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A Blueprint from the Woman Who Helped AdRoll Double its Sales Force and Sales

In the early 1990s, the world’s largest chemical producer, BASF, launched a famous corporate slogan: “We don’t make a lot of the products you buy. We make a lot of the products you buy better.” That’s the spirit of sales operations, according to Diane Lu, most recently AdRoll’s Director of Sales Operations. It centers on enabling deals — helping a company sell better, faster and with more precision. Rarely are sales ops professionals on the front line making sales, but once you have them, there’s no going back.

A decade ago, if you were strolling along San Francisco’s waterfront, you might’ve run into Lu, buying and selling hardware on Pier 38. This was the precursor to her stints at Google, Youtube and AdRoll, where, while Lu was there, her team helped a 500-employee organization to triple its revenue. For Lu, her leadership in sales ops has its origins on that dock, where she first left the back office to run a full sales cycle after a salesperson skipped work to go surfing.

That day Lu discovered two truths: that she’s driven by everything right before and after a sale, and the incredible leverage that sales ops can wield in a company, when done right. In this exclusive interview, she dissects the dynamics and mechanics of the first ten sales ops employees, and the accompanying inflection points for a young, growing sales ops team. Startups seeking to supercharge their sales efforts can learn a lot from Lu’s experience.

Employee Zero: The Founder is Sales Ops

Let’s level. In the early days of sales, a startup — very often just the founder — is solely worried about closing deals and generating revenue. However, after the very first sale, something happens. It’s no longer an anomaly, but a benchmark that’s about to morph into a process. A seasoned sales ops lead sees the start of sales ops, even if it’s not yet apparent to the founder.

“Sales ops begins by a series of small observations-turned-questions around a sale. The kernel of the function is the reflective line of inquiry after the first deal: ‘How could I have closed that faster? Can I find more leads via that channel? What if more people were selling?’” says Lu. “These questions become a series of small decisions to get from point A to B with sales. They’ll be made consciously or subconsciously — but they’ll happen. These choices set up sales ops.”

It’s at this point that Lu often steps in to make the foundation of sales ops solid. She currently advises several early stage startups, including Branch Metrics and Lob, and focuses on the founder, who’s starting to wear a sales ops hat — knowingly or not. Here’s the five-stage evolution that she sees, which gets a startup’s sales ops function from founder to the first hire:

Stage 1: “Just let me sell.” In the really early days, the founder is closing the first customers. Sales ops is an afterthought. The entrepreneur observes what she did and what she would do differently, though she may not act on it the next time around. How to level up: Log how you’d do it better. Document to start making an afterthought into foresight.

Stage 2: “I’m doing it wrong.” Given all the hats they wear, a lot of times founders make sales decisions by what’s tactically easiest to check off the list, not what’s thorough and right. How to level up: It’s mental. Acknowledgement of the wrong action is an active choice (and still shows you see what’s right). Learn what it feels like to put an initial process around this function, even if it’s imperfect.

Stage 3: “That is right, even if I can’t do it. How do I make it repeatable?” Through repetition, the founder is building towards something right, but won’t have bandwidth to repeat the entire process correctly and consistently. How to level up: Remove yourself from the process. Knowing what you know, how would you build the best sales process for someone else to repeat? When you hire, this will be your initial instructions to impart.

Stage 4: “Ok, this is repeatable. What will X number of repetitions generate?” Think about what 1000 more efficient sales cycles will generate. That’ll get you thinking beyond next month and in 6-12 month increments. This is hard if a company is nascent and pre-revenue, but the exercise will create a long-term target. It’s easy to avoid doing so by citing turbulent markets or new competitors. Resist that excuse. How to level up: Set a big sales target, even if it’ll change. It’ll help orient other people to a goal.

Stage 5: “Here’s where we’re going. Help us find our way.” This is the most critical jump — and the gateway to a first sales op post. According to Lu, a founder truly gets sales ops when when he says, ‘This is what we want. Find a way to do it.’ If there’s not a person to say that to, it’s time to hire. Now there’s a stated sales goal and the flexibility for others to execute to get there. How to level up: Formalize the first post in sales ops.

Lu has seen entrepreneurs move through this process time and again, and has identified those who take most naturally to the journey and sales ops function. “I’ve seen founders with operational backgrounds pick up and absorb the value of sales ops faster than those with pure sales backgrounds,” she says, “That’s because very skilled salespeople often rely on their innate skills and don’t need to be as overtly process-oriented. They naturally follow-up and instinctively bucket their targets, so don’t think to systematize those practices for others to replicate. Natural athletes often don’t make the best coaches.”

