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Sales Operations Manager: Simon Owens of Redgate Software

Simon Owens 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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Interviewer: Hello and welcome to a very special episode of Sales Ops Demystified. We’re joined by Simon Owens, currently Sales Operations Manager at Redgate Software. Hello, Simon.

Simon Owens: Hi.

Interviewer: Now, Simon has over 20 years experience in sales and about 25% of that in sales operations, so we’re going to get a perspective here of someone who has extensive experience on the sales side but then, has more recently moved into the operations side.

Simon: Correct, yes.

Interviewer: Let’s kick off with the first question on how originally got into sales operations.

Simon: I still don’t know. I definitely didn’t apply for anything going back in the years. I fell into it basically. As I got into sales management and the roles I was doing, they became- as it gets more and more senior, more analytic, more strategy needed. It just flew from there and I found that I was spending less time managing the sales team and more time looking at the processes and the infrastructure behind it enabling the sales team to go and do their job. Then, you end up getting into that sales ops role, so it’s really hard to say when I first got into sales ops.

Interviewer: There must have been something within you that fell towards the operations side, right? Because–

Simon: Yes.

Interviewer: Could you have just stayed in management and then, gone into self-leadership?

Simon: Yes, I guess the main one was at BT phonebooks. When I was there, we’re in a declining market, so business was a lot harder to get. We didn’t have the resource of the sales ops team behind us. It’s down to the managers to try and come up with ways outside of the box to go and try to generate more revenue and that was analyzing data, analyzing trends, looking at more stuff like that. That was just all the first major ops piece ahead of the management stuff that I started to do.

Once I got into that, we enjoyed it, had some good success there and then, the next role I went to at Konica, again, it was more strategy, customer segmentation this time and how we change our model. Then, I got to Sky which was really analytical. We do have some sales ops people working with us, but a lot of it was down to managers and look at that local presence as well. That’s how that goes on. Each job got more and more sale ops focused. In the end, before I started at Redgate, I was probably doing- 150% of my role was sales ops.

Interviewer: That was at Sky?

Simon: Yes.

Interviewer: Cool, and then, you joined Redgate as pure sales operations–?

Simon: Pure sales ops, yes.

Interviewer: It is your first pure sales op role.

Simon: Pure role, yes.

Interviewer: How’s it going?

Simon: Fantastic. I’ve been actually two years, it’s a great company and it’s a company that I didn’t mind to work for for a while. It looks like it’s a good position.

Interviewer: Cool. In terms of the total resources and sales and then, resources in your ops sales or ops team, what are we talking?

Simon: We are the smallest team in Redgate. Three people including myself and we’ve run about 80-85 salespeople and managers in the business.

Interviewer: Cool. I’ve been asking [unintelligible 00:02:52] on this, I’m trying to understand the perfect ratio and it comes to about one to 20 salespeople or like one ops person to 20 sales reps, so you guys are a little bit over that, right? You’ve got one ops person to 20–

Simon:  25, 30, yes.

Interviewer: Okay, cool.

Simon:  We will need another person next year. With the growth plans we’ve got, with the way the business has changed, with the demands on us as a team and coverage, we will need additional headcount.

Interviewer:  What’s the structure of the three? What are the definition of roles between the three?

Simon:  We’ve got three quite unique roles. I’ve got Lesley who’s in Pasadena, US, and she looks after a lot of the basic salesforce stuff, the American teams and also the sales inbox and reseller quotes, that sort of thing. We’ve got Amanda in the UK who is fantastic at salesforce, really as a salesforce guru in the sales team, salesforce admin. She does a bit of that sales inbox stuff, but primarily it’s more about specific projects that’s about data enhancement, that sort of thing. I sort of get involved in a bit of everything, but really focus on things like the strategy and the commission plans, compensation, how those work and just the governance of when those salespeople start trying to steal deals from each other and try to be the judge and jury on that.

Interviewer: Then the new person you’d bring in, what do you think you would give to them?

Simon:  It’s probably a bit of a cross between what Lesley does and Amanda does and that would probably be in the US because we’re a bit short on coverage over there.

Interviewer:  Cool. Can we talk about quickly, you mentioned salesforce, but the kind of tech stack for Redgate right now?

