When should I be pre-selling to prepare for slow months?

Why waiting until a slow month arrives is already too late

January is your weakest month. Revenue drops 35% from your average. You notice the problem in the second week of January when collections are behind and the pipeline is thin. You start making calls, sending proposals, ramping outreach. But your average deal takes 45 days to close. Even if you started closing deals immediately, the revenue would not arrive until March.

So you white-knuckle through January. You make payroll but it is tight. You delay a vendor payment. You feel stressed about a problem that was entirely predictable.

Pre-selling for slow months means treating your sales calendar like a farmer treats planting season. You do not plant in December and expect to harvest in January. You plant in October (start building pipeline) so that deals are closing in December and January (when you need the revenue most). The math is straightforward once you know two numbers: when your valleys hit and how long your deals take to close.

The two numbers you need to calculate your pre-selling window

This analysis combines data from two systems: your accounting software (for revenue seasonality) and your CRM (for sales cycle length). Here is what you are looking for:

• Your weakest revenue months. Pull a 12-month P&L displayed by month (same report described in our guide on finding your weakest months). Identify the 2-3 months with the lowest revenue. Confirm they repeat year over year.
• Your average sales cycle length. In your CRM, look at the average number of days between deal creation and close date for won deals over the last 12 months. This tells you how far in advance you need to start filling pipeline.
• The pre-sell start date. Subtract your average sales cycle from the first day of each valley month. If January is weak and your cycle is 45 days, you need pipeline building to peak by mid-November. If your cycle is 90 days, you need to start in October.

How to calculate your pre-selling window manually (step by step)

This requires data from both your accounting software and your CRM. Here is the full process:

Step 1: Find your valley months in QuickBooks or Xero

1. 1
   Pull a 12-month P&L by month

   In QuickBooks: Go to Reports → Profit and Loss. Click Customizeand set “Display columns by” to Months. Set the date range to the last 12 months. In Xero: Go to Accounting → Reports → Profit and Loss. Click Compare Periods, set period to 1 month, compare with Previous 11 Periods.

2. 2
   Identify the 2-3 lowest revenue months

   Look at the Total Income (QuickBooks) or Total Revenue (Xero) row across all 12 columns. Note which months are significantly below your average. If possible, compare to the prior year to confirm the pattern repeats.

Step 2: Find your average sales cycle in your CRM

1. 3
   HubSpot: Check average time to close

   Go to Reporting → Reports → Create report. Select Deals. Filter to “Closed won” deals in the last 12 months. Add the Days to close property. Look at the average. Alternatively, check your Sales Analytics → Deal velocity dashboard if you have Sales Hub Professional.

2. 4
   Salesforce: Check average opportunity age

   Go to Reports → New Report → Opportunities. Filter to “Closed Won” in the last 12 months. Add the Age field (days from creation to close). Group by quarter or month and note the average. Salesforce also provides this in the Pipeline Inspection view under deal cycle time.

Step 3: Calculate the pre-sell start date

1. 5
   Subtract your sales cycle from each valley month

   If January is your weakest month and your average cycle is 45 days, count back 45 days from January 1. That puts your pre-sell start at approximately November 15. If your cycle is 90 days, you need to start in early October.

2. 6
   Add a buffer for pipeline falloff

   Not every deal you start will close. If your close rate is 25%, you need 4x the pipeline to hit your target. Start even earlier or increase outreach volume. A good rule: start 1.5x your average cycle length before the valley month.

Why this calculation breaks down without consistent tracking

The formula is simple: valley month minus sales cycle equals pre-sell start date. But in practice, maintaining this is harder than it sounds:

• Your sales cycle length is not fixed. It varies by deal size, customer type, and season. A 45-day average might be 30 days in your peak season and 70 days in your slow season. Using a single average can be misleading.
• CRM data quality matters enormously. If your sales team does not consistently update deal stages and close dates, your average cycle length will be wrong. Deals sitting open for 6 months that were actually lost in week 2 will skew the numbers.
• Valley months shift as your business evolves.New products, new markets, or a shift in your customer base can change which months are weak. Last year's pattern may not be this year's pattern.
• Nobody connects accounting seasons to CRM activity. Your accounting software knows January is weak. Your CRM knows your average cycle is 45 days. But no one is automatically connecting those two facts and telling you to start ramping outreach on November 15.

Or get pre-selling reminders automatically, every month

Bottomline connects to both your accounting software (QuickBooks or Xero) and your CRM (HubSpot or Salesforce). It knows your seasonal revenue pattern and your average sales cycle length. Every month, it checks whether a valley is approaching and, if so, tells you exactly when to start ramping pipeline.

Because Bottomline has both your financial data and your CRM data, it can tell you not just when to pre-sell but how much. It knows your average deal size, your close rate, and the revenue gap you need to fill. Instead of guessing, you get a specific number: “You need 8 more deals in pipeline by November 15 to keep January revenue above your baseline.”