Whenever I'm working out of the house in the morning, I walk on the one-mile beach across the street. I actually find the physical act of just walking to be borrring, so for the last 10 years or so, I pick up the trash left either by careless day-trippers or the junk plastic and lobster rope washed in from the prior night's tide. I realize that in the total scheme of things, my tiny bag of trash is not very impactful, but in my head, it works, and most importantly, it gives me purpose to the walk.
I realized last Friday just how immediate the end of the summer had become in just a few days:
"The Beach People" had totally changed both in quantity and in who they were. No one but a few seniors were on the beach on Friday and only a scattering on Saturday even with good weather.
Even the lifeguard chairs had disappeared by last Friday plus the large refreshment store was already boarded up in prep to defend itself against the upcoming hurricanes and wicked winter storms.
Last week...all of us experienced that same immediacy in our work lives as we moved from the anticipation of the end of summer to the reality of September's Q3 quotas, new end-of-year marketing campaigns, and the first of the dreaded memos from Finance about their timetable, their various reports they need for their 2027 budgeting.
Let's think about the simple example of that one-day event of Halloween that kicks off ads in all the large retailers in mid-July, that moves the candy and costume marketing people into hyper-speed in early August and increases rapidly in intensity and variety so that the balance of that $13B will be spent in the next 45 days. Even at the Derby Center, we take Halloween very seriously...a photo from last year just before the faculty meeting where costumes were very strongly recommended. Work hard-Play hard!
So, theoretically, we have 67 selling days available for selling, so let's round it off to 70. You can use your own calculation of a couple of days for being sick, doc appointments for the kids and whatever else is real life. For those of you who are skilled HubSpot...the absolute best choice btw!...or SFDC users...let the forecasting module do the work, but CRM or not, you need to create an 80% accurate projection of what the next 70 days will look like.
1. To start, assume that there's nothing in your current funnel. What you do know is your projected deal size, of what you're targeting in revenue. For this conceptual process, let's make an assumption of $30k to 50K/deals.
2. In 2025 and H12026, what was the average number of days that it took from an SQL to close those deals? Just do the math. If the number is 120 days, on one hand, we have a major problem since you don't have 102 days, but on the other there's an immediate opportunity to shift your marketing focus and sales intensity from new deals to upselling and expanding existing customers. But let's assume that the days are 60; therefore, we have 70 days available, so we have an opportunity all related to absolute focus and the use and the increased weekly training of your sales team on the use of your sales tools.
3. Now add back the current deals that you have today from your existing sales funnel. Be brutally honest with yourself with the 2025/H126 math and apply that same historical data to what you're projecting for the next 70 days. For us, since we are sales math nerds, we know that it takes...on average... a total of 9 Discovery Meetings to get to 1 closed deal in 60-90 days. Do your own math!
4. What's the result of this back-off-the-envelope math look like? For those of you who already are active HubSpot users, this scenario and five others would have been done in the time that it took you to read this blog. For the rest of you, just be brutally honest with yourself!
This process is much better to understand exactly where you are right now, in the middle of September, than to be telling "Sales Status Stories" to your boss or to the Directors in October. As a board member myself, I will politely, but very pointedly after 30 seconds of listening to sales stories, ask the VP of Sales to whiteboard the math for us in real time describing their specific funnel status. If they're using HubSpot of SFDC, even better. If not, use a whiteboard.
Personally, I find that this selling season is the most invigorating of the year. We have tested sales leaders, defined and proven sales and marketing tools, and a short-term scoreboard. If you want to talk through your own results from your counting of the days, just connect with me at any time. Have a great week selling!
Jack is a Managing Partner of Derby Management, a strategy consulting firm, and founder of the Derby Entrepreneurship Center at Tufts University, where he has taught for 20 years. Every semester is significantly updated, with heavy emphasis in 2026 on AI in Marketing & Sales. At Derby Management, Jack and his team architect and build business strategies focused on sales and marketing processes, tools, and technology platforms.
www.derbymanagement.com | Derby Entrepreneurship Center at Tufts