Welcome folks! 👋

This edition of The Product-Led Geek will take 6 minutes to read and you’ll learn:

• How to extend your PLG motion with strategic outbound email campaigns that reach enterprise customers.

• The three common email outbound failure modes

• How to create focused microcampaigns that leverage product usage data to identify expansion opportunities within larger organisations.

This is a guest post by Alex Shartsis - author of Seed to Sequoia.

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How To Add Outbound To Your PLG Motion

PLG Can Be Limiting

Product led growth (PLG) is phenomenal for fast growth, low-cost sales. No strategy can deliver lower customer acquisition costs at scale. PLG has two major limitations. 

First, even when your growth loops are working, how do you ensure broader adoption and success within larger organizations? How do you find and close more big deals? 

While $100/mo users are easily acquired, guiding enterprise-level engagement ($30k ARR, $100k ARR) often requires a more personalized human touch to foster widespread engagement within complex customer organizations - something automated emails and product growth loops can struggle to create on their own.

Second, PLG might not get you into new networks. 

Whether you are testing a new market segment or simply trying to reach a new region or group of potential customers, depending on your PLG loops it can be hard to gain traction with a new group. 

You need an alternative strategy. 

Maybe outbound email can solve both challenges. 

Email Still Works

Everyone thinks email is dead. 

Other forms of outreach are popular, but email is very much alive and often the best channel. 

Just look at how you spend your day. 

How many hours do you spend in email? 

The tactics we’ll talk about apply on other channels, but email is the most scalable and easiest to implement - so we’ll focus there. 

Email outbound failure modes

You may think email outbound doesn’t work.

Maybe you even tried it. 

The thing is, there are nearly infinite ways to fail in sending cold emails, so let’s cover what not to do first. 

Here are the three main failure modes and how to avoid them. 

1. Bad setup

Email infra is no joke. 

Google, Microsoft and other providers will squash emails with bad setup. 

Instant spam penalty box. Nobody will ever see your emails. 

There are several DNS settings you have to get right, email addresses you have to monitor for spam reports, and more. 

To send emails safely you need a domain that is not the same as your primary domain. 

For example, my company is on skyp.ai - but we send cold emails from useskyp.com or tryskyp.com. 

That way emails we send from skyp.ai - including transactional emails for our customers - are never affected by our outbound campaigns. 

What could be a better indicator of spam than a fresh email on a fresh domain? To avoid this, you have to “warm up” your emails. Otherwise–instant spam penalty box. 

Many use the wrong tool for the job. 

Some platforms are great for marketing, but not as strong for outbound email delivery. 

MailChimp and tools like it are meant for sending marketing emails - not 1:1 outreach. 

The email providers penalize sending that happens all at once. 

It’s a surefire way for them to be marked as spam.

The good news is you can avoid all of the technical mistakes by using the right tool for the job. 

Some tools will set you up properly without you lifting a finger; others will walk you through the setup and validate that you got it right. 

If you’re doing it yourself, it usually takes a few days to two weeks to get properly configured, and requires someone with DNS access (e.g., admin rights on Godaddy or whoever your domain registrar is) and someone with email admin access (e.g., a Google Apps admin). 

If you don’t set it up right, don’t expect outbound to work. 

2. Bad targeting

If you nail the sending so your emails get through but you sent them to the wrong people, you will still fail. 

Worse, you’ll probably waste not only time and money getting meetings with the wrong people, but you will also waste your sales team’s time in meetings with people who are unqualified. 

It’s also pretty demoralizing for the team.

This happens most frequently when you use an agency or an AI SDR. 

Built for volume, they will spam the internet hoping to get you meetings - regardless of whether that meeting might become a customer. 

Outsourcing list building is risky. 

It’s even risky to task it to a new hire, like an eager new AE or SDR. 

Make sure you give firm guidance on who will actually become a customer in order to build a good list - or better, keep doing this yourself or with an experienced hand until they’ve been through a few months of customer conversations. 

3. Bad emails

The easiest way to fail and think you’re doing a great job is to write bad emails. 

Most emails written by novices are far too long. People read on their phones. 

One screen maximum. 

That works out to around 70-80 words. It should feel uncomfortably short to you, the author. 

It’s also very easy to be unfocused. 

People care about their pain, or what job to be done they are trying to get done right now - not your YC class year and especially not your Harvard affiliation. 

They don’t care about your patents or jargon. 

They just care about their pain, and whether you can solve it. 

Recently, AI invented a new way to fail: hyper personalization. 

With the rise of AI list building tools and AI email sending tools, personalization has become a hallmark of AI-written outbound. 

AI SDRs are typically big culprits, because there’s minimal to no human supervision. 

If I get another email talking about being a fan of the “Oakland A’s” I’ll lose it. 

How to avoid writing bad emails is hard to explain. 

There is no quick fix. Tools can definitely help, but choose one that has good defaults, enables the right kind of personalization, and gives you control over prompts so you can fine-tune the content. 

And don’t underestimate the value of customer and domain experts being closely involved in the process. 

Good tools can draft emails that start at a B+/A- and can be made truly A+ with your knowledge of your customer and their journey. 

