, we can do multi-level forecasting. The AE may forecast X dollars but his manager forecast Y and then her senior manager may forecast Z. Those are available in the system. But in doing those weekly calls, we also bring together the stakeholders so that everything is recorded, it’s an opportunity to quickly touch base on anything that may be needed in the upcoming week or what have you, but really, those are the result of up and down conversations throughout the sales organization.

The sales ops usually doesn’t get too involved in those just due to the volume of them, but we try to get the highest level. Like the Americas RAPJ business or MEA business, those we want to get involved in because that’s kind of the summarized view of what opportunities we’re counting on for the quarter.

Tom: Good. Actually, from your experience, what has been a super insightful KPI to try and performance of reps?

Morgan: Yes, that’s a great question. I’ve come up with a bunch on my own that aren’t part of the standard reporting pack, as I’m sure we all tend to do, based on just chasing our little hunches, which I think is one of the greatest things about sales ops is, we get access to the raw data so that we can go down rabbit hole. Sometimes a bad thing or sometimes we can spin ourselves up on all these different avenues, but when we find something we lock on, I think it’s pretty cool.

One of the most interesting elements or KPIs that I’ve been looking at recently is the email-to-meeting ratios. Usually, the report outcomes as inbound emails, outbound emails, meetings, opportunities, contact creation, et cetera, but one of the things that I’ve really found interesting is the email-to-meeting ratio because the specific team that I support, we have some parts of the business that are very developed. We’re not struggling with awareness in any of those accounts. They know us. We’ve been around there, we’ve been walking the halls forever, and then we have others where naturally, through the growth of any organization, we start targeting different areas.

It’s interesting when I compare those sales teams, and especially their email-to-meeting ratios, the amount of outreach that it’ll take, even just for a tenured AE, to get meetings where they already have the relationships built up versus a new hire AE who’s trying to build their own brand as an AE or sales rep within an organization and how telling that can be in the first few months of their employment.

Not only when you have a new territory that’s getting stood up, which naturally involves a lot of seeking out who’s going to be your folks, who might be the advocates as you start a sales cycle and even finding out where businesses are in their sales cycle. Also looking at, as a metric for new hires, what is your messaging? How are you messaging? Is this resonating? If you are a new hire who’s quickly getting to meetings, so you have a low email-to-meeting ratio. What are you doing? How did you figure it out so quick? That we can emulate and spread across our new hire population. That’s just an example of one KPI that I’m specifically looking at that I think can start to tell a bunch of different stories as you tie the data and your deep knowledge of your sales team together.

Tom: Got it. Especially if a new rep is joining, it’s a good indicator of what their run time will be, right?

Morgan: That’s right.

Tom: Cool. That’s, just to clarify, it’s like the total outbound email sent versus total meetings had, and then taking a percentage?

Morgan: Yes, that’s correct. That’s correct. There’s always nuances in the data and that’s where, you, as a sales ops manager, get to impart your wisdom. The sales manager himself or herself knows what the AE is doing and what they’re spending their time on. Similarly, as you get inculcated in the business and you are on those forecasts calls, you’re in the meetings in the hall with the sales managers, et cetera, you start to know. For example, you may have an AE who’s spending a ton of time at an org that they just recently sold something into.

Are they really prospecting? Are they trying to radiate in that org? Or is this more, “The deal’s been concluding and we’re trying to do a little bit of customer success management”, and then we should expect to see that fall off next quarter. There are some nuances, but I would say, even if you’re a new sales ops manager or a sales ops analyst looking at this data, I think it’s still valuable to at least present that information in an unbiased way to the sales manager, or, I’ll just say, to the sales team and let them apply their own judgment to that in order to drive the conversation with their teams.

Tom: Got it. Final question, who has been the one leading light for you in sales operations? Who has inspired you the most?

Morgan: That’s a really difficult question. I’ve been lucky to have worked with some of the most amazing folks in my professional career since taking on the mantle of sales operations, but I would say my guiding light would probably be one of my co-workers, Wanda Droz. She has a fantastic ability to read her audience. She’s never forceful, but she gets her point across. I think part of the reason why she’s so capable is, prior to coming to sales operations as a sales ops manager, she was on the data and analytics team.

She can go super deep in the data. She knows exactly where it’s coming from. She can represent it in intelligent ways that make sense for the sales team based on what kind of information they’re looking for. She can anticipate how that will resonate.

She also keeps a really calm demeanor, in spite of things that can sometimes be stressful. It’s a tough job trying to please so many stakeholders, as we often have to do. We have folks up and down the chain, we have our field facing personnel, we get pulled into ancillary projects, but she handles it all with an impressive demeanor, and she’s also just so willing to share her work with us, which has really helped me grow and become a better sales ops professional myself. Wanda, if you’re listening, thank you so much for the guidance. I look forward to continue to learn from you.

Tom: Thank you. Shout out to Wanda. Here are things I’ve thought like, there’s a few really, really good words just that I wanted to kick off with [laughs], but I wasn’t 100% sure what they meant. One was inculcate. Does that mean like to integrate into?

Morgan: Yes, exactly. To really steep yourself in the business, to really become a part of it.

Tom: There’s one more in there that I didn’t write down, so it’s lost in the interview. I liked your– Something you- actually and you mentioned quite shortly with, I thought powerful if we align out with the VP and we hadn’t talked about that before in– Your relationship with this person who is responsible for the big number is super, super important. I thought that was really– I wanted to highlight that. The second was how you lead and interface with the sales reps and being more of a– because you don’t have the chain of command. You’re not their boss, essentially. You have to develop that relationship and become the trusted advisor. I thought that was really interesting. Then exciting vigilance. I really like the word vigilance describing data quality. There we go.

Morgan: Fantastic.

Tom: I want to thank you. That was actually a pretty long into the end. I want to thank you so much for coming on, giving us your time and sharing those insights and amazing words.


Tom: It was an absolute pleasure.

Morgan: Thank you so much, Tom. Absolutely fantastic to join you. Thank you for the opportunity to speak sales ops and talk shop for a little bit.

Tom: Thank you.

Morgan: All right, thanks.

[00:29:45] [END OF AUDIO]