Joe Ort developed an interest for sales operations during his first role at SiriusDecisions. His final role at the sales and marketing research company was Director of Sales Operations and he has since taken the same title at LiveAction. From collecting data that is actually valuable to producing a dashboard for a board meeting, Joe has done it all. I was keen to delve into Joe’s experience and uncover some gems for the community…
Rory Brown (RB): To start, please can you tell me about Joe Ort and your career to date. I am very interested in your time at Sirius as well. A brief overview would be fantastic.
Joe Ort (JO): I got into B2B when I moved to SiriusDecisions, and I worked there in a Customer Success Manager/SDR type of role for two years. That was my first exposure to sales operations – I was working with sales ops leaders at different companies and seeing how that related to me as a rep. It was interesting to see how the systems worked in the background. I approached the co-founder and said, ‘Hey, this stuff is really interesting. What if I take the reporting and analytics stuff off your plate so you can focus on running the business?’ He liked the idea. So, when we finished the fiscal year, I moved into sales ops. I couldn’t be in a better place to learn it.
I began taking all our data – and being a small company, it was mostly on spreadsheets – and building it into Salesforce. It was a great opportunity to connect and grow with our analysts, and over the next 7 years we continued to scale. Then I was just looking for the next challenge out there. We had put together a really well-run sales organization, with great data, and I wanted to go and do that again. So, I moved to another JMI equity portfolio company, automotiveMastermind before coming to where I am now – LiveAction – which is an enterprise sales motion.
RB: Thanks for the intro. You have mentioned ‘great data’. What are some of the key things one would need to think about in order to ensure that they are on the way to capturing great data?
JO: In the end, data is great, and we have a ton of it these days. But the question is ‘What are you going to do with it?’ So, if you have something in mind that you want to do with it – build that backwards. My time as a sales rep taught me to consider ‘How can I make this as easy as possible for our reps to collect the information I need to analyse and make decisions from, but also make it as simple as possible for the reps’?
Think about the types of things that you are going to want to know and improve upon and then figure out how to weave it into the existing process – causing as little change for the sales motion as possible. That is the big part. What is the data that we need to be able to make the decisions that are going to help us move forward as an organisation and make it scalable?
RB: Yes. So, you want the information that people need, as simplified as possible, without altering the way that they work ideally?
JO: Exactly. You have to be creative. And yes, there’s a process to make sure that it works – but once you have it, you’ve opened a world for yourself as a sales rep in terms of the information you can share with them. You should aim to put things together that show what a typical sales process looks like in terms of days and stage, by type, industry, and the region that you’re in. From there, you can point out deals that are most at risk for your sales team and identify the warning flags.
I started doing this a lot earlier than a lot of the tools out there, so I had to build that stuff on my own. Being able to give that to reps and have them understand: Hey, these are the things that are looking good. That deal is moving along. And if the deals that are forecasting are starting to move to Yellow (of your Red, Yellow, Green), then let’s figure out what’s going on there. Why is that starting to slow down? Is there anything that we need to be doing to move those things forward?
RB: Nice. You mention the RAG system – we call it stage tenancy – and it sounds like you have cut that up depending on deal size and industry. Is that something you have found to be of great value to salespeople?
JO: We had so much data at Sirius. You could say it is the basis of the company. So being able to use that and use it to forecast, putting all the different components together – pipelining, the three-month sales cycle – we got very accurate. We can aggregate all that information and then be able to say, ‘You are calling X for this quarter, we really don’t see it. Change my mind. What do you see out there that we don’t?’ It is an art and a science. We do as much as we can from the science standpoint, and there are still going to be some different things that they know.
RB: Let’s go into that a little bit. If you were going into a new business and starting from scratch, what data points would you prioritise getting visibility of?
JO: It really goes back to your ICP, whatever that may be for you. It could be revenue size, industry, or deal size – maybe how many times a deal is pushed in a quarter – I’ve seen that have an impact. In my experience, after one or two of these points, the win rate tends to drop a lot.
