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January Jump-Start Week 1: Take 15-Minutes to Reflect, Review, and Record Your Wins from 2023

Ryan Walsh, CEO and Founder
Ryan Walsh, CEO and FounderJan 2, 2024

Welcome to the 2024 January Jump-Start! Each week this month, we’ll be sharing a short and simple task that can help you have a successful year in sales.

We’re starting off with an easy one — but many reps don’t make time for: reflecting on the previous year and recording your wins. 

What to Reflect on from 2023

Your reflection should start off with one simple question: Was 2023 a good year for your career? Of course, that leads to a second question: How do you decide what makes for a good year? That’s a personal choice that will be different for everyone — so take a moment to think about how you would define a good year.  

It might be based on whether you hit a target figure for total earnings — but it could also be more nuanced. Did you make enough to pay off debt? Did you hit a target savings goal for buying a home, or for your kid’s college fund?

Or maybe your definition of a “good year” isn’t based on money. Are you selling a product that you believe in? Does your sales org have good leadership that you trust and respect? Do you feel like you’re treated fairly? Do you have a good culture on the sales team? Did you get a promotion or other recognition for your accomplishments?

It could be that what makes a good work year for you isn’t actually your job at all — but instead it’s the life that your job enables you to lead. 

However you define it, your answer to whether or not 2023 was a good year will lead you to a number of different questions you should think about next.

Understanding a Good Year

If yes, 2023 was a good year for your career, the next questions you ask yourself can help you answer why it was good. Some options to consider are:

  • Did you join a new org or move into a new role where you’re happier? How did it make you feel that way?
  • Did you sell more or make more money? How did you make that happen? 
  • Did you learn something new or work hard to improve a skill? How did that make a difference in your work life?

Don’t stop at these examples. Try to come up with questions for yourself to help you understand what made last year good. That will give you the foundation to make a plan to repeat or build on those wins in 2024.

Understanding a Bad Year

2023 was a difficult year for a lot of sellers. Reflecting on what made it a difficult year can help you decide how best to move forward in 2024. Some questions to ask next might be:

  • If you missed your targets, what would you do differently if you could re-do the year? Would better prospecting or pipeline management have yielded different results? Or was there just not sufficient demand for the product that you’re selling?
  • Did your territory or lead flow give you enough to work with?  If not, is that something that can change in 2024? Can you source more of your own leads?
  • Did you lose deals you expected to close? What were the closed-lost reasons, and is overcoming them within your control?
  • If you didn’t make as much money as you wanted or expected, how can you do better in 2024? Are you limited by the compensation structure in your current sales org?

Thinking about what went wrong isn’t fun, so don’t dwell on it too long. Spend only as much time as it takes to identify where things could be better in 2024 — or if you need to find a new role.

Record Your Wins from 2023

It’s surprising how many sellers don’t keep track of their wins. You should! 

If you want to negotiate your comp for your current role — or if you’re interviewing for a new one — having numbers that show your success is critical. Write these numbers down where you won’t lose them:

  • Your top three deals (Bonus: for comparison, your team/company’s top three deals)
  • Your average deal size (Bonus: for comparison, your team/company’s average deal size)
  • Your quarterly and total quota attainment percentages for 2023

Looking back on these numbers, were they what you expected? Any surprises? 

If you’re proud of them, go add them to your resume and/or LinkedIn profile. If you’re not, how do you want them to be different next year?

Rate Your Current Org on RepVue

The last thing to do this week is to leave a new rating on RepVue

Yes, even if you are still in the same role at the same sales org. (You should leave a new rating even if your last rating was sometime in Q4-2023.)

There are a few reasons why you should.

  1. Leaving a new rating now renews your access to RepVue. If you decide to start looking for a new role sometime in the next four months, you’ll be ahead of the game.
  1. Leaving a new rating will really help all your fellow sales professionals who’ve already decided to look for a new role in the new year. 
  1. A lot changes by the end of Q4. There’s a unique urgency, with buyers and sellers both working hard to close deals on last year’s budgets. New ratings give everyone more transparency with the latest data providing a more complete picture.

Once you leave a new rating, you’re all done with this week’s task!

January Jump-Start: Next Week

For week two, we’ll be looking at your Q1 pipeline to help you close more deals. See you then! 

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