Sell yourself the right job: Qualify opportunities for long-term career success

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Being a successful sales leaders starts in qualifying your career opportunities effectively

We all want to be successful sales leaders. But sometimes, that success is out of our hands. And the best way to avoid that is by asking the right questions during the interview process. 

I’m not talking about company culture of flexibility here, I mean getting to grips with the data, metrics, and details on how the sales target was set. If you join the company, what’s your target and what’s the rationale? 

The truth is, often when a startup raises funding, they need to build a sales team. To recruit a sales leader, they just take the on-target earnings and multiply it to get the target. But there’s no history or benchmark to base it on. So failure rates are really high since the number is a bit finger in the air with no real validation. It’s crucial, in my opinion, to get access to the right data and metrics and really immerse yourself in it before making the decision to join a business. 

I learnt this the hard way. Early in my career I was fired from my first VP of Sales role because I didn’t properly qualify the opportunity.

Treat the hiring process like a sales process

As sales leaders, we’re skilled at qualifying sales opportunities. We do it every single day. 

But too often, I see sales leaders fail to do it as effectively in the recruitment process. And I’ve definitely been guilty of this myself in the past.

You interview for a role, the compensation seems fair, and you accept the offer. But in reality, you may be stepping into a position set up for failure, either due to challenges with the role itself or broader company issues. 

That’s why it’s essential that you treat the interview as an opportunity to qualify if the role is the right fit. Is it selling to the right target customers at the right deal size for you?

This will minimize the risk to your career trajectory. 

Qualifying at job offer

Congratulations, you’ve secured a verbal offer. But is it the perfect next step in your sales career? 

For many of the companies we work with, this would have already been covered within the interview process. But if it’s not, now’s the time. I recommend scheduling a separate meeting focused solely on closely examining the proposed terms and figures. 

Ask the founder to come prepared to that meeting with detailed financial data and projections. If they are not fully transparent or fail to provide the requested information, consider it a red flag.

You should spend the time asking what you need to qualify that this is the right role for you. Otherwise, the founder will put pressure on you to hit aggressive targets, the VC will pressure the founder, and you as sales leader will likely be the first to get fired when targets are missed. It’s a constant cycle that can be avoided by thoroughly qualifying job opportunities.

It’s important to thoroughly interview the founder to understand where current revenue is originating, what obstacles they’ve faced, where they’ve won deals, and where they’ve lost deals. This is also an opportunity to potentially meet with the VC investors as well if appropriate. You’ll be reporting to these investors, so meeting with them to grasp their perspective on where the valuation number comes from and how realistic it is given the timeline to hit growth milestones is key. 

Why pushing back propels you forward

There’s always a line, but pushing back to thoroughly qualify an opportunity is absolutely fine. Founders invest heavily in the hiring process, and candidates shouldn’t hesitate to do the same. Long hours, ambitious targets, and potential equity are key factors that demand a detailed qualification process.

From what I see, if a strong sales leader says ‘thank you for the offer, I now need to qualify if this is right for me’, founders are more often than not reassured by this. They would rather someone spend an hour now than spend six months in a role that isn’t the right fit,

Miss hiring at this level is a massive opportunity cost for both parties. 

A confident “yes” now saves everyone from a painful “no” later. Plus, deeper understanding leads to fewer mismatched expectations and a smoother onboarding process. 

Investing 60 minutes in quality qualification benefits everyone involved. It leads to better decisions, reduces wasted time, mitigates against opportunity cost, and creates a strong understanding between the company to ensure you hit the ground running.  

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