As is usual, I don't know. But, what follows is my opinion and the reasoning behind it:

Before I get to what I think is the right time to outsource your SaaS Startup's sales function, here are a few assumptions:

1) You do not have the need for a full time sales person just yet for the region you are exploring outsourcing. The region could be the first region that your startup sells to or the (n+1)th region.

2) You do not have a sales expert as one of the co-founders. People with pre-sales/ solutions consulting background don't count and can often be detrimental to a saas startup's sales prospects.

O.K., now that we have that out the way, here's my opinion: You should outsource the sales function at the first instant you get yourself a qualified lead.

How do you know if a lead is a qualified one: This varies for different solutions but the essence is that a qualified lead is one that will close for you or a competitor and you know you have an equal shot at win product-wise.

Who does the qualification: Ideally you should do that on your own. You know what the product's shortcomings are, the firm's shortcomings are..

Why outsource at the first chance? Why is pretty obvious, so let me try and argue against why not..

1) A lot of founders struggle (some actually enjoy it :)) with trial and error until a point where they figure out the process for selling their B2B SaaS product only to be surprised by something out of the blue with the next opportunity. And only once they've figured out a process that they outsource sales or hire a sales person.

Why reinvent the wheel? There are experts who've been there, done that.. not with the same product.. but you get the idea.. The lesser a salesperson talks about your product, the better are your chances at the sale anyway.. Nobody (except you) cares about the product (yeah, sorry).. Salespeople (who care about their reputation) and prospects care about what the product can help achieve/ avoid etc, as much as possible, without burning bridges internally.

2) Fear that if I outsource at the outset, how am I going to figure out how, you know, for when I bring it back in..

I'm sure there are people (Individuals can be held accountable and trusted with this more than companies) you can outsource to that will document your sales process for when you want to bring it back in. Process is overrated anyway (Recommend reading Ingredients and Formula for a winning Inside Sales Org). 

What not to do:

1) Outsource to save money. 

Outsource what can be done better than you can do yourself, but I think this holds true for any form of outsourcing.

2) Keep it outsourced since it is working.

Bring it back in as soon as you can keep a full time resource busy in-house.

What do you think of my opinion and when do you think is the right time? Do share your views below.. I look forward to reading..

About the Author: Raj Nadar is the founder of Inside Sales On Demand setup to handle outsourced inside sales closures for B2B SaaS Startups. His inside sales orgs have sold into Startups to USD 4.5 billion revenue firms in US, Canada, Spain, South Africa, Iceland, Brazil, UK and Mexico, Sweden, India, Australia, New Zealand, Norway, Finland, Austria, Germany, Ireland, Belgium, Netherlands with deal sizes ranging from USD 600 to 250k per year.

Current Projects: Inside Sales for Making Sense of Large Team Communications | Teamchat, Crowdsourced Software Testing | 99tests

Connect with me? Raj Nadar on Linkedin
                             Raj Nadar on Twitter

I am available on demand as your inside sales resource.

Want to launch your own Inside Sales org?