How To Set Yourself Up for a Wildly Successful Sales Year
How to set yourself up for a Wildly Successful Sales Year with Income Goals, Sales Calendars, Territory Plans, and Account Plans
“If you fail to plan, you plan to fail.” — Benjamin Franklin
It sounds cliché, but in sales it is painfully true.
Every January, thousands of smart, capable sellers log into their CRM, start sending emails, and hope this year will be better than last year… without changing anything about how they operate.
Hope is not a strategy. Systems are. The better you get at reverse engineering how to get to the outcomes you want, the more frictionless the work will become. Plan like an engineer so you can live like an artist.
At the beginning of every sales year, before sending a single prospecting email, I walk myself through the same five-step planning process. It’s the difference between chasing deals all year and engineering them.
Here’s how to do it, and the exact templates I’ve used to hit my quota, and that I now use to lead my team to hitting theirs.
1. Establish your goal income for the year (The Dream Income Playbook)
You can’t reverse-engineer what you don’t define. The first thing you should do every year is decide: How much money do I want to make?
Not your quota. Not what your boss hopes you’ll hit. Your actual dream income.
Once you know that number, map it backwards through your comp plan:
Base salary
Commission rates
Accelerators
Deal sizes
If you’re new to the role, this shows you what’s realistically ahead. If you’re in the same role as last year, it forces an honest question:
“If I repeat last year… what will I actually make?”
From there, you can see exactly how much pipeline, how many deals, and what average deal size you need to close to get to your number. Sales stops being emotional when the math is clear, and starting with your dream income allows you to get clear on your why, your what, and your daily operating system to be able to achieve that what, so you can make that why come true.
Some of my “Why’s” from years past included things like: “I want to be able to take my parents on an all expenses paid vacation.” or “I want to have X$ in my pay from account for my car so I don’t have to think about my car payment for the entire year.” or “I want to take myself on a staycation at the Four Seasons and not think twice about the room rate.” or “I want to pay off my loans.” or “I want to make X$ in a single transaction.” Your why can be as selfless or as selfish as you want it to be, the trick is to have as many as feels authentic for you, so when you inevitably wake up dragging ass mid-Q1 or at the beginning of Q3 when you hit a summer slump that you have something to come back to.
Here’s an example Dream Income Template to show you how the math maths and give you and idea of how this helps you get your goals on paper. Note: You will need to plug in your comp plan in order for it to work in your specific scenario.
2. Know your calendar
Sales is driven by time just as much as talent: End of month. End of quarter. End of year. Industry conferences. Summer vacations. Holidays.
Some of these are deal drivers (use-it-or-lose-it budgets in Q4). Some are deal draggers (trying to get Susan to sign something on the last day of June, while she’s boarding a flight to Europe with her kids). If you understand how the calendar works, you can stop fighting it and start using it.
At the beginning of each year, I sit down and look at every single week of the year, mapping exactly what I know is going on with respect to: the industry I am in (e.g. conferences or major meetings my customers might be having), where the holidays fall, anything my company is putting on to help us drive deals (e.g. user conferences or webinars), and finally when I am planning to be taking time off (e.g. my 10 day vacation at the beg of Q4).
Once this is mapped out, I can easily plan about 8 weeks out at a time, and have a pretty good idea of what my levers are for 1) prospecting, 2) driving deals forward, and 3) closing deals out. I ask myself:
For renewals: When are these going to hit, in context of everything else I will have going on at the same time, and how can I potentially get them done early so I don’t need to worry about them and neither does my client when the time comes and we are dealing with both an End of Quarter, Industry conference, and a Holiday vacation week at the exact same time as the renewal.
For late stage deals: Over the next 8 weeks, when will buyers be motivated? When will they be distracted? How can I use any of this to my advantage when teeing up timing for contracts?
For mid stage deals: Over the next 8 weeks, what is going to get in the way of meetings that drive these deals forward? Time kills deals and motivated buyers are going to work with me to get shit done, calendars are always the arch-enemy when trying to progress pipeline.
For prospecting: Over the next 8 weeks, what is happening in the industry that I can make a theme for my prospecting efforts, or even use in my prospecting to open and close a quickie deal? For example, will a customer need something that I have before they have a industry show in 8 weeks? If so, now is a great time to get that note out.
The more predictable your calendar becomes, the less reactive your selling feels. Simply by having a plan that aligns with your calendar, you can reduce the mental load of having to be creative when you sit down for your daily prospecting block.
Here’s an example of a sales calendar so you can see how to build this for yourself.
3. Know your territory
This is where mediocre sellers and elite sellers part ways. You should know your book of business so well that you can categorize every account into:
A-list
B-list
C-list
Your goal? If you only sold to your A-list, you could still hit quota. To do this well, you need more than just account names. You need context:
Is the company growing or declining?
Is the category growing or declining?
Did they just hire new leadership?
What are their top 3 priorities for the year?
Those combinations tell you everything. Just a quick example of what I mean:
A growing brand in a growing category is optimistic and momentum-driven.
A declining brand in a growing category is in pain—they’re losing ground.
A declining brand in a declining category with new leadership? That’s a company under pressure to change.
By knowing just this level of detail, you start to shape a real point of view on how you can help. At the end of the day, businesses exist to solve problems for people for a profit. And selling feels so much easier and better when you understand what problems the people you are going to be prospecting are most likely facing. It motivates you to want to help them individually, and as a business.
