Streamline Your Headcount Planning Like a Champion


Streamlined planning processes are transforming how companies optimize growth. Use our 5-part checklist to master headcount planning.

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Alexandra DePalma
May 27, 2022

Create flexible and predictable sales forecasts

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Streamline Your Headcount Planning Like a Champion


What’s the first thing that comes to mind when you think of headcount planning? Perhaps you see images of boring, tedious spreadsheets. Or maybe you see yourself bombarding IT with unending data requests that never get addressed.

If that’s true, you’re living in the old era of headcount planning and workforce analytics. And it can leave you feeling helpless, burnt out, and resentful.

But the world of planning has made leaps and bounds in technological innovations, simplifying the Finance and Revenue Operations functions. As a RevOps champion, you work hard to enable Revenue teams with the best support and tech out there.

And you deserve the same.

Welcome to the age of smart technology that saves time, costs, and brainpower for growing or sustaining your #1 position in the market. Here’s how to streamline headcount planning and fast-track your revenue and growth engine with the right tools, technology, and best practices.

How do Revenue teams approach headcount planning?

In the context of Revenue teams, headcount planning is the process of defining and budgeting for the skills, roles, strength, and timelines of the workforce needed to achieve revenue targets.

RevOps professionals are most often tasked with determining an allotment of headcount to meet sales quotas and marketing objectives. Headcount planning optimizes budget and allocation for the roles and skill sets that meet the needs of the business.

Behind-the-scenes look at headcount planning activities

The activities for successful headcount planning can vary from data gathering to cross-functional business partnering, and capacity planning. However, these activities fall into three main buckets of collaboration, historical or predictive analysis, and budget allocation.

Headcount planning activities

Here’s a non-comprehensive list of common tasks performed by RevOps teams under headcount planning:

  • Requirements gathering on talent required to meet strategic goals
  • Data sourcing, validation, and aggregation from ERP, CRM, and HRIS systems
  • Collaborating with Finance business partners to allocate budget
  • Forecasting the present and future headcount needs of the Revenue team to meet targets
  • Increasing or sustaining a high return on investment in talent with the most optimal budget
  • Understanding historical trends from data to feed performance expectations into future forecasts

Key stakeholders involved include Sales and Marketing leaders, Finance teams, executives or senior leadership, investors, HR, and of course, the RevOps team.

Traditional headcount planning is clunky and outdated

Headcount and workforce planning as we know it is a painful, clunky process. Not only do you have to deal with data source gaps and ever-changing environments, but also with overly-complex legacy systems that are hard to utilize.

If you’ve ever had to revise mid-year targets due to the onset of external events (*ahem* covid), you’ll find some comfort in recognizing these common challenges of headcount planning:

  • Difficulty measuring and reporting ROI on talent
  • Prolonged and uninformed decision making
  • Limited visibility on the reliability of data
  • Subjective inputs lowering forecast accuracy
  • Excess information with no means of prioritization

These challenges are more or less a result of systems in dire need of a refresh.

The good news is that there is a way. The not-so-good news: it’s hard work convincing stakeholders to implement systemic changes.

Read on for a customizable checklist that can ease the transition and get you going in no time.

How to streamline your headcount planning process

A streamlined headcount planning process involves system updates, adopting the latest technology, and filling gaps with modern, sustainable solutions. To put it simply: you’re giving the planning process a makeover.

The most effective makeovers go beyond surface-level improvements to address the root cause of problems. Which essentially means that more effective headcount planning requires a complete change in mindset.

To get a head start on changing mindsets, review this 5-part checklist for streamlined headcount planning. As you go through each step, note down what you’re currently doing well, what you can improve, and what is a must-have for your future strategy.

1. Frame the problem and set the stage

You put out hundreds of fires each day. It’s the occupational hazard of being a RevOps professional. You’re solving problems for other teams so often that you forget to look inwards.

Although we’re speaking of headcount planning in particular, this applies broadly. Stable and successful RevOps teams empower dependent teams, but also their own teams and functions.

Your first step is to identify the challenges you currently face in short-term tasks and long-term strategy. It may be useful to split the challenges into themes: lack of resources, low impact yet time consuming tasks, low visibility, and poor or inefficient use of technology.

When performing this exercise, make sure you gather input from team members at all levels and work together to classify challenges as blockers, impediments, or mild inconveniences.

A clear understanding of key challenges and their root causes arms you with the information required to move towards solutions. You’re now able to prioritize and solve specific pain points.

