Alexa, CEO of Pocus, hosts Product-Led Sales (PLS) “Ask Me Anything” sessions with PLS experts to share best practices, frameworks, and insights on this emerging category. These AMAs are an opportunity to ask PLS leaders any question — ranging from hiring to sales compensation to tech stack — in a low-key, casual environment.
The PLS AMAs are for members of the Product-Led Sales community, the place to learn, discuss, and connect with go-to-market (GTM) leaders at product-led companies. The goal of the community is to bring together the most thoughtful and innovative GTM leaders to build the next generation of sales together.
Interested in joining? Request an invite here.
Now, keep reading for a recap of what we discussed with the CEO of Scribe, Jennifer Smith, in our latest AMA chat.
Meet Jennifer, CEO @ Scribe 👋
The idea for Scribe came from Jennifer’s work as a consultant and VC, where she saw how difficult it was for people with precious know-how to effectively unleash that knowledge to the rest of their teams.
The result? Go-to employees spent more time answering questions and building long process docs than doing the work that matters.
She knew there had to be a better way, and when she couldn’t find one, she built it.
In this recap of our AMA conversation with Jennifer, we’ll share the high points of our discussion, including:
- How Scribe migrated from a sales-led to product-led motion, and what that meant for sales incentives
- How to experiment with pricing and packaging
- Building feedback loops that drive revenue impact
- Why the future of sales is product data
How Scribe migrated from sales-led ➡️ product-led
When Scribe opened up a self-serve channel, the sales team was focused on business opportunities with stakeholders not yet on the product. Free users had to contact sales to upgrade.
But, organic usage of their free product was increasing. Handraisers were getting in touch and asking for a self-serve way to get a paid contract so that they could get the necessary data protections and roll out to more of their team, without waiting for sales intervention.
There was so much momentum from the bottom-up. People were championing the tool to colleagues, friends and leaders. So, revenue leadership at Scribe decided to accommodate this segment by introducing a self-serve paid tier — helping them expand adoption throughout user teams.
While the product team was focusing on building great experiences for end-users, sales was still using the traditional playbook, going after top-level stakeholders who hadn’t and maybe never would interact with the product.
However, Jennifer realized this approach was disjointed. So, they pivoted to Product-Led Sales by focusing sales power on intent signals in their self-serve pipeline, instead of chasing cold deals.
🚀 Step 1: Set the tone, firm and fast
Jennifer’s team experienced the same thing most companies do when trying to change their DNA. Everyone got really excited about the idea of shifting the go-to-market motion, then went right back to their old ways of working.
They learned that they needed a complete and quick reset, not a months-long experiment or roll out.
Leadership knew they had to be transparent and receptive, inviting the team to share their ideas and feedback — while also being clear this new direction wasn’t optional. It was all about getting folks fired up to build something new together, and capturing that energy to build momentum and shift nimbly into a product-led motion.
“When it comes to changing mindsets and your company DNA, you have to draw a pretty clear line in the sand. You want people showing up everyday knowing they’re going to work differently, and think differently.”
💬 Step 2: Inform customers, as needed
For the most part, the move to PLS didn’t impact the way existing customers interacted with Scribe. Customer Success continued to support a wide range of customer and deployment sizes.
Luckily, Scribe had already invested in removing admin friction from their payment model, making it easy for admins to manage licensing as usage grows within the account. So while there was work behind the scenes on pricing, packaging, and licensing as the focus shifted to prioritize expansion among existing customers, current users weren’t affected.
If your pivot to a product-led motion does require you to change some things on the customer side, the most important thing is communication. You want to make sure that the transition is clear but also seamless, so customers don’t feel like they signed up with one company and came out on the other side with another.
For more on communicating pricing and packaging updates: PLG guide to pricing and packaging.
Pro tip: Don’t be afraid to experiment with pricing and packaging
Jennifer says pricing and packaging is the most powerful growth lever for companies, which may be why there’s also a lot of fear around experimentation.
But, Jennifer says you should be experimenting with pricing regularly.
Keep developing your personas and each package to make them irresistible to target buyers. Reconsider what you can use to differentiate pricing tiers and go beyond just product features -maybe flexible pricing is a huge value add for your audience, or maybe it’s a new level of customer support.
What does experimentation look like in practice?
1️⃣ Develop a hypothesis to guide your process and success metrics.
2️⃣ Conduct A/B testing. In Scribe’s case there was a lot of A/B testing on new users in order to avoid upsetting existing clients.
3️⃣ Experiment with how customers buy. What channels do buyers use? What does the experience on each look like? What changes can reduce friction and increase efficiency?
For example, Scribe experimented with pushing the self-serve channel as hard as possible. What they learned was that some users want to buy self-serve, and some simply don't.
Realizing they couldn’t get rid of their multiple sales funnels, they decided to develop more sophistication around segmentation to determine which kind of users want to buy in which particular ways and how to make those channels accessible to them.
“We experiment to continually re-ground our understanding of who our users are, what they value, why they buy, and how they wish to buy — then deliver on that.”
Step 3: Align proper incentives
Another challenge of developing a self-serve motion focused on free-to-paid conversion is helping sales overcome the idea that they’re “competing” against the self-serve product — a common objection across companies pivoting to PLG later in life.
