Strategic sales planning: Mastering a blueprint for revenue and sales ops success

As the saying goes, “By failing to prepare, you're preparing to fail.” And perhaps nowhere is this truer than with the sales and operations planning process.

While it might not seem like the most exciting part of operating a sales organization, proactive, detailed sales planning is arguably the most crucial.  

It’s the process whereby you set goals, a shared vision, and a plan of action to get there—the eventual sales plan deliverable including the structure of your team, the sales incentives on offer, and the territories each team is assigned to.  

Benefits of strategic planning for a sales function span far beyond the comfort of shared knowledge around what’s on the horizon. Proper sales planning gives you a meaningful advantage to quickly pivot when required.  

Sometimes referred to as comprehensive 's&op planning', it ultimately means you have constant eyes on every aspect of the sales process, monitoring key performance indicators that show you when it’s time to pivot—fast. This is a major competitive advantage when other sales teams lack the agility to reallocate resources or respond to shifts in-market.

Below, we’ll share the best way to approach your sales plans with core considerations, including some sales planning software options to support you in managing the end-to-end process.  

First up: defining sales and operations planning

Sales planning is the strategic process of outlining your business’ objective and working backwards to create a plan of how you’ll get there. It encompasses everything from understanding your target market, to organizing your sales team structure, assigning territories, managing sales performance, and even the admin around data (tracking and reporting).  

Sales planning keeps your sales associates on track and increases efficiency across the entire organization.  

When team members know which goals and shared vision they’re collectively working towards, and the stakeholders included throughout the process, you limit the chances of veering off course and chasing vanity metrics that don’t actually meet the business’ overarching goals.  

You'll also avoid paying compensation on behaviors that don't drive outcomes. When you have a plan, reps can better prioritize tasks, and you can set realistic commission levels and quotas, as well as account for sales capacity planning for coverage generally, all without blowing your budget out of the water.  

Your approach to sales planning can ultimately improve agility. If competitors are outpacing you and you’re losing market share, for example, proactive sales planning not only helps identify this in advance, but also can provide insights on the strategy and action plan that can get you back on track.

So how should you approach your sales planning? Below are a few of the core areas you'll want to deep dive into ahead of documenting the action plan.

1. Get clear on your sales objectives and shared company vision

To make sales a profitable and effective function, you’ll need to first tie sales objectives back into bigger revenue generation goals.  

Your sales strategy will fluctuate depending on which goal you’re targeting.

Sales key performance indicators that usually tie back into business goals include metrics around:

• Market share  

• Revenue

• Sales efficiency

• Customer lifetime value  

• Churn rate

• Quota attainment  

At this phase of the sales planning process, consider your shared vision as an anchor point for the other stakeholders you're working with. Tessa Whittaker, VP of Revenue Operations at ZoomInfo, said in a recent webinar that sales planners should align on:  

"What is the most important thing that we want to achieve? What are the shared KPIs? And [work] backwards from there.”

She adds when decisions aren’t made with this end vision in mind, the various functions within the business run the risk of prioritizing different things, "[meaning] we’re going to be taking a step sideways or backwards instead of moving in the same direction towards that common goal.”

As for what this looks like in practice, your company may have a big focus on going up market and there's a lot of things required in the rollout of sales methodology and different ways you might manage pipeline or change the way your forecast for this. This is a lot of work upfront you'll need to get a handle on, and it's by outlining your sales plan that you start to see what's required.

As Tessa shares, to ensure all the go-to-market groups are bought into the work ahead with a shared understanding of the "why" and shared broader objective:

“We always bring it back to: ‘This is the shared vision and this is when it's going to make your life easier, and this is what we're working towards in the end'...Having that alignment and that end state vision together really builds trust when you're going through a change and you're asking [reps] to put more effort in at first.”  

To arrive at your sales plan...

Break big-picture goals down into smaller, more achievable targets  

As you do, remember overly ambitious goals can demotivate reps from the effort to reach them, whereas easily achieved targets won’t provide a sense of achievement most reps crave.  

The eventual action plan is the blueprint for how you’ll execute your sales plan. It details who is taking responsibility over which actions, the tasks you’ll complete, and the milestones and deadlines you’ll work together to achieve, and your KPIs.  

Instead of giving your sales team a list of actions to work through on their own accord, prioritize sales activities that will provide immediate impact. Early-stage wins can motivate reps to continue pushing and meet more ambitious quotas.

Former SVP of GTM Strategy & Operations at HubSpot, Sid Kumar, advises co-creating your sales plans with the people who will be executing them:  

“[Bring in] and getting enough feedback from the folks that actually have to go execute these plans after they're signed off. If they understand the input earlier on, and you understand what the [pitfalls] and stakes are, you’re much more likely to come out with an executable plan.”

Related to setting especially achievable, motivational targets...

Review historical data to ensure targets are within reach

Do a deep dive into your sales performance management software to evaluate how realistic the proposed organizational targets may be.  

If you’re trying to increase market share by 5% in the next year but you’ve only managed to achieve a 1.2% increase over the last 12 months, it’s likely not the best target to lay the foundation for your sales plan. A bump of 2% may be more realistic as your recommendation.  

