Interview with Matt Magee, Director of Global Sales Operations, Smarsh

10 min read

Before getting into sales operations, Matt Magee spent ten years working in ‘high-end specialty retail’ amongst other professions. Dissimilar vocations as they may seem, Magee has managed to gather a most suitable skill set for sales ops during this process – and his sales teams’ pipelines seem to have become his new inventories. He also happens to be a keen cyclist, citing the story of Team Ineos as inspiration for implementing marginal gains at Smarsh. I caught up with Matt to learn more about marginal gains, why curiosity questions are a major step towards improving your sales pipeline, and why he loves the problem-solving aspect of being a sales ops leader…

Rory Brown (RB):  It would be great if we could get a steer on who is Matt Magee, and your career to date?

Matt Magee (MM):  I often think back on ‘how in the world did I get here?’ I spent time in financial services, insurance, and I had a whole ten year career in high-end specialty retail before making this massive change of direction into enterprise software about six years ago. I still look at those days in retail, finance and accounting as my formative years, and I draw on so much that I learnt about retail management, inventory management, business processes and so forth.

I look at my different sales teams’ pipeline in a similar fashion to how I managed my inventory when I was in retail. We know how many turns our SMB team is going to get out of their pipeline in a given quarter, which guides us on what kind of pipeline coverage they need to have; and where their pipeline needs to be staged at a specific part of the quarter.  It helps us to have a view on that because we are serving a client base of SMBs with less than 10 employees – clear up to the largest banks in the world. Without a grasp on how those different pipelines need to be managed and staged, unique to those specific teams, it is very difficult to manage the breadth and depth of that business on the sales side alone. So, I rely daily on what I learnt during retail. That is really the foundation of how I got to where I am and how we are doing what we are doing in Sales Ops here at Smarsh.

RB: Looking at your track record, I presume you are a keen cyclist?

MM:  Yes! There are even influences there. The story of the UK cycling team Sky [now Ineos], for example. In a short few years, they went from a start-up team to winning the biggest race in the world. Obviously, they had a great plan which they executed well. But the way I see it, at the core of it is this idea of marginal gains.

I always ask, what small thing we can change today? And the idea is to repeat that over several years. Once we look at one year, three years, five years, we will have completely changed our trajectory. It may be the easiest thing we can do, but it will put us on an entirely different course to where we would have been had we not made the changes. Its not about some massive brand-new sales methodology, it’s the tiny things that make the long-term differences – how do we change something small today that gets us to someplace completely different?

RB:  I read all about Team Sky; I watched a documentary. Applying that to sales ops I think is a wonderful concept.

Let’s say you are a typical sales ops leader. You have got different geographies, different hierarchies, different teams – probably products that sell to different types of businesses.  With all that going on, what are the key core metrics that we can focus on to make sense of how those individual units perform in relation to each other?

MM:  I think you have to zoom out just a little bit. In this day and age where we have big data and all these BI tools to cut and splice it however we want, it is really easy to over-complicate something.  We have to make sure we keep things simple, and so for us, we come back to conversion metrics. We look at the sales funnel from marketing all the way to opportunity, and then how this opportunity converts through the pipeline to won, lost, or closed no bid.  And we look at the time, i.e. how long it takes to do that.  We really have committed to a small set of conversion metrics. It’s about understanding: What are we committed to measuring and What is the value to the business?

Once we simplify things, then we can start to segment. So now I’ve got my SMB team; I’ve got my mid-market team; I’ve got enterprise and strategic accounts channel.  And we set up our systems accordingly to measure those metrics in those segmented focus teams, which makes it a lot easier to cut and splice our data. At this point I can clearly look at our data stream and see what their lead conversion is, what is their pipeline conversion, what are their win rates and how fast do they get there and understand and act on it as it relates to their market segment.

RB:  You mentioned something called a curiosity question, and how it always must be linked back to either time or conversion for the business to care or to do anything about it. 

