Smooth a pipeline with a staggered sales cycle?
Sales is not linear - could you make it smoother by introducing a staggered sales cycle? It's worth considering ... read: "Everything Starts Out Looking Like a Toy" #187

Hi, I’m Greg 👋! I write weekly product essays, including system “handshakes”, the expectations for workflow, and the jobs to be done for data. What is Data Operations? was the first post in the series.
This week’s toy: what if a text file was the solution to tracking time and understanding productivity? It’s so simple you almost wouldn’t think of it unless you’ve tried to-do lists and other approaches and have adopted the pieces that work while avoiding automated stuff that doesn’t work. Edition 187 of this newsletter is here - it’s February 26, 2024.
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The Big Idea
A short long-form essay about data things
⚙️ Smooth a pipeline with a staggered sales cycle?
It’s almost the end of the month. For those sellers that are on a quarter schedule, it’s not quite the end of the quarter, but by month 2 they need to be able to firm up their commits. The sellers on a monthly schedule are in a sprint to the finish (go, sellers!)
The common thread here? More sales get done near the end of the period than at the beginning. As RevOps pros, we’d love to see a perfectly linear (or perhaps even favoring the first part of the period, but team motivation doesn’t work that way.
The commit schedule for a quarterly sales cycle is a bit simpler than a quarterly one because the cycle moves so fast and happen 12 times a year instead of 4. Yet if you’ve ever watched a sales-led monthly cycle it behaves a bit like the quarterly one. Week 1 typically has less activity and closing than week 4, because the sales cycle just ended.
What if there were more sales cycles?
Go on a brief thought experiment with me here. If the sales cycle was a single yearly cycle, a disproportionate amount of sales would happen in the last week of the year. If the sales cycle happened daily, things would be kind of uneven until you got to a point of scale where you had thousands or tens of thousands of yearly sales.
Could there be a middle ground here where half of the salespeople are on a sales cycle that’s offset halfway from their counterparts? In a quarterly cycle, this would mean some start Jan 1, while others start their quarter Feb 15. In a monthly cycle, it might mean that some team members start their month on the first day of the month and others start theirs on the 15th.
The Happy Path: Why Do It?
If this works – especially for the monthly contingent – it means that your team is going through closing cycles more times during the month. You have a built-in incentive for deals to close more often.
You also do your team a favor by letting them follow their natural pattern of taking a breather after completing a sales cycle. It’s entirely reasonable that sales peeps want to take a few days at lower intensity right after pushing hard to the end of the month.
You’ll know if this is working if the number of closed-won deals is more linear during the month than your old method.
Why this is a bad idea…
Caution: this might be a very bad idea for teams that are bound to the traditional quarterly cycle, and especially bad for enterprise deals that take 90-120 days to develop. Adding additional complexity on top of the typical quarter close will not win you any friends with Sales Ops and finance. (Even though the sellers *might* be interested in seeing if they can arbitrage the difference between their staggered quarter close and the quarter close of their prospects.)
It also might not be a good idea because even in a shorter monthly cycle, you are adding complexity to monthly commissions. Do you pay out at mid-cycle to keep the finance team from going bonkers and needing to validate commissions twice a month? Or do you commit to the additional complexity inherent in multiple cycles (SPOILER: more complexity = bad.)
But it’s still intriguing. How can you improve the first half of the sales cycle while maintaining the existing excitement that happens at the close and avoiding the demotivation of sales reps?
Incremental steps without changing the cycle
What are some things we could do to improve sales velocity without actually changing the cycle?
Two things that come to mind as potential strategies to motivate sellers:
“split the cycle” by working on some early-stage items and some later stage items every day. By moving the early pipeline later and driving to a decision, you keep the train moving. Identify a few metrics for reps to count daily.
identify late-stage input metrics that are one step removed from the actual closed-won, and try to make those metrics happen earlier in the cycle and more often. Moving accounts to a late stage as a cadence means more deals completed.
You might not be able to physically move the sales cycle earlier in the month or the quarter, but if you can improve the velocity of sales activities that convert, that’s almost as good of an outcome.
What’s the takeaway? Everyone would like a smoother pipeline, but it’s easier proposed than completed. To get your pipeline looking more like the linear gain you’d like to see, focus on activities that drive deals forward and be consistent about working deals at every stage of the funnel more often.
Links for Reading and Sharing
These are links that caught my 👀
1/ Range Anxiety is overrated - I’m one of the people who thought, “I’ll hold off on considering an EV until the range improves.” In a study conducted by Recurrent, it turns out that people don’t drive that much. The median distance? 22-43 miles daily.
2/ Surprises are bad - Removing uncertainty might be the single most important task for an engineering project (or for most other projects as well). Communicating progress and calling out risks while staying realistic with estimation helps.
3/ Making data easier to read - If LLMs shouldn’t write SQL, what should they do to improve the data experience? Benn Stancil is skeptical that LLMs can write good queries, but maybe that’s not the point. If LLMs can make queries better or point out how a specific query cannot answer a specific question, maybe that’s 80% of the way there.
What to do next
Hit reply if you’ve got links to share, data stories, or want to say hello.
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The next big thing always starts out being dismissed as a “toy.” - Chris Dixon