Part 3: Freemium Trials (and the Death of the Top-Down Model)

“Shamus, thanks again for your time yesterday. After discussing with the team …”


Do you know how this story ends?


“… we’re not moving forward.”


If they went with a competitor, you curse them out (cue the Corporate Bro meme video). But, if they were genuinely interested but can’t commit to a next step because of a budget freeze (80 percent of companies are in this boat), should you automatically DQ them and set a reminder to check back in 6-12 months? 


In Part 3, we’re going to talk about how to set up a freemium trial (yes, I made that term up) and how to get prospects to auto convert into closed/won opportunities.

Disclaimer: This model is designed for SaaS products that require little or no professional services or installation.


Dan McMurtrie - Shamus Miracle Grow Pipeline Series

Dan has a point. 

SaaS companies dream of rattling off buzzwords like this when pitching VC’s.

“We’re sticky and have solid traction.” Let me guess: You’re moving upmarket now?

Oh, by the way, “getting sticky” means the nature of your customers continuing to use your products or services. They “stick” with you.

But, how can you make this happen if they aren’t willing to pay? 


A Freemium Trial. 

Freemium = free and premium.

Trial = contains all of the features of a paid subscription, but only for a limited time.


Remember, this series is about quick hacks to help you create pipeline with minimal resources. Re-creating your top-down model into a bottoms-up strategy is a lot of work–and likely above your pay grade–so let’s save that for a different day.

You’re going to offer a unique premium subscription to users for a limited period of time. At the end of the trial, it’s going to roll over into a paid subscription.

Turns out, others are already doing this:

Jeremy Donovan - Hey Salespeople - Miracle Grow Shamus content series

Yes, I “Celebrated” that post.

In fact, trials are now the new norm. Check out The SaaS Buying Experience: Mapping How Businesses Buy Software to get a deeper understanding of what’s behind the curtain when it comes to buying SaaS nowadays.

Alright, software as a service gang. Here we go.


How to Set Up Your Freemium Trial

Stop trying to convince C-suites to demo your product. 

All of your trials should be designed for your product’s end-users or admin users.

Adopters and users will be your champions (luckily, they are now a big part of the buying process). You can still contact C-suites, but take the pressure off them to make any decisions (for now).

Technical features to think about:

  • Only enable your top 1-3 features that do not require any professional services or setup. Yes, I know your widget has a cool artificial intelligence feature for predicting your next customer, but that’s too much right now.
      • For example, as part of our Enterprise solution at Crunchbase, we offer a Salesforce integration. While this is not the only feature of our Enterprise package, it’s the one clients tend to use right away. So, that’s what we offer in our Sandbox environment. Yes, there’s more functionality to it, but we need to lead with the No. 1 feature to start with. Baby steps.
  • Later on in the trial, you can open up access to other features or tease out the functionality in the paid version.

But first, let’s see which freemium trial option is best for you. There are two different ways you can set this up.


Option A: Individual logins (designed for end users)

  • Pros:
      • End users have the ability to customize their experience
      • You can get buy-in from the entire team right away
  • Cons:
      • You have to manage multiple users, and gathering feedback can be difficult.
      • End users may not test it out and become a bottleneck; “Well, Timmy never had a chance to test it out.” I emailed Timmy 10 times and he never responded! UGH

Examples: Crunchbase Pro, Gong, Outreach


Option B: Sandbox environment (designed for admins) 

  • Pros:
      • Likely only 1-2 people, one login environment ( 
      • Easier to manage and gather feedback from
  • Cons:
      • Admin is likely the only decision-maker, there’s no buy-in from individuals who would be the end users.
      • Bottleneck: “I still need my team to try this now.”

Example: Crunchbase app on the Salesforce App exchange


Bonus tips:

  • If possible, enable your chatbot within the sandbox environment. Field questions while they’re setting it up.
  • Send prerecorded videos of setup (in addition to your 30-page “easy to install” PDF 🙂 .) Keep it under 2 minutes. 
  • Instead of emailing them once a week, send a Google Survey to gather results with a 1-10 scale and only one open-response question at the end. Make it SUPER easy for them to relay feedback.


Compliance/InfoSec/Data Security

Ah, the moguls of your downhill slalom race to a closed/won. Bumpy terrain, but go slow and you’ll make it down in one piece.

  • Ideal: Setup a sandbox environment that is 100 percent hosted off a web browser that does not integrate into your clients’ systems. Load dummy data in there to start. Make sure it’s GDPR, CCPA, etc. compliant. Do anything you can to avoid having to go through compliance/procurement (I imagine no one from procurement is reading this– if so, no offense 🙂 ). Compliance teams are going to do their job and identify any potential risks and how to address them. Even if you have a champion, they are likely going to be asked: “Is this absolutely necessary right now?” Don’t put them in that spot.
  • Fallback: If this isn’t an option and you need to go through compliance, be very upfront about it in the beginning. Send them your proof of value, timeline slide, etc. Don’t try to trick them into thinking it’s an easy process if it’s not. 


Bonus: Get ahead of your objections. Send something like “on average, it’s usually a two-week process to get setup with compliance. Most teams raise questions around X,Y,Z. Here’s our stance on all three, in case your team wants to investigate further.”


Use your existing Proof of Concept contract as a baseline. We’ll make a few tweaks so you don’t have to recreate the wheel. If you don’t have a POC or trial contract setup, you should probably create one. Here’s an example.

What are the top three objections you usually get from prospects on your contracts? Is it truly a dealbreaker? Now is not the time to be a stickler about your business terms. Make sections mutually agreeable if you can. Don’t ask for marketing rights (just yet). Be flexible. (Disclaimer: even though I watch a ton of Law & Order, I’m not a lawyer and you should not take this as legal advice. Please consult your legal counsel before making any changes to your contracts.)

