How to Measure Success in Sales Operations

18 min read

Sales operations is in a state of evolution. As it adapts and finds its feet,a key question is: how do we measure success in this role and how is the sales operations department held accountable?

We asked sales operations leaders how they measure success in their roles.

Julian Harris, Senior Manager of Corporate development and strategy at Classy.org

We use the OKR system. We have OKRs as an operations team in the form of projects that are rolling up to drive the success of the organization. At the end of the day, if we’re missing our revenue and retention numbers, I don’t see that as a successful period. Our job is to drive investment of those teams. Not only hitting our overall numbers but are we getting more effective at doing it? Are we driving improvements in ASPs, are we seeing a higher percentage of reps hitting quota, higher percentage of reps over 80% quota? Those are the things that really drive or move the needle for the organization.

If we’ve got a sales team where two people hitting 200% of quota are driving us to the number, that’s not a recipe for long term success. Those are the things that we may not have a specific OKR dedicated to make X percent as your reps hit quota or help drive that but there are ancillary projects that are geared towards that ultimate goal. At the end of the day at the end of each quarter, each year, if we can help hit on those things that’s a successful sales ops team.

Read our interview with Julian.

Jennifer Laurie, Director of Business Operations at Bonfire Interactive

Our KPIs are the company KPIs.  Since major functions of rev ops are aligning teams and executing on company strategies, our KPI is how successful those teams are and the company is. If we were working on a system or business program, how did that roll out go – did the individuals impacted understand the change and buy into it? How did the company wide roll out go, do teams have all the data and insights they need, and if there is an external aspect of it, how is the overall customer experience? Those are the questions we ask ourselves as we do our project debriefs. 

Read our interview with Lauren.

Zach Thigpen, Head of Operations at Augment CXM

I keep track of the metrics, and the numbers don’t lie. If we’re hitting on particular numbers for the year, and we’re feeding them and there are things that I directly worked on, that’s a pretty good indicator. Part of it is not just improving but just maintaining while you grow.

While you’re growing, there’s new infrastructure and new processes and systems that need to be put into place, because what worked at five reps doesn’t necessarily work at 20 reps. Being able to get out of the way as much as possible while maintaining some sort of consistency and accuracy and controls from a financial and legal aspect, that’s very helpful for the reps.

Read our interview with Zach.

How Brandon Bussey measures success in sales operations

Brandon Bussey, Director of Revenue Operations, Lucid

With my team, we measure sales operations success with four overarching goals. One of the goals is to increase the total amount of bookings. This is important because we have an aggressive growth target, so we need to make sure our goals are aligned with that.

The second goal is increasing average bookings per rep across the board. I’ve seen companies that increase the overall number of bookings but it’s a ‘the rich get richer and the poor get poorer’ situation, which is not success.

The third goal is transparency and visibility upward into our executive team. Our exec team doesn’t have a traditional sales background so a lot of it is educating them and showing them the key metrics. It’s about providing better transparency and visibility upwards and across the wider organisation too.

The last goal is creating a vibrant culture in the orgs that we support. There are a lot of ways we can influence culture. One is how people are paid and how they’re motivated. This is an area where we can have a huge impact. People want to feel successful.

One of Lucid‘s founders came from Google and a lot of our culture has come from the Google model, a key example being OKRs (objectives and key results). Every quarter, we look at what our objectives are and the results that define those. As we’re studying our OKRs, we make sure they impact each of those four metrics, although culture and transparency are not as quantifiable.

One of our objectives is to create an overarching efficient book or territory strategy. And so, our key result was to deliver the timeline and training. Then from a metrics standpoint, we’re tracking whether reps are able to hit their quota given their new book and secondly, looking at book penetration. We’ve set some basic targets using historic data. Historically they were reaching out to X many and we think they should be reaching out to Y many, depending on which segment they’re in.

It’s crucial to make sure you’re not creating your OKRs in a vacuum but thinking of the wider company objectives and making sure your objectives align to those.