2. Build a seamless data lifecycle to meet planning needs

In general, the data lifecycle starts with sourcing the right data and follows through with data preparation, validation, consolidation, usage, and repurposing. This is an important second step in your streamlining journey, because an overwhelmingly large percentage of problems are caused by inaccurate or inaccessible data.

In this stage of streamlining your headcount planning, try to abstract your data requirements. For example, rather than focusing on specific tools, note down your needs and the corresponding data source type. Your data source to requirement map should look roughly like this:

Business Requirement Data Source Type
End-to-end revenue lifecycle management CRM
Cost management HRIS
Financial targets Finance Team

Repeat the exercise for each stage of the data lifecycle to arrive at a comprehensive view of the data you need to efficiently execute headcount planning.

3. Shortlist the best tools for your tech stack

At this stage, you should have a much clearer understanding of your challenges, potential solutions, and the data systems needed to power those solutions. Here’s where you take a critical look at your current technology usage. Ask yourself the following questions:

  1. What tools and tech do I currently use for headcount planning?
  2. Which technologies are saving time and creating an impact?
  3. Do I use these technologies to their full potential?
  4. Are there other supplementary tools I could add to each of these?
  5. Which technologies are holding me back?
  6. How much time and resources are wasted on ineffective technology?
  7. What could I use instead?
  8. What are the urgent needs of my team and the wider organization that I could automate?
  9. What urgent needs could be met with investment in new technology?

Here’s an example of a headcount planning challenge easily solved by technology. How often have you put your name to numbers you’re not sure of?

Perhaps you’re forecasting the risk of attrition in your sales team, but

(a) you don’t know where to source work hours, time utilization, and compensation data from or

(b) you know where to get the data, but you have no idea who owns it or if it’s accurate or even

(c) you can source accurate data but it’s stored across 10 different hard-to-connect systems.

Whew! Sounds painful, right?

This is exactly the type of challenge the right technology can solve. With a business planning platform, for instance, data consolidation from endless integrations happens in a matter of clicks.

In summary: this highly critical step in your checklist forces you to think smarter while optimizing the headcount planning process.

4. Scale and empower your RevOps team

In scenarios like this where you’re trying to standardize and improve your processes, experience goes a long way. While it’s fair to take direction and guidance from other teams, you can’t expect (for example) your Sales team to set up quota and headcount planning systems.

That’s where you swoop in with not just the right tools, but also specialists in your RevOps team. Specialist knowledge of headcount and workforce planning helps you scale that much faster. Once well established, you can bring in the generalists to expand further and keep the ship sailing.

We covered this topic extensively in our webinar, How to Grow and Scale RevOps Teams, with RevOps leaders from Chargebee, RingCentral, and HighSpot on how they built their RevOps superstar team.

5. Showcase the potential impact of streamlined processes to win stakeholder buy-in

Look at it from the perspective of your stakeholders (usually executives and interdepartmental heads). Why should they dedicate time and resources to fixing what seems to be accomplished anyway?

Before addressing these questions, take a moment to understand for yourself what it truly means to streamline a process. “Streamline” seems like a cliched buzzword, but only because so few people implement it the right way.

A streamlined process simplifies the existing approaches and methodologies. As far as headcount planning is concerned, simplification takes place through the right tools, technology, and automation for hours of saved time.

But it also makes cross-functional collaboration a way of life.

Action plan to win stakeholder buy-in and revolutionize your headcount planning

Let’s put it all together to see how you should approach stakeholders to pitch a streamlined headcount planning process:

  • Quantify the damage caused by past planning failures
  • Identify the root causes of the damage (usually inefficiency, inaccurate data, and poor communication)
  • Map each root cause to its potential solution
  • Identify your data needs and corresponding data sources to implement those solutions
  • Stake out the best tools along with their projected impact on efficiently earned revenue
  • Appoint specialists at the early stages of the process and generalists to sustain the engine
  • Consistently communicate impact to stakeholders through headcount metrics: quota-to-OTE ratio, ARR, NDR, time-to-hire, deal volume, pipeline velocity, attrition, ARPU
  • Propose wellness checks to maintain the health of the process

And there you have it.

The idea of streamlined headcount planning is fairly new. There lies your competitive advantage: you now hold the key to focusing on high impact activities.

Headcount planning is often one of the first stages in the overall revenue performance management process. That’s why it’s mission critical to bring efficiency, cost savings, and better utilization of people into the picture.

Here’s to a re-imagined future where headcount inspires images of a well-oiled revenue machine rather than red lines on a gray spreadsheet.

Alexandra DePalma is the Revenue Operations lead at Pigment, where she builds cutting-edge solutions that enable and align revenue teams to exceed their potential.

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