How to Find Your Dream Sales Job (The Job Search Scorecard Series, Part 2)

“Life is long. You can waste time at a job that doesn’t pay well or fulfill you.”

– No one, Ever

Obviously, we all want to find a good sales job, but what’s the fastest, most reliable way to land your dream sales job?

With so much on the line, so much to consider, and so much chemistry between potential employers — it’s easy to lose the forest for the trees.

As someone who’s had a few sales jobs over the past 20 years and been through two downturns, I know it can be hard to stay objective and make a well-informed decision when you’re on the hunt.

That’s why I created a job scorecard to help you speed up your job search and find your dream job. This guide will help you reduce the margin for error, navigate the complexities of the hiring process without uncertainty, and avoid potential disasters.

A Job Scorecard: The Secret Tool for Landing Your Dream Sales Job

It’s easy to get dazzled by an exciting opportunity or forget your due diligence and jump at the first thing that comes your way. I was so dazzled during one interview for a sales job — by the product concept, the leaderships’ vision, the cushy paycheck — that I neglected to ask how the company planned to connect enterprise sales with their go-to-market strategy through their ability to customize the product.

I had no idea what kind of resources or support would be allocated to product iterations, what seat sales leadership had in the boardroom, or how long the runway was for building out the enterprise sales team to keep up with the demands of a complex marketplace.

In the end, I worked my tail feather off for a company that wasn’t ready for an enterprise sales team. Within nine months, they disbanded the entire enterprise sales team from the CRO down (OUCH).

I learned the hard way that it’s critical to have a system when searching for a sales job that holds you accountable to peeling back the important layers versus getting distracted by perks.

A job scorecard helps you collect your thoughts, define your dream job, and distinguish the standouts from the rest.

After all, a dream job is a nebulous concept. One person’s dream could be another person’s nightmare.

A scorecard allows you to evaluate each opportunity objectively while accounting for what’s important to you, your experiences, your perspective, and your personal goals.

This requires a healthy dose of self-awareness, but getting real with yourself is way better than being wooed by an employer that’s not meant to be.

Consider, too, that we’re in a market none of us have seen before:

Add all this up and you have a scenario in which employers are running around frantically trying to figure out how to hire good salespeople when they’re bombarded with candidates and actively topgrading their existing team.

Meanwhile, the best employers won’t jump at just anyone. They didn’t before the pandemic, and they certainly won’t now.

Having an unbiased system for choosing the best opportunity helps you avoid making emotional decisions. It also helps you evaluate each opportunity with your best interests in mind.

In fact, I get heartwarming responses about the power of the job scorecard regularly.

Start Here: Define Your Dream Job

To create a job scorecard, you need to first do some soul searching to define what the right job looks like for you, and why. This is probably the number-one job search tip I can give you.

Many of the people I talk to who are looking for a change don’t know what it is they like and dislike about their current position. They don’t have a meaningful understanding of how their career has brought them to this point. And to make matters worse, they can’t define what’s important to them.

Without a sense of what your ideal job looks like, how are you going to know when you see it?

Clarity is key to finding your dream role, but it’s also an attractive trait to hiring managers.

After all, turnover in sales is expensive, and the best companies aren’t going to be too keen on hiring someone who doesn’t have clear direction.

It raises other red flags too. If you don’t know what you’re looking for, and you can’t articulate it, how does that reflect on your ability to be successful with a complex buyer journey?

Set aside a time, sit down with a notebook, and ask yourself two questions:

If I look 6–12 months ahead, and I’m crushing it (my goals, life, etc.), what would it look like? Why?

And even more importantly, if I was struggling and hated my life, what would it look like? Why?

Write down everything that comes to mind. When detailing these best/worst scenarios, be sure to address all the factors. For example:

  • Stability / reduced risk
  • Salary
  • Work expectations
  • Leadership
  • Growth
  • Company culture
  • Work goals
  • Personal goals
  • Lifestyle outside of work

Be very specific about the quantitative and qualitative details of your dream job.

What’s expected of you on a daily basis? How are you treated? How do you feel about your job? Your ability to earn money?