RB: That’s great. Let’s take a step back to the first thing we talked about: Where do you start on the journey to collecting good data? Sitting down with sales leaders or salespeople, I presume you get people asking for information that is largely irrelevant or lacking value. How do you control that process?
JO: I have put together a big matrix that has the KPIs and metrics down the rows. Across the columns we have things like: Who cares about this department-wise? Who is impacted by this from a role perspective? Then, how do we want to look at that from a dimension standpoint?
Bookings, retention, discovery calls – all those metrics and KPIs we would consider and put it down one side. And then going forward, we would look at: What is the priority? How important is this to that role or to that group? We would start to prioritise around the criterion: What are the most important things that we need to get out of the business?
The aim is to get everybody on the same page and be concise about the metrics that we are going to go out and measure. There is so much stuff that you must be able to prioritise. It is important to limit the confusion and enable the team to focus.
RB: I really like that idea. Having worked out what people want to see, you now know that there is going to be a few little bits of data capture that you must add in – which presumably is going to come somewhere along the sales process.
What tactics have you seen work well for sneaking those in and getting salespeople to always comply with them? How do you make it part of their life? That is the hardest bit, right?
JO: That is the hardest. If you have got something simple, for example, we need a better understanding of the types of meetings that we are doing, you can make it a simple action for them on the Salesforce Lightning app. It can be a simple Log a Meeting button, which the rep can simply click and move along with their day.
You have got to try to find ways to make it simple, to the point where it is not going to be such a burden for them to relay this information. It is a Change Management piece, and you have to get people involved. It will not be the easiest thing, and you’ll need reinforcement from top down.
RB: I suppose there is always the old ‘mandatory field’ trick!
Let’s move to reporting to management or even to the Board. There is a real skill in presenting information to these people. Often, I think it is far simpler than people might at first perceive.
How do you go about producing a dashboard for a Board of Senior Leadership meeting? What are the key concepts that make it usable and impactful?
JO: I think it goes to: What is the story that you are trying to tell? All the data that you present should be supporting the story you are trying to tell. If it doesn’t, it’s irrelevant. If you are looking back on the quarter, start with the ‘This is where we finished’. And then start digging into the ‘Why’. Why did we hit this quarter? Well, we hit the accounts that we were expecting to. Once you ask that next level question of Why, you start peeling into it. Hey, we missed this quarter – Why? Well, the retention rate was lower. Why? Well we lost a couple of key accounts. Why? It’s all about drilling down into it.
That is more beneficial than showing the same reports and the same data every single time. Keep that stuff in the appendix – we still want to look at it – and we still want to know about it. But you first need to investigate the impact on performance and then pull out those stats. Make the correlation explicit on each slide and keep the story intact. You have done the qualitative and quantitative analysis – so figure those things out yourself. Don’t leave it to people to figure out what you’re trying to tell them with the data, give them the answer.
You’re telling a story, highlighting the answers on the slides, and making sure it’s all connected and everything ties out. That is beneficial and it saves time.
RB: Yes, I am sure. It sounds like what you are suggesting is that is each quarterly board deck is new. It is telling the story at that time.
JO: You don’t want to just do the same thing. That is not what they are there for. They are going to ask the next question, and you are going to spend time after the Board Meeting scrambling to get those answers anyway. So why not be prepared going in? Looking at all that data and being able understand what to do next is what truly matters. Data is just data. The key is what you do with it.
RB: There must be a bit of a skill, or an art to that. We’re not saying that someone could just rock up having never done data analysis before and immediately tell a good story. Surely it takes a bit of honing, right?
JO: Yes, it is something that comes with time and experience. You must learn to ‘peel the onion’ and know what the next question is going to be. It’s about understanding: What are the potential reasons for this? You can’t just sit behind your reports; you must get up and talk to people. There must be an underlying story behind some of this stuff.
