Sales Ops Insights Series: Interview with Jeremey Donovan

Apr 21, 2020

As the Head of Sales Strategy and Sales Operations at SalesLoft, Jeremey Donovan has had plenty of experience on what makes a successful sales and sales ops team. He has also provided strategy and leadership at other large companies, such as CB Insights, Gerson Lehrman Group, and American Management Association. He is also a professor at NYU School of Professional Studies teaching courses related to data and sales.

In addition to experience in the field, Jeremey’s podcast Hey Salespeople and blog SellingSherpa dive into the art and science of sales. He is the author of five books, including the bestseller “How to Deliver a TED talk.” He also provides thought leadership and sales advice through his LinkedIn account.

We sat down with Jeremey to get his insights into leading sales ops, technology that he can’t live without, and why you won’t find him binge-ing on any Netflix shows.

To listen to the whole interview:


Question #1: What are your current favorite books, podcasts, blogs for keeping up the sales ops industry news?

I’m a massive consumer of information, and all of the above, especially books I would say, as well as some forums. So on the book side, I really do try to read almost every sales book that is published within reason. And I publish summaries of those books both on LinkedIn, and then I also have a blog where I post those summaries for other sales people to read, which is at SellingSherpa.

And then, favorite books, I read all kinds of nonfiction and fiction, but in the sales ops and strategy world, one of my favorite old time books is Strategic Selling. There are a few newer ones that are less known, Secrets of Question-Based Selling. I really liked Keenan’s book Gap Selling.

So there are so many of them, but for me, I concentrate more on books than podcasts. I don’t listen to that many sales podcasts, just because of the nature of my commute. And then with blogs, the blogs that I most follow are Gong, Chorus, The Bridge Group, TOPO, John Barrows. So those are some good sources. But those are sales and sales ops for sure.

(interviewer) And I think it’s fair to give a little plug to your own podcast, Hey Salespeople, for people looking for podcasts out there since you don’t listen to as many yourself.

And I’m remiss in not mentioning Modern Sales Pros. I should’ve led with that. It’s not quite a blog, a podcast, or a book, it’s more in your etcetera category. So Modern Sales Pros for sales ops folks who don’t know it, I’m shocked, but it is a very old school Google group, almost like a sort of email listserv. But it’s a place where sales ops professionals congregate to ask and answer questions.

And what’s great about it is it’s extremely tightly moderated, and there’s no self promotion; there’s no selling. It really is people asking legit, often complicated, questions or checking out vendors and trying to get objective feedback, and so on. So yeah, Modern Sales Pros I guess would be my number one favorite, and it took me a while to get there.

Question #2: What is one piece of technology that your sales team can’t live without, and how do you use that on a daily basis?

To talk more broadly about our tech stack, there are a ton of different tools we use. If you think about the flow of the way that sales professionals operate, the very first thing that they need to do is find contacts and accounts, and the two vital tools for us there are ZoomInfo and LinkedIn Sales Navigator. So those we definitely cannot live without on the sales or sales op side.

We drink our own champagne with the SalesLoft platform for engagement, but we do use a number of other tools that kind of support that ecosystem. We love gift giving platforms, and we’re using two of those right now: Sendoso and Alyce. They’re both great and have slightly different use cases. So those are highly complementary, and our salespeople can’t live without them.

And then there’s some stuff that sales people don’t even honestly know about where we’re doing backend routing. For example, when inbound leads come in, or we have other workflows, we use a combination of different things. Workato is a great partner for us there as well as Chili Piper, which we use for a round robin routing. So there’s a lot of stuff.

And then of course Salesforce, love it or hate it. I actually do love it. We’ll talk more about CRM, but I’m a big fan of Salesforce, but I guess we can get there when we get there.

Question #3: What is your typical day to day as a leader?

As I’ve gone through my career, as old as I am, I have not always been a sales ops person. I actually started my career as a semiconductor engineer. I then moved into product development, product management, product marketing, corporate marketing. I was a CMO and a CRO at one point, and I guess in my crusty old age I realized that I really love sales strategy and operations. I’ve been doing that for quite some time.

The other evolution I’ve been going through, which kind of gets to a long winded answer to this question, is that I’ve gone through waves in my life of where I like to do what could be referred to as individual contributor work and leadership and management work.

I am currently in a wave that I really enjoy being a player coach, which I don’t usually advise for most roles, but I’ve got two really able partners at Salesloft amongst others. One is our Head of Sales Enablement, Sean Fowler, whose title is a misnomer. He’s also a sales strategy and ops person. And then I’ve got another partner in crime, Jason Moore, also a sales strategy and ops person. And we divide and conquer with the teams that we lead.

For me personally, because of that player coach thing, I would say I probably spend half my time project managing stuff that has been then delegated out to other people. So that’s assigning, checking in. Strategy is all about people crossing technology, so just making sure that those projects are working. So I’ve sort of described it as leadership coaching and project management.