Simon: Probably not a lot of difference in most other businesses similar to us. Salesforce is our CRM. We use that for a number of years, but it is heavily customized version, which is something that sort of [unintelligible 00:04:34] a little bit now because we find that products don’t necessarily integrate as smoothly as they should, so I think we’re having to go back and redesign that a little bit.

We use Engagio in marketing, HubSpot as well. We’ve got a product called InsightSquared, which we’ve been pushing within the last few months as a tool for managers to really delve into their sales pipeline and hopefully, get into the forecasting area and Power BI is our single source of truth for revenues. That’s where the managers go to look up what, how much we’ve done this month or period.

Interviewer:  What insights can InsightSquared bring out from the data in salesforce to help with forecasting? Give us just one example.

Simon:  For us, it’s really that visibility of the pipeline. We’ve got more into the accounts model, which is more unpredictable than a transactional sales model. You can’t just think we’re going to do 10 or 20 or 50,000 a day. Deals can be quite lumpy. They can come in at various times, but it’s understanding what the reps are doing on that and while all it does is really replicate what you can do in salesforce, it does it in a much more graphical, better way, you can drill down into it a lot easier.

The managers can look at what deals are closing for someone in the next 30 days and keep drilling down into that. The biggest thing we saw at the start of it was there was loads of deals forecasting to close this week that had been an open stage for 200 days, were still in open stage, there’s been no engagement with the customer for two months, yet it’s closing in two days time and that’s not going to happen but we’re forecasting that.

Interviewer: Got it.

Simon: Now, the sales manager has been on top of that with the reps, you look at what’s closing this week for example and you see that everything is in procurement, everything has got- virtually everything has got actually the dates of the last couple of days and you can see that actually we can believe what we’re doing here. It gives the managers a great resource there to look into what the teams are doing, where we are as a business.

Interviewer: Got it, you mentioned Amanda doing data quality-

Simon: Yes.

Interviewer: – projects. How are you holistically dealing with the quality of the data and so forth?

Simon: That’s the big thing because data is a living breathing object that is never going to be perfect and it’s never going to do everything that you want. Just trying to understand what data we’ve got and how we got to it. A lot of the data we’ve got has come from places like DMB, but some those have been custom input, some of it’s been rep input.

It’s how do we distinguish between those. When we do a clean, how do we do that clean? Do we look at the actual business entity itself? For example, we did a lot of work with them but the company’s based on employee sides. If we do it just on the employee side, we do that for the business, we’ll do that for the group, for the subsidiaries, parents, and all that. It’s really trying to take a step back and understand what we’re trying to do and trying to have it as consistent as possible, but that isn’t always the case.

Interviewer: Yes, I do totally agree that you might do with some data products and then think, “We’re fine now,” but actually it’s something that’s going to keep integrating and you have to keep doing stuff.

Simon: You’ve got to keep doing it almost every day if you can, which we don’t do. One of the other things you to get rid of a lot of excess data and we’ve got a lot of excess data now which are going through the process of trying to get rid of and just make sure that our process is more streamlined so that the data we hold is less and better quality. We’ve had some [unintelligible 00:07:50] the data is good. It’s not perfect, it’s not fantastic.

The real thing about data is knowing when and how to use it. The big thing is I’ll do a report for somebody today, somebody does a very similar report in a couple of days time, gets different data results when you’ve taken at a different time and sometimes people don’t get that. Let’s try to educate people about just because I did report a week ago, it doesn’t mean you’ll get the same numbers next time because things do move in that period.

Interviewer: There is also an educational piece as well.

Simon: Definitely.

Interviewer: Moving on to the sales reps now, you mentioned that the sales team has doubled in the past two years.

Simon: Yes.

Interviewer: Do you have any tips onboarding? Actually, you probably had to been involved in that process?

Simon: Yes, we’ve been onboarding a lot of people over the last couple of years. We’ve been lucky that now we’re getting a lot of people in the renewals, inside sales levels that they’re moving up to STR level, then moving into the AE level where you don’t need to necessarily do a lot of product training because they’ve been doing a very similar job and they understand the company and everything else.

