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The Winrate Newsletter
Issue 3: The June July Strategy
Issue 3: The June July Strategy
This week we are switching up the format. Winrate company updates will resume next week!
I’ve always been fascinated by June/July strategy. June is my favorite month in Sales and July is one the hardest to get right. So this week's issue will focus on what I’ve tried this time of year to be successful.
So why do I love June?
You get December-like momentum and a reciprocated push from prospects to “get things done before July 4th”. In Sales June is seasonally and psychologically a powerful month. Discounts and incentives are seemingly more authentic and effective. The weather is nice, deals have movement, and the H1 pipe has reached maturity and is ready to close out.
Then as soon as the action ends… most buyers take off the first week or two of July.
So with a light pipe and only 2-3 weeks of selling, what do Sellers do? What should they do? I’ve tried to execute on July a bunch of different ways. Let’s get into it.
First things first, this July is a blessing. It’s a long July. Let me explain.
A normal month is around ~20ish selling days in length (less weekends, holidays). July is always shorter. This month starts on a Monday and lines up perfectly with a mid-week ending.
Even with many buyers taking off July 1st through July 5th this year, there are still 18 selling days. So almost a full 20! I would encourage the entire Revenue Org to mimic buyer behavior and take the full week off if they can.
In order for this to make sense, I would want my teams to have been focused on preparing a clean, new (fresh), and well prospected list before the end of June.
Unfortunately prospecting and CRM cleanliness are what many teams focus on this week, while IMO they should be unplugged and recharging for H2.
Leaders need to be intentional about preparing their teams to rest while buyers are resting. This requires discipline, communication, and top down reminders throughout the entire month of June. If a Sales org is aligned on this, everyone can have a great week off in July and the org can come back flying for week 2. When done right it’s an incredible thing to witness.
To emphasize why I believe this July is favorable, let’s take a look at a different scenario. July of 2021 was much more challenging on the schedule, I’ll explain why.
In this scenario the holiday is on a Sunday, meaning it will be observed on Monday, SO some buyers will use PTO for the 2nd and the 6th creating a 5 day weekend. When this happens in July, the “Family Vacation” typically hits a later “full week” in the month. So a few days after they returned from the 5 day weekend, many took another full week off during the 12-16, 19-23, or 26-30th. Total gangster move for them and their families, but this opportunistic double dip, while I don’t blame them in the least, creates near impossible conditions for a rep trying to build back their pipe!
A July like that leaves only ~10-15 biz days to progress any given deal… and even less depending on when the opportunity was created. Luckily, I am predicting a more favorable vacation schedule this July, with a majority of scheduled vacations happening this week, with some bleeding into early next. But not much more than that.
Some Leaders are surprised that I am an advocate for Sellers taking off a full week to start July? I wasn’t always this way.
Encouraging this week off for sellers is strategic. They need to rest, they will perform better if they do, and there are few calendar weeks in the entire year where such a high percentage of buyers are off. Meaning it’s one of the lowest ROI weeks on activity all year.
Some years I played it straight with the corporate holiday calendar, nothing more nothing less… and other years I even did what were called “double sessions” where every day of July, I would work long hours 7:30am - 7:30pm and would encourage others to join as we “outworked the holiday deficit”.
Those were some “character building” summers, I remember them now as being “young and dumb”.
While I am and will always be a fan of outworking the competition, we weren’t gaining much additional ground by doing this every day in July. Especially not that first week.
After 3-4 days in a row of double sessions your eyes would start to cross and your brain would turn to mush. Any recovery gained from a couple of days off was quickly gone. We didn’t rest enough and then we went too far in the other direction. We weren’t disciplined.
The real trick is staying disciplined in June so that your pipeline is clean and tight so that you don’t need to spend the first week of July “cleaning up the list”. This sets you up to rest the first week, so that you can return refreshed and ready to go!
Then instead of “double sessions” every day for the rest of July… I would commit 1 or 2 per week staggered on a Tuesday and Thursday. This gives you a day in between “sprints” which is more than manageable, especially after a full week off. You won’t go cross-eyed, but you will get a huge lead headed into H2.
If you slipped up in June on the prospecting front, take a day or two of double-sessions to catch up, and be more mindful next year. Whatever you do, take some time to rest. You’re only halfway home.
Lastly, I will leave you with a July Warning! Beware of Zombie Mode.

Sellers, you can’t think clearly if you aren’t rested. I’ve seen reps who are a little burned out, their eyes are glazed over, and they never address the prospecting and clean list issue, and then opt in for “double sessions” in July. This is Zombie mode. It is a HUGE mistake. They endlessly dial and pound the same stale list from H1. This is an all sweat, no smarts strategy. Zombie mode can kill your July, your Q3, and your year.
Leaders look out for this! It’s on you to make sure they pull their heads up, take the time they need, set a clean strategy and execute on it. As of right now every July zombie on your team can be cured. 2 weeks from now, it’s way too late. So get on it!
Sellers, pause and make sure you are excited about a NEW and updated list headed into July. If you take anything from this issue of the newsletter, this is it. Stop what you are doing, take a few days off, and get yourself excited about that list before you lock back into the grind.
In summary, the best way to have a productive July is to stay disciplined in June, rest during the beginning of July while buyers are off, then with a clean and fresh list, return energized and ready to hit a couple of “double sessions” per week. If you do this you will be way out front come August!
Happy 4th of July everyone!
Winrate 3 is live on Spotify. Each playlist is a different theme. WR3 is designed for the BBQ, lake, beach, or wherever you find yourself this weekend. (Link below)