And then the other half of my day is rolling up my sleeves and getting down in the dirty inside of Salesforce. Or, believe it or not, because I have that engineering background, I still write a lot of code. I still do a lot of analysis in Excel and other BI types of tools. So I think like most people there is almost no typical work day.

But it’s a happier day for me when I can block. I actually refer to them as deep work blocks in my calendar. So I’ll block two to three hours with just no meetings where I very specifically deep dive on making progress on a project that I’m working on. That is the individual contributor work side of what I do.

Question #4: How do you work with marketing and do you think they provide high quality leads?

The topic of sales and marketing alignment seems to be a perennial one, decades long complication. And having worked on both sides of the fence, there was a time where I worked on the demand gen side, and we would create all these leads, and then we would scratch our heads about why sales would not engage on those leads. And we tried to find ever more creative ways to provide incentives, carrots and or sticks for them to engage with those leads.

A high quality lead to me is someone who really, really raises their hand. And by that I mean they request a demo, or they fill out a contact-us request. That to me is high quality lead to our salespeople. Back when I was in marketing we’d do webinars; we’d have white paper downloads; we’d have all this content, demand generation stuff that we would do, and I really wanted our reps to engage with those leads. But now I kind of see on the other side that those leads, there’s probably another word. I don’t even want to call them leads. They’re somebody who has a passing interest.

My ideal would be that you’re providing information and brand exposure with some of those pieces of content marketing, but you will always want to have a call to action so that they can raise their hand.  And when they do raise their hand, you’re ready. So I have not had a lot of success in trying to directly engage those people until they actually raised their hand.

That said, on the partnership with marketing more broadly, we’re tied at the hip in a lot of ways at SalesLoft. One way is, just like everybody these days, we’re very account-based, and our marketing team is responsible for the account segmentation and tiering that we do. And it’s really important that the sales team and the marketing team meet regularly to look at lists of accounts. This makes sure that we’re targeting the right people, because we really want to reinforce each other.

One really tactical, practical, actionable way we do that is we have something called a sales engagement score. We compute this in Salesforce. Basically, we’re looking at how engaged a rep or reps are on an account, and we tally up a score based on calls, and emails, and social touches. And then that sales engagement score actually feeds our account based marketing execution. Marketing might target someone, then the rep gets involved, and they sort of play off each other, increasing the degree of engagement. So I think that that’s a specific tactic that’s been very effective for us.

Question #5: What are your thoughts on CRM and data integrity? What is the best way to keep the data clean between different systems?

We think of CRM Salesforce as a system of record. So because we have our own system of execution, we don’t rely on Salesforce as a system of execution. If we did then I probably wouldn’t be as much of a fan. But as a system of record, I find it’s a good system of record.

I guess part of one’s happiness with the CRM is your happiness with your own data integrity. We have pretty good data integrity because we log all activities: social, email, phone. Everything is logged. So we have just really good data on that side. Our account data is enriched by ZoomInfo as I mentioned earlier. So that data is pretty clean all the time. Our contact data we’re constantly enhancing either from ZoomInfo or updating based on information that we gather via LinkedIn. So the input data is very good.

And then on the CRM side, it does the things I needed to do. I can generate almost any report I want. I can build dashboards. The search functionality is very good. The responsiveness most of the time is very snappy. I think my happiness with Salesforce also increased dramatically when I made the leap from classic to lightning. At first I was very reluctant. I switched over. Two weeks later I gave up. And then I had to give it another go. And then once I did, I was totally hooked.

And then you asked about integrations. We use a lot of integrations, and if anything, they certainly help with data integrity. Some of those integrations are process integrations. For example, the Workato integration I mentioned earlier. Some of those integrations are data integrations, like ZoomInfo, or Datahug, or any other of the data enhancement things. Another one we use is to track references. We use a company called ReferenceEdge for that. It’s almost too many to list integrations into Salesforce, and they are all serving different needs.

Question #6: Speaking of reporting and Salesforce, how do you create accurate forecasts for your team?

That’s a great question, and it’s been very top of mind for me recently. In RevOps one of our primary responsibilities is sales forecasting. In this case, we actually triangulate between three or four different methods. One method is the roll up. Basically, think of it as a weighted pipeline of the reps. To support that we ask our reps to forecast not only their base case number, but also a best case and the worst case for the deal. So we automatically have a range.

We try to be as sophisticated as we possibly can to weigh that pipeline. We weigh by the usual thing, weighted by stage, which we calibrate based on a 90 day moving average. We’ll calibrate the forecast probabilities based on both stage and by segments, since we operate in a few different market segments. So that gives us a pretty good forecast roll up.

The other thing that we do is that some parts of our business have faster sales cycles. So if you’re at the beginning of the quarter, and you’re going to call a quarter, and your sales cycle is short, then not everything is going to be in the pipeline. So we have a few different approaches that we use to estimate the trend or the run rate in our business that gives us that other piece.

