Tackling Digital Product Management: Part 4

Welcome, Housekeeping & Productside Overview

Roger Snyder | 00:00:00–00:05:00
Hello everyone, good morning or good afternoon or good evening, depending on where you are in the world. My name is Roger Snyder and I’m the Vice President of Marketing at Productside. Thank you for joining us today.

We’re continuing our “Tackling Digital Product Management” series, and today we’re discussing Part 4: Pricing the Flavors of “Free.” It’s a really exciting topic because “free” has become such a critical part of how we design and grow digital products.

I’m also excited to introduce our excellent panelists. We’ve got a larger group than usual, so I’m going to ask each of them to introduce themselves briefly.

Roger Snyder | 00:00:00–00:05:00
First up, we have Chris Seidell, Senior Director of Growth at SurveyMonkey. Chris, tell us a little bit about yourself.

Chris Seidell | 00:00:00–00:05:00
Hey all, thanks for having me today. I’m really excited to talk about all things pricing and flavors of free. I lead the growth product practice at SurveyMonkey. I’ve been at the company for a number of years.

“Growth product” means different things in different places, but for us it’s really about running lots of experiments to figure out how we can grow our high-value user base, and how we can get people into the right plans and products that fit them best.

Roger Snyder | 00:00:00–00:05:00
Fantastic, thanks Chris. Next up is Kyle Poyar, VP of Growth at OpenView. Kyle, tell us about yourself.

Kyle Poyar | 00:00:00–00:05:00
Hey everyone, I’m an Operating Partner at OpenView. We’re a VC firm investing in B2B SaaS companies at the expansion stage — generally Series A, B, or C — when they’re going through periods of rapid growth post-investment.

We have a group that rolls up its sleeves and works hand in hand with portfolio companies on things like go-to-market strategy, pricing and packaging, customer success, and product-led growth. OpenView actually coined the term “product-led growth” about five years ago, and that’s been a major focus of our investing and advisory work since then.

Before OpenView, I was at Simon-Kucher, the world’s largest consulting firm focused on pricing and packaging. So this is definitely one of my favorite topics.

Roger Snyder | 00:00:00–00:05:00
That’s great. And I love that your firm coined the term product-led growth, Kyle. Your portfolio includes companies like Calendly, Deputy, and Expensify — some great examples.

Last but not least, we have David Nash, Productside’s VP of Products and Services. David?

David Nash | 00:00:00–00:05:00
Good morning everybody. We’re delighted to have you with us today.

A quick word on our panelists before I talk about myself. First, about Chris: me and millions of other customers use SurveyMonkey every day. We bought into the paid, enterprise version years ago. It’s really the backbone of our business. So I’m delighted to have Chris with us because SurveyMonkey is such a big part of our lives.

About Kyle: if there’s one person to read on product-led growth, it’s Kyle. I read him every day. He writes prolifically on this area. If you don’t follow him on LinkedIn, you should.

As for me, my role at Productside is on curriculum and product creation. After a career building products and product teams for B2B and enterprise SaaS companies, I joined Productside about a year ago. We’ve brought a whole new curriculum around digital product management to market, where we go deep on product-led growth. So I could not be more excited to do this series — especially with these guests.

Community, Housekeeping & Leadership Series Context

Roger Snyder | 00:05:00–00:12:00
Thanks David. It’s interesting — we’re all over the world today. That’s one of the benefits of the last year: we can come together so easily. Kyle, you were saying you’re going to get a snowstorm today in Boston?

Kyle Poyar | 00:05:00–00:12:00
Yeah, we’re getting a nor’easter. It always seems to happen right when you start celebrating the beginning of spring.

Roger Snyder | 00:05:00–00:12:00
And Chris, is it foggy up there like it is down here in Santa Cruz?

Chris Seidell | 00:05:00–00:12:00
We’re actually nice and sunny right now, so I’ll take that. I was complaining yesterday about how chilly it was, but after hearing what Kyle’s about to go through, I should probably be quiet.