For example, it’s not enough to say, “I want to work for a company that sets reasonable sales quotas.”

Specify what a reasonable sales quota is for you. Define what a great salary would be, what a great relationship with your VP of sales would look like, and so on.

Next, mark each item on your list as “must-have” or “must-avoid.” Think of your musts as the deal-makers and the deal-breakers of your job scorecard.

Use your musts to define your own unique “best sales job.”

These specifics enable you to cross-reference your ideal opportunity with your current role and easily identify any roles that aren’t a good fit.

Be thoughtful in this process, and give yourself plenty of time. Knowing what you want (and want to avoid) is the first step in guiding yourself to where you want to be.

Your Dream Sales Job: 15 Key Questions

Here’s where we hone in on the tangible factors that go into your job scorecard.

According to the Harvard Business Review, The validity or predictive power of a typical unstructured interview is around 20%.

This means that you only have a 1 in 5 five chance of accepting the right offer if you don’t have a system in place to help you choose.

Below are the specific questions I use as part of my discovery process with prospective employers. Your answers to this series of questions will help you design your job interview scorecard, thus giving you a structure for future interviews.

  1. Why am I leaving my existing job? Are my prospective opportunities better than what I’m leaving behind? What have I done to try to address my issues? Can they be resolved?
  2. Given the market conditions, is it really the right time to make a move? If I do move, what’s the risk?
  3. When I’ve been the happiest in my job, how would I describe what that looked like? Why?
  4. What lessons have I learned, and how can I apply that to my next role?
  5. What part of my job have I done best in? Where have I struggled? What contributed to my success or failure?
  6. Are there repeat patterns between jobs that have caused me angst?
  7. If I make a move, what does a better role look like? More importantly, why?
  8. What kind of leadership have I thrived under the most?
  9. What kind of company / leadership would allow me to recreate my best deals?
  10. How do I like to work with my buyers?
  11. What industries are compelling, and what gets me excited to learn more?
  12. What kind of products or services do I like to sell?
  13. What kind of team do I work the best with?
  14. Have I ever worked remotely before? Do I seriously have the chops for it?
  15. How soon do I expect to make money? What’s required to earn that money? Am I up for that?

This personal Q&A session allows you to define the critical traits that you need from a would-be employer and populate your scorecard.

Create Your Job Scorecard

Once you’ve defined what’s important to you and why, it’s time to create your scorecard.

Uses the information you determined above about your ideal sales job to populate the top row of a spreadsheet. In the left column, you will put the different opportunities.

Rank each opportunity on a scale of 1–10 in each category based on their answers during your interview, then calculate the average.

Determine your threshold for a minimum acceptable score and voila! — you have a clear-cut, non-emotional evaluation that you can use to compare job opportunities.

Personally, I set my threshold at 7.5 because I’m only willing to tolerate a 25% miss-rate with a potential employer. But whatever your threshold is, pay attention to where the company failed to meet your standards to make sure you’re not compromising on one of your must-haves.

Research each company and role, and review your scorecard before an interview. Then ask insightful questions that relate to each category during the interview.

Since you’ve done your work ahead of time, you won’t get bamboozled and forget key points. In turn, you’ll be more relaxed, confident, and impressive to potential employers because you came prepared.

Since it accounts for every factor from culture to chemistry to cash, this scorecard will help you objectively assess the strengths and weaknesses of each would-be employer. It also challenges you to quantify and qualify each category to make a well-informed decision that’s right for you. This is your life and career after all!

You can download my job scorecard template here.

Using a Job Scorecard Template: Do’s and Don’ts

Like coding a piece of sophisticated software, your scorecard is only effective if it’s built and used correctly.

Here are a few tips to help you get the most out of your scorecard, from creation to interviewing to negotiation to accepting the offer.


DO: Get specific about what success and failure means

I said it above but it bears repeating: It’s 100% essential to set a target if you want your job scorecard to get results.

This means taking note of what you’ve learned, what you want and don’t want, and the difference between reality and perception.