Yes, in the US, we’ve gone through some massive growth. We’ve had somebody out there who really focus on sales enablement, making sure there’s a learning resource back there. We use our presales engineers and awful lot, but we also use the young people in the business. The AEs will take other UAEs or STRs through that thing because they can relate especially closely to what is relevant in the real world and not just a technical sheets or a feature sheet, but actually what it does for the customer and what it can solve for them.

We’ve got, obviously, Amanda who does some of the salesforce specific training. I’ll take some the managers through other bits and pieces, but it is a really effective effort. We’ve got a great people team there that set up the basics. I think a lot of the time it’s getting that right. When they turn off of work on the first day, they’ve got a laptop. In one of my jobs, I had to turn off and buy my own laptop and expenses, that environment. You want everything to be smooth, everything to be there, and the manager’s dipping in and out of the training using people like us or people in their marketing when they need to.

Interviewer: Got it. Okay, that makes sense. Empowering the other resources in the company to do that and then you’re just the puppet master at the back.

Simon: A bit like that, yes. We’re just there behind the scenes maybe coordinating a few bits and using sales enablement to then really look at individual learning areas and to do all the testing and benchmarking there. Make sure we’re doing things properly.

Interviewer: If you had to influence the salesperson to start using a new process and maybe if not, what they want to do, how would you go about that? Have you done that previously?

Simon: Salesforce is making it mandatory. They can’t do a thing without doing it, but that sometimes can get people’s backs up. A lot of the time it’s about communication with them. It’s about understanding what we’re trying to solve by this new process or new feature we’re putting in. What is it we’re trying to do? What are the problems with the way of doing it at the moment? Make sure that it’s really clear to them.

They can actually see, “Okay, this way of doing it isn’t perfect. It might look perfect to me, but I can see how it’s causing back end problems in finance or we can’t make sure how many leads we’re getting in marketing or something else that’s having a real big impact to the business. They can understand the reason why we need to change. The impact that’s going to have on them, as in if it’s like a marketing issue, we can get better marketing data, better leads. Well, that’s a bit of a win-win and then we do put the process in.

This was about making sure we try and communicate that with them, not just before we do it, but as we do it. We can get their feedback and we can say that this is what we were planning on doing. What are your thoughts? Do you see any–? Because sometimes they can spot the issues that we won’t. Any particular issues here? and they go, “Yes, there’s that you haven’t considered.” Okay, we can go back, we’d visit that, change the process slightly and put it back in and then it’s really–

You can get them on board. We always try and make sure we have that sort of– Sales champions as well in different teams so that they can be the immediate go-to person for the team. Then, obviously, we’ve got sales Ops and maybe the IT core function to go in there and help out if needed.

Interviewer: Got it. What are you doing in the moment to make reps more productive?

Simon: Trying to basically take as much of the back end stuff away from them as possible and try and make it more around getting them time on the phone. I’ve always been really keen to look at the sales reps or people in sales should be spending as much time as possible in front of customers or talking to customers in some way or doing something with a customer and not worrying about back end problems or what commission they’re going to get paid this month or anything else.

Just try to take that away from them and it’s very much like sport in that respect where you’ve got Ben Stokes who wins the Ashes for England and wins the World Cup for England,

but actually, although he said fantastic cricketer, there’s a team behind him making sure he’s doing the right things, making sure it’s in the right training, the right exercise, getting into the ground on time, making sure he’s got enough bats in his bag, all that sort of stuff. I think a lot of it is making sure that we’re putting our sales teams in that position, where they don’t have to think. They can just think, “Right, today, I’ve got these leads to follow up, these customers to call.” Then it just goes really smoothly.

Interviewer: The cricket analogy, I like it.

Simon: Very timely.

Interviewer: Do you think that the way to measure, accurately measure time spent selling because you’re saying that’s an important metric right?

Simon: Yes.

Interviewer: Can you actually measure how many, how long the salesperson is spending selling and then track that every time to see if you guys are doing a good job?

Simon: You can in some roles. I’ve done that successfully in some roles, but I think in a lot of roles is different, especially when you’re in more of a consultative sales process where you need to understand and spend time researching the customer. How do you quantify that? That’s really important.