Roger Snyder | 00:05:00–00:12:00
I was just visiting David in Portland earlier this week and it was nice and sunny there too.

Let’s do a couple of housekeeping items before we dive in.

First, we encourage you to join our Product Management Leadership community on LinkedIn. It helps you stay engaged with other product professionals, learn what people are thinking about, and share best practices. Nicole, our amazing person behind the curtain, will paste the link to our LinkedIn group into the chat.

Roger Snyder | 00:05:00–00:12:00
We really love interacting with you. During this webinar, please ask questions and give feedback. We actually have fewer slides than usual today so we can spend more time on Q&A.

Use the Questions box on the right side of your GoToWebinar panel to type in questions at any time. We’ll handle some questions as we go and leave time at the end as well.

Let me answer the most popular question right now: “Can I watch this webinar later?” The answer is yes. All attendees will receive an email with a link to the recording once the webinar is over.

Another frequent question is about slides. “Can I get a copy of the slides?” The answer to that one is no, because some of the content includes copyrighted materials that we’re not at liberty to distribute. But you will be able to rewatch the webinar, so you can revisit any part you like.

Roger Snyder | 00:05:00–00:12:00
For those who don’t know Productside, just a quick overview. Our mission is to empower product professionals with the knowledge and tools to build products that matter.

When we say “products that matter,” we mean:

• Products that matter to your customers
• Products that matter to your business
• Products that matter to you as a product manager

Unlike many organizations, we focus specifically on the needs of product professionals. We help both individuals and teams improve skills, processes, and outcomes. If you want to learn more, visit Productside.com.

Roger Snyder | 00:05:00–00:12:00
Today’s topic is part of our Product Management Leadership webinar series, under the broader theme “Implications of Change.”

There’s a lot changing in our profession, and digital product management and product-led growth are a big part of that. We’re excited to present this installment on pricing and packaging “free” in that context.

Let’s take a look at who’s with us today.

Roger Snyder | 00:05:00–00:12:00
Looking at registrations from last night, nearly half of you are product managers and product marketers. Around 20% are directors or VPs of product management or product marketing. We’ve also got product owners and a variety of “other” roles — people who work closely with product or who are curious about the discipline.

So it’s a good cross-section, and I think everyone will get value from this discussion on product-led growth today.

Poll: How Do You Use “Free” Today?

David Nash | 00:12:00–00:20:00
Thanks, Roger. Let’s get this ship moving.

I’d like to open with a quick poll. Think about a product you use every day — you probably use several — but focus on one that’s become really important to you.

Tell us: are you using a free trial version of that product? A freemium / free-forever version? Or have you already upgraded to a paid version — and maybe expect to upgrade further?

If you have products in multiple situations, check all that apply. We’d love to see how “free” shows up in your own tool stack.

Roger Snyder | 00:12:00–00:20:00
So if you’re using multiple products, and some are free trial, some are freemium, and some are paid, go ahead and check multiple boxes. We’ll give you a moment to respond.

David Nash | 00:12:00–00:20:00
While we wait for responses, I’ll mention: Kyle’s going to share some very interesting data in a few minutes about how different models of “free” show up across hundreds of SaaS companies, so this poll will be a fun contrast.

Roger Snyder | 00:12:00–00:20:00
All right, let’s close the poll and see what we got.

We see that:

• 44% of you are using a free trial version of at least one product,
• 61% are using a freemium / free-forever version, and
• 63% are using some kind of paid version — and maybe planning a future upgrade.

So all three styles are clearly in wide use across our audience.

David Nash | 00:12:00–00:20:00
Exactly. And what jumps out to me is that a large majority of you have or will open your wallets after using a free trial or a freemium product.

That’s the heart of today’s topic — how we design those “flavors of free” so they encourage people to fall in love with our products and then pay for them.

