Interview with Cris Santos, Director, EMEA & LATAM Sales Strategy & Operations, Docusign

7 min read

For those of you focusing on sales and marketing alignment right now, this is a must read! I got together a couple of weeks ago with Cris Santos, Director Sales Strategy & Ops at Docusign to talk about sales ops as a priority, a strategy driver, and the all elusive whirring sales and marketing machine.

Rory Brown (RB): Can you tell us about your career?

Cris Santos (CS): I think my passion for operations and strategy comes from my first professional experience as a naval officer. When I was in college, I wanted to be a diplomat. I always believed I could change the world for better and one of the easiest and fastest ways to do that was to be in the military. I was a naval officer for four years and that’s where I started working in strategy and operations and where I learnt that the two disciplines are interconnected.  

Then it was a fairly easy transition from the military world to the business world. I started in sales. I was fortunate enough that the company I joined, Allianz, were launching into new markets and because of my international relations experience, I was given the opportunity to take part in SWOT analyses. Then I decided to leave sales and just focus on the strategy and Ops side of Sales and that’s when I joined BMC Software, which became a really good business school for me as they were a mature business, well established in the market, and had very seasoned business professionals and sales ops people. So I was able to learn what worked well.

However, I like putting my stamp on stuff and building from scratch and that’s why I moved to the start-up world. I did that for a short time, in a small Irish tech company where I was covering sales and marketing operations. It was a really good experience, but I left because the company was too small, and I needed to be in a company that had aspirations to be something bigger.

I’ve been at DocuSign for almost four years and I was the first international sales ops hire and one of the first hires in the overall EMEA organisation. They wanted someone who could execute on the tactical day-to-day, but also develop a strategy. Actually, I think it’s critical to strategise, before you start hiring and opening offices.

RB: It’s interesting you say that because for some companies, hiring sales operations is an afterthought. What would you say are the arguments for having your sales ops prior to building out a significant sales team?

CS: Sales ops should be one of the first hires a company makes. And I’m not talking about someone who puts reports together. I’m talking about a seasoned leader who has plans and goals. If we look at the recent trend in business, when a lot of American companies expand overseas, they are now hiring sales ops at the same time as the sales leader. To use a military analogy, they are bringing their Chief of Staff or their lieutenant. You often hear about sales ops supporting sales, but sales ops partners with sales. We are peers regardless of job titles. And that’s how I see my relationship with my stakeholders. They bounce ideas with me and vice versa.

I really like the idea of calling it sales strategy and operations instead of just Sales Ops. To quote from the Art of War, “Tactics without strategy is the noise before defeat”. You need a plan and a strategy before the tactics to achieve a goal.

RB: Do you have an example of a strategy play? And then is there an example of strategy and then applying tactics?

CS: When I joined DocuSign, the team was very small here in EMEA. In three years, we wanted EMEA to be X% of the total revenue of the company. We had that goal from finance. So, what we had to do was firstly ask ourselves, how are we going to build our teams in these areas? Do we just need sellers? No, we need to align with marketing and start building pipeline. So, we’ve established that in order to be successful, we need to bring pipeline to the business. How are we going to do it?

One of the first things we did was set up a pipeline council meeting. These are weekly meetings for marketing, sales and sales ops discuss how we’re tracking against our pipeline targets. It’s a forum for accountability and for people to discuss what activities they’re doing. Even if all lights are green, we can analyse which events have been successful and then it’s about replicating them.

RB: Let’s home in on sales and marketing operations. One of the areas people struggle with is how much sales ops know about the marketing funnel and vice versa. And that can be where the disasters happen. What are the pitfalls to look out for?

CS: Seeing it as two separate departments is the first mistake. For me, marketing creates the demand for sales. Sales can’t exist without marketing and vice versa. Having that broken relationship is very common in companies. At DocuSign, we removed that wall across the two organizations and we got the marketing and sales leaders together to discuss targets. And we concluded that there is no such thing as a separate sales target and a marketing target. I think it’s that lack of accountability that can create that tension between marketing and sales. So we put together a new measurement on the compensation plan to align both departments.  

At the end of the day, organisations are made of people, so we need to make sure we get those people together. We have the marketing team spread across different countries so they’re not sitting here with the main sales team,but we go and see them all the time, they come to see us, and we have regular contact over the phone. I think that explains a lot of the success here at DocuSign; people are very open to dialogue and willing to cooperate in a holistic way.

RB: The next question goes a bit deeper into the nuts and bolts of the handoff. When an MQL comes in, what is the handoff moment like?

CS: We make sure we have the right systems and processes in place to be as efficient and fast as possible. One of the first things we did was to reassess the lead scoring system and we worked with marketing on that to make sure that we are focusing our time on the best leads. However, even if they’re not an MQL, we continuously monitor them and we’ve invested a lot in a sales development organisation that helps with that machine. We have people in charge of processing those leads so we’re on top of everything that’s coming in. We have inbound reps and then we have the outbound team. We’ve created a sizable sales development organisation, similar to what Salesforce, for example, have created.

RB: I love the fact that sales ops get involve with that lead scoring. Are there any SLAs in place?

CS: Precisely. We have SLAs for the sales development reps. They need to process leads in 24 hours. In the four years I’ve been here we’ve definitely improved on that. We’ve specialised the SDR roles to some focus on leads from events, others focus on leads from webinars and so on.

We have tools to monitor what the reps are doing. In EMEA, we were the first to adopt a gamification tool. We started using a certain tool and gamifying the process. We’ve since changed tools, but we’ve kept gamification. We have screens across the floors where we track opportunities and how fast those opps are qualified. It’s on full display and it works really well as we can see from the fact that here in EMEA they have the highest productivity per head. It’s also good for morale and culture. It’s the fun of competitions and being on the leaderboard and we’ve really seen the results.

RB: I’m interested in how you define success in sales operations.

CS: 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 on your blog 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.

RB: Do you have any specific examples of these innovations?

CS: One of the innovations was gamification. Another one we did with the sales enablement team was revamping our forecasting methodology at the sales rep level, not just manager level. Because forecasting starts with the reps. So, we trained them to take a mathematically driven approach to their forecasting and combine it with their own qualitative opinion about the deals they are working on.

Since this interview took place, Cris has moved to a new role as Head of Revenue Strategy and Operations for EMEA and India at Pluralsight.

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

At Kluster, we’re big fans of sales operations…

We recognise the growing importance of sales operations. No longer seen as the function that provides spreadsheets, sales operations is integral to building a repeatable, scalable sales machine.

That’s why we built Kluster. We make analytics and forecasting systems for you so you can spend time doing what you do best: uncovering trends and delivering growth defining insights.

Kluster gives you total visibility into the effectiveness of your sales machine and helps you generate credible forecasts to revenue leaders and the board.

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