Read our interview with Brandon.

How Justin Kersey measures success in sales operations

Justin Kersey, VP of Sales, UK, Merrill Corporation

One of the general ways to measure success in sales operations is generating more revenue per sales head. And that bridges across sales ops and sales enablement because we have to upskill sellers on a regular basis to make sure that they know the latest product features, they know the latest selling styles, they know the latest buying personas within our market. We also need to ensure that we’re serving up the right information and coaching them through the sales process with relevant information about the organisations we’re selling to and driving new business towards them as well.

So, it’s really about supporting that full go-to-market strategy. Ultimately, we’re moving more towards revenue ops as opposed to sales ops because I think it generally starts with the marketing organisation at the top of the funnel feeding into SDRs and making sure that you’re continually cycling these people through that funnel. If they get to a stage where they’re not in a buying position, then we should pull them back up to the right place to continue to nurture those relationships and see them through the rest of the funnel. Sales ops’ job is to support from a data and analytics and tools perspective to make sure that we’re capturing all the right information, serving it up at the right times and just generally supporting the go-to-market strategy across the organization.

And if you’re doing all that effectively, you can correlate the average revenue gain per head to your work on X, Y and Z.

Read our interview with Justin.

Stephen Haltom

Stephen Haltom, Director of Sales Operations, AppDynamics

For me, success is when I get the direct validation and the direct feedback from the sales leaders that what you’ve provided is truly valuable because, at least in my experience, a lot of sales ops leaders come in Gung Ho with great ideas about how they’re going to change the world of sales. And a lot of it winds up not resonating, not being relevant, and not being the top priority for the sales leader. If you have your priorities and they’re not aligned with the core concerns and the priorities of the sales leader, it doesn’t invalidate the work you’re doing, but it’s just less likely to make an impact with them. For me, it’s really important to align with what your Sales Leader cares about, not just what you think is important.

In terms of quantitatively measuring success, for me that’s when a finding of mine leads to a decision being made.

Read our interview with Stephen.

Robin Yeoman

Robin Yeoman, Director of International Sales Operations, Snowflake Computing

We are very driven by OKRs, knowing exactly what it is you’re going to achieve that quarter and then being able to keep that priority list so that if another project comes in, you can very quickly rejig that list. So using the example of a new data tool, implementation can take a lot of time, but if the benefits outweigh some of the other projects, it might be worth doing. And if it saves in time in the long term or solves other issues that you’ve got, it’s definitely worth doing.

It’s almost like storytelling. You picture what could happen, you model whether this will have an effect on another department or another part of your team and you look at what you’re able to roll out and what you regard as success. And then you talk about how you measure that success.

A very basic example of an OKR we use at Snowflake is about hiring in our team, ensuring that we meet the targets to fall in with the ratios. Ratios are very important in sales ops, for example how many SDs report into an RD etc.

Another example is making sure any data tools or any other tools you’re getting are in your OKR and are signed off with clear mile stones. And then there’s enablement sessions. We committed to running a certain amount of what we call ‘lunch and learn’ sessions. So, we have to hit a certain number of sessions every quarter and have them documented, recorded and then put it in a place where people can watch them. And that could be about rolling out changes to Salesforce or how to forecast, for example. And it’s just delivered in a way that only takes an hour out of the salespeople’s week. It’s recorded, and sometimes it has quizzes added to it just to test that people are actually doing it. So as an OKR it’s quite simple but effective.

Read our interview with Robin.

Barrett Kelly, Global Sales Operations Manager, Exari

We follow the agile methodology. We have quarterly goals and everything we do feeds into those goals. When new tasks come in, you throw it into the backlog and constantly evaluate the backlog to see if anything needs to be brought into the current quarter. It’s having a focused approach. And then you can start measuring your achievements against your goals.