What would be a couple of examples of curiosity questions, how do we make sure it links back to selling more efficiently or faster? 

MM: At Smarsh, we capture and archive electronic communications. That enables companies to build trust with their clients that, hey, we’re on the up and up, we’re communicating good things that are compliant within regulations and we are telling you the truth! That allows customers to have faith in the companies they do business with. And we sell those two services separately from each other or combined in a single solution. Being curious about how we could dig deeper into understanding our pipeline; it occurred to me that  these different solutions will have different sales cycles and behaviours. So, I decided to figure out a way to segment those and how we analyse that data, enabling us to look at how long it takes to complete a deal of one type versus another and use it to refine our forecast and the ideal composition of our pipeline.   

The curiosity question could be: “well, these things must behave differently from each other, right?”  Maybe they do; maybe they don’t.  Since we’re measuring time on all our opportunities, I know now: different solutions move at different rates – one type being measurably faster than another.  Now we can go back to our benchmarks – OK, this is an enterprise deal, a busy client; we know these take longer. It is already Q2 and you have got a deal that is not yet in ‘commit’ – maybe this should be throwing red flags, right? Well, no; not if we know it is a type that moves faster…We know we’re still in the green zone there. Things don’t need to be yellow or red yet. 

RB:  Yes, OK. That is really good.  Presumably then, this information that you produce gets into the hands of sales leaders and team managers so they can get to decent conversations quicker.

MM: Right. Yes. We have a ton of very complicated data. It is important that we simplify this so that it drives directly at what the business and the sales team is trying to accomplish and is easily digestible so that we can make meaningful business decisions from it.  That’s where keeping it simple is a benefit. It is easy to get really complicated but does it really change the outcome? And does it really change what you are going to do with the information? If you can come back and the data shows that it does, then maybe you should start measuring it.  But if it is negligible to zero, don’t measure it; keep it simple. We have dashboards and reports that highlight when an opportunity may be in danger of slipping or may be forecasted incorrectly based on this data and it has driven deeper adoption of our methodology and forecast accuracy.

RB:  Great. I think we will come back to this marginal gain topic. 

So, if we go back to that concept, could you give me some examples of what you might specify as a marginal gain? And do tell me more about how the sports model fits in the world of working as well.

MM:  Here is an interesting one; it is something that is almost brain-dead simple, but over time has revolutionized the way our salespeople look at their time, their pipeline, and what they are doing. About two years ago, we began implementing an idea we call ‘Dollars a Day’.  We would look at a salesperson’s output relative to the timeframe of a day, and how much it was worth in total.

 So, for example, if you close a deal worth $200 and you spent 200 days on it, then you are making $1 a day on that. Whereas if you can cut that in half, you are making $2 a day and you are more efficient. It is a simple efficiency metric. We also came to understand that it is possible to get emotionally connected to some stuff in our pipeline. We may think ‘well it is a valuable customer and I’ve got a good relationship with them, and we get on really well, so it is good business’, but is it really worth the amount of time that you are spending on it?  

This doesn’t necessarily mean that small deals are bad – it is just a matter of dedicating the right amount of time to them so that you can fit more deals into a given timeframe. Instead of working five $200 deals, you are working one $1,000 deal which, oh by the way, takes just as much time and effort to do as the $2,000 deal, so let’s work two or three of those in the same timeframe. So now you are making more; you are more efficient. You are learning to work the big ones faster and that snowballs on itself now. Just little changes, turning that dial just a little bit, and eventually turning several of them so that over time, that curve goes up.  I hope that is answering your question.

RB:  It is, definitely. I think it goes back to what you say – and a lot of people say – you can make a tiny tweak at the top of the funnel and then the waterfall effect is quite a dramatic one, but it takes time for that cycle to happen, right?

MM: Yes, and they need to be willing to experiment a little bit too. I was in a sales organization where they would make a change and then not be sold on it long enough to measure the result. Just about the time they were finally starting to get results, they would change the methodology. You have got to be sold on it long enough to find out if it’s really going to work or not.

