Be Specific About What You Want
A 9 Point Checklist for Sales Reps Looking at a New Role
How to Land Your Dream Tech Sales Job
Demystifying the 10K for Sales Professionals: Evan Kelsay
This episode is brought to you thanks to Outreach, QuotaPath, and Vidyard who all happen to have open sales roles. To learn more about them and all of our sponsors who support this podcast and this community, click over to top1.fm/sponsors
In todayâs bonus episode on the Sales Success Stories podcast I want to talk about doing your due diligence on a new sales role. This is something that has come up over and over again in this community because the position you find yourself in, in terms of the company youâre selling for, the industry, and in large part who youâre working for can have a massively outsized impact on your success in sales, and Iâve threatened for way too long to create some type of resource to help with these decisions. Well, hereâs your resources thanks to a thread in the Sales Success Community Slack that Luke started, with some significant contributions from Eddie Baez and David Weiss.
Before we get into the due diligence on the company youâre considering going to work for. Iâd highly recommend you do some due diligence on yourself. I even wrote a story about this for the first Sales Success Stories book and shared that audio from that piece a few years ago. If youâll go to top1.fm/dd for due diligence Iâll include links to all of the resources like that that come up.
The title of that piece was âBe Specific About What You Want.â The idea is that you really need to give careful consideration to whatâs going to be the right fit for you. One of the most important considerations is who youâre selling to and what youâre selling. Youâre going to spend a lot of time interacting with your buyers. They should probably be people you enjoy spending time with. For me thatâs sales and marketing professionals because they tend to be more optimistic and forward-looking, which is important to me because Iâve also sold to HR, Finance, and IT types who tend to be the opposite. Theyâre typically way more pessimistic and risk-averse. You should also consider what size of organization is right for you. Will you benefit from great training, a well-known brand, and a lot of resources that a large organization offers, recognizing that there will likely be some additional bureaucracy and internal complexity that comes with that, or will you thrive working for a small company where you can be more nimble and creative, but where youâll probably need to figure out a lot of things on your own and will need to wear some additional hats?
Finally, youâll want to make sure that youâre targeting the right role and give careful consideration to the price point that youâll be selling at. Jason Lemkin of SaaStr who I donât always agree with, wrote a pretty good piece about 9 reasons good salespeople fail, and he makes a really good point about watching great sales reps thrive at a 20K price point who canât make it selling something thatâs 2K and vice versa. Again, Iâve got that link for you at top1.fm/dd
Alright, so now youâve found a company that youâre interested in going to work for who you think will be a good fit for you. This is where the real due diligence begins because youâre about to commit 100% of your professional effort to this company, and you want to make sure that you get a good return.
Iâd recommend you start with the solution. Do you believe in what they sell? If you donât believe in the product, itâs nearly impossible to find success. In many ways, sales is simply a transference of belief. So take a look at their offering. Look at their customers. Ideally, you have somebody in your network who uses the solution who can share their honest opinion. Now if you donât already know somebody, you can always reach out cold to a reference the have on their website. This is also an incredible way to set yourself apart in the hiring process. If you want to dig really deep into that idea, listen to the conversation I had with Jacob Gebrewold on How to Land Your Dream Tech Sales Job. The other thing you can do is to reach out to another sales professional in that industry to get their perspective. This just happened recently in the community as well. Sometimes something sounds really good from the outside, but you might learn from somebody thatâs in the middle of it that while this solution sounds like a good idea on paper, most companies arenât investing in this type of solution and itâs a really hard sales. Definitely something you want to know BEFORE you take the leap.
Solid product. Great. Now, what about the company itself? I would dig into culture and financials in that order. Culture is absolutely critical and this is kind of a personal hack and shortcut, but you can learn a lot just by looking at the CEO. What is their background? Do they come from a sales background or did they build their career in product or finance? Personally, thatâs more or less my order of preference. A top leader whoâs spent some time selling often sets up a really great culture because they understand sales. Anybody that comes from a customer-centric place like product, marketing, or customer service can institute a strong culture based on the customer as well. Itâs not a red flag necessarily, but you might want to be just a bit more wary if the most senior leader in the organization comes from a purely financial or engineering type background.
