Are You Hiring a Sales Rep or Head of Sales?

Are You Hiring a Sales Rep or Head of Sales?

One of the first “big hires” at many startups is, the “Head of Sales” or “VP of Sales.” It is also the hire, that many people seem to get wrong.

There are a number of common mistakes that I see made, when people are hiring for this role. We will go through those mistakes in this post.


Hiring a Sales Rep or VP of Sales

The first and most common mistake, that we see being made is confusion between a Sales Rep / Closer /VP of Sales.

When startups want to transition out of “founder lead sales” and develop a more mature sales process, we often see the first sales hire being made.

It is not uncommon for founders, to want someone who can recommend the right tools (for their current position), build the process, write the scripts,  send the emails, make the calls and create the sales material.

There is nothing wrong with that expectation. Its entirely necessary, within a startup. What you need to be aware of is, that your typical SDR, Closer or VP of Sales, will not be able to do all of those things.

The VP of Sales, is often the worst person to employ at this point. Because anyone with experience in that role, will have spent large amounts of time supporting a sales team, hiring, training, reporting and interacting with the wider business.

These are not skills that are critical at “early stage” companies.

You need someone who is capable of building the basic sales process. But most importantly, can do the daily work required of sales teams.

Do not fall into the trap of hiring a VP of Sales, then becoming dissapointed when they do not deliver on what you expected. That is not and never was, their speciality.


Great Experience – Wrong Company

The second mistake that we see being made is, the hiring of people with great experience, at the wrong places. What does that mean?

It means that you are hiring people to move your business from its current position to a more desirable position. That is a process that will happen continually.

The mistake that people make here is, they hire people that have a great resume or great experience, working in fantastic companies. But that doesn’t mean they have ever taken a company in your position, to the desired position.

So whilst they can look great on paper with great experience, it might be at the wrong company.

When hiring someone, look for people with experience transitioning from the position you are in, to where you want to be. Not just experience in the role.


There Might Not be a Right Time

When it comes to hiring VP’s specifically, there might not ever be a right time. Thats because you never know when good people will be available.

There is a small caveat to this rule, which is – You shouldn’t be looking to hire any VP, until you have achieved at least $1 million in revenue.

Once that milestone has been passed, sometimes you just have to take the right VP, at the wrong time. The good people are in high demand and they may become available at a time that isn’t perfect for you.

Most of the time, its better to take them, than pass up on the opportunity and hope they are available when you really need them.

So long as the financials work, you are going to build the best team this way.

Yes its true, from time to time it might mean changing your strategy slightly. But the long term benefits are worth it.



headshot of Dan Wheatley, Straight Talk Consulting founder

By Dan Wheatley, Co-Founder

CEO/Co-Founder of Straight Talk Consulting, a business consultancy that gets our hands dirty. We work with organisations to achieve product market fit before transitioning into scalable and repeatable growth