Secondly, I spend a lot of time managing software and working to improve our data hygiene to ensure better visibility and reporting. Communication with the teams and trying to get feedback from the management team are very important as well. Lastly another big piece for me is personal satisfaction, making sure I like what I’m doing and I’m going after goals that are going to make the company better.

Read our interview with Barrett.

Cris Santos, Director, EMEA & LATAM Sales Strategy & Operations

Everyone has a different perspective on this. I’m not officially measured on that, but I’m a big believer in measuring myself by the sales team I support hitting their target.

I think the way to measure the effectiveness of sales ops is closed business. How much business are the team that you’re supporting closing. That’s number one.

Secondly, a lot of people say, sales ops gives you the report. But it’s what you do with it. I actually read in Brandon Bussey’s interview that sometimes it’s not the amount of data you work on, it’s how much of that is actionable. And I totally agree. I’ve seen, even here at DocuSign, my team create tons of dashboards. And you end up not talking about what those numbers actually represent. So, another measurement of success is continually making your reports more efficient and drive decisions and ideas around the trends you’ve identified.

I think sales ops should be measured on innovations too. I ask for two innovations for my team per quarter, including two innovations from me. Sometimes an innovation is just tweaking something that’s working but could be done better. I always say that good sales ops strategists and ops people should always be unhappy with the status quo. They should always aim for more and to drive change.

Read our interview with Cris.

Mark Feldman, Head of Revenue Operations, Localytics

You should only be thinking about one thing: Revenue. I was going to say Bookings and Revenue but we are in an enterprise model so we have long sales cycles. Bookings is a leading indicator, but it really just comes down to revenue.

At Localytics we use OKRs, although they are still evolving over time. We are rebuilding a lot of our data and operations, so it is the percentage of reporting that is self-serve out of the system, versus a Google sheet. One of my key results is 0% of reports done in Google sheets. Right now, it is probably about 80% so there’s a bit of work to do there.

We are developing a database of all of the accounts in our target market and all of the decision-making units’ contact information, and then being able to report on the account funnel with those accounts. So, over time our key results will be in metrics of moving people or accounts through that funnel. And then looking at how rev ops can support that by fixing the plumbing and greasing the wheels to make things more efficient and scalable and providing a business intelligence layer that allows decision makers to make improvements that will increase velocity, shorten deal time, and increase average revenue per customer.

Read our interview with Mark.

Jonathan Bunford, Director of Sales Operations, Ada

At all three startups I’ve been at we have used OKRs. I can definitely say it hasn’t gone perfectly at all of the three! It is a learning curve, especially if it is not part of your natural process. One of the benefits of using OKRS (assuming you don’t over-engineer it) is it provides clear visibility across the organization.

Discussing key targets company-wide opens the door for really interesting conversations, and is a helpful way to keep organizations, teams and individuals all aligned.

Sometimes it can be a little nerve-wracking thinking that you are responsible for a number, but that is normal in the world of sales. In sales, you have a number and if you don’t hit that number, we have to talk about it. It should really apply to everybody. It is just a little harder sometimes in an operational role.

I really enjoy training related OKRs, things to empower the team. Everybody who joins Ada in a role that uses Salesforce gets a basic level of training. But at the end of the day, when people want complex reporting they will come to me. So, one of my OKRs this quarter is to roll out advanced report training. Then a key result would be to decrease the number of report requests by a percentage. Or ensuring that a certain number of people have been trained.

Read our interview with Jonathan.

Denis Malkov, Director of Revenue Operations, PandaDoc

Success for rev ops is maximising conversion and velocity, or funnel. We are not quota-based, obviously. Measurement for any overhead team like ours is a little more difficult and a little more project-based but we consider ourselves the stewards of the funnel. We do target ourselves to a certain lead to MQL conversion rate and then marketing qualified to opportunity. Between opportunity and closed won, obviously, we have less control as that is more sales. Then moving beyond closed won into retention, that is more customer success.