The Five Golden Rules of Product-Led Growth

David Nash | 00:12:00–00:20:00
For those who have joined earlier parts of this series, you’ve seen these before. I want to quickly recap our five golden rules of product-led growth, because they’re the foundation for everything we’ll talk about today.

1. Know thy user.
You need to know exactly who’s coming to your product, how often, what they’re doing, where they’re getting value, and where they’re dropping off. That means instrumenting your product, understanding behavior, and tracking metrics at a very detailed level.

2. Give before you get.
This is today’s focus. The idea is that when you onboard new users, you want them to activate and reach an “aha” moment before you ask for payment. A classic example: The New York Times and other digital publishers give you a handful of free articles each month so you can get hooked before the paywall.

3. Obsess about growth.
Before you can monetize something, you have to manage it. Before you can manage it, you must measure it. That means you measure not just revenue, but the entire funnel and engagement cycle — from sign-up to activation, retention, expansion, and referral.

4. Make it easy and make it fun.
Especially in B2B, the buyer is often not the user. If we want to be product-led, we need to focus on the user experience: onboarding, activation, and everyday use. Get them to their first moment of joy — and then repeat — as quickly as you can.

5. It takes a village.
Even though we put the product and the user experience at the center, PLG is not just “a product team thing.” The most successful PLG companies have sales, marketing, success, support, and leadership all aligned around user value and product usage.

Zoom as a Value Metrics & Pricing Example

David Nash | 00:20:00–00:26:00
Let’s make this concrete with a product we all know: Zoom.

Think about Zoom’s pricing page. Without showing every pixel here, I’ll describe the key elements that relate to value metrics.

A value metric is something:

• Users are willing to pay more for
• That directly relates to the value they get
• That’s easy to understand and easy for you to package
• That scales as they use the product more

In Zoom’s case, there are at least four value metrics that matter:

1. Number of participants
   Zoom is generous — up to 100 participants on the free plan. But as your meetings grow, and especially if you’re running webinars or large events, you’re willing to pay for higher participant limits.
2. Meeting time
   For free, you can run a group meeting for up to 40 minutes. That’s enough for some quick syncs, family calls, and small meetings, but it’s limiting for business meetings. Zoom tested a lot of usage data and found 40 minutes to be the right moment to place the paywall. That’s a perfect example of “give before you get” tied to a value metric.
3. Support
   If I’m using the free version, my expectations for support are low. Maybe I’ll submit an email and wait. But if Zoom is mission-critical to my business, I’m absolutely willing to pay for better support, faster response times, and stronger SLAs.
4. Storage
   Recording meetings and storing them in the cloud is another clearly monetizable value metric. The more I record and store, the more value I get, and the more I’m willing to pay.
5. In each of Zoom’s paid tiers, you can see these value metrics scale up as the price increases. There are lots of other features in each column, but users don’t upgrade because of vanity URLs — they upgrade for participants, time, support, and storage.

That’s the difference between features and value metrics.

Poll: Are You Actually Practicing Product-Led Growth?

David Nash | 00:26:00–00:32:00
Let’s do one more poll and see how much of this is happening in your organizations today.

Check all that apply:

• Are you offering a free trial or a freemium version?
• Are you driving self-service buying and onboarding?
• Are you doing in-product onboarding — not just emailing people?
• Are you using product analytics to make decisions?
• Are you actively generating product-qualified leads (PQLs) from your product usage?

If you don’t recall the term PQL, it’s simply someone who’s already used your product and demonstrated meaningful engagement — they’re much more likely to buy than someone who’s only filled out a form.

Roger Snyder | 00:26:00–00:32:00
We’re collecting responses… and yes, that PQL concept also includes building product virality — helping existing users bring new users in directly from the product.

Roger Snyder | 00:26:00–00:32:00
Let’s close the poll and share the results.

