The Stealth Role of the Sales Ops Leader

A job that barely existed a few years ago is becoming increasingly essential to growing companies. Behind every great sales team, there’s a sales operations leader quietly powering the machine.

BY HEIDI MITCHELL                                                                                                            ILLUSTRATIONS BY PAUL BLOW 

Two years ago, Tony Pham was brought into the SaaS company, Cloudinary, to create a formal process and implement tools that would help the sales team do what they do best. “Before that, the company found leads and figured out how to contact decision-makers and close deals through word of mouth,” says the Senior Manager of Sales Operations, whose background is in auditing. Over time, Pham worked with every customer-facing group, determining the touchpoints and ways by which teams communicated internally and externally, figuring out how to move sales down the pipeline from demand generation to the actual sale, all the way to customer support and even billing. “It’s really a bridge job,” says Pham, whose position had him reporting to the Vice President of Sales. “You have to understand technology and systems, but you also have to under- stand the business itself. My job is all about bringing in the stakeholders and end users and making sure tools they need will work at that point of time.”

Pham keeps up with emerging tech through a virtual group called Modern Sales Pros (unrelated to The Modern Sale), along with chat groups with friends in the field, and hours of research and test driving. “The job requires a lot of relationship building, especially with the sales folks inside. You need to gain their trust, and ultimately become the voice of reason that can calmly facilitate the company’s goals. Often there is some relief that I’m there now, since I take on the administrative and operational responsibilities so the sales managers can focus on what they do best: selling and meeting quotas.” He obviously killed it in this increasingly-in-demand role; Cloudinary grew from 60 to around 200 employees and Pham was just recruited to the tech-recruiting platform Codility as Director of Revenue Operations, reporting to the Chief Revenue Officer.

Just a few years ago, not many sales organizations would even know what a sales operations manager was, let alone have one on staff. CSO Insights, a research arm of the Miller Heiman Group, just began tracking the “sales operations” role in it’s 2018 Sales Operations Optimization Study. That study reported that about 80.5% of all technology companies today have a dedicated sales operations function, while across all other industries combined, that number drops down to 54.6%. They looked at 16 different sales-related activities and found that sales ops touched 15 of them, ranging from enablement to forecasting accuracy to territory definition and compensation management. No wonder the research firm defines a sales operations manager as “a strategic function, designed to provide a platform for sales productivity and performance by providing integrated methods, processes, tools, technologies, and analytics for the entire sales force and senior executives.” The role itself is as dynamic and powerful as whomever takes it on, and is sometimes an art, sometimes a science.

“Sales operations is becoming an increasingly powerful and important role,” says Marianne Borenstein, Chief Client Officer of Collective[i], the technology and network used by the world’s leading sales organizations to implement and operationalize AI-enabled sales transformation. She calls modern sales/revenue ops leaders “trusted advisors to the C-suite and the secret weapon of the sales team,” who “implement essential technologies and deliver mission-critical intelligence that is literally transforming how companies predict, manage, and grow revenue.” The sales ops leader is a force multiplier — according to SiriusDecisions, a B2B research and ad- visory firm, the “link between the develop- ment and the execution of the sales strategy and go-to-market strategy.” And he or she can be invaluable.

Chris Durrant, managing partner of the Salt Lake City recruiting firm Big 3 Consulting, says that about five years ago, when the position first emerged, candidates were considered “almost administration.” But in the past two years, he’s seen a sevenfold increase in requests, and a significant increase in compensation, some- times doubled. Companies, he says, typically seek candidates who have experience with Salesforce (including its Configure/ Price/Quote solution, SteelBrick, and AI analytics system, Einstein), plus some data analytics and even product management or development gigs. In some cases, they ideally have worked in sales, too. They’re practically unicorns. “These people are in high demand and you cannot find them, particularly in the Bay Area and New York City,” Durrant says. “When I do, and they decide to make a move, they have many opportunities.” Undeterred, the headhunter remains on a quest for people who can create a commission structure, quotas, co-ordinate internal relationships between finance, sales, and marketing, and manage Salesforce activity and reporting.

Often companies need more than one person to get the job done. “Sales ops is becoming its own division,” Durrant adds. “You have a leader and then people below them. In most circumstances they report to the VP of Sales, in many cases doing the things the VP of Sales doesn’t want to do: putting together all the reporting, analyzing the sales team, presenting at board meetings, making recommendations for specific solutions. An AI platform could make this person’s role easier, but sales operations is here to stay.” Durrant believes that not having a sales ops manager on staff can reflect negatively on the leadership, especially for a large or high-growth company. “Sales people notoriously do not pay attention to detail. They want to sell and interact with people. But there is part of the job that has to be done, which is operational,” he says. “A VP of Sales can do it, but they’d have to work long hours and probably still come across as inadequate. For the most part, senior leadership is aware that this is a role that is needed.” And they will find the budget for it.

