The Hidden Trap of OTE
The Cost of Sales Roles Where You Can't Close Deals
Last week I shared that I’d be working with Sam Marelich on a question that always seems to surface via questions from you, the audience, X, or social circles where the topic of sales roles comes up.
How do I know I’m making a good choice in a sales role, for both my career and earning potential?
To answer that question, Sam and I have put together perspectives laid out in a series of posts over the coming weeks. These will help you to better evaluate roles so that you can have a better understanding of what A GOOD Role looks like and how to best set yourself up for success.
Over the coming weeks Sam will be sharing FREE video modules from his course. In this post and future ones in this series. He also has a newsletter, where reps learn more about the perspective of hiring managers, which you can check out here.
If you’re interested in exploring the course, you can check it out here. For all Hacking Sales subscribers, you get the a 50% discount, by using “HACKING” promo code.
Here’s a sneak peek at what’s covered:
• How people actually make (lots of) money in sales
• How to work with external recruiters
• How to create a perfect resume
• What LinkedIn looks like if you are a recruiter
• How to evaluate new account executive roles
• What you need to consider as a first sales hire
• What to do if you’ve just been fired
• What to do if you don't want to change jobs today, but want to set yourself up for long term success
*Use “HACKING” promo code for your 50% discount
Here’s what we’re covering today:
What’s important to you? Your Main Framework
What does my next move look like?
Resources to get a sense of where to go
What are the characteristics of the company I’m looking for?
Researching companies
Evaluating a New Role and Company
What’s important to you: Your Main Framework
What does my next move look like?
If you ask, you shall receive.
And the quality of your questions determines the quality of your responses.
The reality is that when most people are evaluating new roles, or even LOOKING for new jobs, they’re mostly passive and reactive.
The biggest reason people don’t get what they want is simply for the fact that they aren’t specific:
“I just want a job”
“I just want a sales job”
“I just want a sales job in x industry”
The reality is that people don’t care about you. However, they WILL help. The challenge is that the less specific YOU are, the less able THEY are able to help.
So how do you come up with a sense of what you want?
Resources to get a sense of where to go
Here are some resources that can help you navigate the landscape, especially if you’re in tech and looking for new industries and roles to scope out. This doesn’t have to be exhaustive. It’s just a way to get a sense of where YOU WANT to go.
Matt Turck’s MADD landscape - great overview of the AI, ML, and Data landscape (along with companies that provide applications to specific industries).
CB insights - Google “CB insights top (insert AI, or ML, Blockchain, or healthtech, or xyz) companies. You can sign up for a free trial for 7 days to continue accessing more reports and more in depth information on a specific company. Use it to get a sense of where the top companies fall in each respective ecosystem.
Builtin NYC - same as above (google “top (insert AI, ML, blockchain, or xyz industry) companies”. I’m in NYC, but you can obviously use it for your respective location or remote.
The goal here isn’t to just find any job, but one that you WANT.
Remember however, at this phase, you're just window shopping.
IF you do have a job currently, even better (and we’ll cover the topic of abundance and mindset in later posts in this series).
What are the characteristics of the company you’re looking for?
There’s a spectrum of sales opportunities within tech. Generally speaking, you’ll find characteristics of companies with the below in mind depending on their maturity.
Early Stage, Series A/B: anywhere from 50 - 200 people (this is a good indicator that the team is on to something but there is still probably risk, need to understand that and see what has been done so far from a sales perspective in the org in order to “de-risk” as best I can)
Growth: anywhere from 250 - 500 people (most likely have established something repeatable and are hiring to execute on playbooks but there are still a lot of learnings
Enterprise/established: your Databricks, Snowflakes, Amazon’s of the world. Processes and ICP’s will be laid out with well refined sales playbooks.
You can get more detailed than this however for the purposes of today, it’s a starting point and a suitable framework to give you a sense of what matches up to you and how to be more targeted and efficient in your approach.
It also directly relates to sales prospecting. You'll notice that there is a lot more upfront work, but with that work, comes more tailored positioning and messaging for you as a candidate and navigating your career.
Researching companies
The resources below give you a good sense of what direction to go towards industries/roles where you can make money.
From a sales perspective, Repvue is a great lens into things like quota attainment, culture, overall sentiment from the sales team.
From a product perspective, Blind is a great for engineers - but it’s useful because your sales numbers are only as good as the product you’re selling.
Now, these aren’t the BEST resources for companies that are early stage (ie series A/B as mentioned above).
Sam has a free guide written for companies on when they should hire their first salesperson - it’s not geared towards reps, but rather towards companies, but this should help you answer the question: is this company developed enough for me to join?
If they are unestablished companies, here’s your best rule of thumb:
Has the founder been there and done that before, successfully?
What is their revenue? Good rule of thumb is $500k in ARR AT LEAST.
Evaluating a Role and Company
Here’s the most important part. Because after you’ve established what YOU want. Then you need to understand how to be successful you can be in those roles.
Questions to that will give you a better understanding of the role:
Have you (hiring manager or founder) done this before?
Why did you choose this company?
What is the reason behind growth?
What does the pipeline look like?
How are they booking meetings?
How hard is it for them to book meetings with their customer profile?
If they’re an unestablished company, you’re just trying to understand what are the levers you can apply as to what is working currently. Along with a hypothesis that is showing traction. You can download my free territory plan which outlines the mechanics of all aspects of a sales cycle.
The goal here is to give you direction on how to vet the organization and leadership. If people you’re speaking with can speak honestly, and intelligently, about the challenges in the role - it’s a good sign.
Now, this is easier as you go into companies with more funding, revenue, scale, employees and brand equity. For unestablished companies, you are inherently taking a risk. As is the case with all small startups.
The most important thing to help get access to roles easier and information on organizations you’re interested in?
NETWORK.
In our next article we’ll cover how to network to find a job, FREE videos from Sam on how to best position yourself with external recruiters and a FREE sample of a resume template.
You can also join Sam’s newsletter here - it’s once a week and aimed at hiring managers (but reps can learn a lot too).
Finally, remember to use the promo code “HACKING” at checkout for 50% off if you end up purchasing Sam’s Course.
As always, thanks for reading and see you all next week. If you have any questions or thoughts, shoot me a DM or email andrew@hackingsales.xyz.
See you all next week.
-Andrew K
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