You can also get some really good clues about culture just by reading reviews about the company. Glassdoor, PayScale, and RepVue can all offer some interesting insights. But the most important thing you can do is to talk to people. You should work to have a conversation with at least one member of every team youâll be interacting with on a regular basis. Obviously, youâll want to talk to others on your immediate team to get their perspective, but talk to a solution consultant or sales engineer, talk to somebody in marketing, talk to somebody in customer service, and somebody in product. This will give you a broad-based view of the company and its challenges beyond just a myopic sales view.
As youâre talking to some of those sales peers, this is probably a good time to learn a little bit about comp. Validate how many people are at or above quota. Are targets reasonable, or are you being sold a dream based on âfaux T E,â shoutout to Elaine for making me aware of this one. OTE is an acronym for On Target Earnings. Itâs the amount of total compensation between base and commission you should expect to receive at 100% of plan. Unfortunately, there are a lot of organizations where very few people actually see that kind of W-2 and thus, Faux TE. You should also ask about turnover. Iâve found this to be one of the best indicators of organizational health. If thereâs a lot of turnover, be very very careful. Itâs almost always a very bad sign.
On the financial side, for the larger public companies, this is a lot easier and Eddie Baez recommends looking at their earnings calls and financials. Their shareholder memos and messages from senior leadership with provide useful background on the operating environment and the firm’s corporate objectives.
For an incredible resource on how to make the best use of public company documents like this. Check out Evan Kelsayâs highly entertaining Sales Success Summit presentation on Demystifying the 10K for Sales Professionals. Again top1.fm/dd.
If the company youâre considering isnât public, you can look at Crunchbase to find out details about their fundraising activities, and this is just an areas that youâll need to lean into and ask some more explicit questions about.
The last piece is critically important, and thatâs the due diligence you need to do around your potential new manager. This relationship can make or break everything. Make sure you understand their style and their approach, but here you really need to get outside of what they tell you and validate. Certainly, talk to other people on the team about their perspective, but the most powerful thing you can do is use LinkedIn to find reps that have worked with them in the past. You can ask all the same questions about their style and what itâs like to work for them, but the most telling thing of all is probably in their answer to your question about whether or not they would work for this person again and why. Remember itâs super important to get outside of the organization for these detail. Find one or two people who donât care whether or not you end up going to work for this company to find the truth.
All of that sounds like a lot, doesnât it? Because it is, but every career decision you make is critical to your overall personal trajectory. Going in the wrong direction even for a year or a year and a half can have a major impact long term, while the same is true if you make a great decision and work for an incredible company under super-strong leaders. Trust your gut! If something doesnât feel right, thereâs probably a reason for that. Donât chase the dollars and the title. Theyâre important considerations for sure, but in almost every case Iâve ever seen that theyâve been the primary driver, the person who accepted the promise of the big dollars and the big title has regretted it. Too often they just donât materialize. So be a little bit skeptical. You might even build a scorecard to help you be a little bit more objective in a very emotional decision.
Finally, you canât talk to too many people. Thereâs literally no such thing as too many conversations. Talk to people in and around the organization, but lean on your network and your mentors. Join the Sales Success Community Slack and lean in there. To do that, you just need to hold some $SALES coins and your link today is SalesCoin.co/dd. Now if you havenât created an account yet, go to SalesCoin.co/start and then share your username and wallet ID at salescoin.co/form so I can send you your first $10 worth.
Iâm sure weâll be continuing the conversation on Slack, and you can also ask even more specific questions. Itâs a pretty incredible collection of humans. Many of whom youâve heard here on this podcast.
Good luck in your search and may your next sales role, or the decision to stay where you are, put you on the path to greatness. Thanks for listening!
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