When Lu works with founders, most of the early work is to help them put repeatable, structural support around their sales process, no matter how naturally they come to sales ops. “Especially if they’re intuitively good at sales or the charismatic and charming founder, that’s when there’s heavy lifting,” she says. “Once they’re ready to deconstruct and standardize the sales ops process, they’re primed to start delegating the responsibility. They’re prepared to not build it for themselves, but for the first sales ops person they’re about to hire.”

Employee One: The Lone Ranger

Lu gives an honest take of the relationship between a founder and first sales op hire. “There’s no doubt that it’s a big opportunity for the first sales ops person, but it’s almost certainly going to be a tough couple of years,” she says. “The strategy will live nearly completely with the founder, who’ll have little time to collaborate, and the execution will depend almost entirely with the sales ops person. It’s not uncommon for the hire to have several managers — from a sales manager to a sales development representative (SDR) to the founder — over the first few years.”

To top it off, this first hire will not only be new to the role, but also likely professionally green. “While the seniority level of the first hire tends to change with the size of the company, it’stypical that your first sales ops hire is junior — about two years out of school,” says Lu. “As they’ll be independently putting out fires daily, they’ll need to embody specific characteristics to counterbalance the founder and lay the groundwork for the sales ops team.”

In sales ops, the satisfaction of a job well done often lives with you. You have to be okay with that.

You’re likely to find a first sales ops hire coming from a few different backgrounds. “One is they happen to be a bright, technically-minded sales or SDR person. Then there are business analysts, who are driven by finding and fixing inefficiencies,” says Lu. “It may seem counterintuitive, but I like to hire candidates who have spent some time being externally facing. They’ve seen customers and know who it is they’re impacting. They need to have the analytical chops, but also be rooted in how their work changes the sales experience.”

While she wouldn’t call this profile one in a million, there’s a precise combination of traits to search for in order to set up the first hire — and future sales ops team — for success. “I’ve started building sales ops teams several times, and love the personality that goes with sales ops. I feel like I could pick them out of a lineup.” They are:

Scrappy. “They’re not going to have a lot of technical resources. There’ll be no designated developers or earmarked time from colleagues to help. They’ll need the ability and gumption to beg, borrow and steal to get something done,” says Lu. “At the one-person stage, a lot of sales ops is automation. Unless the person happens to be a developer by background, he’ll need to find an engineer to help write a script or get leads off the Internet. Creativity and scrappiness plays a large role.”

To test this attribute: Get examples of how they’ve built more with less. Look to find individuals that have a get-it-done attitude and don’t let roadblocks get in the way. This is where creative thinking and bending the rules comes into play, and where the people who ask for forgiveness rather than permission thrive.

Opportunistically lazy. “The flip side of coin of being very efficiency-minded is being opportunistically lazy. I apply this trait to myself, and not in a bad way,” says Lu. “Sometimes the greatest efficiency innovations come out of laziness. Look for the guy who’s going to automate his job instead of do it.”

To test this attribute: Find out if they are driven by the pure joy of getting something done. Are they a person who likes checking things off the list? Will they go back to their list to write a completed task just to cross it off? In the early days, sales ops has to be in it for the pure joy of getting something done and making something better.

Street smart. “Being smart goes without saying. Book smarts help of course, especially if they can learn to spec out or code what they need. But most importantly, they must find ways to act on their inclination to automate and direct their scrappiness,” says Lu.

To test this attribute: It’s not always the case, but those with street smarts actively observe, while those with book smarts tend to passively absorb. Ask the candidate to pinpoint the earliest signal that an improvement was needed. Take note if it was through firsthand experience or via another source or secondary research.

Not too structured. “Sales ops still belongs to the sales floor. The first hire will have to roll with the punches and be flexible enough to get along with the sales team,” says Lu. “Those who will construct constraints — say only allow three projects in the pipeline at any given time — are too rigid and tend not to do as well.”

To test this attribute: Inquire about moments when they’ve had to react to unexpected changes. The ones who freeze up or consistently dig in their heels might not be the right match. Those who work to understand the change and craft a plan B will be a better fit.

Ethical. “Yes, candidates should be scrappy, efficiency-minded, not constrained by rules and smart. But if you take those qualities on their own, you could get a shark. You’d probably get a very successful, but not quite ethical sales ops lead,” says Lu.