You can’t just pick up the phone and prospect somebody. You need to understand that business, what pains they might be having, their immediate team. A lot of that stuff goes on in the background. They might need to go away and check some technical information about at school that we might be recommending to them. There’s a lot of stuff that you can’t actually measure. What you can look for is general sales activity and that could give you a steer as to whether we should be doing more or less. Just because somebody does a lot of activity, it doesn’t mean they’re the greatest salesperson.

Interviewer: True.

Simon: I’ve known salespeople that have had probably the weakest number of sales activities, but you give them five fleets, they’ll post four for you. It’s a good indicator, but it’s not [unintelligible 00:14:04].

Interviewer: Sure. Can we quickly jump to forecasting? We touched on that earlier with InsightSquared. What is your role in the forecasting process? Are you actually creating the forecast and then giving it to the managers? Or do you get to give the managers the tools and then go forecast?

Simon: We’re a little bit behind the times in that. We’re still using excel spreadsheets, which might surprise a lot of people and be a bit shock. We are looking at ways we can get that a bit automated. Yes, some of that sits with me and apologies to VP of sales, but I forgot to do it yesterday because I was off. It’s not perfect and that’s why we’re looking at other ways.

Basically, obviously salesforce is holding loaded information there for the opportunities that we have, but for the quarter, for a big chunk of my revenue for almost 10% of our revenue or more, it’s a transactional sale with a 14-day sales cycle. We can’t look at what we’re going to do for the next quarter. You can only look at

 historic data and we’ve put that memory into forecast machine.

With the accounts team, again, it can be a bit lumpy now because we’ve got some big deals coming in. You know, some of our deals can be certain six figures, so get a couple of those in and then it changes slightly, so it’s understanding that. Each manager puts in their own team’s number in terms of commits, like lists, best case scenario and that just gets totted up and uses forecast moving forward, but it’s probably not scientific as it should be, but yes, if we do this in a year’s time, I might have a different answer for you.

Interviewer:  They submit to you and then you kind of forecast it and–

Simon:  It goes straight to the forecast spreadsheet. Each person goes in there and– It’s really the manager or VP of sales.

Interviewer: Got it, okay, nice. Then you’ve also given them info credit tool to help them manage the reps.

Simon:  Yes, obviously, we’ll set up various dashboards for them and we pause to make sure they can accurately track the forecast. We can go back with, “Look, historically, on web revenue, we do X amount per day. We’ve got so many days left, this is what we think we’re going to come in with.” We do look at historic trends because yes– We’re not a particularly seasonal business, but some quarters or the end of quarters is better than the other. Even on web revenue, we won’t just do $10,000 a day. We might do 6,000, 7,000, 8,000 at the start of the month and then ramp up at the end and do 12,000, 15,000. Just trying to look at those little quirks as well.

Interviewer:  Nice and then the question that we don’t normally ask about the different– You’ve spent time with being a salesperson, a sales manager and then sales operations. Do you think there is a different skill set required for sales manager versus sale operations person? Or do you think that the same person could be equally effective at both?

Simon:  I think you can be equally effective at both. Again, to chuck a sports analogy, you can have football managers that are very charismatic and engaging and take people with them on that journey, without necessarily being the best tactical person, but then you have other people that are very much into the tactics. Like there are some [unintelligible 00:17:00] sort of managers who pretty much go for that and rather than personality and they can still do the same thing.

I think having worked in sales has given me a massive help because it makes me understand what the challenges are personally for the managers, personally for the reps, but also for the wide business as a whole and I think, certain comp plans, the first thing you do as a sales rep is, how can I make the most out of this? What loopholes are in there that I can look at? Having done the job of looking for those loop poles myself and managing those, then you start to get to know what’s fair for the business and most fair for the individual. I think it definitely helps having that sales background and I don’t see any reason why somebody can’t move between one or the other.

Interviewer:  Okay, are you saying that sales experience is necessary to succeed in sales ops?

Simon:  I wouldn’t say it’s necessary, but I’d say it’s a big help. It’s a big help.

Interviewer:  I was wondering about that. Okay, cool. Moving on to metrics. Throughout your career in management and operations, what has been a metric that you found incredibly insightful

 or useful?

Simon: It depends on the role I’ve been doing at the time, what we’ve been trying to measure. BT, for example, it was activity-based. If we measure activity and the activity was good, pretty much the numbers would stack up at the end.

Interviewer: For example, a number of phone calls in a day.

