Free Trials: Do they see the benefit?

“Do they see the benefit?” is what my business coach always asks me when we’re going down the list of where prospects are in the sales process. It’s all about structuring a sales process that helps the customer see that the benefits far outweigh the costs. Pricing less than customer value is a good thing! My customers are nonprofit job training programs and public schools, so I have an especially uphill battle.

We sell an automated mock interviewing tool called Talk Hiring to career readiness programs. When we were in our free pilot stage, we asked how prospective customers wanted to evaluate Talk Hiring, and three aspects kept popping up.

Once I figured out that this is often how Talk Hiring was being evaluated, it made it really clear how we should structure our free trials. We need a free trial process that has the following characteristics:

What we settled on


To give a little more context, I felt like it would be helpful to give you some background on how I structure my sales process.

  1. Initial contact. About 40% of my prospects come from referrals (thanks Apollo —, another 40% come from cold emails, and the other 20% come from events, social media, and other smaller sources.
  2. Try to start a free trial as quickly as possible. Some programs want to talk with me first, others don’t want to. The only step required from them to start a free trial is to e-sign a free trial agreement (thanks Contractbook —
  3. Once the agreement is signed, do an onboarding meeting to outline best practices for rollout, walk through the tool, talk through the goals of the trial, etc. Write up the notes in a shared Google Doc that can be referenced throughout the trial.
  4. Track usage during the trial (thanks Metabase —, and give nudges along the way.
  5. Once the trial is over, shut off their account and see if they want to purchase. The details of what happens in step five is definitely worthy of another blog post!
  6. If they want to purchase, send over a paid contract agreement via Contractbook and an invoice via Stripe.