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The 10 Deadly Sins of Sales Ops

Salespeople can’t sell alone. Don’t set them up to fail.


Salespeople can’t sell alone. Every great sales organization is backed by an equally great Sales Operations team, who design, manage, and streamline your entire go-to-market strategy.

We sat down with Hilary Headlee, the head of Sales Operations & Enablement at Zoom, a video-first unified communications platform home to billions of meeting minutes every month.

I’ve seen it happen dozens of times. Companies with product-market fit will scale quickly and organically, only to suddenly… slow down. Sales begin to drop. Churn spikes. And while nobody can articulate exactly what went wrong, it’s clear that something was missed.

Building a sales organization is like designing and growing a garden from scratch. You focus on cultivating dozens or hundreds of different plants, some different varieties – account executives, business development representatives, sales managers – all the while dealing with whatever weather happens to come your way – competitors raising funding, changing regulations, and customers going out of business.

Sales Operations is everything you do in your sales garden to kill weeds. Sure, you might think you won’t need to at the beginning – it’s just empty dirt – but failing to plan for the inevitable need for clean data, defined communication methods, or data-driven sales strategies will stop your sales organization in its tracks.

The dire impacts of leaving weeds in your garden can hide in plain sight:

  1. Account reps may quit.

    In this competitive environment, Sales professionals accustomed to more organized workplaces might begin to leave for competitors.

  2. Infighting.

    Internal teams might start to shirk responsibility over the nitty gritty that falls between departments. “That’s not my job” may become a common excuse.

  3. Customer service may suffer.

    Without clear internal processes to solve customer-facing issues, your customer service team will be forced to make ad-hoc decisions about the most important parts of your business.

At some point, you have to decide to deal with the weeds.

I’ve committed and seen each of these sins as part of my fifteen years working in Sales Ops across six different companies. Learn from my mistakes, and kill some weeds. 💀

Dirty Data

Every part of your sales organization produces dirty data, unorganized and left to mildew in poorly named folders. Lists of prospects jumbled together in Excel, incomplete Salesforce records, and sales scripts scribbled on the backs of expense reports – all missed opportunities to learn about what actually drives sales of your product.

Moreover, dirty data leads to bad learnings. In an age where anybody can run complex reports about the state of their pipeline or previous sales, leaving incomplete or incorrect data accessible can actually lead workers to incorrect strategies and fewer sales.

Dirty data is not caused by bad tech. It’s caused by bad process.

Thankfully, we can fix process:

  1. Determine if the dirty data is incorrect or incomplete.

    Dirty data falls into two buckets: incorrect or incomplete. Incorrect data is dangerous – it can actively destroy a sales team’s ability to improve. Incomplete data is less actively dangerous, but almost always undesirable.

  2. Find the culprits.

    Figure out who can create, move, change, or delete data. If any part of your answer includes “reps” – you’ve got a problem. If any part of your answer includes “customers” – you have an even bigger problem.

  3. Incorrect data? Revoke access.

    If the dirty data is just plain wrong, you should likely start revoking access from teams (or customers!) who are inputting it.

  4. Incomplete data? Start negotiating.

    Reps will almost always want more data to route leads more efficiently. Asking customers for more data up front almost always decreases the volume of leads. Negotiate with your internal teams – either they’ll need to start inputting data themselves, or accept that they’ll always have B+ data.

Cleaning up your data is just the first step.

Beyond understanding which databases are incomplete, duplicates, or just plain wrong, you need to work across your organization to specifically delegate capturing, verifying, and updating that data in the long-run. That might mean working with an existing data science or business insights team… or lobbying to build one from scratch.

Nix all the Noise

“Why didn’t you do what I asked you to do? I sent you an email about it.”

Dilbert can be right sometimes.
Dilbert can be right sometimes.

Everybody – engineering, product, design, finance, sales – has things they need other people to do. Whether that’s informing customers of new features, getting approval for a specific expense, or implementing a new process for your sales team.

But, communication is hard, especially when talking to large groups of people at scale asynchronously. Everybody will miss things when there is no process. It’s unreasonable to email teams a long, complicated to-do list and expect them to follow through.

“Check the box” communication isn’t enough.

It’s your job to facilitate and structure efficient communication between teams.

  1. Recurring update meetings.

    Instead of asking engineering to send ad-hoc email updates with new features, set up recurring meetings between the engineering lead and everybody that will touch the new features. Instead of email blasting out new sales processes, set up a monthly all-hands to clearly explain the reasoning behind a new process.