But the main part of the marketing to sales funnel is where rev ops gets its discrete KPIs from.

We have benchmarks. MQL to opportunity: 20% plus, which a lot of companies would consider pretty high, but again for a heavily inbound and a high intent driven business, it’s our bread and butter.

And 20% plus for MQL to opportunity. And then for marketing suspected, which is the first time that we are scoring these leads and passing them into an SDR’s hands, that shows that our lead scoring engine is operating correctly and efficiently and that we are sending the right leads to our SDRs. We typically look at it like 80% – 90% of MSL to MQL.

Read our interview with Denis.

Melinda Forest, Sales Operations Manager, Decibel

In the same way that you are looking at metrics for the marketing and sales team, you measure the marketing and sales ops person on the improvement of those metrics. If lead and opportunity value, volume and velocity are indeed improved upon, that is a measurement on me.

We define success through new processes  put in place, integrations to the system that have streamlined workflow, and progressive productivity of the sales workforce. If we see an increase to pipeline, that is a measurement on the sales operations team. If we see a shortened sales cycle, that is a measurement on us as well.

I think people throw out stats all the time, ‘you should see 30% growth and that’s due to your sales operations person’. I can’t necessarily say that, because, hypothetically, only 30% of what I do relates to the sales team; 30% to marketing, 30% to finance, 10% to management and business intelligence. I think we have a hand in everything, and any type of growth is significant. If you are doing your job right, you are streamlining process; you are helping all departments achieve their metrics.

If they are not, I think likewise you can say, sales ops need to step it up.

Read our interview with Melinda.

Catalin Tilimpea, Director of Global Sales Operations, Arm

I believe that sales ops has to be thought of as part of sales, and I strongly believe that it is best if you measure sales and sales ops together based on sales results, like dollar figures.

I am a strong believer in objective metrics, preferably numeric and making sure that they are exactly the same metric for sales and for sales ops. The sales ops professional that works with sales needs to feel that they are part of the team, so they have to be incentivised on the same basis. That bond is very important. You have got to feel that you are working in the team and you are cheering when that number goes up.

I think that is a very powerful motivator. You are like the co-pilot, but you are in the same race and at the end there is going to be some reward, of the same type, for the co-pilot, just as for the pilot. 

Read our interview with Catalin.

Kirsty Charlton, Head of Sales Operations, Signal AI

There’s a document which our old sales ops manager from Vision Critical sent to me. It’s the anatomy of the world class sales operation. It says for every sales ops function, these are the 19 areas you should be looking at, from CRM ownership to commission structure and everything in between. I set out a team exercise using that document. For each one of those 19 facets of sales ops, the team assessed how we were performing on a scale of 1 – 5 and how much impact could we have if we got it right on a scale of 1 – 5. And I mapped it out on a board and anything that we’re not good at but we could have huge impact on we made a priority for us to work on.

From that, we’ve come up with two overarching OKRs. The first objective is to define and implement a repeatable, global, and scalable sales process. We want it developed through data and utilised by all reps. The three key results are to reduce RAMP time to four months, have the reps working a min of 36 ops looking forward and reduce our sales cycle by 50%. It’s ambitious, but that’s the idea of OKRs. You’re meant to only be 70% confident you can hit them.

The second one is massive. It’s evolving the culture of the sales management team from an anecdotal and reactive one to a team that’s data backed and proactive. A key result of this is forecast accuracy. At the moment we have open head count, we’re not analysing how many accounts are being worked. We can reactively look and say you’ve got enough. But we don’t have anyone proactively analysing whether X person has had a bad month. So another key result is for every manager to go into 1:1s with data so they can actually coach the reps. Instead of ‘how’s everything going?’ they can have data backed conversations.

Read our interview with Kirsty.

Adam Daigian, VP Growth & Revenue, Hustle

I think there are a couple of different ways to look at it. One, you absolutely have to consider your internal customers’ NPS. If your sales organisation hates your revenue ops organisation, it is painful for everybody. 