RB: Yes. That’s a good question… If you are thinking about implementing any kind of new process, or at least trying one out, what formula, what criteria can you use to understand how long it is going to take to for us to understand if this has actually been successful or not?

Where do we pull the cord?

MM:  The challenge right now for us, is that we are a dynamic, high-growth company.  We have recently gone through a massive merge and like many companies, there is a lot coming at us. So how do you carve out time to step back and think critically about that?  You don’t get a lot of time to really plan and plot something.  Some of that is good because it forces you to be efficient, but you must be purposeful – which means knowing exactly what the results are that you want. We are about to make a change on one of our teams soon and I know what the results are that I’m trying to get – but what are my leading indicators?

You have got to step back and figure out what the metrics are that are going to lead you to whether this is actually working or not. And then to start measuring those, you have got to have a baseline to know whether it is good or bad.

RB: Getting to some more fun stuff I suppose: What would you say is your favourite and least favourite part of being a sales ops rev ops leader?

MM: I describe my role as the connective tissue between sales and the rest of the company.  So, one of my concerns is: How do we help create good, valuable, cross-functional relationships between sales and the rest of the company, and make sure that sales isn’t creating problems downstream for the rest of the company – especially ones that can be easily solved. Going back to marginal gains, it was really taxing on our accounting department the number of errors that were on contracts when I started. Over 40 per cent of contracts that came in had an error that needed fixed. Those are easy bugs to squash so let’s put processes in that prevent the ones that are preventable early.

Make it easy for sales to do the right thing, and hard to do the wrong thing so that when contracts get created, most of those errors are eliminated.  Errors are down now below 10 per cent.  Most teams are under 5 per cent; and one team last quarter was at 0 per cent.  Every single one of their contracts was perfect when it came back. We don’t need to be dumping garbage downstream on other teams. That part of it – the inter-departmental relationships, cooperative problem solving – to put a fancy term on it – that is energizing for me. I’m a problem solver by nature.  That is one of those things that I really get energized by. Working together to create greater good for the business and make a better business tends to make us a better sales team as well. 

The part I don’t enjoy… This is going to sound a little altruistic, but this a whole lot better than what I could be doing…  So, if I’m starting to get down on myself, or starting to feel like this is a drag – it could be a whole heck of a lot worse. I’m fortunate that the business and my job is presenting me with this problem.  Some days I must remind myself.

RB:  That is a good politician’s answer. [Laughter] It has been hard to get that from people, the things they don’t like; I don’t blame you.

The last thing we need to ask – and this has been a very interesting question for me – is how you currently measure success in sales operations.  What does that look like?

MM:  Turning sales into a centre of excellence for the rest of the company and trying to innovate and improve in a way that may prompt the rest of the business look at sales and sales operations and say ‘Wow, we want some of that’, is what’s important to me. We want to keep learning and improving so that the aggregate effect to the entire business is getting better, smarter, more data driven, looking for marginal gains and just generally improving overall. Then turning around and seeing what we can learn from others who are similarly pushing the limits.

We pin everything back to those certain core metrics. Are we getting those to move in the right direction? Are bookings on the rise? And if yes, are we doing it in a way that is scalable? We look at how fast we are doing it, we look at our success rate, and we look for new ways to find success. Are we not just doing it with volume, but are we doing it in quality and good business? All of this really comes back to one big question: Are we doing things to help the company succeed?  Are we selling business that turns into revenue quickly? So we landed a massive deal; but what does it take for the company – in both calorie burn and resources – to get that to where we actually start realizing that revenue?  

And there are some qualitative and quantitative measures to that too. I like to see when people are coming to sales operations and saying, ‘tell me more about how you guys are doing this.’  I think that is a great leading indicator that you are being successful – you are getting the right kind of attention.

RB:  Nice, OK.  I like that.

There has been some really useful stuff in there. Thanks for sharing with us.

Want to get more insights from sales ops leaders? Check out our other posts in the sales ops interview series.

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