7 Reasons Why That Software Sales Job Might Not Be For You

By October 21, 2015Software Sales
7 Reasons Why The Software Sales Job Might Not Be For You

Things that you might not have considered when going for a software sales job

During my 17 years in IT Sales Recruitment the most critical conversations I’ve had with candidates have always been around which job offer they should accept. This could be an internal move with the same employer or the choice of two or more offers to go to pastures new.

Those raising their head above the parapet to explore Tech Sales opportunities at the moment could be overwhelmed by the sheer volume of sales jobs available in what is certainly the most candidate driven market I can remember (and I can remember when we faxed CVs)!

The more ‘seasoned’ IT sales professionals I’ve had the pleasure of working with over the years usually know what’s involved in making the right career choice and will take their time when it comes to weighing up the risk vs rewards.

In most cases they already have a good idea of what their next move looks like and have let me know 3, 6 or even 9 months before we eventually talk turkey.

“Weird to think it could take as long to grow a baby as place a passive candidate.”

Or maybe not so weird; this is a person’s career we are talking about and it is a sad but true observation that many of us will spend more time during a typical working week with our colleagues than our children.

It still surprises me when IT sales folk take the transactional approach;

  •  only talking to head hunters when they need a new job
  •  …..and fixating on a basic salary.

When it does come to the crunch and you have made the mental decision to move here are 7 points to help you qualify an IT Sales opportunity before you make your career choice:

1. Show me the money!

Would you rather earn £150k for doing a great job or earn £90k for showing up? OK don’t answer that question but do consider how you are going to earn your OTE rather than fixating on the basic salary.

To do this you need the underlying data which will validate if your OTE is achievable. What’s the revenue target, average deal size, typical length of sales cycle, commission plan? If there is a ramp up period then is there a guarantee? Are there pre-IPO shares or RSUs and, if so, what’s the strike price and vesting period?

2. Joining the A team?

The OTE may seem achievable but if there is already one or more Sales Execs doing a similar role at the company then their performance could be further proof. When did they join and how are they doing? Don’t just buy into the boss, ask to meet the team.

3. Leadership

Meeting your first line software sales manager should always be part of the process. A lot does rely on chemistry and gut feel, however take the opportunity to make the interview a two way street with questions about their management style or how their team would describe them. A company’s success can usually be attributed to the leadership team.

Have a look at the bios of the CEO and EVP/SVP Sales, you can do this on their website or a simple Google or LinkedIn search. What’s their track record like?

In a large corporate it’s often impractical to request a conversation with the CEO but my advice would be to go as high as you can to get the big picture or company ‘vision’. It demonstrates you are a candidate that thinks about the bigger picture, which in itself will stand you in good sense.

4. Do they want you to sell ice to Eskimos?

What will you be selling and who will you be selling it to? There is no right or wrong answers here other than to recognise your own ability and weigh up the risk vs rewards.

Are you a consultative value based seller or do you thrive on high volume, fast-paced transactional sales? Do you have the customer network and ability to take a disruptive new offering to market or would you excel with a broad solution suite across a defined set of accounts? High risk scenarios would be selling a product which isn’t ready yet or selling something new to a vertical market or type of decision maker that you have no experience of dealing with. Moving from a technical sale to a business sale or vice-versa is perfectly achievable but only advisable with a proven solution that has reached critical mass.

Likewise selling a product which is in danger of becoming ‘old hat’ or too commoditized would be a bad medium to long term move…anyone want to buy that fax machine?

5. Career progression or slippery pole?

Not everybody has leadership aspirations, however our natural setting as software sales people is to want to see some type of career progression. Ask what are the different career path options? If you get an answer with clearly defined time scales and some examples of others who have followed this path then you are on to a winner. If not then it might be time to think again

6. Culture

Remember you could be spending more time at work than with your family so it helps if you fit in. Asking about their company culture is standard nowadays. There are ways to ask about work/life balance without appearing too needy such as; “is everyone expected in the office when they are not with customers?” Or, “how often do you like to get the team together”?

As a sales person asking about how the company engages with customers on a deal can be important too.

Is there a high degree of autonomy or is it more of a team matrix environment? Glassdoor.com can provide some good insight on company culture but be careful that you are not put off by someone else’s sour grapes.

7. Worst case scenario

The final thing to consider is how will this move look on my CV if it all goes belly up? My advice if or when this does happen is to make the call early. I see too many CVs with 11 month stints where people have stuck it out only to have the decision made for them before the year is up.

With regard to the company, a big brand name does help because people will assume that XYZ Corp does not hire idiots and you have just decided it’s not for you. However it can also be excusable to have a short stint at a start-up that didn’t make it for reasons beyond your control e.g. no series B funding, product bombed etc.

The key is to not make the same mistake twice in a row. If your start-up gamble didn’t pay off, you need some big brand stability on the CV or if you were stifled in the corporate environment, why not go for the smaller software vendor.
Not all career changes are planned but conceiving your next ideal move should be.



P.S. Need help deciding on your next software sales job move. Call us here at Go-Teem for a confidential conversation on +441457 865 034

Jim Kinread

Jim Kinread

Jim Kinread is the M.D of Teem, a leading organisation in the specialist IT sales recruitment arena. Jim has 17 years experience in the sector and leads his team of senior search consultants to help both software companies to achieve their global growth strategy and professionals to achieve their career goals.
Jim Kinread

About Jim Kinread

Jim Kinread is the M.D of Teem, a leading organisation in the specialist IT sales recruitment arena. Jim has 17 years experience in the sector and leads his team of senior search consultants to help both software companies to achieve their global growth strategy and professionals to achieve their career goals.