Your Next Sales Career Opportunity: A Conversation on Mistakes to Avoid

By: Chad Peets on April 25th, 2019

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Your Next Sales Career Opportunity: A Conversation on Mistakes to Avoid

Categories: Sales Transformation  |  sales challenges  |  Sales Productivity

Chad Peets is a Managing Director of Sutter Hill Ventures. He is responsible for GTM hiring globally and has placed more than 2500 software sales executives. Chad shared his recent conversation with John McMahon with The Command Center blog.  McMahon is a Force Management customer, a sales veteran and an adviser to some of the world's most successful software companies.  This post is part two of the conversation. Read part one here


In the last conversation with John, we discussed components to consider when picking your next sales career opportunity. We reviewed the "3 Why’s" and five critical factors that should help you analyze if the company is going to be the right one for your next move. In this post, we discuss the mistakes people make when deciding on their next move. John provides some good food for thought as you consider your next opportunity. 

Blog Graphic - Conversation PT2


 Picking Your Next Sales Opportunity


What are the classic mistakes people make when choosing their next opportunity?

Many people don’t evaluate their skills to the stage of the company. We aren’t honest with ourselves when it comes to assessing our skill set. So, we think of all companies, regardless of stage or product as equal. We don’t consider how the environment in different stages requires a different skill set to be successful.

You've seen this movie many times. Mid-level managers who were successful in a startup company take a new opportunity as CRO during the early adopter stage. They believe they’ve had experience in early-stage startups but, in reality, they joined the startup, after the early adopters’ phase and during the scale stage when all the pieces are in place. 

As CRO, they fail miserably. They last anywhere from 5 days to 6 months. They expected that all the infrastructure and support they experienced in a scaling startup company would be there at this very early stage company. Their skill set didn’t match, and they didn’t want to scrounge. They didn’t understand that it was their job to scrounge for everything because the company has no infrastructure support. Everything from buying a laptop, discovering the ideal customer profile, finding the best uses cases, creating the sales process and sales messaging, hiring reps, building comp plans while building the pipeline and closing deals. Many times, their skill set, and personal strengths are a better match for a scaling stage company.Blog Quote PT2.2

Confusing opportunity with the position is another classic mistake. It happens ALL the time. The person describes two companies, one of which meets all the criteria, the 3 Whys and items like market size, market growth, but the opportunity is a VP-Western US position. The other company doesn’t match most of the requirements, but is offering a much larger title like CRO. It becomes clear they should accept the better opportunity with a lesser position, but after we hang up, their ego gets the best of them, and they decide on the company with the larger title.

Nine to twelve months later they call me back to say I was right about not taking the job with the big title. The company failed, or the person failed because they weren’t a good fit for the product or stage of the company and now, they’re out of a job. They let their ego control the decision, and they threw away their analysis of the best opportunity. They head straight off into the danger zone. Remember, the number one reason startups fail is product-market fit. That means you need to look beyond the title, and focus on the opportunity the role will provide you. 

I know many people that have made this mistake and a few that have made the same mistake multiple times. Now their resume is a piece of swiss cheese, and they’re having a tough time finding any position.

What other mistakes have you witnessed?

One of the biggest mistakes is not precisely defining what you’re looking for in the next company. One I hear often is, “A recruiter called me.” Whenever someone wants to speak to me about an opportunity simply because a recruiter called them, I love to ask three questions:

The first is “Why would you change?” People need to give careful consideration to why they would change jobs. It can’t be that you change jobs just because a recruiter called. Is there something driving you away from your current situation or is it something specific about the opportunity that is attracting you?

Second is “What other opportunities are you looking exploring? I love this question because most times the answer to this question is that they haven’t considered any other opportunities. If the only company you’re looking at is the one a recruiter presented, chances are you’re making a mistake. Would you consider looking at only one house and buying that house because a real estate agent called you?

