Depending on whom you listen to, employers claim it is once again a job seeker's market, which may sound weird given the world is still reeling from a global pandemic. Capable professionals will always be in high demand, but frankly some care needs to be taken in choosing a company that is the right fit for you to keep growing.

Why? Just a single bad decision can result in lots of frustration while your learning can grind to a halt. A quote below sums it up well for me:

When a manager with a reputation for brilliance tackles a business with a reputation for bad economics, it is usually the reputation of the business that remains intact.  - Warren Buffett

Although one can never know for sure, let's explore how you as a sales professional can improve the chances of your next company being the right fit for you.

Table of contents

  • First, carefully consider the following...
  • Questions to ask throughout the interview process
  • Conducting independent research
  • Requesting to check the following details
  • What if you identify "red flags"?
  • Last ideas and closing thoughts

Invite for a discussion

I've been building this list on and off in the past couple of years while sometimes adding new ideas. If you don't agree or would like to contribute, feel free to drop a comment below. You can also subscribe to the LBS newsletter and join a community discussion for this article.


Let's get started.

First, consider and ask yourself the following

Take your time to honestly ponder the following simple questions:

1. Do I use the product or would I buy it myself?
2. Will I work for people I respect and admire?
3. Would I enjoy working with my collegues?

These are absolutely critical points to reflect upon, especially if you are early in your career. Even if you just get two yeses out of three, you're already off to a great start. Are you interested where these questions come from? They are mentioned in Charlie Munger's compiled speeches that I've summarized on this site. He is one of the most famous investors out there, and I agree with him wholeheartedly.

Number 3 is a difficult one to know in advance, so how can we increase our chances of knowing more?  

Questions to ask throughout the interview process

In no particular order, feel free to shuffle them as you like:

1. Why are you here  (why does the person work at the company) and what are you most proud about?
2. What is the biggest pain point for you as the VP or Account Executive?
3. Why do you lose deals?
4. What is the pipeline amount, where does it come from, what is the division between each source?
5. How many demos a week does an Account Executive have?
6. What is the sales team structure?
7. What are the average conversion rates?
8. Average duration to close a deal?
9. Average deal size?
10. How is the overall sales funnel and sales process structured?
11. Can you show me your CRM?
12. What is the structure of your internal sales meeting?
13. What is your ICP (Ideal Customer Profile) and a typical compelling event?

Reading these you might wonder if some of the questions are too sensitive to bring up, or whether you get any truthful answers?

For the former, if you have managed to get through initial screenings and continued with one or more rounds of interviews, why wouldn't you deserve to hear answers to these questions? Alternatively, what kind of answers do you then expect to get when you actually start working? Embrace the tension and dig for answers. As in for the latter, I claim that it's important to at least hear some answers even if they are off the mark. Silence or trouble with answering can be a bad signal.

If you intend to be targeting top-level executives and the C-level, try to ask and understand the value message, what kind of workshops or other value-driven milestones are designed to be part of the sales process, and get a grasp on what is hopefully a clear and realistically laid out timeline for predictable closing.

Conduct independent research

It might be a good idea to read some recent Glassdoor reviews from current and former employees. There are often also country-specific Glassdoor equivalents available like Kununu in Germany.

Other data points that I personally like to check is the historical development in employee count as enabled by LinkedIn Premium, or even some historical revenue numbers or other financial indicators. For this we have many transparent and freely available portals in Finland, even when the entity in question only employs a couple of people. On Crunchbase you can find lots of useful startup information, including data on recent funding rounds.

Particularly in the SaaS (Software as a Service) industry, following review platforms might be useful to get an additional customer perspective:

  • Capterra
  • G2Crowd
  • Trustradius
  • Gartner Peer Insights
  • Siftery
  • Trustpilot
  • Google Maps Reviews
  • FinancesOnline
  • And many more...

Ace tips:

  • Use LinkedIn to look for previous employees of the company, contact them and ask if it is possible to have a conversation on their recent experience
  • Request a demo as a realistic target customer and see how the process works, get a feel for the company through their "customer's eyes"

Regarding the first one, remember to take answers you get with a grain of salt. The second point may also be a questionable approach depending on whom you ask. As discussed earlier, these are only some additional chances for you to gain a better gut-feeling before making your decision.

Requesting to check the following details

These might be worth reviewing to get a better idea of organizational readiness:

1. Pre-sales materials and presentations
2. Discovery call and demo structure
3. Customer case studies and references
4. IT and security certifications
5. Qualification critera in use
6. What kind of training or coaching is provided to salespeople?

What if you identify some "red flags"?

You've asked some questions but aren't getting answers you expect or something feels off, what now?

1. For you, there is now more perceived risk  => Ask for a better agreement (e.g. increased salary, or other favorable conditions).

2. Ask about pricing of products and services, get an understanding of the discount capability particularly if you've identified problems with organizational readiness. Maybe the strategic priority is to get new logos instead of just cold-hard revenue. If so, ask to see the the go-to-market strategy. GTM should be cohesive and comprehensive, because throwing reps into a new territory without proper support is rarely a good idea.

3. There is always an option to not join the company and look elsewhere.

Last ideas and closing thoughts

If you're about to start in a quota-carrying sales role it might be a good idea to assess the relationship between your quota (sales target) and your OTE (on-target earnings). OTE is your base salary + commission you receive when you've reached your 100% sales quota. A reasonable sanity check to make is that one should be expected to close revenue worth approximately 4-6x of OTE depending on organizational characteristics like product readiness, market maturity and comparable track record of previous performance in the company.

It is always a good idea to count the realisticness of achieving your quota to your best ability by breaking up the numbers into quarterly and monthly targets. Next, think about a plan of activity volume down to weekly and daily levels. Questions to ask yourself might be:

  • How many demos do I need per week to achieve my revenue goals?
  • How many sales qualified leads do I need to work on at any given time?
  • How many phone calls should I make per day?
  • Etc, etc.  

You've now decided to go for the role? Congratulations!

I've written an article on how to be successful when starting in a new sales position, go and check it out! On the other hand you might be also interested to find out more about careers of the past vs. careers of the future or how to sharpen your sales skills.