1The Sales Operations Playbook By Sales Operations Professionals

The Sales Operations Playbook

By Sales Operations Professionals

2The Sales Operations Playbook By Sales Operations Professionals

Table of Contents

The Rise of Sales Operations .............................................................................................. 3

Who Are These Sales Ops People, and Why Have They Become So Important? ........... 5

Defining Your Sales Model and Sales Team Organization ............................ 7

Rules of Engagement .................................................................................................................... 11

The Sales Ops Toolbox ........................................................................................................... 12

Need to Have Versus Nice to Have ........................................................................................... 13

Now and Later ............................................................................................................................... 14

Ease of Use ..................................................................................................................................... 15

Compatibility with Rest of Tool Stack ..................................................................................... 15

Cost .................................................................................................................................................. 16

Shopping Tips ................................................................................................................................ 16

Reports and Analysis .............................................................................................................. 18Sales Development Reps ............................................................................................................. 18

Account Executives ...................................................................................................................... 18

Communicating the Importance of Sales Ops ................................................... 20

Winning the Respect of Sales Reps ........................................................................................ 20

Gaining the Confidence of Leadership .................................................................................... 21

Carrying the Bag .......................................................................................................................... 23

Conclusion ...................................................................................................................................... 24

3

Sales has always been the art of persuasion. It’s about convincing someone that your product or solution not only will make their life easier. It’s indispensable. That ability to sell is a rare talent. It’s why the best salespeople always have been heroes at their companies.

But every star needs a supporting cast. And there long have been people on sales teams who handled the administrative tasks that helped keep the sales engine running smoothly. They stayed in the background while the sales stars, well, shined.

Over the years, though, the business world has changed. The basic tools of sales evolved from Rolodexes to spreadsheets to CRM systems to today’s sophisticated, cloud-based CRMs. Yes, sales remains an art. But now it’s also becoming a science. And those humble admins who once labored in quiet obscurity? They are stepping out of the shadows with their mastery of data.

Welcome to the Sales Operations Era.

Sales Ops is becoming the heart-and-soul of the modern revenue-generation team. These are the team members who are driving success in their organizations by making sense of the new wealth of sales data that is transforming business. These are the practitioners who are:

• Designing the sales process for organizations • Managing the technology stacks that have revolutionized sales through data and automation

• Serving as trusted lieutenants for leadership when making key decisions

The Rise of Sales Operations

Sales operations has been around for

awhile, but it used to do the janitorial

work like dealing with compensation,”

said Peter Kazanjy, founder of the

Modern Sales Pros, a leading sales

operations forum. “But it’s different

now. The way sales teams used to

be run was, ‘We’re going to hire as

many folks as we can, we’re going to

motivate them, and we’re going to tell

them that we’re going to fire them if

they don’t hit their numbers.’ Today,

it’s more about being a systems thinker

and an analyst. I think of sales ops as

the human representation of the sales

organization’s left brain.

The Sales Operations Playbook By Sales Operations Professionals

““

4The Sales Operations Playbook By Sales Operations Professionals

From a historical perspective, Xerox often is credited with creating – or at least defining – the Sales Ops role in the 1970s as a way to better support sales leadership. But the responsibilities have grown exponentially with the reliance on data.

The right side of the brain continues to be the salespeople who are good at developing relationships and constructing deals. But equally important are Sales Ops pros, who are taking the torrent of data, making order out of the chaos and using it to increase revenue.

“They are the hidden keys to a sales team,” said Craig Rosenberg, the co-founder and chief analyst at research firm TOPO. “It’s why VPs of Sales are bringing these Sales Ops people with them wherever they go. They’ve become foundational for success in a sales organization. They’re a partner in crime that every sales leader needs. They’re like the fixers. They’re smoothing out roadblocks. It’s beautiful what they do. The sales leader gets all the glory, but they know full well who is helping make it happen.”

For this eBook, we interviewed front-line Sales Ops practitioners as well as top sales thought-leaders with one goal: What should everyone know about modern Sales Operations? What are the challenges and responsibilities they encounter on a daily basis? How do they go about thinking through the Sales Operations Playbook at their organizations? Some of the specific topics include:

• Defining your sales model and organizing your team • Reporting and sales analysis • Sales tools and encouraging adoption • Communicating the importance of the role

You will learn from leading practitioners, in their own words, and get the inside scoop on actionable tips and tactics that can be applied to your business. The goal, simply put, is to take some of the mystery out of Sales Ops.

A lot of people would look at it as the brains of the operation. There’s no replacement for true, raw sales talent. But our job is to focus that talent in a smarter way. Whether that’s through better data analysis or just a broader evaluation of your go-to-market model, Sales Ops provides foundation and focus.

