Who to hire for my start-up? Gray hair or jeans

By Mark LaRosa on December 18th, 2008

In speaking to so many start-up entrepreneurs, I get the same question over and over again:  what type of sales person should I be hiring?

This is a very interesting dilemma for start-up companies as they begin to build their sales plan, and as they try their best to get to profitability.  You have a serious choice.  Do you hire someone who is experienced in sales or do you hire a junior, super-energetic salesperson.

Of course… you want both!  And – often you can find that person in the experienced salesperson.  But what we are really talking about here is not energy level – its COST.   When I say experienced sales person, its just a euphemism for EXPENSIVE sales person.  A proven sales person, someone who has closed lots of very large accounts, has earned the right to have more base salary – especially at a start-up where there is so much risk – knowing this person can go to a more established company and make a lot of money.

This means that the tendency of a start-up is to find a less expensive sales person who they think can pull it off.  And many will be able to.  After all, I started my career as an entrepreneur and I was selling my software.  I had no experience in sales.  I was a programmer.  Yet, I figured it out and was able to close some very large accounts.  However, I lost a lot of accounts along the way, and also had some experienced sales people involved with the company that gave me gobs of great advice along the way.   You are going to be paying for on-the-job experience with a more junior salesperson, so how best to mitigate this and get the sales you need.

The options, as I see them, for a start-up are:

• If you have a CEO or other management type who has hard-core sales experience, then hire the junior sales person and save yourself some money.  And I mean real quota carrying sales experience – not just an ability to sell.  That manager can guide and train the salesperson, help them avoid the obstacles, power through objections, and quickly get up to speed on how to close deals.  Without this, you are likely to get lots of activity – but not lots of money.  A new salesperson typically needs their energies channeled – especially near the end of a sale because that is when it gets hard – and the path of least resistance will take their activities to new prospects where all conversations are lovey-dovey.  Managing activities and the pipeline are going to take a portion of the CEO or other management person’s time, but having management oversight will be critical – or lots of cycles will be burned without sales.

• If you don’t have a management team member that has done hard-core sales, then hire yourself a true VP of Sales.  If he/she is all you can afford, then that VP of Sales can carry a quota until he/she makes enough sales to justify another team member.  While this person will cost you more money than a junior salesperson, you will actually be spending money wisely.  This person should more than make up for their expense.  They should be able to set in place the right sales structure, and get some anchor accounts will will cement your sales strategy moving forward.

• Third option:  Hire the young salesperson, and then have an external advisor that is a sales guru (board member, outsourced sales management firm, partner firm) work with the sales person and manage their activities.  Get that person involved early on and the experienced person can shape the strategy and guide the junior sales person.  This junior salesperson, if conditioned to rely on the advice of the expert, can be guided by the senior salesperson in terms of what steps to take next, when to call again, how to handle certain objections, which accounts to prioritize, how to get past a gatekeeper, how to break a log-jam, when to negotiate on price, when to know you are getting the brush-off, etc.  He/she can also be the grey hair to call in when they call in their senior management for either a webinar or a face-to-face.  If you have someone committed to the success of your company, this can be a great option for a start-up.  If you have angel funding, you may learn that some of your angel investors can be, and would be willing to be, this person to you.  (Disclaimer:  I try to keep this blog pure sales advice – but I feel the need to disclose that outsourced salea management and advice is what QuotaCrush is about)

Its certainly a tough decision for a start-up, and the costs surrounding sales (not just salary but travel, entertainment, etc) are one of those difficult pills to swallow.  But like in anything else, its not wise to go cheap on the sales side, unless you can back-up the junior sales people with some real sales management.  I honestly believe that companies with great sales typically have solid sales management and structure behind it.