Also: know where your accounts are located. In a world that is obsessed with AI, where content is cheap, one way to stand out as a seller in today’s market is to make it a point to see your customers in person. Shake hands. Look them in the eye. Make them laugh. Deliver value. Take them out to a lunch. Send a thank you note. Those little things make a big difference.
When you are thinking about planning a trip, you should plan to make the most of it and try to see every account in that area. By starting the year with a map of your territory and knowing what accounts are where, you can make the most out of any trip simply by pulling up your territory plan, sorting by city, and then ripping some notes out to book meetings.
Here’s a copy of the Territory and Account Planning Template that’s taken me many iterations to perfect, for this step fill out tabs “Account List” and “Territory Plan.”
4. Build account plans for your A-listers
This step alone will make you feel like a different salesperson.
For every A-list account, map:
Build an org chart starting at the top and working your way down, use Linkedin and make assumptions where you need to
Using internet research identify what problems the business is likely facing (press releases about fund raising, partnerships, etc. are a great source of help here. For publicly traded companies, read the annual report for the keys to the kingdom. ChatGPT can help you!) and who at the top of the company is likely focused on solving those problems. Note: Executive leadership are not always going to be directly involved in your deals, but they are the people who set the list of priority problems to solve and determine which of those problems have solutions that get funded, so by understanding who the ultimate authority is on solving these problems you can set yourself up for a sales process that will have less friction.
Then, for each problem, write down how your product solves those problems and who at the top you are selling it to. Again, you may not sell directly to this person, but you will likely be prospecting them and then hear from someone in their chain of command.
Now, give yourself an action plan. You know the account, you know the problems, you know the people with the problems, and you know how you can help… Identify 3 things you are going to do and put dates to them.
Once this is on paper, your prospecting becomes lethal—in the best way.
We’ve all seen generic sales emails.
We’ve also all had that moment when something shows up in our feed and we think:
“How did they get inside my brain?”
That’s the goal.
Relevance beats volume every time. (Don’t get me wrong, volume helps, but generic a** sales prospecting emails don’t convert).
Here’s a copy of the Territory and Account Planning Template that’s taken me many iterations to perfect, for this step fill out tabs “A List Account Map” and “A List Contact List.”
5. Build a real prospecting cadence
You cannot rely on one email.
You need a 12-step, 6–8 week cadence that includes:
Multiple emails
LinkedIn touches
Follow-ups
Personalization layered on top of automation
The goal is not to annoy people.The goal is to stay present long enough for timing and relevance to intersect.
Every touch should either:
Teach something
Show insight
Or make them feel seen
People answer sales emails when they feel understood, not when they feel hunted. You can be persistent and respectful at the same time. Lots of research in B2B sales indicates that it takes 12 touches for a person to even realize that you exist.
People don’t ignore you because you’re bad. They ignore you because:
They’re in meetings
They’re traveling
They’re putting out fires
They’re scanning, not reading
When you’re thinking about your 12 touches, know that each touch doesn’t need to “sell.”
The game you are playing here is: developing familiarity, showing that you’re consistent and care about serving them, by delivering value.
By touch 6, your name probably looks recognizable.
By touch 9, they feel like they’ve seen you before.
By touch 12, maybe just maybe they feel safe to reply.
Your prospecting isn’t about convincing, it’s about becoming familiar enough that replying feels easy. And that the person replying to you feels like they’ll walk away from an appointment with you having learned something about their business and how they could approach the business problems they are trying to solve with a little bit more ease.
Your prospecting is also not about re-inventing the wheel with every single touchpoint. You can repurpose the same 2 or 3 key insights over the course of the campaign (and hey, even reuse those again in future campaigns) as long as you are constantly focused on the person you are prospecting, and how you can help them, and HOW THEY WILL RECEIVE YOUR MESSAGES.
Here are some thought leadership pieces from Gong’s Research Lab on prospecting and outreach that are worth a read:
Here’s an example of a 12 step cadence, timed out, and what is included in each of the 12 steps:
Tue Jun 3 – Email delivering valuable insight #1 about one of the problems this person cares about
Thu Jun 5 – Email with abbreviated insight from #1
Mon Jun 9 – Linkedin connect request (<300 characters) with abbreviated insight from #1
Wed Jun 11 – Email with valuable insight #2 about one of the problems this person cares about AND a phone call or text message offering to discuss valuable insight #1 and #2
Fri Jun 13 – Email with abbreviated insight from #2
Tue Jun 17 – Email nudge
Wed Jun 18 – Linkedin inmail, potentially another phone call or text
Mon Jun 23 – Email about the linkedin inmail and previous attempts to connect
Fri Jun 27 – Phone call or text message about the previous attempts to connect, offering to discuss valuable insights #1 and #2
Mon Jun 30 – Email with value #3
Tue Jul 8 – Calendar dart to review the valuable insights #1-3 that have been shared
Thu Jul 10 – Email with abbreviated insight from #3, and saying you’ll leave them alone for a week or two but you’ll be back
The Big Idea
Sales is not always about being louder, hustling harder, or volume, volume, volume. Sales is about being more prepared, delivering value at every step of the way, and remembering that you are there to help solve this individual’s problems.
And when you: know your number, know your calendar, know your accounts, know their problems, and show up with a plan…
You stop chasing deals and start creating them. And that is how you turn a new sales year into your best one yet. LFG!