It is hard to maintain a solid internal customer NPS because your internal customers are usually pretty tough and not always particularly understanding of your road map or competing priorities. But again, it is important that you deliver on expectations and you maintain a strong relationship with your internal customers.

Clearly, whatever the core KPIs within a revenue organisation are, rev ops has to play an important role in and be a driver of lifting those metrics.

And last but not least, you can look for efficiencies elsewhere too because revenue ops is also connected to other functions, like product, marketing, finance etc. So there are opportunities to measure success by looking into efficiencies that you drive for these other organisations.

Read our interview with Adam.

Jessie Schreiber, Director of Sales Operations, Program Management, Ibotta

Sales enablement and sales ops sometimes have shared goals. One of them recently is something that is more industry standard. We needed to see the appropriate percentage of opportunities in Salesforce go through each of the stages, because in the past everything had been going in at ‘verbal accept’. So we had no pipeline visibility.

We set a very specific goal. If we had seen that only X% of opportunities sat in stage 2 previously, and for how long, we went in and applied specific percentages to drive a Y% increase, so that the sales managers were able to see all the opportunities throughout the entire funnel.

Here is another broader example. We are trying to make Salesforce a single data entry point solution for all revenue generating activities. In the past, we had a different system that we call “Admin” (customized administration interface on Rails), which we are now transitioning out of. Both of them now are technically active, but I’m trying to move everyone out of the old one. Part of that was looking at how many of our campaigns get initiated in Salesforce and then pushed to the other – versus created in “Admin.” Those are obviously very tangible and specific tools in the stage that our company is at.

Read our interview with Jessie.

Rebecca Silverstein, Manager of Sales Operations, Smartling

We divide things into projects using OKRs: This is our objective, this is what the result looks like and these are the things that we need to do to get there in this time period. I know that some people also use a form of NPS score to understand if their work is actually making an impact on the team. It’s always good to ask whether the work we do is helpful and what we could have done better.

Read our interview with Rebecca.

Matt Magee, Director of Global Sales Operations, Smarsh

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.

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?

And there are some qualitative 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.

Read our interview with Matt.

Neel Suri, Director – Sales Optimization & Technology, Newsela

I think the biggest thing is ultimately hitting the number – impacting the business in a big way.  Some will say it is about having perfect data, governance, and a tightly controlled environment – All of which do make a difference. But if you’re not hitting the number, none of that stuff is important.

So, I think the definition of success is being able to show that the work that you are doing, the initiatives you are pursuing, and the change you are implementing is moving the needle, driving more sales, and driving increased velocity.

Sales productivity is certainly a key component, and this can be measured in different ways. For example, in a technology sense, you could focus on reducing the amount of time a rep is occupied from engaging with a customer. Another focus could be, how quickly are we ramping our new reps, so they are contributing to the bottom line?  

I’ve also tried to measure our success through internal data collection. After my first year here, I sent out a survey to the sales organisation. We had a series of questions focused on getting feedback about their personal experience with the company and how supported they felt. Ultimately what I wanted to do was get an annual NPS score to monitor our progress. 

Read our interview with Neel.

Sofiya Ulyak, Director of Sales Operations, Star

Sales operations itself is a niche responsibility within the company that people may not realise the value of. And I think the only way to measure whether sales operations are successful is by looking at how well the sales team is hitting their goals. That is the only quantitative measure of sales operations. If the sales team is successful, it means that sales operations is moving in the right direction, it means that we are investing the effort and time into it and some tiny portion of that success belongs to us.

When looking into our qualitative success, it’s the perception of the team as well as feedback, we ask people what we should improve on or if we are going in the right direction. Feedback that our CRM is easy to work with; our onboarding works well; the process is clear; and so forth; is always positive. It means that the Lego blocks we pick are the right ones and the entire team shares the vision of the result.

Read our interview with Sofiya.

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