– Elaine Mao, Sales Operations,

Strategy and Business

Development at Uber

““

5The Sales Operations Playbook By Sales Operations Professionals

Who are these sales ops people, and why have they become so important?

“So many people are left asking: ‘What is this sales ops thing?” Kazanjy said. “It’s not an uncommon discussion, even in a group of practitioners.”

The answer can depend on who is being asked. But as a general rule, Sales Operations is in charge of building a smooth, repeatable sales process. It is responsible for properly training, supporting and effectively measuring the success of the sales team. In short, it’s about making an organization as efficient as possible.

Sale Ops pros are the new engineers of the sales process. Without that process, a B2B sales team is set up for failure.

Kazanjy likes to use the metaphor of Sales Ops playing the role of product manager for a sales team, They’re deciding what features are “shipped” to the sales organization to get the most of the team.

Kendall Grant, Sales Operations Manager at Fastly, looks at it a little differently.

Sales Ops is essentially the COO of the sales team. They’re responsible for making sure that sales is efficient as possible as well as setting up sales for success. We have a day-to-day responsibility to keep an eye on the business, making sure we’re closing out opportunities properly. We’re managing the pipeline. We’re closing deals. We’re calculating commissions. We’re also responsible for all the back-office stuff. We’re making sure everything is functioning smoothly behind-the-scenes so the revenue we’re bringing in is accounted for and verified.

“

“The role can be something of a balancing act between being a “fixer” focused on daily tasks such as running reports and a “strategist” who is doing the crucial forecasting that makes sure the business is running on all cylinders. As Grant explained, they have a larger responsibility to keep an eye on the big picture and to ensure every rep has what he or she needs to be successful. They are the people with all the answers . . . and not just when it comes to password information for forgetful reps. They are much more than that.

The exact role they play will depend largely on what sales leadership expects from them, said Channing Ferrer, the vice president of sales operations and strategy at HubSpot. One of the core priorities that organizations need to answer, he added, is if Sales Ops will be purely operational (managing the CRM) or strategic (designing and building sales organization). In other words, will they be fixer, strategist, or a hybrid of both.

Traditionally, Sales Ops might have been considered an afterthought. “What happens

6The Sales Operations Playbook By Sales Operations Professionals

more often is companies want their first, second, third, fourth, fifth hires to be people who can bring in revenue,” said Dhiraj Singh, inside sales and operations manager at MemSQL. “They want them each carrying a bag. But the smart way is to think about a foundation built on Sales Operations. Just having a CRM, getting your data collected, having that data preserved is a start. It helps to have a structure – whether or not you have a Sales Ops person. It makes a lot of sense when later on you’re trying to scale.”

Sales Ops pros told us that they see their role as using data to understand everything about the selling process. What went into successful deals? What can we learn from unsuccessful ones? What could we have done better? What can be tweaked? Answering questions like those help organizations predict, with a greater degree of certainty, what might happen with future deals.

They also walk a fine line in how they interact with the rest of the sales team. Sales Ops specialists are entrusted with helping sales reps achieve their number. But their primary responsibility is to the business as whole. Sometimes, practitioners say, those dual objectives can be at cross-purposes and put them in difficult spots.

“I have this awkward position sometimes,” said Jin Daikoku, director of inside sales at cloud app security company Netskope. “I’m trying to be their buddy and friend, and make sure they’re enabled. But I have to be the cop sometimes and say – ‘Hey, this isn’t your account.’ Inevitably, I’m the one making the judgement calls. I imagine that every sales ops person finds themselves in that situation from time to time.”

Sales Ops can be a “pretty wide umbrella,” Daikoku added. In fact

because the role can be so broad, practitioners can struggle to find ways to describe what exactly they do. It’s the fireman putting out sales fires . . . It’s like the swim coach who keeps the sales team in their own lanes . . . It’s the puppet master pulling the strings from behind the scenes . . . It’s the sales team’s guardian angel.

For Jonathon J. Leon Guerrero, who oversees Sales Ops at LeanData, it’s more like being the offensive coordinator on a football team.“You’re not in the game, but you’re calling the plays for sales,” Leon Guerrero explained. “Salespeople can be like quarterbacks and call audibles sometimes. But you’re still the one designing the overall process for them.”

Here’s a deeper look into the plays that Sales Ops is calling.

There doesn’t seem to be one standard approach or definition of Sales Ops. Some are more

designed toward people, process and technology. That’s where my background is. I see it more as a business analyst function who can help with defining and refining processes. But some are looking for ways to build models and plan. If you ask 50 people what sales operations means to them, you might get four dozen different answers.