2. Deeply understand your target market and segmentation

Your target market is ideal customer profile you’re selling to, so part of the sales planning process is understanding their characteristics in-depth. Their interests, background, motivations, and pain points are factors in the actions your sales team will ultimately take for engaging these prospects.

You need to ensure your sales plan accounts for the fact that not all of your target market will share the same qualities. Certain products will inevitably be more suited to different segments of the market. Instead of speaking to all (and subsequently speaking to nobody), segment your target audience and define the products prospects with certain characteristics will be most likely to be interested in.

• For example, with an accounting software company, there are often plans for self-serve individuals, small businesses, and mid-market to enterprise brands.

• Self-employed or self-serve individuals have a completely different set of challenges or use cases to go-to-market with than enterprise brands. There are also fewer people involved in the purchase decision process, and their prior experience with accounting tools is likely less in-depth than other segments. The go-to-market sales approach you’d take for this account would differ dramatically from targeting an enterprise brand.

Remember to lean on insight from product marketing who have packaged plans with different features to reach every demographic; also, consult marketing and customer success teams to understand how the business will cover the full spectrum of the customer lifecycle—not just the campaigns for acquisition, but the features and positioning proven to engage post-purchase.  

The more data you can get to build a sales plan specific to how you'll acquire different market segments and buyer personas, the more accurately you can target and qualify leads that turn into paying customers.  

3. Map your sales process in detail: determine sales operations from end-to-end

After understanding your target market, in this stage, you’ll map out the entire sales process; who’s responsible for what (the operational aspect), and the goals of each stage.

Sales leaders will often work very closely with Revenue or Sales Ops as part of this undertaking.

As Sid Kumar shared with us:  

"Typically, you're gonna have a set of guardrails that you have from a corporate objective standpoint...You’re working closely with finance to develop, but then [layering in] RevOps is really the how. How are you going to make those numbers happen? What output do you need from which teams, and in what quantity and mix?"

To kickstart this part of your sales planning process, evaluate historical sales performance data and map the entire linear sales process from start to finish. This might look something like:

1. Prospecting

2. Qualifying leads

3. Making the first contact

4. Providing a demo or consultation

5. Handling sales objections

6. Negotiating terms

7. Closing the deal and signing contracts

Here, gather data on the average conversion rate from one stage to the next. If you find that most leads drop off between demo and objection handling, how can you fill that gap? The answer might be planning for additional follow-up training or placing bigger incentives on deals that linger in this stage for a certain time.

Once you know what the end-to-end sales function looks like at your organization, detail the activities you’ll complete at each stage and the sales techniques you’ll rely on to progress.  

In the case of prospecting, for example, your approach might include cold calling leads based on your research and competitive analysis, or leaning on existing relationships with customers to get intros to new leads.  

The techniques might seem simple or obvious as you map your plan, but failing to document your ideal sales process could cause inconsistencies from rep to rep. The customer experience differs from lead to lead as a result.  Where, in actuality, you want more adherence to sales processes overall.

4. Determine the organization or structure of your sales team

Sales representatives ultimately put your plan into action, so structuring your team to leverage the most value from their skills and experience, or even product knowledge, is key.

Merge qualitative (customer surveys, peer feedback, and manager observations) and quantitative (quota attainment, revenue generated, NPS) data to do a micro analysis on each team member.  

• What do they excel at?  

• Which tasks motivate them most? What’s their personality like?  

• What personal development goals are they working towards?  

Answers to these questions help you assign responsibilities so reps are not only productive, but also motivated. They get to double-down on what they’re best at and you reap the rewards.

Once you’ve identified your rep’s strengths and weaknesses, figure out where they sit in the sales process. Popular sales team structure models include:  

• Hunter-farmer, where “hunters” focus on generating new business and “farmers” nurture existing customer relationships.  

• Assembly line, where sales representatives focus on acquiring new customers, account executives close the deal, and customer success agents ensure you’re following through on your promises.

Also consider your sales capacity—how much money your team can realistically generate over the coming months. The last thing you want is to set an ambitious team-wide goal of $1 million but force reps to work around the clock to make it possible.

Instead, consult CRM data to find your current sales output using metrics like quota attainment or sales rep performance data. This will provide a realistic idea of how much your agents typically sell pre-sales plan.  

A new direction and sales strategy can sometimes spark motivation and help agents be more effective, so a slight increase in current capacity is reasonable. If your current annual capacity is $15,000 per rep and you’re managing a team of five, for example, your team could realistically bring in $80,000 over the coming year.

As you organize your sales team, consider rhythms of business and remember sales isn’t a solo sport—ideally you integrate other business functions into this part of your sales plan.  

Tessa Whittaker at ZoomInfo ensures for RevOps, Marketing, and Sales alignment this way with “pipe councils”—regular meetings in which leaders from all departments (marketing, sales, and customer success) go through the pipeline to review the numbers and outline the next steps. Operationally, you may want to have a similar rhythm of business meeting baked into your sales planning.

