I recently sat down with Paul De Barros to reflect on his journey from AE to sales manager to head of sales at companies like Box, PandaDoc, Chargebee, Hopin, and Notably. Now as a Limited Partner at Stage 2 Capital and advisor to founders building their first sales team - we discussed his PLG learnings, trends, and predictions.

What are the most important aspects of GTM in a PLG motion?

Not getting distracted. 

There will always be bright, shiny objects creating a glare in your focus and pulling people's attention away. And, because PLG is such a long-game, it’s really important to stay focused on the game plan and stay confident that it will pay off down the line — and not give up and revert back to what’s worked in the past.  

So staying focused is key and setting up swim lanes within the team can safeguard that. 

For example, having a structured cadence — maybe with one team acting as the “speed team” that jumps in when there’s a certain PQL or a certain leads threshold. Say five users from one account have been active this week — have a team ready to execute a speed play on that. 

And then have a team that’s meant to be thinking more holistically, like on a six month horizon. The expansion-upsell team. 

Have this AE team get alerts when the play is less about immediacy and more about overall business impact. Allowing them time to think through what that signal really means and then having the next call to action in a week, two weeks, or within that month.

How will sales and customer success differentiate (or blur) in PLG motions?  

Specialization within teams will always exist. 

When PLG is done right, sales definitely looks much more consultative or educational and many times the lines between these two functions can become blurred. 

Customer support is becoming more involved with upselling, and AE’s are taking on more of an educational role in the buying process.

But I think there will always be a need for specialization. NPS and retention rates continue to be more and more important, but at the same time you likely will need a team who can just go out and get new logos. 

So companies have to figure out what makes the most sense for their specific motion — who should be focusing on what and at what stage of the buying journey.  

There’s definitely a growing science to all of it. For example, there’s a company that’s just launching called Gradient Works. They have a whole science to how teams should build territories, getting away from the traditional zip code approach and implementing a way more strategic balancing method that suits a PLG motion so much better in most cases.  

So that’s just another interesting shift that was already taking place in the industry but seems to be getting accelerated by PLG.   

How should PLG companies scale education for sales reps? 

Plan ahead and avoid being reactionary. 

Think through what's going to be really important for the team to know over the next couple of months. For example, when you pause and take a second to look up, what are a couple of those trends and patterns you’re going to see more of?

It’s really easy to be reactionary and say, “Oh, this competitor’s popping up,” or “Oh, the execs are telling us that we need to re-think our messaging.”

But when you’re constantly implementing things ad-hocly, it still takes two to six weeks of repetition for these things to sink into the team's flow.

So it's key to look up and provide that information ahead of time whenever possible.

There's this quote by Stephen King (this book) that in order to write consistently, you need to read consistently. So he learned how to read in “small sips and long swallows,” — carrying a book under his arm everywhere he went and reading every time he had even just a free 30-seconds in line at the grocery store, at the post office, etc.

I think that relates so much to sales in the post-2020 world where everyone is always “on” and everything is done over Zoom. After selling all day, the last thing an AE wants to do is another Zoom call for training and planning or learning.

Instead, plan ahead and give the team new information in small sips.

I think most people can pick it up better anyways in smaller ‘sips’ and be ready to implement the learnings when the time is right.

What are the key skills for AE’s to have in PLG? 

I look for curiosity and preparation.

Regardless of PLG, my old CEO at Chargebee, Krish—who was amazing—always talked about hiring for people's strengths. Look for a strength, identify what it is that they can bring, and just hire for that. Then coach them up on the rest.

All those company-specific skills are something that, if you're a good coach and manager or if you have a good enablement team, should come in month one and month two, but just hire for their strengths from the beginning.

But to your point, there's a secret sauce that works well in a PLG motion that you have to look for. I always start by looking for flat-out curiosity.

There’s a couple ways to pressure-test curiosity. How do they do research? How do they prepare for the interview? What did they ask? Who did they talk to? 

And then I imagine when they're talking to customers, where do they start their questioning? Do they start with a curiosity about the business or about big news that's facing them or is it more about what their next quarter is going to look like?