– Jason Paquette, director of sales operations at MongoDB

“

“

7The Sales Operations Playbook By Sales Operations Professionals

Defining Your Sales Model and Sales Team Organization

Sales operations isn’t just about checking boxes and running reports in the here and now. It’s also about looking forward and adjusting the overall sales strategy. Examining the sales team and its goals and evaluating different methodologies are important functions Sales Ops serves. The insights gathered after careful analysis dictate what type of sales model the organization should adopt and how the sales team is structured. Those decisions can influence the success of the team for the months to come.

So where should Sales Ops start when tasked with designing a sales model? Pendo’s sales operations manager, Kristen Podger, suggests “evaluating the current data and identifying what’s working, what’s not and what can realistically be expected. From there, you can make forecasts and projections based on analysis.”

Identify your ultimate goal and then work backward. Talk with the executive team, figure out your main objective, and then work backwards from there.

“ “

When deciding on a sales model, there isn’t a “one size fits all” answer. As Podger said, a thorough examination of the business and its goals is needed. And while that may seem labor-intensive, getting an overall look at the health of your pipeline and where you’re seeing the greatest successes is never a bad idea.

Some points to consider when deciding on a sales model:

Are you looking to land a ton of end users who require little customer education, or larger, enterprise accounts that expect dedicated support?

Are your goals attainable? Are they in line with reality?

What is your Average Selling Price (ASP)?

What is your Customer Acquisition Cost (CAC)?

8The Sales Operations Playbook By Sales Operations Professionals

The answers to these questions will influence the approach you should choose. So what are your options? For SaaS companies, the sales models have been broken down into three, distinct categories:

Customer Self-Service: higher

volume, lower cost. This model

has the least amount of rep

interaction. But depending on

your product, it may require more

customer support.

Transactional: the ‘Goldilocks’

model. Scalable and customizable

to fit a variety of offerings.

Enterprise: lower volume, but

higher ASP. Your offering and the

support you provide should justify

the higher price tag.

Three SaaS Sales Models

Complexity(CAC & TCS)

Pric

e

High

HighLow

Self-Service

Transactional Enterprise

Startup Graveyard

Price and complexity define a strategic spectrum of sales approaches for SaaS startups that gravitate strongly toward three distinct SaaS sales models: self-service, transactional and enterprise.

Source

9The Sales Operations Playbook By Sales Operations Professionals

Chances are, your organization’s sales model will be a blend of all three. But remember to keep it simple. “You don’t want to overcomplicate things,” Podger says. “More is not necessarily better.” You don’t want to make it so hard for a customer to buy your product or service that they get frustrated and give up.

The next decision Sales Ops will influence is the ratio of Inbound reps to Outbound. Even if you have kept a careful eye on your conversion rates, this is something that may require some trial and error.

Let’s take a look at both:

Outbound

Every successful company will have a combination of both. Make sure to examine your product, the industry in which it sits and how your customers are buying it. Remember, you can adjust your approach to fit your company’s needs.

Inbound is a low-cost, high-touch model with the ability to capture thousands of potential customers. But there are limitations. According to SiriusDecisions, 67 percent of the buyer’s journey is now done digitally. Online searches are prospects’ first course of action before contacting sales reps. As a result, they have more information than ever about a product before engaging with a vendor. That means you have to provide high-quality content and have a strong ranking on search engines for your Inbound efforts to drive in leads. If you focus your content efforts on specific keywords as your company grows, achieving a high ranking on search engines shouldn’t be that difficult.

Inbound

You know your prospect is interested in your product because they came to you. They raised their hand, so to speak. And unlike Outbound, Inbound sales continues to generate leads even when you stop working. Unfortunately, as you scale, your Inbound channels – content, ads, SEO – can get maxed out, which is another reason why you always want to combination of both approaches. You may also have a higher churn rate because your Inbound stream of leads is too broad, and the potential customers you attract may not be a good fit for your product or solution.

Predictable and scalable. Deals may be larger because your reps have gathered important data on prospects before reaching out, and are targeting companies that fit your ideal customer profile. This approach does require more time and can be off-putting for prospects who don’t appreciate being cold-called/emailed.

10

As your business grows, it might make sense to increase your Outbound efforts. It can open opportunities with bigger clients and larger budgets – many of whom aren’t looking for you. While labor-intensive, Outbound enables you to target a specific type of buyer and ultimately improve conversion rates. Mikita Mikado, co-founder and CEO of PandaDoc, recalled when his company shifted its “sales approach to marry Inbound and Outbound strategies. We improved both the quantity and quality of leads in our sales pipeline. Within six months, our sales performance grew by 320 percent.”

Your approach will evolve over time. It’s very common for startups to focus on Inbound and, after a few quarters, bring on more Outbound SDRs to improve lead quality, go up-market and reduce churn.

Here at Pendo, we started with just an account

executive team. But after really taking a hard look

at our goals, we knew we needed to build out our

business development team to prospect and qualify

leads. It kind of naturally evolved into a 1:1 model

(1 BDR to 1 Account Executive), and that’s been

working. Based on where we’re going, we’ll need to

figure out how we can maximize how the team is

producing, without biting off more than we can chew.

