I left the NH beach last night to drive to the Vermont office for a day filled with sales calls starting in 10 minutes at 9.
Clearly the fall season is fully in charge here on the busiest leaf-peeping week of the year... except that the trees are already mostly bare due to a wicked dry summa'.
- 29 on the thermometer on the office building across the driveway.
- I just lit the first woodstove fire of the season.
- A new cord of wood is being dropped off at the woodshed this morning.
- There's a thick carpet of leaves and frost-covered plants everywhere.
- The same 5 young men show up at 8 tomorrow for our semi-annual "Big Clean".
we have 50 more Selling Days!
Looking at Q4 in the same way I think about another Vermont winter, success in this quarter is all about being at a level of "fingers-in-the-dirt", day-by-day, week-by-week planning and execution. On the calendar, it may look like we have 12 weeks, but in the actuality of looking at that same calendar from the buyer's side of the desk, it's 10 at most. This crisp fall morning with frost on the pumpkin, let's think about a few tactics that we can put in motion immediately to move through these 0 weeks with higher productivity of our time and sharper focus on achieving quota.
USE AI Automation for more Precision Targeting
Use AI-driven analytics to identify high-conversion accounts. We use Chat of course, but we tend to use CoPilot and Claude more since they directly tie into our HubSpot platforms which gives us immediate visualization of where to focus our time. Choose your own tools, of course, but that simple activity will allow you to deliver much more highly personalized content and be able to specifically score the use of such tools as case studies and demos that you're using in your sales process.
Focus on New/New or Existing Customers?
With 50 days left, success is about where and how you want to spend your time. The concept sounds simple, and it may be that in your own company, those decisions have already been made through structured handoffs to different types of salespeople or to different departments such as Customer Success. If that is not the case, then the somewhat obvious decision would be to focus on upselling with different products and services. By itself, it sounds like an overly simple solution, but it could also complicate results for 2026 by limiting the addition of new accounts.
The bottom line here is that any “A” level professional B2B salesperson recognizes that at best, they have only 25-30 hours a week to actually sell, so the equation quickly comes down to the “Time is Money” formula, and how you plan those selling hours.
Buddy up with Marketing as Your Best Friend
As a class, as salespeople, we are very good at what we do. As marketing people, we’re terrible!
- We make stuff up!
- We talk about features!
- We hunt around for hours for out-of-date slide decks and waste time trying to change them.
This is exactly the time to buddy up with your marketing people-whether that’s one person or a department of 20. They’re experts at what they do, and they are also focused on the same success as you. Sit down with them on Monday for 45 minutes and go over your Q4 plan and ask their advice.
Have a great day selling today and enjoy this weekend picking up a couple of pumpkins!
It's time to begin your business planning for what lies ahead in 2026.
Think about taking a half day in October or early November to begin your business and sales planning process for 2026. Here's our free how-to ebooks for a few ideas:
"Writing the Winning Sales Plan"
"Writing the Winning Business Plan"
"Writing the Winning Marketing Plan"
"The Marketing of Me"
We outline ideas on structure, models, process funnels, productivity tools and how to recruit, hire and onboard the best people. A few hands-on guides for real managers written by real managers with their fingers in the dirt.
Connect with me any time at jack@derbymanagement.com and let's discuss your own 2026 planning!
