Flip the Switch: When Customer Success Should Feed your Sales Team

I had dinner with a bunch of SaaS peeps earlier this week and the conversation at the table provided inspiration for this post.

The conversation centered around the challenges of fitting a SaaS offering with a freemium and/or free-trial model into the traditional Marketing - Sales - Customer Success work flow.  

And by traditional Marketing - Sales - Customer Success work flow, I mean the normal “order of operations” for (inbound) deal flow, conversion and activation. You know…it looks something like this:


Marketing (more specifically, Lead Gen) drives in a bunch of leads that get delivered directly to the sales team. Depending on the structure of the sales team (are you using SDRs, etc), the sales team goes to work trying to convert as many of them as possible to actual, paying customers. Once a deal is closed & a contract signed, the newly minted customer is ‘tossed over the fence’ to the Customer Success team who runs onboarding and ongoing support. 

Make total sense - in the context of a more traditional software business. And it more-or-less makes sense in the context of an ‘enterprise’ SaaS offering.

But what about a business that has a freemium offering, or a free trial period, that drives a ton of signups at the top of the funnel. I talked to someone last night who ran sales for a SaaS app that was driving 600-1,000 signups PER DAY to their freemium offering. That’s a huge monthly flow into top-of-the-funnel. But the question was - what are these people that are signing up for the freemium offer or trial?

Are they prospects?

Are they leads?

Are they users?

Are they customers?

Well…yes. They are all these things. 

But if they are all these things, how do we deal with them in the context of the traditional “order of operations”? I would argue that you don’t. I would argue that this model demands a bit of a rewrite to the traditional flow.

Why a rewrite?

This freemium/trial flow brings poses two main challenges to the normal workflow:

First of all, a freemium model generates a ton of volume (if it’s working). A ton of ‘leads’ coming into the top of the funnel. Way more than a cost-effective sales team can handle.

Secondly, these top-of-the-funnel leads are actually users. The business has made the decision to let prospects try the product for free before making a purchase decision. So the traditional ‘sales qualifying’ process (as sales people know it) isn’t really applicable. 

What do you do?

Flip the Switch - Customer Success moves up 

The good news is that a large amount of freemium/trial traffic is mostly a good problem to have. But it does demand some significant changes IMHO. My suggestion is to flip the normal ‘order of operations’ and make it look more like this:

marketing_customer success_sales

In my opinion, you have to treat all of these signups as users/customers. This means that the ‘qualification’ of whether or not these new users will become paid conversions should happen by the Customer Success team. Not the sales team.

Why? Because the qualification of these users will be based on more than what sales people are used to assessing. They should be qualified based on normal qualification measures (size of opportunity, use case, industry, etc)…as well as ACTUAL USER DATA.

This is why your Customer Success team will be much better suited to handle this qualification. Not to mention that they will be much better suited to actually impact it. The usage piece, I mean.

They will have the skills and mentality to understand what users are prime for conversion and/or growth. They should be able to shape a model based on user behavior that will really help determine those free users most likely to convert. 


Few things need to happen to make this work:

1. Sales, Marketing & Customer Success all need to have a good idea of what a sales qualified lead looks like from a more traditional perspective. You will likely determine that the sales team is only going to get involved with opportunities that have the potential to be a certain size (expressed in revenue). Things like:

  • Size of company

  • Industry

  • Use case

  • Title of user

  • Etc.

With that model in place, every signup (as best you can) should be qualified on these criteria. Of course you won’t be able to determine this for every signup (especially if you are doing big numbers), but you should do the best you can.

2. Next, Customer success needs to have a model of behavior that can be used to predict conversion. If you have historic data on free customers that converted and their user behavior prior to conversion, you can use a tool like Totango or Gainsight to see if any patterns emerge. If you are early stage and don’t have that data, you are going to have to make some assumptions (ie - users who do these 3 things are more likely to convert). Don’t wait until you have ‘enough data’ to put this process in place. Do the best you can with what you’ve got and get to work. 

3. Then you should put together an execution plan that will help you to optimize conversions and revenue. It could look something like this:


And, by the way, this should go without saying, but it probably doesn’t in many companies. With large amounts of freemium/trial signups, it is essential that your Customer Success team works very closely with your product team to absolutely nail the early experience (call it The First 30-Day Experience) of your users. I’m not just talking about in-app onboarding (although that is important), I’m talking about the first 30-day experience. The goal of your freemium plan should be to drive more signups than any one team can manage - so much of this needs to come right from the product.

If you have a Product team who doesn’t like to work closely with the Customer team (because who are these non-designers/engineers telling me how to build MY product?!?), then I suggest you abandon your freemium plans. Your Customer team absolutely must be a part of designing this experience. 

Couple big take-aways

  1. It’s important to recognize that the SaaS model and the Post-Sale World challenges every piece of the traditional software business operations model. So, don’t be afraid to break ‘normal’ molds and processes to try something that works better for your business.

  2. Customer Success, as a function, continues to grow in importance in the SaaS world. It is quickly becoming the ‘glue’ that holds SaaS businesses together. Great to see.

Hope this line of thinking helps. Love your feedback…