B2B SaaS – Creating a Sales Dept?

Hi everyone! I am an entrepreneur that has successfully met all of my initial goals. Now I need to take it to the next level but don't know how.

History

Back in 2002 I created a software app as a side project that performs a particular kind of data analysis for medium-to-large companies. It made some nice extra income on the side. In 2011 I left my full time job and decided to make an online version of the app. It released in 2012. Since there were so many companies who bought the old software from 2002-2012 the online tool took off pretty well. I currently have close to 50 paying client companies (~200 sites). All recurring revenue.

Now

The main challenge is sales and marketing. Because of my programming background and personality I am more of a sales engineer than a salesperson. I tend to make deals smaller than they could be instead of larger. I am likely undercharging by a lot. But how do you create a sales department from scratch when you aren't a salesperson?

I have budget but the risk is very high to simply hire a salesperson. If the first two people I hire don't work out that could burn through the expansion budget (at least until next year). My understanding is that the best way to get 2 good sales people is to hire 10 of them and see who works out. I can't afford that and I have little sales support structure in place. I have a pile of old customer contacts and can implement pretty much any tech solution quickly (CRM, VOIP, etc). But what is a good strategy for a small business?

Some more details

  • Customers are primarily North American medium to large companies.
  • Almost no travel is required. Since the software is online, the customers expect to do most everything online. I only take 1-2 business trips a year.
  • Company is entirely virtual. So work-from-home. Employees could live anywhere if they have good Internet and a quiet place to work.

Things I think I know

  • Salespeople are difficult to hire even with a good structure in place. Many companies spend as much effort marketing to salespeople as they do to customers.
  • Salespeople can be difficult to manage, especially in companies with poorly defined boundaries (battle of wills over compensation, responsibilities, protecting domain by sabotaging other salespeople, etc).
  • A good salesperson in the tech industry should be able to make 6 figures (salary + commissions) within 2 years.

Options

  • Hire a single salesperson – I expect that I would need to offer ~$50k salary plus 10% commission. If they matched last year's new sales (that required no sales effort) then total compensation would be over $75k. I would have enough budget for up to two failures. In my past experience this was not a good strategy because the first salesperson who was successful would carve out their domain and protect it making it much more difficult for a 2nd and 3rd salesperson to be successful.
  • Hire two salespeople – Same compensation. But I would only have enough budget for 1 failure. If both hires did not work out then I would have to wait a year for enough budget to try again. If they both work out then I would learn much more quickly about reasonable sales performance. Very likely to lose the lower performer after a while. But if first person works out then budget for a replacement would not be an issue.
  • Another solution I am not considering?

I appreciate any input you can offer!

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