-Kristen Podger, Pendo

““

11The Sales Operations Playbook By Sales Operations Professionals

Rules of Engagement

Now that you have decided on your team’s structure, you need to define the rules of engagement for your reps. This includes choosing whether your reps work specific territories (geographic, technographic, firmographic), use a round-robin approach to divvy up leads, or a combination of both. The term “rules” may sound restrictive – especially for startups that are used to “shooting from the hip.” But without a commitment to fair lead distribution, your reps may feel they’re getting shortchanged and complain that they don’t have enough to work. And when reps are hustling to hit quota each month, those rules will help reduce that uncertainty and potentially unhealthy competition between colleagues.

To help define the rules that work best for your company, start asking questions and thinking through scenarios. “What happens when a customer lead comes in? What happens when a lead from an active opportunity comes in? What happens to a net-new lead? “Those are all different,” said LeanData’s Jonathon J. Leon Guerrero. “You have to think about what to do with them. And you have to define what people own. Who owns customer accounts? Who owns target accounts? You need to decide who is going to have account ownership and who is going to own what leads.”

Many companies find territories effective in fostering focus among their sales teams. Aaron Ross, co-author of Predictable Revenue,

described territories as “another example of Specialization, which works by helping people focus, collaborate, and learn to become experts. That’s the main reason to use territories, in whatever form you go with.”

Implementing territories is not without hurdles.

• Territories, no matter what criteria you use to design them, will never be 100 percent fair

• They’re difficult to create and can cause friction between salespeople

• Once implemented, they’re a challenge to manage and adjust (especially as the size of your sales team grows)

All that said, the benefits outweigh the cost. “By not having territories, things run amuck: sales reps have less focus, less emotional ownership and more infighting,” said Ross. You can’t afford mistakes like those if your goal is rapid growth.

Fortunately, there are now sales tools and technology available that enable sales ops to create rules, build automated workflows and track reps activity.

12The Sales Operations Playbook By Sales Operations Professionals

The Sales Ops Toolbox

No area illustrates the growing importance of Sales Operations more than the sales stack. Technology has transformed the way B2B companies sell their products. Unprecedented efficiencies have been created by automating previously manual tasks – giving sales teams an ability to engage prospects in more meaningful ways. Cloud-based CRM systems like Salesforce are a central part of that revolution by becoming the system of record for sales teams.

“Historically, salespeople had more primacy because they held the customer relationship,” said Pete Kazanjy of the Modern Sales Pros. “They had an information advantage. Now, that customer relationship lives in the CRM. We can find individuals inside a company. We can engage them at scale. There’s no monopoly on that relationship. The power and dynamic has shifted. The Sales Operations person’s role is to be in pursuit of what’s best for the business.”

But it’s much more than just the CRM. The popularity of Salesforce has created a robust ecosystem of supporting SaaS solutions to help businesses grow their revenue. There are tools to find and acquire leads, enrich leads, manage leads, predict which leads are most likely to become customers and . . . well, you get the idea.

ProspectData

Linkedin

ContactData

PredictiveAnalysis

SalesIntelligence

SocialApplications

Sales EmailApplications

MarketingAutomation

Phone/Headset

DialingAutomation

Email/Calendar

MarketingAutomation

Reportingand Analytics

Gamification

CRM

Pre-CallResearch

SDROutreach

SDRLive Call Nurture Analysis

13The Sales Operations Playbook By Sales Operations Professionals

Scott Brinker, the editor of the popular chiefmartec.com blog, counted up a remarkable 3,874 companies for his latest Marketing Technology Landscape supergraphic. He estimates that when you combine sales and marketing tools, there probably are about 5,000 vendors. It’s a mammoth task making sense of this rapidly changing world.

Sales Ops part of that comes in determining which sales tools can help a business, training the team on their use, managing the technology stack as well as evaluating new possible solutions. That means they have a larger role in designing the sales engine – and a budget to make purchase decisions.

The Sales Ops’ pros we interviewed consistently talked about how managing tools takes up an increasing part of their work day. When practitioners get together at meetups, it’s common for conversations to turn to comparing stacks. And there are a multitude of criteria that go into creating a powerful tech stack.

“There’s just so much out there,” said Netskope’s Jin Daikoku.

“It’s easy to become a shopaholic and say, ‘If I buy this, this and

this, it will be awesome!’ Theoretically, they all add leverage, will

make you more money and pay for themselves. But you really

have to budget the time and mindshare of the reps because

they can only use so many tools at one time, and you can only

teach them so much.”