RB: That is great. Really good stuff there.
Let’s move onto forecasting. You said it was at your last company where you created a forecasting system. If we start with the process, what does a good forecasting process look like? How do you engineer that?
JO: I think the process and the data collection is different depending on the type of business you are in. If you look at my experience in that transactional business model, every Monday we would do our forecast call. Once we got the data, we could look at the different conversion rates for the different types of meetings that we were having, whether we have scheduled enough meetings to estimate our projections, and so forth.
We always made sure we had enough data. From there we would see clearly whether we are pacing ahead or falling behind where we should be at this point in the month. For example, normally we would be 20% of where we finish one-third way through the month – How does that compare to where we are at right now? It’s important to be aware of that and applying these findings. Being able to say, ‘Hey, we need more meetings, SDR Team. Let’s go.’
RB: I really like that system. People often talk about forecast accuracy and forecast visibility. It is all very well being accurate and saying, hey, I have got 99% accuracy four hours before close. But have you got 99% accuracy four weeks before close?
How did you find that balance in getting accuracy as far out as possible? I think people sometimes people have unrealistic expectations as to what is achievable, if the data is not actually there to support it. What do you think is realistic to aim for?
JO: Yes, it is very tough, especially where I am at now. At Sirius the number was +/- 5%, if you can get there. And then +/- 10% you are still good. It is hard though. I think from an aggregate level we have done a pretty good job here, achieving within the 10% number. But if you look by rep, it is wildly different. You have got people doing between 200-300% of what they forecast. It is by no means easy to get good at this. Even in that transactional business where you think you have got enough data to be able to figure this stuff out, there are wild swings in terms of the accuracy of the managers and the reps at that level as well.
In the past we have tried to just look at what our pipeline looks like for each of those periods, and snapshot that week over week. We also look at how particular pipelines have converted historically to try to project how we think we will finish. But from a rep level there are so many different variables and processes involved that it is really hard to get very accurate.
RB: Yes. Of course.
Another question – and this is certainly one area where we help our clients – it is a newer thing, particularly over here – people are starting to use maybe one, two, three different forecasting systems, understanding how they are all performing differently and using those for context.
What experience have you had with that? Have you tried that and if so, have you found it useful?
JO: Good question. When we looked at the transactional business, we would have our ops forecast, our reps forecast, and the management commit. We would have the different components and try to measure the accuracy of each of those. When you come to the board, you must give them a precise number, it can’t be left so open to question. So being able to have those different data points to support why you have come up with that, was always important.
RB: Who do you think the responsibility for the integrity of the forecasts submit number lies with?
JO: Well, for better or worse, that’s us. We’re the data so we try to give the realistic view on those things and analyse the different data points. Your sales leader is going to believe what they do based on their knowledge of all the deals. But they can’t talk to each prospect to understand where they are at.
If you are uncertain, you need to partner with the sales leader and say: ‘This is what the data is telling us; your number is a little more optimistic than what I think we can achieve, and why. Have that conversation, because you don’t want them to be putting a number out there that is unrealistic. You must make sure you are on the same page and are able to support why they are submitting the number that they are.
RB: Great. The last one on forecasting: What do you think, in your experience, is the best way to visualise a forecast to the Board? Presuming it is not just a number, and there is some context around it.
JO: I think it has been different for every company I have been at. Initially at Sirius it was just kind of a number. At Mastermind it was more of a process – we would show all the different cuts we were coming up with, and then the number that we were going to produce.
Now, with Insight, they look at it week over week, at a much deeper level. They are much more data driven, so they ask questions like: What is the weighted pipeline and current pipeline? What are those coverage ratios? They dig much deeper into each component and the measuring that week over week. So really, it depends on the organisation that you are reporting into.
RB: That is great. Thank you.
I notice in your last role you covered sales and marketing ops, which sounds like no small feat. How did you find that? How do you make sales and marketing stick together and almost be one funnel – one system?