Tessa says that everyone leaves the meeting with the same action plan: “Here are the opportunities we need to address, here’s what we need to go and do, and then aligning on that and coming back together and making sure that we’re making progress towards those goals.”  

4. Plan your sales territories and capacity  

You’re working with a finite number of resources, be that time from your sales team or budget you’re able to allocate to commissions. Sales territory mapping ensures you’re spreading those resources as efficiently as possible, while also motivating your agents with fair and equitable opportunities.  

Without a sales territory plan, you might have sales representatives working in saturated markets where opportunities are plentiful. They’re ranking in commissions and feel satisfied with their role.

On the other hand, agents who’ve been allocated to less lucrative territories feel like they’ve they have to work harder to find opportunities and close deals because the territory is less plentiful. As a result, their commission payouts remain stagnant. These reps are at-risk of leaving, and you’ll risk ending up paying 6 to 9 times their average monthly salary to replace them and retrain new agents.

Instead of making this a likely outcome of your sales plan, consider how you structure your sales territories. For example, you could define them as:

• Geographic territories, which are split based on ZIP code, town, or state.

• Account-based territories, which are segmented on characteristics like company size, product line, or revenue potential.  

Though, there are quite a few structures for sales territories to consider beyond the two methods above.

For example, an ecommerce software brand that’s targeting marketing managers at mid-market brands might have a goal to increase market share by 1.5% over the next two quarters. As part of your sales plan, you’d take a combined approach and split territories by region, but also by customer segment. You might have three sales teams targeting New York, each targeting customers that use one of three sales channels: social media, an ecommerce website, and in-person.  

Customers with an existing online presence are higher priority because you can claw back market share from the competitor they’re currently using, so you’d assign more resources—be that more experienced reps or more generous incentives—to this territory.

Once you’ve defined your territories based on the resources required and opportunities available (you can model and simulate the affect of your potential territories in your sales plan using SPM platforms like Forma.ai), finally assign team members to each one.  

Think about their skills and experience, incentive program or commission level, and sales performance history. For example: reps on a generous incentive program might be best suited to saturated markets since there’s a strong motivator to sell and stand out from competitors already dominating that territory.  

On leveraging sales planning tools and technology

There’s a fine balance between relying on gut instinct and historical data when sales planning. Your gut can point you in the right direction for your analysis, but data acts as the confirmation that your hypothesis was true (or not). That’s the secret to making decisions with the most likelihood of success.  

“The ability to leverage data, insights, along with qualitative inputs from your field teams around making changes when you have sufficient conviction, as opposed to waiting until the next planning period, or just having arbitrary times where you’re going to move your business.”
— Sid Kumar, Former SVP of GTM Strategy & Operations, HubSpot  

Essential tools for sales and operations planning include:

• Customer relationship management software

• HR, accounting, and payroll software  

• Sales performance management platforms like Forma.ai—particularly those that track incentives, sales compensation, and quota attainment.

When evaluating data from any sales planning tools, Sid Kumar recommends considering:  

“How do you get signals of potential risks upcoming that could impact performance? Conversely, what are the signals you’re going to look at to capitalize on certain favorable changes?”  

Most SPM platforms with sales planning capabilities will have reporting and analytics features to show the leading key performance indicators you set in the goal-setting stage.  

When using these, Sid Kumar recommends to zoom out and broaden the scope:  

“We often get very focused on attainment relative to an annual plan, or you focus on year-on-year or month-on-month as a measure of performance. Those are measures—I certainly won’t take anything away from that—but what I think is really important is that you take a look at trending metrics over an extended period of time.”  

He recommends asking: “What does your business look like in a steady state, where macro is stable, where we don’t have a global pandemic, and how do these leading indicators behave then?”

Measuring and adjusting your sales plan

Sales planning isn’t a process that can be replicated in a linear fashion. Think of it more as an ongoing operation—a consistent analysis of your existing strategy to identify areas for improvement. Only when you have your finger on the pulse and know what’s happening inside your sales organization can you improve agility and quickly pivot to take advantage of new opportunities.

The simplest way to do this is by switching to a mindset of continuous improvement. Instead of checking in on your sales performance data quarterly, make it a week over week ritual.  

Sid Kumar says:  

“We’ve gotten very prescriptive about this core set of leading indicators for sales and other functions too, but we’re going to look at these core leading indicators really maniacally week on week, and we’re going to look for signals or changes in the macro, or changes in customer behavior, and using that as a litmus test of helping us understand: do we need to revisit any assumptions or do we stay the course?”

Become more agile in your sales planning process

The world of sales has never been more turbulent. Markets are evolving at a rapid pace, competitors are experimenting with new sales tactics, and consumers are more picky about the brands they engage with than ever before. The secret to keeping up is to constantly monitor performance data and fine-tune your sales plans accordingly.  

As Sid Kumar summarized:

“Be very open to being wrong, and be open to iterating over time as your business evolves, as you have reason to challenge your original assumptions...Have the conviction not to wait if you have enough data points and evidence that you should be changing.”  
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