Channing Ferrer, of HubSpot, believes in the philosophy that data and infrastructure are more important that individual tools. That starts with the foundational system – a strong CRM. “If your process is working really well, you don’t need a lot of tools,” he said. But once it becomes obvious that the process needs tweaking, that’s when Ferrer explores adding tools to create greater efficiencies.

So, let’s take a deeper dive into the thought-process that goes into designing a high-performing tool stack.

Need to Have Versus Nice to Have

Functionality always is the primary question that Sales Operations needs to answer when evaluating a tool. Deciding if something is a “must-have” isn’t always easy. Will a technology be a difference-maker for an organization? Will there be measurable ROI that can be shown to the sales leadership. Or is something just another shiny new toy?

“It seems like these days everyone is always talking about tool, tool, tool,” Kelsey Barber, systems engineer at Uber. “What can we buy? What do we need to improve our process? But a lot of times I feel like tools sit on the shelf and collect dust. So a big part of my job is figuring out how we can best utilize what we already have by creating a better process around it.”

That’s a challenge because the right tool for business can be a game-changer. The wrong one? It’s destined to become the dust-collector that Barber was referencing. The answers, Barber said, will be different for every business.

14

At Google we really don’t have like

a million vendors,” said Mayukh

Chowdhury, a quantitative business analyst. “We try to minimize the number of tools and look at overall efficiency. . . . I think talking about tools is interesting. But I honestly think tools solve about 20 percent of the problem while the other 80 percent is process-driven. Once you have a proven process, then a tool becomes more viable.

Now and Later

Every organization chooses a technology tool to solve a specific pain point that it’s feeling right now. The business needs immediate relief. Sales Ops pros, though, are not just into quick fixes. They’re in the game for the long haul, and they make decisions based on how something will help their business down the road.

Will a product be scalable as a business grows and evolves?

“Maybe you only have a small team today, but you have to be thinking about how if that tool will deliver the same value if you’re growing by three times, year over year,” said Alex Miller, formerly with Zinc and now the sales operations manager at ProsperWorks. “Will this tool work the same way as it does now, or will it bend?”

That’s why it means a lot to Miller when vendors take the time to spell out their product road map – giving potential clients a better sense of where they’re going with their solution. This way, he can make a more informed decision about whether or not there’s a long-term fit for his organization.

“I’m a huge believer in that idea of ‘measure four times, cut once,’” he added. “No

one likes having to rip out a tool and replacing it with something else six months

down the line. That’s just a huge distraction for your sales team. You want to find

a vendor who is going to be a good partner for the next five years.”

“

“

15The Sales Operations Playbook By Sales Operations Professionals

Ease of Use

If a tool is too complicated, too hard to implement or too time-consuming, the sales team simply will ignore it. That defeats the purpose of adding something in the first place. After all, one of the main goals of technology is to make reps more productive.

Dhiraj Singh, who oversees Sales Operations at MemSQL, said he strives to utilize tools only that reduce on-the-job barriers – not add to them. That results in greater adoption by the sales team.

“My point of view is automating as much as possible to make it easy for the team,” he said. “That’s why we invest so much, per person, on a tech stack that maximizes selling time and minimizes the time on tasks like prep work such as researching companies. Using process and technology to reduce all of that non-selling time is always the goal in operations. That’s the puzzle we’re trying to solve.”

The greater the ease of use, the more the tool actually will be used, added ProsperWorks’ Alex Miller.

“You have to be mindful that the job of sales reps is not to push buttons and turn knobs,” he said. “They generate revenue. So you don’t want to bring on tools that are distractions, have a long ramp-up and ultimately don’t bring value to their job. At the end of the day, we want our reps doing more activities and not acting like Salesforce administrators.”

Compatibility with Rest of Tool Stack

Technology is the machinery of a modern sales engine. At its very best, a sale process will perform like a highly tuned race car. But while those sports cars are extremely sophisticated, they also can incredibly fragile. Even the smallest changes can cause problems.

That’s why managing tech stacks has become a challenge – and sometimes even a nightmare. There’s always a concern that making any change will throw a monkeywrench into the entire stack.

Compatibility matters. That’s why there is such a focus in operations to make sure tools “play well” with one another. It begins with CRM integration. There’s a common phrase in Sales Operations: “If it’s not in Salesforce, it didn’t happen.” That means tools need to work with the CRM – ensuring consistent data that’s being shared and updated in real-time.

“Our methodology is to make sure that everything flows through Salesforce,” said MemSQL’s Singh. “We want everything to live within Salesforce. You really want a 360-degree view of every prospect and every customer no matter where the information comes from. We try to avoid a lot of customization within Salesforce. You want to build a connection between Salesforce and the tool so you have an idea how they’re interacting.”

16The Sales Operations Playbook By Sales Operations Professionals

Cost

Every business has to live within a budget. An organization may want something, but it has to afford the solution.