  2. Time-boxed times for important emails.

    Instead of expecting reps to watch their inboxes all day, force managers and teams to only send specific types of emails during specific times. For instance, at Zoom, we only send out Salesforce tips during the first two Mondays of every month.

  3. Always use the same subject lines.

    Condition your employees to pay close attention to any emails that include a specific subject line or emoji.

  4. Update all listservs and chat rooms quickly.

    Email mailing lists, channels, chat groups – it’s overwhelming for everyone, let alone new employees. Build a process to include new team members to every required group, instead of expecting that “they’ll eventually get an invite.”

All of these serve to do one thing: dial down internal noise for your reps. Your job is to maximize the amount of time they can focus on talking to customers, not to ping them incessantly.

Cluelessly Confusing Correlations

Your clean data isn’t powerful alone: you need context around it.

As your reps, managers, and sales leaders begin to run reports, surprising things will emerge. Individual days where conversion rates spike by 50%. Periods where closed deals drop by double digits. A week where reps simply can’t seem to make any sales to certain parts of the country.

There are often larger, qualitative drivers behind these shifts. On that successful day, you might have run a discounted sales campaign. That period where closed deals dropped by double digits? That was the week of the company off-site. That part of the country with no sales? That was the week where the site went down, so nobody could access the sign-up flow.

If you’re drawing conclusions individual parts of your sales funnel, you’ll almost always miss the true insight or problem. Your data needs context, consistently reviewed and audited to make sure it’s correctly tagged as it happens… rather than six months later.

Managers Mis-Managing

The quickest way to blow up any Sales Ops team: turn their inbox into a feature request hotline for every rep in your sales organization.

“A person isn’t a process.”

Let your team actually reach Inbox Zero. Rather than establish individual relationships with every rep – and calling that a process – work with Sales Managers to identify what specific pieces of information their teams constantly request, or when their entire team’s productivity grinds to a halt. One of the greatest skills a Sales Manager can bring to Sales Operations is pattern identification in complaints and requests, which can then be translated to the outcomes needed to solve the problems.

Then, build a process for your Sales managers to bubble the information up to the correct person. We call this an “information intake process”:

  1. First, intake.

    Determine where you’ll collect this data – a dedicated inbox? JIRA tickets? A web form? You should ask for enough information to know whether the issue is worth investigating, but not enough to waste people’s time. Five questions is a good benchmark.

  2. Second, scope.

    Set up time to have a conversation with the stakeholder to see what outcomes they’re looking to change, and what metrics they’re looking to drive with their proposed update or change.

  3. Third, prioritize.

    Use some sort of ranking or scoring system to benchmark each specific request against every other request currently in your queue.

  4. Fourth, communicate.

    Communicate your prioritization queue and reasoning to everybody, even if their request is at the bottom of the stack. Managers will appreciate the feedback to better hone later submissions, and you won’t run the risk of alienating individuals whose requests are not fulfilled.

Optimize to streamline every type of communication for your reps. It’s far more efficient for your reps to have a single POC – their direct manager – for everything, instead of managing three different email chains with different people on the Sales Ops team.

Prodigious Piles of Projects

Sales Ops teams can quickly drown in projects.

When your responsibility is – most simply – to “make things better, faster,” it’s hard to justify saying no to projects that could have practical outcomes, but most likely are only marginal improvements above current practices or may not be your responsibility in the first place.

Saying no is harder than it looks. When everybody wants your help, optimize for high-impact, well-executed campaigns that are tied to measurable results instead of just assuming your work is making a positive impact:

  1. Prioritize projects based on impact.

    Trying to decide between projects? Your favorite phrase should be: “How much, by when?” Use this to benchmark how much of an impact your various projects might have on the business.

  2. Feel confident saying no to projects that clearly don’t belong in Sales Ops.

    You’ll be asked to take on random projects that should be the responsibility of a dedicated engineering operations or customer service operations team. Say no and explain your reasoning with data. You can also use their demonstrated need to help the project owner lobby for more resources for a new dedicated ops team in their vertical.

  3. De-prioritize projects that aren't as impactful.

    If you benchmark every project with specific metrics and goals, you’ll have an easily-prioritized list of your highest impact projects. Use this list to say no to everything that’s not quite as impactful.

Fighting for Fame

As teams grow and revenues increase, hyper-specialized teams will form around previously core responsibilities of a Sales Ops team.

Salesforce management is quickly swallowed by a centralized Business Systems or IT department, data analysis is consumed by a dedicated Data Science team, and compensation benchmarking is moved to a Finance team.

It’ll feel like your job is getting carved up in front of your eyes. It’ll be terrifying.

This is natural and healthy. Lean into it.