For Jennifer, it’s about changing the mentality to viewing self-serve as a feeder source. It’s just the very beginning of an account’s usage potential. What are the points of friction that may be keeping high-potential users in this tier? What opportunities can sales introduce or experiences can they capitalize on to help these people realize it’s time to migrate to paid plans?
Reward your sellers based on these goals, instead of pure revenue acquisition. Product-Led Sales is about helping, not directly selling.
“The most beautiful version of this motion is when a user hits something in the product that helps them realize they need more, and they can easily get more by indicating that they’re ready to upgrade. Then boom — they’re talking to a sales rep.”
How to find the enterprise tipping point: Ask ‘why now?’ 🤔
Jennifer didn’t just worry about self-serve vs. sales cannibalization during the early shift to PLS. She and her sales team continue to analyze and optimize their packaging and product usage signals on a regular basis.
Since many of Scribe’s free-to-paid conversions are initiated by the user, the question she always thinks about is “Why now?” What is it that makes customers go from using a free self-serve version of the product one day, to starting a conversation about moving to an enterprise plan the next? What prompted the change? A feature gate? A usage tier?
To uncover these ‘tipping points’ or product usage signals that indicate an account is ready for sales, do a regression analysis of usage and other factors like, industry and job function, of your best customers and how they got there. Then, target similar users who are a step, or two, behind those.
Free-to-paid conversion Grammarly example:
Grammarly has simple packaging and pricing, with clear differentiation between tiers. Teams looking to collaborate on writing assignments fall into the Business tier, while users who need more advanced features like full-sentence re-writes would benefit from the Premium tier.
Here are two free-to-paid conversion playbooks they could run:
#1 Target account conversions: Reach out to new users (from target account companies) within the first 14 days to provide support and white-glove onboarding to speed up the sales cycle.
- Active usage > 4 days
- Frequent feature use= tone detection
- Domain = target account
#2 Freemium conversions: Surface long-time loyal users who haven't yet made the upgrade and convert into paying customers.
- Weekly active user
- 20% higher rate of words analyzed than the average in freemium plan
- ICP-fit: potential for expansion to larger ACV
Building feedback loops with impact 💥
Especially for early-stage companies in the product-led growth (PLG) space that are striving to build hyper-relevant features for end-users, the feedback loop from sales and/or customer support to product is critical.
Jennifer advises to keep this in mind when building your motions and teams. It’s easier to make feedback a part of your culture by hiring people who are inspired by building feedback systems, gathering insights from customers, and sharing that information to positively impact the product roadmap.
The other key element of building and maintaining an effective feedback loop is all about, once again, asking why.
Your product organization can’t be afraid to ask why. Why is sales or support asking for a feature? Why are customers asking for a feature? Why do they think this is the best way to solve their problem?
This line of questioning helps product get down to the actual pain-point, and come up with the appropriate solution — which is often not the same one that customers, sales, or support ask for.
At Scribe, understanding this has led to developing more robust training for sales and support. Now, they ask more of the “whys” up front, so that they can gather richer customer feedback for the product team.
How you handle feedback influences company culture
While the connection may not be immediately obvious, the thoughtful feedback loop that Scribe has developed actually helps strengthen their culture and value.
Jennifer has seen it happen before where an enterprise customer puts a lot of money on the table to try to sway a company to build a feature just for them.
One of the hardest things she has to do is not only turn down offers like these, but crush the excitement of the salesperson on the deal.
And while she explains that this isn’t always the best course of action, it often is.
Why? Because as a PLG company, building for the majority of your end-users should always be the goal. It’s the culture your organization is built on, and the underlying factor behind the KPIs for which every process is optimized.
When leadership deviates from these guiding factors, it diverts resources, negatively impacts KPIs, and confuses everyone underneath them on what their priorities are.
As painful as turning down a big offer from an enterprise customer can be, Jennifer adds that, in a surprising number of cases, they usually see the reasoning behind it. She strives to create the understanding that this decision is still in their best interest. By continuing to follow their intended roadmap, Scribe is creating the best possible product in the space, which ultimately benefits all of its customers.
And of course, the conversation never starts with a flat-out “no.” Instead, Scribe will work with customers to resize the scope of deployment with the goal of giving them the best possible experience, without compromising their roadmap or culture. Jennifer says the reception to this flexibility is usually positive and leads to trusting, long-term partnerships.
The future of sales is product data 🔮
Jennifer shares that, compared to the top-down sales model they used to follow, today their bottom-up sales model leverages a lot more data.
Those early signals taught the team to pivot, and helped them build a powerful PLG engine that’s only gaining in revenue. Without thoroughly analyzing and trusting that data, they might still be where they started.
The first and most important step Scribe’s sales org took in becoming data-driven was getting familiar with product data, looking at it before every call. Jennifer trained her team to analyze how users and customers were engaging with their product before jumping into calls.
This made a world of difference, the future of sales is about making decisions and gauging intent based on product usage data.
Product data provides the kind of view PLG companies need to develop a holistic understanding of customers and deliver value.
Join the Pocus community for more expert insights
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