That’s because, as Roxanne Tashjian, Senior Vice President of Global Sales Effectiveness and Optimization at Monster, says, sales ops leaders “are the glue between all the groups.” Though Tashjian’s title is unusual, her responsibilities are those of a sales ops leader: making sure sales has what they need from marketing and other groups, and doing all the due diligence before implementing any new tools so onboarding is seamless. And even that can require outside resources. When Tashjian recognized Monster had a sales productivity issue and needed to fix its lead flow process, she brought in Sirius- Decisions to isolate the problem. Then she took a deeper dive with Seattle-based Slalom Consulting and ended up running a technical assessment and implementing an 18- to 24-month roadmap to reimplement Salesforce. She had the budget in her own division, but that’s not always the case, which makes funding major changes challenging for sales ops leaders. “Every time someone comes on board [in the C-Suite], you have to convince them that your project is a priority for the company,” she says. Tashjian, whose experience includes years at Dell EMC and cybersecurity firm Fire- Eye, has a lot of help; her team consists of sales enablement, go-to-market, sales strategy, reporting and analytics, commu- nications, and systems strategists — eight direct-reports in all, and she reports to the Chief Commercial Officer. “My number one responsibility is making sure sales has whatever they need to increase productivity,” she says. “So I need to be able to talk to finance, services, pricing, and marketing to be sure I’m being as effective as possible to impact sales.”

In its short life, the sales ops leader role has primarily meant working behind the scenes, using metrics and predictive models to help facilitate sales, but at some companies it’s morphing into a management position with more visibility. Matt Veitch, Director of Sales Operations at Austin-based AI company Hypergiant, sees his job as “the person who creates your blueprint for success,” he says. “We provide a feedback loop to marketing so they know what is working and what is not. Your sales rep may be flooding in all these deals but maybe they’re not converting. I’m the one that can create an efficient sales funnel and push everything through it.” He’s not the “heavy,” which is typically the role of the VP of Sales; instead, says Veitch, “I’m going to teach you how to keep your pipeline managed, how to put your best foot forward, and how to stay organized to generate more business.” As the right arm of the VP of Sales, his role requires problem-solving, agility, and some fancy footwork. Veitch has seen first-hand how investing in a sales ops manager pays off. In his experience, a company’s ability to attract new talent and new funding has much to do with having a strong sales ops person on staff. “This shows everyone you have systems in place to get it all done, that you know where deals are getting stuck and how you can push them through,” Veitch says. “And to be honest, without this role, you’re fly- ing blind.” And missing out on a lot of potential closes.

In the past two years, recruiter Chris Durrant has seen a sevenfold increase in requests for Sales Operations Leaders, and a significant increase in compensation — sometimes doubled.

 

The key to success of the sales operations manager is to be deliberate — and not reflexively leap to new tools as solutions. “We all too often jump to tools,” cautions Kevin Raybon, Chairman of the Global Sales Operations Association and a thought leader in the field. “However, studies show that culture has a much bigger impact than tools or training do for productivity.” Sales ops leaders can easily spend all their time evaluating technologies, he says, “and they have a host of vendors very willing to take up their time and help them feel important. But in many cases, they are not making the most of what they already have, and are falling victim to thinking they always need something new.” The sales ops leader should instead build a solid plan to help the CRO hit her objectives and, eventually, thoughtfully help select the tech that will make a difference. “A good sales ops leader knows the current state of the sales team and where any friction is coming from, and can then look into the market for tools that can begin to address the challenge,” says Raybon. “Sales ops leaders allow the CRO to be on the business while they are in the business.”

Tony Pham is definitely in the business at Cloudinary. He’s seen the need for someone to connect the dots across sales, marketing, and other aspects of his company becoming more and more crucial. “Companies are realizing that sales ops, which is strategic, can be more important than tactical roles like analysts,” Pham says. Kevin Raybon agrees. “At some point in the life of a company, the sales leader will find that she is buried in operational details and not working on the strategic items that will move the company forward,” he says. “This is when having a professional sales operations leader is critical.”

Metrics of Success for the Sales Ops Leader

They go by different names — Sales Operations Leaders, Sales Operations Managers, Director of Sales Enablement, Head of Sales Effectiveness and Enablement — but what- ever the in-house title, the central role is the same: support and drive frontline sales teams to enable them to sell better, faster, and more efficiently. So how is a VP of Sales or CRO able to measure their sales ops leaders’ success? Kevin Raybon, Chairman of the Global Sales Operations Association (sopsa.org), offers a checklist.

  • Is the firm hitting its revenue targets?
  • Is the cost of sales in control?
  • How productive is sales?
  • For every dollar I put into sales, how many do
  • I get back? Is that ratio improving? How accurate are my forecasts?
  • What percentage of my sellers are hitting quota? Is it growing?
  • What do the salespeople and managers say (in surveys…and over coffee)?
  • How quickly do new hires reach quota
  • Am I retaining my best people?
  • How many of my new hires were recruited by my sales team?
  • Do my sales people get value from the big events like sales kickoff and training?

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