Should vendors offer free trials or pilots to win enterprise deals?

AJ Tennant · Oct 23, 2024

Vendors should be very willing to do small land deals with mega customers, but only with commercial and executive alignment on explicit success criteria that unlock the seven-figure contract

Time-bound, specific success criteria tied directly to dollars are what convert a small paid POC into a seven-figure contract

Scope: requires executive-level alignment on the criteria

16:43 20Sales: Biggest Lessons Scaling Slack from $6M to $1BN in ARR | How to Build a Customer Success Machine and Where Most Go Wrong | The Framework to Hire All Sales Reps: Take-Home Assignments, Hiring Panels and more with AJ Tennant @ Glean

Patrick Forquer · May 11, 2026

Pilots run on test or publicly available documents to dodge infosec review are a recipe for low engagement and generally fail; qualification should require give-get — agreed use cases, stakeholders, success criteria and metrics up front

Getting the buyer through the painful front-end work is itself the signal that there's a real deal there

Scope: infosec processes at big firms and Deloitte are nontrivial

28:24 20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

Rich Liu · Jun 7, 2023

Building a freemium-style trial into an enterprise contract — free for six months with hands-on implementation, pay only if it's amazing — is a highly effective way to overcome buyer skepticism and land expansion

People.ai used this on him at TripActions during the pandemic; despite his skepticism and an existing analytics stack, they stood it up successfully and he signed for the broader platform

Scope: not the only way to do it; cited as one example, from a while back

47:48 20Sales: PLG and Early Adopter Sales are Gone, How to do Sales Forecasting in 2023, Why You Cannot Do PLG and Enterprise from Day 1 at the Same Time and Which is Easier to Start, How to Onboard, Manage and Scale Reps with Rich Liu, CRO @ Everlaw

Chad Peets · Jan 9, 2026

Enterprise buyers now want to buy proven outcomes, which means letting them fully integrate and trial the product in their own workflows before purchase — something not seen before

Buyers want to know in fact that the solution will deliver the outcome, so the sales engineer role is changing and forward deployed engineers are a real need

24:27 20Sales: Why the Best Sales People are F**** in the Head | Why Remote Work is BS | Why Europe is a Nightmare for Recruiting Sales Teams | How to Build a Sales Machine | What Everyone Gets Wrong Today in Sales with Chad Peets

Patrick Forquer · May 11, 2026

Giving the product away for free is counterproductive because customers who pay nothing won't devote the resources and attention needed to adopt it

The vendor can have the best team, but transformation fails unless customers lean in and want to change — and price is what makes them lean in

Scope: Legora still tries to be flexible and easy to work with

25:12 20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

Harry Stebbings · May 11, 2026

People commit to what they pay for, as shown by a behavioral economics study where free park yoga classes had 52% attendance versus 92% when priced at $35

A behavioural study of park yoga classes showed 52% attendance when free versus 92% when charged $35

25:46 20VC: Inside Legora: $100M ARR in 18 Months | Jude Law Generated $50M in Sales Pipeline: The Economics Broken Down | Competing Against Harvey, the 800 Pound Gorilla | Why Legora is Undervalued at $5.5BN with Patrick Forquer, CRO @ Legora

Ishan Mukherjee · Apr 4, 2025

Startups competing with incumbents should keep the product open and ungated even when it's embarrassing, rather than gating it behind demos and implementation

Incumbent enterprise software is gated by demos and implementation with three-to-nine-month time to value; an open product reduces sales friction, and if you're a shipping machine you can ship your way out of any holes since you're not hiding anything

13:12 Ungated open product even when embarrassing

Ishan Mukherjee · Apr 4, 2025

Enterprises will buy beta software if you de-risk it with a 30-day paid evaluation that lets them downgrade to freemium if ROI isn't proven

Competing on time to value; the guarantee removes the risk of buying unproven software

56:07 Paid evaluation with downgrade guarantee

Kevin Egan · Jul 12, 2023

Salesforce doesn't get enough credit for being one of the original product-led growth companies.

It was among the first to offer prospects a free 30-day trial, and its sales team used the trial to configure the service around the customer's business problems, which drove very high conversion rates.

4:11 Trial plus sales assisted configuration converts

Raaz Herzberg · Dec 12, 2025

You can only win by running a generous, unpressured proof of value — if the customer sees value you win, and if they don't, the failure conversation is the most valuable feedback you can get

Enterprise relationships are long-term partnerships, so exposing gaps is worth more than forcing a close on schedule

39:02 Generous unpressured pov because a failed one yields the best feedback