Behind the Scenes: How We Cracked Enterprise PLG Motion for a B2B SaaS

👋 Henry here, I’m building a software product to provide readers here a ton of value. I’d love to be able to talk to some of you about your growth, GTM and monetisation - with the promise I won’t sell you.

I understand how valuable people’s time is, so anyone who books in a call will get a breakdown of their growth problems and some free consulting work. I appreciate any of you that help 😃

Insights from today’s article:

• 🎮 Why PLG Champions Close Enterprise Deals Faster Than SDRs

• 🔄 The "Fake Automated Email" Hook That Got Past 2024's Spam Filters

• 🎭 Why Making Your Product Look Bigger Than It Is Can Drive Enterprise FOMO

Ever wonder what happens when traditional enterprise sales meets product-led growth? I recently helped a B2B SaaS company tackle this exact challenge, and this is a case study I’m so excited to share with you.

The Problem: Breaking the Traditional Enterprise Sales Model

Here's what we were dealing with: The company had stumbled onto something interesting - their close rates jumped from 11% to 25% when opportunities came through their PLG motion. Why? Because they had internal champions who could get them in front of the right buyers.

But there was a catch…

With $10k ACVs, the traditional enterprise sales motion just wasn't cutting it anymore. Think about it: SDRs, AEs, customer success teams, and 2-3 month sales cycles? In today's market, those economics simply don't work.

The Challenge of Attribution

First, we needed to figure out how to measure success. B2B SaaS attribution is notoriously messy. Was it the December cold email? The LinkedIn ad from last week? That billboard at SFO?

Let me tell you a secret: it's rarely just one touchpoint. It's the collective impact that builds awareness, so when a buyer finally needs your solution, you're already on their radar.

So we took an unconventional approach: working with a specific target account list. No one else in the organization would market to or prospect these accounts. Clean attribution, clear results.

Getting Surgical with Account Selection

Here's where it gets interesting. Instead of casting a wide net, we went narrow. Really narrow, 3 accounts to be specific.

Why? Because we needed density. We needed everyone at these target companies talking about us. You can't create buzz if you're spread too thin.

But we didn't stop there. We filtered even further, specifically looking for companies where we'd already signed a competitor. (Stick with me - I’ll explain why later on.)

With our hyper-targeted list in hand, instead of going after buyers immediately, we scraped LinkedIn and Apollo for potential product champions - the actual users who could become our internal advocates.

LinkedIn ads became our secret weapon here. Why? Because we could target specific companies and actually name them in the creative. Personal touch at scale.

🎭 Why Making Your Product Look Bigger Than It Is Can Drive Enterprise FOMO

Now things get fun. We built:

• Small custom audiences on Facebook and LinkedIn

• 1% lookalikes for broader reach

• High-frequency educational ads

• Objection-handling ads to the same audiences

But here's the twist: we also ran what looked like third-party news articles about the company on LinkedIn and Facebook. The goal? Make prospects feel FOMO by making the company seem larger than life.

We even ran case studies and advertorials showing how competitors were using the product. Nothing drives interest quite like seeing your competition succeed.

The Landing Page Hack

This is where being hyper-targeted paid off. We built custom landing pages for each target company that:

• Called out their company by name

• Showed their competitors profiles

• Offered company-specific discount codes (e.g., "GRAMMARLY20" for Grammarly)

From previous anecdotal experience, I've seen this boost conversion rates by 30%. Yes, it's hard to scale, but for targeted enterprise accounts? Worth every minute.

🔄 The "Fake Automated Email" Hook That Got Past 2024's Spam Filters

The entire idea of this campaign was to hit the prospect company from as many angles as humanly possible.

Cold email is obviously an important channel but to be candid, between AI generated slop and huge deliverability issues in 2024 it’s getting much, much harder to stand out.

So instead of plain-text cold emails, we sent branded emails that looked like automated transaction alerts. The hook?

"👀 Competitor A just Spied on [Your Company]" or

"3 Employees at Competitor A Just Spied on [Your Company]"

Each email pointed to those personalized landing pages showing company details and a sign-up link. Sneaky? Maybe.

Redesigning Onboarding for Virality

But it’s only worth so much just getting them to sign up. The real goal was to actually drive enterprise adoption and to do that we decided to redesign their onboarding to prioritise inviting colleagues over everything else.

When going through onboarding users would see:

1. An offer for a year free of the Premium product just by inviting 2 colleagues

2. Pre-populated share screens with actual employee names and photos from LinkedIn

This was really important. It’s a lot of mental workload to figure out who to invite to a product, whether it will reflect badly on you if they don’t like it etc. so it’s important to take as much decision making off their hands by giving them specific suggestions.

But again this is really tough to scale. It was only possible because we knew the company, and the job title of our end user ICP which meant we could scrape LinkedIn.

Whenever somebody starts onboarding with an email from a certain domain e.g. @grammarly.com they’d see tailored recommendations.

The other lesson we learnt? It’s much more effective to put the share screen in front of a blurred company profile, making it visually more obvious that this was the final step before they could dive in and see what info the product had on their company. Psychology really matters.

The Conversion Push

After two weeks of education and awareness, we switched gears launching conversion-focused ads with time-based scarcity and discounts to the PLG product aiming to get as much density as possible.

Converting Users from PLG to Meeting Booked

Now that we had successfully gotten the density we wanted we had to actually start getting meetings to pitch the enterprise sale.

I’d previously built a solution for someone else that segmented the PLG users into a bunch of different buckets. For this specific campaign there were 2 segments specifically that worked really well.

• Free Trial Conversion: any user in our ICP that started a trial but didn’t convert got an extra 2 week trial automatically

• Ready for Seat Expansion: when we had 3-5 active users after 2+ weeks we then would reach out via email and in-app to get on a call and get intros to managers

Moving Up the Org

After establishing this foundation, we:

1. Targeted C-suite and management with LinkedIn ads showing adoption ("16 [Your Company] employees are using ____")

2. Cold called product users and management

Here's what's fascinating: those cold calls performed way better than the company's standard rates. Why? Because prospects had been hearing about us for weeks. We weren't cold anymore - we were warm bordering on hot.

The Key Insights

Looking back, what made this work was:

1. Hyper-targeted approach enabling personalization

2. Multi-channel presence building perceived scale

3. Smart use of competitive intelligence

4. Viral mechanics baked into the product

5. Traditional sales tactics amplified by digital warming

But perhaps most importantly, we proved that enterprise sales doesn't have to mean long cycles and expensive sales teams. Sometimes, you just need to rethink the playbook.