JO: My experience at Sirius was largely orientated around the goal of organising to align sales, marketing, and product. When I showed up to Mastermind, I imagined I would be partnering closely with whoever was running marketing ops – but they said ‘Well, that is going to be you’. In that transactional business, we really had to make sure the two groups were aligned. That is obviously very tough in some companies – to be able to get to that level of synergy yet be clear about who sources what.
You need to have the same reporting component, and nomenclature is incredibly important – making sure everyone is talking the same language. Everyone must be working towards the same goals and understand the breakdown of what is going to be a sales source versus a marketing source. In my experience, getting to that level of granularity while staying aligned with your Board plan – all the way down to the rep level – is the best method to be successful.
RB: Sure. And when a lead passes from marketing through an SDR to an AE, a contact is passing from a machine to two different human beings – at any stage of that process it can fall apart.
How do you keep that secure? I have heard things about SLAs being used, and that sort of stuff. What have you seen really working there and how to you keep it in place?
JO: Primarily, keep all the information so that it is accessible to everyone. Then it just goes back to visibility and communication. Make sure that part of that forecast call explains where exactly you are in the process and which are the leads that are outside the SLA. Routinely follow up on every lead and be certain that everyone is on the same page. If you have got the data that says ‘We need to progress this thing in X number of days, and it starts to fall outside of that’ you have to be all over it. And you can’t do that unless you have the visibility and the reporting in place to be able to do that.
RB: That is really good. One other question I have been asking everyone is a little bit broader, but it is quite a challenge for a lot of people.
How do we measure what success looks like for a sales operations function? What have you seen there?
JO: That is not easy. To me it always comes down to productivity. Ask yourself – if you look at different projects, different enablement initiatives, different tool implementations – are we gradually getting more out of the team? It could be in the shape of more calls and more meetings from the SDR function, or more bookings/billings from your AEs.
If we are doing what we need to be doing from a sales ops perspective, we are going to see the output. All the things that we are going to do are going to have an impact, whether it is an activity-based thing – making people more efficient – or giving them the data that they need to be more effective. Applying this should then result in increased conversion rates and those types of things. Whatever it may be, the bottom line is: Are we making our sales team more productive?
RB: To give some structure around what that process would look like, what I’m hearing is: We are going to try a new initiative – it could be in technology, process, or whatever – and these are the metrics that we intend to influence. It could be the average deal value per rep, or conversion rate at this stage.
Would you need to establish that before? So then when you make improvements you can track back and see what is improving and why?
JO: That was always the missing step for me. I would go back and try to prove all the great work I did, but I never base-lined myself. It is not easy to go back and do that. You want to make sure to get that baseline, so you can go back and shout from the rooftops hey, look at all the great stuff we have been doing. It’s natural to just keep ploughing ahead and get carried away with so much going on, so you forget to do the analysis. We tried to consciously do this at Mastermind, raising the flag and celebrating all the successes that we had as an organisation – it’s important to take that second to pause and reflect. But you can’t do that unless you have got the baseline to show how much of an improvement you have made.
RB: Nice. So, the argument would be, if you are going to start an initiative, first you must think about what metric that is going to move the needle on; and whether it is worthwhile if it is not going to change a metric?
JO: The harder ones are the ones that usually have the soft impact, so things like ‘comp accuracy’ or something related to a ‘quality of life’ type of thing. Perhaps where the sales reps aren’t sure that we are able to accurately and timely calculate commissions or get data for people. Quality of Life is tougher but those are things people appreciate. You need to balance that with the hard numbers.
RB: Well, taking blood tests and proving reductions in cortisone levels isn’t very likely to happen!
We have covered some really good stuff there. There was a lot of structure and process in there that I think is going to be valuable for people coming and reading our resources. Thank you very much.
Want to get more insights from sales ops leaders? Check out our other interviews in the sales ops interview series.
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