To test this attribute: Ask about the last time they built a cool tool. Suss out if they shared it with the whole company or kept it close to the vest. People who share these shortcuts internally aren’t looking to use it as a competitive edge, but to the benefit of the entire company. This becomes critical as sales ops often is the tie-breaker in sales scenarios.

If you’re able to find this profile for your first sales ops hire, know that they’ll need to be motivated differently than the sales function around them. “The career ladder is different for the first hire of sales ops. If they are a former salesperson or business analyst, they might be taking a pay cut, but gaining a chance to carve out a whole new function in an organization,” says Lu. “The career path will give you intimate (even if intermittent) access to the founder and sales leadership, and the cross-functional exposure is huge.”

If you do sales ops and do it well, you’re in demand by every department across the enterprise.

It was before Lu’s time, but the first sales op hire at Adroll initially joined the company as an SDR. “He was versatile and so leadership constantly sent him side projects, because he had the skills and demeanor to execute them,” says Lu. “For a while he was on his own improving the sales process one fire and side project at a time. When I joined to lead the team, we were able to groom him from a general sales op analyst to a Salesforce-certified project manager, who could follow a more functional or technical career track managing sales ops projects.”

The takeaway is that the first sales ops hire may come in as a junior generalist, but will be on a fast-track to charting and contributing to all facets of a sales organization — and the company as a whole. “Craig has grown up and risen through the ranks at Adroll. He’s a known entity, well-liked throughout the organization and has worked with every department.”

Employees Two and Three: Welcome to the Wolfpack

When Lu joined Adroll to lead sales ops, she was the fourth hire on the team. The team she joined was hierarchically flat, but had already gone from supporting 20 salespeople to serving a sales force of 250. The impetus for sales ops growth was in parallel with increased headcount of the sales team. “Hires one to three happens fairly quick, because in early startup days, it’s about throwing bodies at problems. Most issues are still being solved manually versus, say automation, because when you’re two or three people, you usually can’t fix problems at scale,” says Lu. “It’s more of a set of equals dividing and conquering with occasional flashes of leadership — a bit like wolves in a wolfpack.”

The characteristics of the second and third sales ops members largely mirror the attributes of the first hire, but hint at the beginnings of career paths (functional or technical), but the team still will operate as generalists until headcount increases. “At this stage, it’s the first time you start to get the different flavors of sales ops. One person may come from customer success, so focuses on delivering much more on the people side, and may be geared toward the internal impact of sales ops on the company,” says Lu. “If it’s not the background of the first hire, there will likely be an addition to the team from sales or a former SDR, who wants to make their former teams technically better by putting future leads in Salesforce or helping build workflows. They’re the ones helping you before there’s automated lead routing by responding to inbound leads or doing all the copy that will one day be used for automated emails. These second and third members essentially build the templates that will eventually become standard protocol and language for the sales op function down the line.”

It may be counterintuitive, but the second and third hires are young risk-takers. There’s just enough groundwork laid by the first hire to have something to launch from to solve big challenges creatively and quickly. “For startups, these hires are two to three years into their career, but the immediate exposure they get to leadership is astronomical, as many could report to the CEO or founder early on,” says Lu. “At startups experiencing explosive growth, these are visible roles for early employees. Early on at AdRoll, I met with the CRO weekly.”

Employees Four Through Ten: Truly a Team

The stretch of hiring from employee four to ten marks another transition for sales ops. The flat structure takes on hierarchy, the team starts to specialize, and sales ops become much more proactive in its contributions to the sales organization. By the time sales op reaches ten people, the team is supporting a sales force that is 500 people strong.

“Growing from single to double digits marks the end of the wolf pack and the formation of a team. It’s no longer about day-to-day management, it’s year-to-year planning,” says Lu. “After the third hire, establish a clear manager — a more senior leader who can keep the team coordinated and see getting things done differently. Execution is a strategy and is building a better way forward for sales. That’s the true moment when a sales ops teamcomes to be.”

Seek the moment when execution is not just about getting things crossed off the list, but a strategic prompt to determine what should be done next.

For Lu, this is the sweet spot to truly level up sales ops — and the stretch in which she joined AdRoll to scale the team. “I loved that entry point. I think that was the most exciting moment to come in. It’s early enough that you move quickly, do things fast and feel the impact. But you have enough people and you have the critical mass to start putting structure in place,” says Lu. “I think the greatest ratio of opportunity to wins. Early on at Adroll, I made a 90-day plan. A year later, an exec asked me to send it to him, asking me how much I accomplished. ‘All of it,’ I said. ‘Nearly 300 days ago.’ That’s how fast we were hitting targets.” Here’s how Lu did it:

Start directing your data.