“It’s why the first question I always ask is price,” said

Jonathon J. Leon Guerrero of LeanData. “I’ll treat it like I’m

shopping. If it's too expensive, why will I tease myself? Price

always has to come first.”

The one caveat is that if an organization’s need is exceptionally pressing, it usually will find the budget. Also, “cost” doesn’t always mean cutting checks. There are other costs associated with adding and removing technologies, such as time lost by the sales team.

“If something is working, you’re not going to want to go through the process of ripping it out,” said Netskope’s Daikoku. “You won’t do that if something is only marginally better. There’s a real cost of retooling and jumping to something new. Besides, the sales team might get comfortable with a tool and not want to change even if there’s something better out there.”

Shopping Tips

You want recommendations for good restaurants? You might ask friends. You want guidance about tool stacks? You seek out other Sales Ops pros.

“There’s a lot of us now,” Singh said. “There’s some kind of meetup or function we can go to every couple of weeks, and those are great places to ask questions. But every time I go to one, I leave feeling like there’s 10 more things that need my attention.”

Miller also seeks out the opinion of peers – both at gatherings or through online forums.

“I do a lot of research online and look at reviews like at G2 Crowd,” he added. That’s always a good starting point. You don’t want to go into a selection blind. You want to have a wealth of knowledge.”

But at the end of the day, added MongoDB’s Jason Paquette, it’s about being a diligent consumer. That means doing thoughtful trials of any solution you might think of adding. A vendor has a bold claim about its product? Fine. Let’s test.

“You drag vendors through the mud to prove their worth – and

I say that in a facetious way, of course,” Paquette said. “But you

have to evaluate thoroughly. If somebody says they’re going to

save you time, well then how much? Make them prove it.”

17The Sales Operations Playbook By Sales Operations Professionals

You honestly just can’t keep buying stuff. It’s too much to manage. We had too much stuff and it was creating havoc because we were trying to hook in all of these different tools with our CRM. So for us, it was better to be really diligent about what we needed and then consolidate. I think we’re pretty lean now. We’re hyper-focused on making our people extremely efficient in using what we have.

– Doug Landis, the chief storyteller at Box,

on why his company has less than a dozen

solutions in its sales stack

Some people like to have all-in-one tools. But for me, that falls into the trap of ‘jack-of-all-trades, master-of-none’. I prefer to use one tool for prospecting, a tool for sales cadence and so on. I would rather have specialization. But the key is that they all have to be compatible.

– Jonathon J. Leon Guerrero, who is in charge of Sales Ops at LeanData

“ ““ “

18The Sales Operations Playbook By Sales Operations Professionals

Reports and Analysis

Account Executives

• Win rate (closed won divided by number

of opps worked)

• Sales cycle (broken into stages)

• Average deal size

Sales Development Reps

• Sales activities (calls, emails)

• Opportunities/demos booked (SQLs)

• Pipeline created (total dollar amount of

opps created)

Most sales teams now live and breathe within their CRMs, tracking the progress of their deals and logging activities. So it makes sense for Sales Ops to leverage the CRM’s ability to analyze and evaluate that data. At the same time, it’s easy to experience information overload. So how do you know which metrics are important to track and which just add noise to the mix?

First, remember that every business is different. There are dozens of ways you can measure your team and, unfortunately, there isn’t a list of must-have metrics you should be tracking. With that said, there are definitely some data points most of the sales ops professionals we interviewed say they keep an eye on. Here they are for SDR and AE roles:

19The Sales Operations Playbook By Sales Operations Professionals

I think the most important one is pipeline growth. We deal with enterprise-sized deals that take months to close, so we’re putting a lot of focus into making sure that our pipeline is big enough that it’s creating good revenue growth. It’s a good indicator.

- Alex Miller, ProsperWorks,

formerly of Zinc

“

“

MemSQL’s Dhiraj Singh focuses on activities and meetings set when measuring his SDRs. “The straightforward ones are meetings and opportunities created. For the things that do close, we use revenue recognition. It helps us understand if [SDRs] are creating good opportunities. For Inbound, we’re looking to see if things are qualified before they’re pushed through. On the Outbound side, we’re making sure they’re focused on the right people. Then there are the individual metrics. Emails. Calls. We’re dealing with a pretty difficult sales process. It’s a high-value product that’s very complex and technical. So I’m looking for people who are taking initiative and who are actively trying to speak to prospects as much as possible.”

ProsperWorks’ Alex Miller believes closed-won is the important metric to measure Account Executives. But when he was at Zinc, they used a metric that unified the entire company. “It looks at our revenue and churn rate. Of our customers, are we doing more upsells than we are receiving churns? Are we having people buy more of Zinc than we do leaving the platform? That number is important to our investors.”