DO: Take regular notes about your career

I recommend that anyone who’s considering a move carry a notebook, whether paper or in an app. This way, whenever you find yourself thinking about your career and what’s important to you, you can jot down your ideas.

This is especially true when you’re talking to other people about your job. So much self-knowledge that would be overlooked or forgotten gets uncovered when talking with people close to you.

Taking notes as you go eases the process of defining your goals while also helping solidify them in your mind. Pay attention to any themes that reappear in your notes, and assign them extra weight for being top-of-mind (aka more important).

DO: Run your scorecard by trustworthy peers

Discuss what you’ve written with your “advisory board” — a group of no more than 3–5 people you trust to give you straight-up, unfiltered feedback with your best interests at heart. People such as a mentor, old boss, colleague, spouse, career coach, etc.

Create a safe space for them to provide feedback (aka don’t get defensive). Listen, look for the themes, and make notes so you can compare their thoughts to what you’ve uncovered.

Having people point out important blindspots is priceless.

DO: Keep your scorecard current with your career goals

I recommend reviewing your scorecard whenever you hit critical mass or a new, intriguing opportunity comes your way.

Even if you’re not looking to make a move right now, being ready to evaluate an opportunity is a great way to learn and evaluate your career goals. This way, when the right opportunity does present itself, you’ll feel prepared and ready to leap at a moment’s notice.

Tools like MyPath create a digital space to track what matters most. You can map and track your sales journey, making it easy to keep your scorecard up to date.

DON’T: Skip sections of the scorecard during interviews

Don’t get caught up in the story you start to tell yourself when you’re being seduced by a big salary or cushy perks. The beauty of the job scorecard is that it keeps you focused on the right factors during the interview process. But that’s only true if you stick to it and use all of it!

Make sure to use it throughout the interview and record all your answers to compare opportunities.

DON’T: Update your scorecard during a series of interviews

Your evaluation tool for every opportunity must be consistent. That said, if you realize something life-altering, by all means, adjust your scorecard accordingly. Just be sure to go back and update your previous interview scores with the new criteria to maintain accuracy.

DON’T: Create your scorecard without a peer review

We’re all independent adults here, but you need to run your completed personal job scorecard by people you trust. I can’t emphasize this enough.

Unlike you, these people will be able to identify blind spots and unreasonable expectations in your scorecard that could leave you repeatedly accepting bad sales jobs.

DON’T: Abandon your scorecard for anything

Maybe you were referred by a friend in the company or just have a great feeling about this one. It doesn’t matter — always use your scorecard when interviewing.

This is your career, and you need to take charge of it. Being diligent about using your scorecard is the best way to maximize your chances of making the right choice.

DON’T: Leave your current job just yet

Before jumping ship, be sure to use your new scorecard to understand your current position.

Are the issues situational and, therefore, fixable? Or perhaps you’re just having a bad month or quarter and feeling the stress of that.

It’s best not to act rashly when you’re feeling emotional, and instead, refer to your scorecard to help you see things more clearly.

Implement Your Job Scorecard

Of all the job search strategies I could share, the job scorecard is by far the best. But creating it isn’t enough. You must use it if you’re going to have a successful job search.

Here’s what you need to remember:

  1. Know your “why.” How are you supposed to find a job you love if you don’t know what motivates you? Even with a scorecard, it’s a real challenge to find a dream gig without asking yourself the fundamental question, What do I want from my job, and why?
  2. Create your scorecard. Use the job interview scorecard template I created to start or create your own from scratch.
  3. Evaluate your current gig against your dream gig. Doing so will reveal if you should actually be looking for new work and highlight the big question you need to answer. Just remember, the grass isn’t always greener…

Being true to yourself means saying no to some opportunities. Even ones that, on the surface, look good.

The more you know, the stronger you’ll be. Stand firm with your values, and never settle for something that doesn’t make sense. Never try to jam a square peg in a round hole when making an important life decision.

The power of the job scorecard has never let me down and has proven itself to be a priceless tool to reduce the margin for error.

Want to see what companies are putting on their hiring scorecards? Want to up your interview game? Check out Part 1 of my Scorecard Series, where I discuss how employers should approach the scorecard process.

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