After Lu joined Adroll, the sales op team made a lot of strides toward being a data-oriented company. “At that point, a lot of our sales were more transactional in nature: the deal closed, it was handed off, debugged, next!” says Lu. “I wanted to make sales ops an active agent in helping AdRoll become more of a partner to its clients. ”

Use the wealth of sales data to tell a story. For AdRoll, this meant giving their sales force market trends and context to better understand their customers. “I think the problem is is that you can’t be a company of transactional data points and still sell the partnership story.” says Lu. “It sounds granular, but a lot of what we did was put trending data in our CRM so that salespeople could actually pull up and look at the spending patterns over time.”

For other teams across the organization, this trending data was also important for revenue forecasting, but sales used it to tell a story with clients. “We could go into a big agency who had five different clients with Adroll, and we say, ‘Three of your clients are doing really well, two of them aren’t, let’s go through the optimizations and compare.’ After that, we weren’t happy with being a reactive sales organization anymore.”

Use tools in tandem.

With a higher headcount and greater skillset on the team, Lu wanted to better equip AdRoll’s sales team with more than improved SalesForce reporting or better workflows. “Increasingly, each deal we saw was a technical sale. There’s so much information out there,” says Lu. “Sales is no longer calling someone to let them know what their product is. That takes one Google search. And a few more to know your potential, pitfalls and your three closest competitors. To differentiate is something different. You’re cutting off the whole top of the sales funnel.”

One way Lu helped Adroll get the edge was predictive scoring, which helped sales much earlier in the cycle. “We implemented very data-driven lead gen. To create a powerful system, we combined the strengths of tools, such as sales intelligence platform Datanyze and lead scoring model Infer. Datanyze told us which companies were using which technologies and Infer directed us to which leads were more likely to sell,” says Lu. “Taken together, we were able to see the leads that were using technologies that were more likely to be our customers. So, for example, we might determine that the companies using Kissmetrics were more likely to be Adroll customers. Then we could go back to Datanyze and mine those leads back and score them more heavily.” Bottom line: be creative by hacking and patching tools together.

Most sales ops wins are unknown. But salespeople start to notice when quality leads start surfacing from the garbage.

End exclusively blended roles.

Up until hire number four, the sales op team is composed of high horsepower generalists, mostly because they are early in their careers. Versatility and speed were the valued attributes that helped them fight fires and help enable sales. “That’s why I start early hires, who are often junior, as generalists. Even if the team has developed specialists, you should make sure young hires experience the range of a generalist position. That way, they’ll dabble in configurations, build reports, work across departments, and do light project management.”

Around a time a manager starts to lead sales ops should also trigger the creation of formal specialized roles and career paths. “In my experience, when the team gets larger than three, it’s time to create specific functionary roles, which also corresponds with ownership,” says Lu. “The way that I’ve helped sales ops teams specialize is into two main categories: technically-minded, in which you work on systems and tools; or data-driven, in which you work in lead segmentation or more functional program management.”

There are some sales ops specializations that you should avoid. “I don’t recommend structuring in terms of customer segment. For example, that a person is focused on mid-market US sales or another is dedicated to agency sales,” says Lu. “In quickly growing companies, sales structures are going to reorganize too often for sales ops to rely on it for its own structure. Organizing it by technically-minded or data-driven cohorts gives you much more flexibility in prioritization.”

I knew we were an independent, functioning unit when the founder swapped tl;dr emails for one-line notes that read: Make it happen.

Sales ops is frequently an unheralded function, but a critically important one to any startup’s sales organizations. It begins as a founder’s thoughtful reflection on how to improve a sale and grows into highly-leveraged small team that can help hundreds of salespeople sell faster, better and more precisely. And that’s only the beginning. Of course, it depends on a startup’s growth, but a sales ops team beyond ten people will support a global sales force of over 500 people.

“Keep in mind that a sales ops team works very keenly in efficiencies and automation, so a really good sales ops should stay quite lean because they’ll automate parts of their own jobs, too,” says Lu. “As sales ops grows in parallel with the sales force, it’s important that it doesn’t lose its sense of urgency. Yes, you’re more skilled and better organized, but don’t let the stability of structure bring complacency,” says Lu. “Quota-driven salespeople will stay hungry. It’s sales ops’ job to keep their fridge full, palate sharp and the good stuff on their plates.”

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