As you may have figured out, Sales Ops always are looking for ways to gain a greater visibility into the health of their funnel, as well as measure the strengths and weaknesses of the team. Constant monitoring is essential to keeping the engine running smoothly as well as identify problems before they cause major damage to your business.

“It’s like foreshadowing,” LeanData’s Jonathon J. Leon Guerrero said. “You’re anticipating what’s going to happen. You’re not assuming. It allows you to get ready. You base it on your metrics. You know what to expect. There are no surprises.”

After analyzing the data, you may notice there are parts of your funnel that are leaking, or that prospects are getting stuck at a particular stage of the buying process. With CRMs like Salesforce, the amount of information you can track and display in reports and dashboards is nearly limitless. But many sales ops pros warn against getting bogged down in minutia.

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Communicating the Importance of Sales Ops

Data is the lifeblood of Sales Ops pros. At the same time, many of their colleagues might not be as comfortable with data. (And no, that’s probably not a news flash.) So savvy Sales Ops pros have learned they must clearly convey sometimes complicated mathematical processes in clear layman's language to the rest of the organization. By extension, they’re also communicating the importance of their role. That means fostering productive relationships with the rank-and-file sales team, organization leadership as well as marketing colleagues.

That’s not always easy. Just because Sales Ops analyzes the data, it doesn’t mean an organization will see the worth – or act upon it. And it can become even more difficult as organizations grow.

“Sales ops at bigger companies is harder than at the smaller, ‘cool kid’ tech companies,” said Craig Rosenberg of TOPO. “Just ask a Sales Ops guy at a major company with thousands of reps and partners as well as global complexities. And remember when you’re dealing with sales, these aren’t fall-in-line, tell-me-what-to-do kind of guys. They think they’re all entrepreneurs. So rounding up the troops isn’t easy. Sales Ops can face incredible challenges.”

Here are some of the strategies Sales Ops can craft to navigate those challenges.

Winning the Respect of Sales Reps

One aspect of the Sales Ops role is enforcing rules. Not only are they designing a process, but they are making sure reps follow it. But the reality, as Rosenberg said, is that organizing salespeople can be a lot like herding cats. They’re absolutely convinced they know how to close deals and they often don’t want anyone “interfering.”

Also, there’s an inherent dichotomy to the job of Sales Ops. One element is to make life easier for the sales team (Guardian Angel). But another part is to look out for what’s best for the company in ways that might irritate individual reps (Hall Monitor). It’s a fine line to walk.

21The Sales Operations Playbook By Sales Operations Professionals

“One of the more difficult parts of the job is being judge, jury

and police officer,” said Ryan Axelson, the director of sales

analytics and CRM at Invuity. “You don’t make a lot of friends

in some circumstances. It’s a tough job to be in. You have to

come down and make some decisions when people are selling

in someone else’s territory, and you’re the bad guy because you

have to call them out on it.”

That’s why Sales Ops specialists say it’s crucial to build a level of trust. For Dhiraj Singh, of MemSQL, that means clearly communicating why something he recommends is needed. He said transparency is especially important at early stage startups where things move fast. Sometimes, he said, sales strategy changes quickly simply because the data behind those decisions also changes quickly. If that’s not clearly explained, the thought-process can be lost on the team.

“Your team always needs to understand why a decision was made the first time and why it’s changing now,” Singh said. “It needs to be logical, straightforward and based on data. It shows that decisions are coming from a well-informed place and gives you the freedom to experiment. It also shows people that you’re using data to correct-course when needed. All parties involved need to understand that sound reasoning and logic are being used.”

That said, something else helps strengthen the position of Sales Ops: strong management buy-in.

“You do not want to be the person preaching everything, applying processes and making methodology changes without support,” Singh added. “But your biggest asset is going to be your VP of sales and your sales manager. They’re going to have far more power over their reports to make things happen. That’s extremely important.”

Gaining the Confidence of Leadership

Pete Kazanjy, the Modern Sales Pros founder, said he’s seeing a rise in the profile of Sales Ops at organizations. But while adoption has grown, that doesn’t necessarily mean that all leaders see the value of process-driven sales. Part of the Sales Ops job is persuading leadership to see the wisdom of melding analytic insights with the expertise of salespeople who excel at building deals.

“Some don’t get why performance metrics might be helpful,” Kazanjy said. “Someone with an engineering background sure gets it. But a sales manager who shoots from the hip might not. That’s why some people look at Sales Ops and say, ‘Manna from heaven!’ and other people say, ‘Uh, who is this pain-in-the-butt

22The Sales Operations Playbook By Sales Operations Professionals

“Sales might say: ‘Oh my god, it’s so annoying documenting this,” Kazanjy said. “Why are you making the team do this?’ But then you can show the data about why they are actually losing deals. If that moves the needle 20 percent on competitive deals, and you’re now winning two more of 10 deals just by logging this stuff correctly. That’s a smart ROI argument. Things are rarely that cut and dry, of course. But it helps out Sales Ops in a big way when you make a persuasive case.”