Simon: Phone calls, customer visits, how many times you’ve sold [unintelligible 00:18:20] talking part of that level there but on a business such as RedGate, it would be things like average deal size and sales cycle. the amount of touches and engagement you have with a customer. The win rate as well because you don’t want to just burn through leads that you’re getting but then you don’t want people just keeping- having a really good win rate because they’ve kept everything open still and they’re working it even if it’s two years old.

That person never has any loss, you don’t want to see that either. I guess it depends where you are and what you’re trying to drive as well. It’s a behavior thing. Are you trying to drive revenue? Are you trying to drive longevity with your customers by maybe tying them into a longer renewal cycle? You’re selling this three-year support deal rather than one-year support deal. Is that important for you?

Actually, within the business, you’ll have different people focus on different things as well. They might focus on net yields. Our dollar retention value is absolutely critical to them. For somebody else, it’s just the win rate and average deal size. For somebody else, it might be more activity-based because it’s more of a transaction of sales.

Interviewer: Got it.

Simon: It really does varies with what you’re trying to measure.

Interviewer: Final question. Who in sales operations has taught you the most?

Simon: That’s a hard question. That’s a really hard one to come up with. Because I’ve sort of drifted into sales ops, I didn’t have anybody guiding me down there. Currently, I’ve got two great sales ops people. Amanda and Lesley.

Interviewer: Shout out to Amanda and Lesley.

Simon: I big shout out to those two, I hope they’re watching at some point. They’ve been really inspirational for me because I’ve got a great team behind me so I could focus on things important to me in the other parts of the business. Some of the sales managers I’ve had over the years, it’s not just about sales, it’s about managing people because when you’re in sales ops, in the management level and the leadership level there, it’s about engagement of stakeholders.

It’s about getting other people on board who are probably maybe not onto your wavelength or maybe don’t agree with what you’re trying to do. You’ve actually got to do a selling job on them and I’ve had some really fantastic managers over the years. I got with Steve at [unintelligible 00:20:27] control for example. At Sky, we had a great leadership team there but also had some really bad managers over the years.

I probably learned as much from those, I won’t name them, as I have the good ones because you see how they take or they’re not taken people on that journey with them. How they engage, what they do and what they look at or what they don’t look at and you can see plans are obviously going to fail, but they’re just going ahead with because they haven’t looked at the wider picture or the details sometimes. I’ve picked up lots- stolen lots of bits of information, stolen loads of tips, stolen those

resource over the years and just taking that into what I do now.

There’s no one person, it’s just a combination of things, but yes, I think managing up is a really important thing when you’re in sales ops because you’re often reporting to a very senior person in the business, you’re dealing with some very, very senior people across the business, the exec team. Sometimes you need to be confident in what you’re doing and actually push back a lot of the times. Well, we do things because they’re right not because somebody has told you what they want to hear.

Interviewer: Agreed. Now let me share what I’ve particularly enjoyed here in this conversation. The idea that this quality is not like one-off the things, it’s like a living thing within your [unintelligible 00:21:37] keep tending to. Then, I liked the sports analogy you said. I really like how looking at a salesperson like Ben Stokes and you’re [unintelligible 00:21:47] in the background, giving them everything that they need to go and close the deals.

Then, the difference between the ops and [unintelligible 00:21:54] type, out-of-school leader, and then the more emotional maybe [unintelligible 00:22:00] I don’t know if that’s [unintelligible 00:22:01] or not. The difference in skillset in a manager and operations and actually, how you can be either but still be successful.

Simon: I think having a balance of the two like in most things is a good thing to happen because sometimes you need that because you have to drag people along, but sometimes you’ve got to rely on that technical backup. The technical the backup is the evidence behind it. You can take people with you with an inspirational message, but then you need to have some backup data as well to prove what you’re saying is correct.

Interviewer: Would you say you have the two– This might be a hard question to answer, but you have the two sides of like the manager, the inspirational and then the [unintelligible 00:22:39].

Simon: I think so, yes. I hope so.

Interviewer: On that note, Simon, thank you so much for coming over.

Simon: It’s okay.

Interviewer: It’s been great.

Simon: Thanks a lot.

[00:22:51] [END OF AUDIO]


Simon Owens of Redgate Software