The third question is “What’s your criteria?” Many people haven’t thought through specifically what they want and why they want it in their next opportunity. So, I always ask, “If you haven’t thought through your criteria, how would you suppose I help you? Would you consider blindly buying a house without having defining specifics for bedrooms, bathrooms and other amenities? No, you wouldn’t. So, think about it, write it down.

Is there a type of product do you want to sell? Should the company be small or mid-sized? Do you want to stay in a specific domain? Are there particular buyers you want to target? What’s the company culture? What stage of a company interests you? 

What about a considering career path in the decision?

Most salespeople want a shortcut to the CRO position which, as we discussed, can be risky. A great question people should ask themselves is, “If I take this opportunity, how will it help me in the following opportunity?”

If you want to build a career, you have to think about more than just the financial side of a new opportunity and what product or industry you want. Do you know your career goals? If so, what is the ideal career path to reach your goal? What steps do you need to take? Discover how your next move will help you develop as a rep or a leader so a few years from now you can take the next step in the career path toward your ultimate goal. 

What other mistakes do people make when reviewing the company?

Blog Quote PT2They place an inordinate amount of weight on the VC firm that invested in the company. Why does it matter which big-name venture firm invested? So what? The majority of investments VC’s make fail miserably. Depending upon the data you research, around 80% of all VC investments fail. VC’s get to make eight investment mistakes and can still look like heroes, if one or two become winners. When you change jobs, you get one shot, not ten. So, pick your next opportunity carefully.

Being careful is especially true during the early funding rounds of a company. CB Insights tracked more than 1,100 tech companies that raised seed rounds in the US in 2008-2010. Less than half managed to obtain a second round of funding. Two of every three companies end up either dead or just self-sustaining, and less than one percent became unicorns.

They have “happy ears.” During the interview process, people believe all the information they hear. They have “happy ears.” They don’t ask enough questions during the interview process and don’t take the initiative to investigate claims made by the company through resources like LinkedIn and their network.

They don’t perform “backdoor reference checks” Use LinkedIn to get a backdoor reference. Find someone who knows people at the company. Network to them and ask them what it is like to work at the company. Get specifics on items like:

Sales rep performance - What percentage of all reps made quota last year? What percentage of productive reps made quota? How much did the top sales rep make? How many sales reps did they add in the prior year? How many reps do they plan on adding this year? How many reps were promoted to manager last year?

Attrition - What is the attrition rate in the company? Check LinkedIn for reps that were at the company but are no longer there? How many current reps in your local office and how many reps left? Why did they leave?

Culture - Is it a sales-driven culture, an engineering culture or a bureaucratic culture? The interview process can give you insights into working at the company. How long is the interview process? If it takes over a month for the interview process, you should start asking why it takes this company so long to hire sales reps if they are genuinely growing fast?

How many people are engaged in the interview process? Who is involved in the interview process? As an example, if Sales, Systems Engineers, HR, Marketing and Services are all included in the sales rep interview process, wouldn’t you wonder if you’re joining a Sales driven culture or a committee culture? 

How long does it take to get an offer letter to you after they verbally offer you the position? If it takes a week to get a sales rep offer letter, you’ll have to question how long it is going to take you to process orders, obtain discount approvals and get feedback on customer support issues.

Quality of the sales force - Using LinkedIn, you can quickly understand the quality of the sales force by looking into the background of the reps and leaders at different levels of the company. Are these “A” players? Do they have experience in startups, mid-size or big, bureaucratic, slow-moving companies? Doing research will give you a reasonable idea of the quality of the sales force. Your career potential will be directly related to the quality of the people around you and the ability of your leadership to train you and develop your skills. You need to question the quality of the leadership team, how they onboard, train and evolve their teams.

John, you’ve given some great advice here for sales professionals as they consider their next career opportunity. If you were to sum all of this up into one mantra, what would you say? 

I would sum it up by these four things - 1.  Do your homework on the company; 2.  Be honest with yourself;
3.  Don't be enamored by the title or other bright shiny items and, 4.  Only you can decide what is best for you. 


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