PLG: How to Turn A Free Sign-Up Into An Enterprise Logo

Another busy week in ‘the city that never sleeps’.

Beyond meeting founders and LPs all day, I’m slowly eating my way through New York City.

I’ll take all the Big Apple food recommendations that you have!

Anyway, let’s get into it.

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Turning a free sign-up into an enterprise logo involves a multi-step process that requires careful planning, design, and execution. 

Hubspot recently released a blog on how to effectively optimize the freemium conversion rate; see link/visual below:

5 key steps in the process:

1. Set the right product limitations for your free account.

To improve freemium conversion rates, it’s essential to set appropriate product limitations for free accounts. Offering too many features on the free plan can reduce the incentive for users to upgrade, so monitoring data usage and adjusting limitations can help create a value gap that encourages users to upgrade.

2. Include a full-feature free trial.

You can maximize user engagement by offering both a full-featured free trial and a limited free-forever plan. This combined approach helps users experience the full functionality initially and, if they don’t upgrade, the transition to the free plan with limited features can highlight the value of the paid service, encouraging them to upgrade.

3. Focus on customer success.

In freemium models, it’s crucial for free users to swiftly recognize the product’s value upon sign-up, and the key to achieving this is by prioritizing customer success.The most important thing is to always ensure that users are getting value out of your product.

4. Remind users to upgrade at every turn.

When encouraging users to upgrade, it’s essential to be explicit about their limited plan and offer them the option to switch to a paid version with fewer restrictions, as subtlety may not effectively prompt action.

5. Take a more hands-on approach to inside sales.

Establishing an inside sales team can enhance freemium conversion rates for enterprise-level B2B products by focusing on identifying and directly engaging high-priority leads.

You can read the full HubSpot blog here , encapsulating the entire scope on how to effectively take value from the freemium model.


Freemium to premium is one thing but how do we turn a sign-up into a wall-wall, big enterprise logo?

Let’s hear from two experienced go-to-market leaders who have “been there done that” at some of the best PLG companies in SaaS.

Mark Ghiasy, Head of Revenue & Growth

  • If the product marketing is spot on, and there is good top of funnel traffic, free and paid sign ups will happen naturally.

  • Free trial sign ups at an enterprise account could happen for different reasons: a user is doing some technical d.d for their boss because they have a project / or a initiative coming up and they are doing a bake off on features / functions across a broad range of vendors .

  • That same user will not be able to purchase because of corporate policy on shadow I.T ( i.e they will get in trouble if they try to buy and expense it back ).

  • A paid sign up will prob more likely than not come from a SMB / MM segment account because they have less purchasing restrictions than that of enterprise.

In terms of trial engagement – there are some product cue’s and the sales process that should be overlaid:

  • From a product POV, you would expect the product to have natural trial limits ( i.e restrictions for the user to get the hint that the test drive that they are embarking on, is for demo purposes only – and they can not take it on the freeway and do 100 miles / hour ) & at the same time, they get the same experience as a live user and can appreciate the utility / value of the product / platform in a real world environment.

  • From a sales POV, you would expect an enterprise seller to get onto that free trial at the enterprise account very quickly – and try to qualify if they are wanting to self-evaluate or need some help ( and if they self-evaluate how to best engage).

  • Seller / user ( champion ) relationship is key: this will determine whether or not you can get in front of the executive / buyer and if you can close a small land / or the larger expand in the first instance.

Elena Hutchison, Former Executive VP & Chief Strategy Officer

The tricky thing here is how you build from the thing that attracted the individual user (quick signup to solve problem ‘x’) to something an enterprise scale buyer sees business value in solving across a sufficient scale of users and yet hasn’t solved yet.

You’re almost always solving something totally different for the enterprise buyer versus what the value prop was for the PLG user (maybe it’s adding a layer of analytics across users, meeting a higher bar for security/reliability, etc) but now you’ve also got to do it head to head with whatever else already exists in their tech stack and could meet the use case.


👀 More for your eyeballs

Whether you’re a VC looking to invest in the next Zuck or an employee trying to evaluate your next career move – how do you identify if a founder has what it takes to go all the way? Great article by Auren Hoffman on this topic below.


👂 More for your eardrums:

We had the infamous Sam McKenna founder of #SamSales on the hot seat this week for an extremely tactical framework for building on LinkedIn. Check it out below:


🚀 Start-ups to watch: 

Writer announced their $100M Series B, building the full-stack generative AI platform for enterprises. Couldn’t be more proud of this team’s execution!


🔥Hottest GTM job of the week:

Account Executive at Marqii, more details here.

See more top GTM jobs here


That’s all this week.

Appreciate you rocking with us until the end.

We’re always up for topic suggestions from readers for future newsletters so let us know what you’re currently wrestling with and we’ll try to cover it in one of our next editions.

Have a great weekend.

Barker ✌️

Before helping found GTMfund, Scott spent 4 years at Outreach as Director of Strategic Engagement. He was in charge of aligning key relationships with VCs, BoDs, ecosystem partners and community members to drive revenue and strategic initiatives across Outreach. Scott initially ran revenue/partnerships for Sales Hacker (which was acquired by Outreach in 2018). Prior to Sales Hacker, he led and built outbound Business Development teams at Payfirma and MediaValet. Scott also advises for a number of high growth start-ups and is the host/author of The GTM Podcast and The GTM Newsletter. At GTMfund, Scott leads all fundraising efforts and runs the media arm of the firm. He’s also responsible for assessing investments, team management, LP/community relationships and GTM support for founders.

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