    • Move your contracts into an online, click-through term. You can use a tool like Wufoo to do this.
    • Change your Times New Roman ALL CAPITALIZATION contract (which screams “redline me”) to a softer font like Arial or Calibri. Include a cute watermark of your logo. Make it less intimidating and more business-friendly.
    • Put in a defined number of seats or outline the sandbox login (go off the average number of users you usually grant to clients) so they don’t need to make changes to the contract. Only include the legal terms that are directly related to the trial experience (for now). Try to cut out the stuff that doesn’t matter until they become a paid client.

Bonus: If you want to charge them for this trial, charge them a small amount like $500. It will help you get approved in their systems and set up with procurement so when they are ready to upgrade, the legal paperwork will be done. 

    • Conversions: Under your Fees section, include a clause that states they will auto convert at a certain date. Check the schedule below to see how long your trial should be.
    • Fee section: AE’s should be sending each prospect their own individual pricing chart depending on their use case (usage, number of users, etc.) include a clause like “as set forth in the Schedule provided to you by your Account Executive.” (Another legal disclaimer that I’m not a lawyer. Please don’t copy and paste this into your contracts.) 
    • Amendment: Once prospects are ready to move forward with a full license, they should only be signing an amendment and not a new contract. You can add an Exhibit A for any funky terms you both need to agree to that isn’t boilerplate. This gives you time to negotiate those terms in parallel to the free trial.

Important Note: Make sure you mark every trial in your CRM as a “COVID-19 trial.” If needed, you can renegotiate any terms upon renewal.

The goal of this is to create as little friction as possible for your end users to start using your product. 

Remember, you want to be a sticky vendor. None of this will happen if you can’t get them set up on a trial to test it out.


Freemium FAQ

Q: How long should these trials be?

1 month (industry standard):

      • Generally, this is for sub-$10,000 contract value
      • Semi-transactional sale
      • Email check ins and demo videos
      • No extensions

3 months:

      • $10,000 to $30,000-plus deals
      • Usually an onboarding call, one or two check-in calls, more hand-holding.
      • ROI is not immediate; run stress tests and sample scenarios.
      • Give them the option to extend (written notice) if needed, but put in a hard cap for maximum trial (6 months).

6-plus months:

      • You better have a high six-figure (or seven-figure) deal on the line. That’s a lot of time and resources to dedicate to a trial. 


Q: Who should manage these trials?

Account executives.

Offer a Spiff or bonus for customer success managers if they are not normally part of the presale process but need to get involved. 

Remember those great anonymous quotes you received from your recently signed clients from Part 1? Start sprinkling those into your check in emails/calls. Bridge the gap between what they are demo’ing and the long-term goal. You don’t need to show all of this ROI on day one, but show them the path they are heading down and why they are heading in the right direction.

Have informal check-ins and stop the formal Quarterly Business Reviews. They are not a paying customer (yet).


Q: Who’s eligible for this?

Don’t put this on your website unless you plan to shift your business to a freemium offering. This should be offered on a case-by-case basis. It’s not a free for forever model, it’s a freemium trial. You still need to manage these.

Past: Any closed/lost due to timing or budget from the last 60 days.

Present: Any leads that you’re about to disqualify due to price/timing, but meet every other BANT criteria. Let them know they qualify for a special trial. 


Q: How do we convert these into closed/won?

You should have clear conversion metrics in place before getting them set up. That being said, prospects are going to look to you for guidance (no one likes being handed a blank canvas and put on the spot to paint the Mona Lisa). 

Before asking your prospects what their conversion metrics are, pull the top three reasons people buy your product(s). You should proactively offer these as a conversion metric to your prospect and let them adjust, if needed.

No fluff metrics like “This can be a value add to our organization.


Q: Should this be counted as “open” pipeline?

Depends. There’s no silver bullet answer. Sales leadership should make the decision if this should be counted as pipeline or not. 

At a minimum, tag all of these opportunities so you can track them.


Q: What if they don’t convert?

You should have detailed feedback on why they didn’t covert. Create a Slack channel and drop in all of the feedback from surveys, emails, phone calls, etc.

Escalate what you learn to your product team, because it’s 10 times better than any user research initiative.


Tips for Success

Managers: Be flexible with your reps. Maybe you wouldn’t normally approve a free 6-month POC, but trust your reps and give them the freedom to run the show. Encourage them to act like a detective and investigate and gather as much evidence as possible (Who? What? When? Where? How?). This feedback may help save your job if you don’t hit your ARR goals.

IC’s: You’re no longer a one-trick pony. Learn the full sales cycle. Take a “relationship first” approach for these trials and put in the extra work to collective feedback. No harassing or trying to come down on prospects about converting. Yes, maybe they did hit your conversion metrics, but none of this:


A reminder: These prospects don’t owe you shit. Be grateful they’re willing to champion your product and give it a whirl. It’s the best you can ask for right now, as you don’t know what else might be going on behind the scenes. Build the relationship, it will pay off over time. 


Freemium Model Key Takeaways

    • Shift some of the paid features into the freemium trial, but not all of them. Make it as seamless as possible to get them set up.
    • They won’t see the full incremental value during the trial. It’s your job to get them on a path to show them how they can unlock this potential with the paid version. 
    • Train AE’s to become full-cycle reps. 
    • Gather as much feedback as possible. This feedback may help shape your H2 product roadmap. Or, save your job to show why prospects aren’t buying.
    • Trials will help avoid churn.


Do you know who sells the most at the farmers market? 

The humus stand that offers the most generous samples.


– Shamus (the sales guy)



Find this article helpful? Check out the rest of this series!

  • Originally published May 12, 2020