Instead of grasping at straws of responsibility, focus on building strong relationships with each of these ancillary teams. As stresses, deadlines, and emotions come and go, I can’t understate how important this will be:

  1. Have a transition plan.

    Plan out and clearly communicate exactly when, why, and how transitions of responsibilities are happening. The more you communicate, the smoother the transition will go.

  2. Treat ownership as a group activity.

    Attempting to assign a single owner to a large umbrella of responsibilities is myopic. As your teams grow, Sales Ops becomes increasingly cross-functional, working with dozens of internal teams on various projects. Clearly define who is driving, approving, and contributing to each process and hold everybody accountable, not just the single “owner.”

  3. Build an ongoing communication plan.

    Your job isn’t done when the transition is complete. Decide with every stakeholder how frequently you’ll meet. Especially with systems, data, and commissions, even if you’ve transitioned ownership to a different team, your sales team will ultimately hold you responsible.

Fighting for Factual Fairness

It is not your job to deliver “fairness” to every sales team.

As much as we’d all love to solve every team’s problem with the perfect distribution of leads or new commission structure, it’s simply not realistic.

Fair is a feeling. The best way to provide fairness is through consistency.

Instead, focus on providing consistency through process, policy, and systems. Compensation, quotas, vacation policies, KPIs, and exceptions – all are too personal to be fair for everybody.

Focus on consistency by obsessively tracking every decision you make, and the justification used to make that decision.

  • Defining non-standard deals.

    You should be able to point to specific, consistent reasons why some are accepted and some are denied. Whether the deal is a marquee deal, when the deal was made in your sales cycle, and how certain discounts were applied should all be recorded obsessively.

  • Allowing quota relief.

    It’s hard to understate how important this is when discussing any type of quota relief or adjustment. Defined, consistent rules will help guide you towards the right decisions when faced with an impossible choice.

The world, unfortunately, isn't always fair.
The world, unfortunately, isn't always fair.

Mastering Manual Methods

You need to build a system that works for people, so people don’t have to work the system.

When building compensation or sales coverage models for hundreds of reps, there will be things that you miss that unintentionally tip the scales in someone's favor. Here's what you can do next:

  1. Find the outliers.

    Look for these outliers and learn from them. And while there should be consequences for clear intentional and unethical behavior, there's a fine line between a fireable offense and an intelligent strategy that you can build around.

  2. Manually document the task.

    You should be able to easily and specifically document the process you’re trying to automate. If you can’t do it yourself, it’s unreasonable for you to expect a computer or algorithm to be able to do it.

  3. Then attempt to automate.

    Only after you’re able to clearly and concisely explain the process can you attempt to automate it.

The systems you build must reflect the processes you have and the policies guiding them.

If the process you’re building still feels like a process – arduous, clunky, time-consuming, boring – a few weeks after it’s implemented, review what's not working and see where you can fix or if you have to start over.

Day-to-Day Data

We produce tens of thousands of new data points every day at work, some of which are lagging indicators of our success – sales, for instance – and some of which are leading indicators of our success, like like high quality leads and conversion percentages.

People can tell any story with any piece of data. Without any controls on how data analysis is run and the process through which those reports are surfaced throughout the rest of the company, they may accidentally write a fairy tale… or a horror story.

Instead, write clear, company-wide documentation about the types and locations of data that people should pull to analyze. A best practice is to build folders in Salesforce, Tableau, or Domo that house the key data.

Thinking you’re alone.

Sales Ops takes a village, even if you’re an employee of one.

Turning down low-impact projects, tediously cleaning up datasets, negotiating with teams to build scalable policies – it’s professionally draining to fix the plumbing of your sales organization all year.

Don’t think you need to solve it yourself. Connect with the greater Sales Ops community – on LinkedIn, at conferences, over Twitter. Benchmark your experiences with their expertise. Everybody wins when you’re happier and more productive at the office.

I’m not a public speaker, or a writer. My mentor Karen Colligan encouraged me to speak at four conferences last year, and I did.

And while I certainly enjoyed traveling to Atlanta, Boston, San Diego, and San Francisco to talk all things Sales Ops, the people I met along the way are what I remember.

Networking isn’t about the network. It’s about learning.

Thankful to all of my mentors!
Thankful to all of my mentors!

I’ve learned immensely from people who were willing to take a chance on me: Kyle Porter, Manny Medina, Doug Landis, Jill Rowley, Joe Chernov, Lars Nilsson, Dennis Dube, Max Altschuler, and of course, the most impressive Michelle Obama and Billie Jean King.

Interested in working at Zoom? Let me know. We’re always hiring!