The core issue you need to fix is not providing clear, helpful, relevant and timely value.

Specific Tactics to Leverage PLG in Enterprise Sales

Start with the data.

You need a scalable way to give your sales team access to customer usage data. 

You can reference Ben’s handy playbook guide as a starting point or refresher on the topic:

Behavioral analytics tools like Amplitude and PostHog are great.

Depending on your data pipelines, you might also get data from the likes of Looker, Segment, Hightouch or Census. 

Using ChatGPT, Claude or other AI tools almost anyone can write queries that unearth exactly what you need to know - and most of these tools will enable you to send reports to your sales team. 

The key is knowing what questions you want answered. 

Don’t make your sales team come up with the questions. 

You want them out there talking to customers, not digging through data. 

Nobody got into sales because they like writing SQL queries. 

Your product, marketing or leadership team are best positioned to figure out what questions would drive more and better sales conversations. Here are some ideas: 

1. What customers who are part of larger enterprises recently took a key action that typically leads to a purchase? 

2. Who is signed up and using the app that is from a larger organization, or an organization that resembles our typical enterprise customer? 

3. Who recently experienced a major success in the app, and is part of a company that looks like our enterprise customers? 

Create focus by filtering your questioning through the lens of “... at a company that looks like our enterprise customers.” 

Being engaged and using your service is not enough. 

There’s no point in chasing unqualified businesses, so be clear about the qualifications for your higher tier enterprise offerings. 

Ask your data the questions that reveal intent and momentum towards a larger purchase - but filter to just the companies that can afford the service. 

More Juice from the Squeeze

Now that you have the data, use email to enhance adoption at current customers. 

Use Apollo.io or other enrichment tools to fill in your understanding of your actual customers and find emails of adjacent groups, lookalikes, or managers in order to speed adoption. 

Don’t expect your customers - even the happy ones - to tell their colleagues about you. Be proactive. 

The lookalike program can expand across other, non-customer companies. 

Look across similar companies and have AE/SDRs reach out with case studies, quick tips, webinars, events or other ways to engage. 

Don’t lead with “book a meeting” - these people may never have heard of you. 

At the same time, beware that the content and tone don't come across as ingenuine, cheesy, or obviously salesy. 

This is a common trap when you lean into trying to be helpful without truly understanding the recipient's needs or offering genuine and appropriate value. 

The goal should be to build trust and demonstrate expertise, not to overtly push your product or service. 

If your message feels forced or manipulative, it will likely be met with skepticism and disinterest, undermining any potential for a positive connection.

Just be brief and to the point - offering reasonable, believable value. 

Trigger Moments–for Sales

PLG usually means you’ve automated a lot of key trigger moments. 

Add outbound, 1:1 automation to that.

For example, when I recently signed up for ZeroBounce, an AE reached out. I’m fairly certain the outreach was automatic - but it was also super useful. 

Now I had someone I could go to that wasn’t an anonymous support chatbot. 

Yes, it’s great to have a human in the loop but if the trigger is obvious and the email content is obvious, automate it. 

Microcampaigns for the Win

Success in microcampaigns comes from focus and using the right tools. 

Start with short lists - 100-250 people, max. 

Target very similar roles and companies, so the messaging resonates. 

The messaging should be obvious–it should almost write itself when you put together the list. By empowering SDRs or marketing to target potential new users based on what you’ve learned from your PLG engagement, you can bring new companies into the top of the funnel in a scalable way. 

Focus also on key jobs-to-be-done that those prospects have or may encounter, leveraging publicly available data. 

Perhaps new tariffs have been announced. Are you selling communication software that your customers (or future customers) will need to use to communicate changes? Perhaps you’re selling accounting software, and accounting for new taxes will be…taxing. 

Hiring can also be a great signal that’s external to your product but highly relevant to adoption. 

For example if you were selling accounting or finance software, look for companies hiring controllers or CFOs - either currently hiring or just closed a new hire. 

They’ll be more receptive to a change, and that kind of observation will get your email noticed and replied to - unlike non sequiturs about local sports teams. 

However you come up with the focus, focus is key. 

You also need the right tools to execute on microcampaigns. 

Just because your CRM says it can send emails doesn’t mean it’s any good at that. Your chosen tool needs to make it very easy for anyone to create personalized campaigns, and equally easy for you to take what works and add it to your playbook for the whole team. 

Level Up PLG Growth With Outreach by Humans

Typical sales outbound frequently fails - but it fails for reasons.

• Bad setup

• Bad targeting

• Bad emails

PLG was never about making human-led sales unnecessary, despite a lot of hype to that effect.

Outbound leveraging PLG can be an exceptionally effective strategy. 

PLG companies sit on a high-intent list and can easily model lookalikes. 

They know a lot more about their customers’ use, engagement patterns, and journey than most companies. 

They can execute outbound sales extremely well with all of that data. 

Great supporting toolchains enable you to take the key data or information you know about your prospects and fit it into great emails that expand your deals faster, or bring more leads into your funnel. 

Don’t let all that customer knowledge go to waste in a purely inhuman, automated world.

If you do, you’ll be leaving money on the table.

THAT’S A WRAP

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— Ben

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