Four Quick Steps to Improve Sales Planning

Yuri Yakubov
July 9, 2024
Jul 9, 2024
Four Quick Steps to Improve Sales Planning


  • Sales is not an abstract spreadsheet. Sales planning works best when done cross-functionally. Sales Ops, Finance, Sales Leadership, and Marketing all need to understand that sales is alive, evolving and requires care.
  • Sales leaders (not just the sales leader) need a say in the final plan. A bought-in sales team will be more successful than a skeptical one.
  • Build a sales plan based on reality. If you’re assuming metrics will improve to achieve your plan, be ready with answers on how they’ll improve.

Sales planning is the most important responsibility of Sales Operations and Sales Finance teams. Correctly planning your head count, territories and quota is crucial to helping your sales team efficiently hit their quota. Not hitting quotas leads to attrition, which is costly and impacts morale and productivity. Unfortunately, the task of sales planning is often handed to someone in Sales Operations or Finance to make the numbers work in Excel without an understanding of the realities that sales teams face; for instance, one can’t assume that last year’s attainment will transfer to this year — while head count increases by 25% — without having a plan for how you’ll get there.

I’ve seen and led sales planning at companies ranging from a 400-person Series B startup to a 40,000-person Fortune 500 company and through that experience have identified key steps to set your sales team up for success:

  1. Start from history. Building up your plan from your actual results will allow you to set a baseline to start from and evaluate whether your bottom-up plan aligns with your leadership’s top-down plan. Some of the key questions to consider are: What renewals do you have coming up? How much have you historically been able to grow your installed base? What did you do for new business last year, and how can you grow that this year?
  2. Layer in TAM. Where is your opportunity to grow? Historicals offer a great baseline to start from but are an incomplete picture of potential. It is important to layer in your addressable market so that you can capture growth opportunities in markets where they have not had success in the past. Is your customers’ business booming in the Pacific Northwest, but you only have one rep there? Understanding insights like that will help you allocate headcount and investment.
  3. Identify gaps between historical performance and TAM. Create a companywide plan for bridging the gap. Growing a new market cannot be seen as just sales’ responsibility. All stakeholders — Marketing, Customer Success, Product — need to be committed to supporting growth.
  4. Get buy-in from your sales team. It is crucial that the sales team sees a path to achieving their plan. If you cannot create that, you risk salespeople and managers punting on the year because they don’t believe they can get to their number. Provide opportunities for feedback, and explain the key assumptions used in the plan and how they’re tied to reality. If you’re assuming that your average sales price will grow 10%, what is that assumption based on? Can sales leaders rebalance quotas within their own team?

Once you’ve completed your planning process, set yourself up for future success by understanding the key drivers of your plan and tracking against those metrics. By including these metrics in your operating cadence, you will be able to diagnose early if you are at a risk of falling behind your number and make adjustments on the fly more effectively.

Taking these steps is not just a Sales Finance or Sales Operations responsibility. It is important for sales leadership to include those responsible for planning in meetings throughout the year so that sales is real to them — not just an abstract spreadsheet.

None of the above will guarantee that you will hit your plan, but it can create a more realistic plan and bought-in sales team that will maximize your chances of having a good year.

Yuri Yakubov

Yuri Yakubov

Yuri Yakubov is the head of business operations and finance at TigerEye. Before joining as the fourth employee, he guided go-to-market operations teams at Autodesk, PlanGrid and Tesla. His diverse background includes roles in economic consulting at Cornerstone Research, analytics at Pacific Gas & Electric, and strategic finance at SolarCity. Yuri played a key role in scaling operational teams and was instrumental in integrating PlanGrid into Autodesk following its $875 million acquisition in 2018. He holds an MBA and bachelor's degrees in economics and business from UC Berkeley. Outside of work, Yuri stays busy with his two young children and dog.