And then the third thing that we do is we do ask managers periodically to commit to, we call it a bid. So the managers see their roll up of all the business on their team; they see that best case, worst case, and then they apply a little bit of their intuition and instinct to call their number. We actually make a game out of it. That’s why we call it the bid. Each month we do it and the winner wins, I think, $500 if they’re closest to their bid for their business segment.

Question #7: How have you set up your comp structure for your team, and how do you use this to align with your sales strategies and goals?

On the sales team we are pretty traditional, we have SDRs*, we have AEs*, and we have account managers. For SDRs, they’re paid. Besides their base salary, the variable comp is on two components. One is meetings that had been held and marked as qualified by account executives, called SQLs*. There’s all kinds of names, but basically a meeting held and marked as qualified and accepted into the pipeline by a rep. That’s our primary variable comp metric.

And then we also give them a percentage of the ARR* for the business that ultimately closes that they help source. I think those two metrics are probably the two most common in the sales development world.

In the AE world it is exactly what you would expect. It’s a percentage of quota. So all of our reps have an OTE*, and they’ve got a variable comp tied to that. We actually set quarterly targets, but we pay them monthly. And then the account managers are similar. They have a certain quota they need to hit.

On the sales op side that’s much harder, because how do you actually measure what sales ops people do? We’ve set the comp structure as bonus based, and for most of us it simply is a percentage of the company’s attainment. We’re all working towards the same goal. And if the company does 110% of the goal, then we get paid 110% of the bonus. Especially with respect to the part of your question around aligning to our strategies, there’s no better alignment in sales ops than just to align to your revenue goal.

One is on the sales ops side and then the second is on the sales enablement side. On the sales ops side, I think commissions is a pretty mature area. I would not expect massive innovation on that side. On the territory side, I do think that there’s room for innovation. I think it is a real headache for companies to manage their territories today, both initial territory assignment as well as ongoing territory updates.

We’ve had this massive account based marketing trend that’s bled over into account-based anything. Now the question is, “How is that account-based thing going to trickle over into the world of territory and sales ops?”

Another place is on forecasting and analytics. There are two barriers, as we talked about before, to doing that successfully. One is quality data, and then the next is the quality algorithms that sit on top of the data. The data’s very much the prerequisite. So as sales ops folks are waking up to unclean data, I would hope there’s going to be a continuing move afoot to capture more of that activity and effectiveness and results data. This way you can layer that data on top of more sophisticated algorithms, whatever you want to call them, AI, ML for doing that.

I think those are some great areas, which does mean that the profile for the successful sales ops professional, I’m biased I guess, is going to continue to become a much more analytical mathlete. I’m less of a pro on the enablement side, but I think the place that sales enablement is really concentrating on across, not just SalesLoft, but elsewhere is ramping reps.

And I think the change there is to really look at the data and see when the rate of productivity begins to flatten. You have this rapid increase in productivity when you first hire people and then it starts to naturally flatten out as they become effective at their jobs. Looking at that curve and then tying that ultimately to things that they can do, whether it’s sales process or training, coaching or whatever, I think that’s one area.

For enablement, if I learned one big thing over the course of my career on enablement, we talk mostly about rep enablement, but hands down the most important thing you can do is enable your first line sales managers. As companies understand that, I would expect significantly more investment in sales manager enablement over the next few years.

Bonus: Any other last tips or insights about how to be successful sales ops professional, inside and outside of work.  

Yeah, I promised to share a couple hobbies. So I don’t watch television. That’s an unusual thing in that I don’t do that, but that’s how I get more time back in my life. But besides the cats that I have to feed and take care of, and the Guinea pigs as well, my two weird habits, one is that I got into archery a little while back. So I spend a few hours a week shooting arrows at a target. So it’s one of my hobbies. And there’s no rhyme or reason to why I picked that up.

Major Takeaways

Jeremey knows how important the right technology is for keeping his team efficient and productive. By keeping a close watch on not only what technology they use, but why they use it, they keep clean data and don’t weigh down their operations with technology they won’t use.

Quality data is the future of sales ops and critical to making sales as successful as possible. Cleaning and maintaining data quality should be the top priority for any sales ops manager and company leadership.

Lastly, Jeremey predicts that sales forecasting and analytics will become increasingly important in sales ops. Data will only become even more vital as the algorithms for forecasting grow more sophisticated. Forecasting and analytics are an indispensable part of sales ops and are a major part of the future.


*SDR: Sales Development Rep

* AE: Account Executive

*SQL: Sales Qualified Leads

*ARR: Annual Recurring Revenue for term subscription agreements. ARR= (Overall Subscription Cost Per Year + Recurring Revenue from Add-Ons or Upgrades) – Revenue Lost from Cancellations

*OTE: On-Target Earnings