As a salesperson, once you have put in ~2 years into your first account executive role, you start to have options in the marketplace.

Even in recessionary times like today, it hasn’t been uncommon for me to get 1-2 messages a week from recruiters pitching new opportunities both at startups and public companies.

One recruiter went so far as to email me directly at my company email address!

Don’t forget the opportunity cost of switching roles

The truth is, when you are in sales, the opportunity cost of switching jobs is unlike in other roles. For one, you are leaving an existing pipeline of potential customers you have at your current role. If you were to jump to a new role, you would need to build a book of business completely from scratch.

Depending on the maturity of the company’s lead generation processes, it could take anywhere from 3-6 months before you close your first deals.

So before you pounce on a shiny object in the form of a job description with a higher OTE (on-target-earnings), remind yourself of this.

Now, let’s say you are starting to look – which could be for a variety of reasons. According to this article from Forma.ai, some of the most common reasons may be:

• Unfair quotas or compensation plans

• Career stagnation

• Loss of belief in the company’s strategy

• A bad manager

From my experience, these are all valid reasons to start looking around.

For me, the motivation to start looking was when I was realized I was neither learning nor earning. I have always valued learning, and it was one of the reasons I joined a seed stage startup as an early sales rep.

Other sales people may consider this crazy, but I was really excited at the prospect of selling a product that was at the forefront of innovation in an early industry.

After around 2 years, however, being the top salesperson – a big fish in a small pond – got old. Not to mention, new sales management came in, and began slicing up territories with no plans to bring leads with the increased headcount.

Suddenly, my path to earning became fuzzy, and I was truthfully not learning much anymore.

A framework for looking at new roles

So, whatever your reasons, let’s say you are now open to new roles. I have seen a lot of frameworks of how to evaluate new roles (shoutout to Brandon Fluharty who has a really nice system around this, check it out here), but my favorite ones look at the following factors :

1. People – leadership and peers

2. Product market fit and industry

3. Compensation

Brandon’s frameworks take into account additional factors like company culture, but I am generalizing culture into the “People” category. Let me break down below how I view each of these criteria.

1. People: This is no doubt the most important part of any new role you are evaluating. It is not “do I like the people I am interviewing with?”.
   
   Rather, when you are interviewing with the company, here are the questions I would look to answer for myself:
   
   – Are these A players? Will they push me to excel and get better?

– Does leadership have a solid short-term and long-term vision for the company?

– Do my peers seem like competent people I would enjoy working with, and who wouldn’t make my life difficult by being unresponsive or unwilling to help me?
   
   People make up the culture of a company. If the people you talk to seem like A players who do not have toxic personalities, that is a great signal.
   
   If you want to excel in your career, it will benefit you to work around other hardworking, smart individuals as they will push you to constantly improve.
   

2. Product market fit and industry: I lumped these together because they can potentially go hand in hand.
   
   When I look at the company’s industry, I would want to know if this is a growing space where the total addressable market (TAM) is only increasing. It’s easier to sell in a growing industry vs a stagnating one.
   
   However, be careful not to go into an industry that is too early. I made that mistake, and it is truly a grind as a startup salesperson when your company is figuring out product market fit and you are in an early, not yet mature industry.
   
   Product market fit is a bit harder to gauge, but the reason it is important is because it will influence how quickly you will ramp up to quota in your new role.
   
   Pick a company with good product market fit, and you can come in and win new business quickly.
   
   On the other hand, if you join a company still trying to find product market fit, buckle up and get ready for a longer term ramp.
   
   If you are going to take a role like this, make sure the base salary is high – closer to the $150K-200K range. It is likely you will not make the full OTE in your 1st year.
   
   Product market fit also implies the company should be winning new logos – potentially even enterprise logos. Ask about this. Many startups are just not enterprise-ready, meaning they don’t understand the compliance or features needed in the product, and as a result, it makes sales team’s job harder.
   
   Here are some questions you can ask to dig deeper:
   
   – Can you tell me about some of the logos you have closed over the past year?

– What’s the conversion from proof of concept (POCs) to paid customers? (they may not have data on this yet, but worth asking)

– What is the net revenue retention (NRR) of the business? This will tell you if existing customers are not seeing value in the product after year 1, and are churning.

3. Compensation: I put this one as least important, but let’s face it – we’re in sales – comp matters!
   
   The reason I put compensation last, especially if you are joining a startup, is your compensation will be heavily dependent on putting yourself in the right environment.
   
   If you don’t do the due diligence here, it doesn’t matter how high an OTE number gets thrown at you, it will not be achievable. Build the groundwork to figure out culture, product, and the short / long term success indicators for the company you are interviewing with, and this will tell you if your quota is achievable.
   
   A good rule of thumb on compensation is 50/50 between your base salary and variable commissions. Keep in mind, everything is negotiable, especially if you have to leave a pipeline and successful track record at your current company.
   
   Don’t be afraid to ask for what you need – a higher base, higher commission rate, more equity, etc.

Don’t get emotional, try to be objective

I absolutely loved the 2 years I spent at my last SaaS startup (except for towards the end). I joined in their seed stage as an early account executive, and continued through their Series B raise.

While no one hit quota, I was leading the pack at around 60% attainment. So, I was seen as a top performer.

The reality is, however, startups are really hard – for founders, for leadership, for employees and even our customers! The startup’s growth was not the typical VC growth rocket ship, and naturally, sales was the first to be scrutinized.

The board’s solution to this growth conundrum was to bring in new sales leadership and hire more salespeople. Because duh! Just add more numbers to a spreadsheet.

Most of the people I worked with were great people. But, I always felt like we moved a bit slower than I would’ve liked.

Our technical and product leadership was a bit weak. However, these things were manageable for a period of time, until they all started compounding on top of one another. When sales hiring became spreadsheet math, territories were split up while quotas went up, and no long term plan was presented to bring in more marketing people to generate leads – it was time to go.

I could no longer justify playing the long game and waiting for the product and market to catch up, if I had no chance of earning while we figured it out.

You may have different reasons for leaving, but just know, it may not be an easy decision.

If you create a job change evaluation template for yourself, the odds are higher that you will make the decision logically and not emotionally. If I had allowed my emotions to take over, I would’ve stayed at my previous company, even though a lot of warning signs were there, at least for me in my role.

In conclusion, changing jobs as a salesperson is never a straightforward decision. Putting frameworks in place, like the ones I will link below from other content creators, will make these decisions a lot less emotional, and hopefully set you up for success in your next role.

Don’t feel guilty or scared, change is a reality of life. We just need to make sure we are embracing change for the right reasons and opportunities!

Resources

• Brandon Fluharty’s Career Change Evaluation System (I used this quite heavily while evaluating the role I ultimately accepted)

• Marcus Chan’s Highest Paying Sales Jobs (I would start around 15:00 to see his job evaluation process)