And then I imagine their preparation process in a real scenario with customers. Would they start their conversations zoomed out, thinking about the business strategy as a whole and the current environment they're in? Or would they just jump straight into the zoomed-in questions about the workflow and team-specific strategy?

It creates more of a natural conversation when people display curiosity for the business as a whole instead of just diving straight into the pointed questions about a certain workflow. 

But this can manifest in a lot of different ways, and you just have to gauge how the person is wired to assess problems and search for solutions. 

The second thing I look for is preparation. 

I’ll just ask people directly: How do you prepare for meetings? How would you prep or do the pre-work for a big client meeting or flush out a big presentation deck? Who would you collaborate with to develop this deck or prepare for a big meeting? I'm looking for little details in the way they organize their process. Things like: how much lead time they build in, how much research they do. Do they split it up and democratize it? Do they start prepping 48 hours before? Do they have an internal check in call the day before?

I think being prepared is super key in PLG motions because, for example, if you’re going into meetings with product-led folks, you can’t just start from square one. Some of these users have been active for six months. You need to be able to adapt to many different contexts. 

So curiosity and preparation — those are two that you can definitely include in your interview process. You can work with your enablement and hiring team to find and cultivate these skills.

They don't have to all be questions that the sales manager asks verbatim. But the 1st and 2nd steps of your hiring process should create a filter of who rises to the top, like the creme de la creme of who has that secret sauce that you're looking for.

What trends are you seeing in PLG lately?

Getting users to the ‘aha’ moment faster. 

I’ll give a shout out to Mark Roberge and Stage 2 Capital here. Mark was one of the biggest presentations at SaaStr recently. His talk focused on finding the aha moment in product-led growth. Some people call it a leading indicator, some people call it an activation metric. He calls it an aha moment. 

And he walked through where that is, what that is, and how companies can try to get moments that are closer to the initial entry into the product.

Taking a look at little things like: what are you going to do with your sign up flow, or your login page? How many fields, how gated? Everyone's trying to just figure out the right balance. But really honing in on: once you get into the product, what do you want that first experience to be?

A lot of what Stage 2 Capital does with the Science of Scaling is teaching folks how to get that aha moment early on. And what I'm seeing as an overall trend is teams trying to make the product organically let the natural gravity of the user flow push you right in to that moment faster.

Or for more complex products we're seeing people do more guiding. There's the idea of a progress bar, there's the idea of an in-app checklist — those are two common levers to pull to really try to guide end users.

So you're trying to get them to go up a staircase and these tools are the handrail and that's what kind of guides the user up to the next level.

How do PLG companies know when to introduce sales?  

Qualitative user research. 

This is another trend I'm seeing. You can always look for signals inside your product but you also need to go out and have user interviews.

It’s really important to maintain that muscle —  the process of running qualitative user research. Lately, even with the economic dip in the past six months and companies tightening the belt, so to speak, we're seeing a huge refocus around user research teams.

Big and small companies are all saying we need to prioritize this every month or every quarter — to go out and do user research. We're hearing teams put out mandates, like, if you're a product manager, you need to have five user interviews with customers or with prospects every month, or every quarter.

But that's a big trend, everyone’s doing a lot more user research. 

Anything else you’re excited about or just a closing thought? 

PLG takes time.

I was listening to the Grit podcast by Kleiner Perkins and they interviewed Steve Case, the AOL founder. The big takeaway for me was: time matters. He talked about how it took seven to ten years after AOL went public to really hit product market fit and eventually explode. 

And I just think this concept relates so well to the way PLG companies are growing today where you really can’t see any obvious signs in the beginning. But if you've seen examples like Figma, and the recent big splash with the Adobe acquisition, where it takes years before any traction really hits—they had 5 years before really starting to crank on the revenue.

In that vein, we’re still in the early innings with PLG in general. There’s going to be more people who come out and win this whole thing, and no one is really seeing it happen right now but in seven to ten years another wave will hit. And then you’ll see all these companies that are playing the long game like PandaDoc and Chargebee — they’re sticking to how they think they can help customers and where they add value and if everyone needs that solution and wants to experience it in that way, they’ll be the winners.