Jason Paquette, of MongoDB, adds that it’s important to “read your audience.” Some VPs may be process oriented. But others may not understand the intricacies of operations.

So you have to learn to speak the language,” he said. “Maybe even if what we do is very in the weeds, you should

avoid getting too detailed. It’s a balancing act. Understanding your audience helps

govern how you balance that.

“

“poindexter making my reps do all this busy work when they should be selling and closing?’ It sometimes can be viewed as a loss of control if somebody else is dealing with reporting and analytics.”

His advice to win over those skeptical leaders:

• Have a methodology that shows leadership that you’ve done your homework

• Be a good internal salesperson

The irony, Kazanjy adds, is that Sales Ops must excel at making a compelling case for any initiatives. You know, sell it. He uses the example of a company that’s losing competitive deals and not having the data to figure out why. To diagnose the problem, Sales Ops wants to survey the team and add a new documentation process that requires logging more information in Salesforce. Initially, a sales leader – and the team – might not see the value.

23The Sales Operations Playbook By Sales Operations Professionals

Practitioners come from a variety of backgrounds – including finance, business analysis and engineering. But perhaps the most common career progression is for specialists to begin their careers as sales reps before moving into operations. A common refrain we heard is that having experience “carrying the bag” can be a great advantage in Sales Ops.

“I think it’s almost a requirement of being in Sales Ops that you should have some sort of sales experience,” said Axelson, who also is the executive consultant for BrassCarrot, a sales operations and sales enablement firm. “Sales is an amazing profession. It’s exciting. But at the same time, it’s incredibly frustrating. I would urge every Sales Ops person to do a year carrying a bag. Figure out what that’s all about, and then you will have so much more knowledge and expertise. It will give you street cred with the rest of the team, too.”

The idea is Sales Ops will have a better idea about the day-to-day life of a rep. It’s different when you’ve felt first-hand both the exhilaration and utter fear of trying to hit your number in the last days of a quarter. Singh, for instance, started as an SDR and then was promoted to Account Executive at a small company. Now that he’s in Sales Ops, he still spends time shadowing reps.

“It just gives you a lot of empathy,” he added. “You can think back to your days of being in their shoes and seeing issues from their

perspective. It’s really helpful. My role is to look at everything they do and try to figure out if there’s a way to automate any of it or reduce the pain or lower any barriers. So living in their shoes is very helpful.”

That sentiment is echoed by Jonathon J. Leon Guerrero of LeanData. He said he always remembers advice giving to him by a manager.

“He told me to never lose my sales background,” Leon

Guerrero recalled. “Understanding the data is important, but

don’t ever forget who you’re helping.”

Carrying the Bag

24The Sales Operations Playbook By Sales Operations Professionals

Data, of course, is just another way of saying information. For smart B2B organizations, information is power. By harnessing the explosion of information now available thanks to new technologies, Sales Operations is creating more efficient processes that have revolutionized modern business.

The world of selling really has changed. That change is going to continue, too, because Sales Ops pros never settle for the status quo. They are always looking for a better way and asking: why?

“They are eternally curious people,” said TOPO’s Craig Rosenberg.

Not only are they curious, but in the future they likely will have more responsibility and a larger seat at the decision-making table. Executives and managers will increasingly look to Sales Operations for guidance, whether that’s providing raw data on sales’ performance or actively analyzing the funnel to diagnose issues and prescribe solutions.

As more and more businesses focus on building a sales structure with a foundation of technology, process and people, operations will only continue to rise in stature.

Furthermore, sales operations will be tasked with continuing to consolidate the sales stack. A leaner, more streamlined sales process with fewer, yet more capable, tools will be the goal. That means constantly reevaluating the current stack and looking for opportunities to reduce its size and cost while increasing its effectiveness.

This much is certain: the role will continue to evolve and grow in scope. And it’s why there are more chapters to be written in The Sales Operations Playbook.

Conclusion

25The Sales Operations Playbook By Sales Operations Professionals

About LeanData

LeanData simplifies the complexity of the B2B sales process through better

lead management. LeanData’s strategic solution makes sales teams more efficient

by matching leads to accounts and automatically routing them to the correct

owner. A member of the Salesforce AppExchange, LeanData maximizes the value of every lead by providing richer

insights into accounts so businesses can increase sales velocity and close more deals.

Learn more at www.leandatainc.com

About Datanyze

Datanyze is the leader in technographics -- real-time insights based on a company’s

technology choices and buying signals. Technographics help you find great

accounts, engage them in timely, value-driven conversations, and convert them

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