We see something like this:

• Around 45% are offering free trials or freemium
• Around 40–45% are offering self-service buying and in-product onboarding
• About 50% are using product analytics for decision-making
• And around 30% are actively building product-qualified leads from in-product behavior

So there’s clearly adoption, but also a lot of room to grow.

Kyle Poyar | 00:26:00–00:32:00
To me, that says there’s still significant upside for this group around PLG. The best product-led companies check all of those boxes. The good news is many of you already have product analytics — that’s the foundation. Without it, everything else becomes guesswork.

What “Good” Looks Like: OpenView PLG Benchmarks

David Nash | 00:32:00–00:40:00
I want to show one page from OpenView’s SaaS metrics survey. Over 400 companies responded, ranging from a few million up to $100 million in ARR.

If you ask, “What does good look like in PLG?” — this is it.

Among the best product-led companies:

• Around 90% offer a free trial
• More than 50% offer freemium
• Nearly 70% are using product analytics in a serious way

And when you compare PLG companies to non-PLG companies, the PLG group consistently shows stronger adoption of free trials, freemium, and analytics — and stronger growth.

So if you’re asking yourself where to go next, that’s a great benchmark.

SurveyMonkey’s Journey: Free, Paywalls & Try-Before-You-Buy

Chris Seidell | 00:40:00–00:52:00
Thanks, David. Let me walk through how this played out at SurveyMonkey over the last twenty-plus years.

If we go all the way back, SurveyMonkey started at the very end of the ’90s. Our founder built it basically in his dorm room. The mission was simple: make web-based surveys accessible and powerful, without having to hire an agency.

Back then there were lots of survey firms — expensive, agency-style offerings. The idea was: “The internet exists now, software is cheaper, why not put that power directly in the hands of researchers, students, teachers, marketers?”

If you looked at the site in the early 2000s — and I’ve seen the archive screenshots — it was pretty wild. The UX would make today’s designers cringe, but one thing is clear: there were two product offerings even then:

• A basic free subscription
• A professional paid subscription at about $19/month

We needed free as a land-grab tool. Survey software was already fairly competitive. We had to attract as many people as possible and make it truly easy to start.

The challenge was: there was no real bridge from free to paid. No free trial. No in-product paywall. You basically had to pre-commit: sign up for paid on the website, without really experiencing the higher-end features.

As we grew, we did what a lot of companies do: we piled on features. We added more capabilities for the paid tiers. We added more SKUs to segment different customer types. The thinking was: “If we just make the paid tiers more powerful, more people will convert.”

But for a long time, fewer than 1 in 100 users were paying us.

So the next phase was: optimize the pitch. We invested heavily in the pricing page UX, the messaging, the side-by-side comparison charts. We A/B tested copy, layouts, buttons — all the classic conversion rate optimization plays.

Again, we were still mostly focused on the promise of value, not letting people experience that value.

That helped a little, but it didn’t fundamentally change conversion. We were still at something like 1% paid.

The real inflection came when we started asking: “How do we show the value of these paid features in-product, rather than just talk about them on a pricing page?”

We introduced in-product paywalls.

For example: you’re building a survey on the free plan, you see an advanced question type, you click it, and you can start to configure it. You can get pretty far. Then at a certain moment — say, when you try to add more responses or export data — we surface a paywall that says, “To use this capability, you’ll need to upgrade.”

That works because by then you’re not just reading a description; you’ve seen the value. You’ve started to build something that matters to you. You can imagine how it will help you.

Even that wasn’t the end of the journey. We eventually moved toward what we call “try-before-you-buy” inside a freemium model.

In that model:

• We essentially allow you to use everything you need to configure your project
• You can build the survey, set up logic, tweak design, preview it, even sometimes test it
• Then, at the moment you’re ready to launch or export or scale, we ask you to upgrade

This model is not a time-limited trial. It’s not “You have 14 days and then everything locks.” It’s more contextual and usage-based.

When we did that, we moved from roughly 1 in 100 to 2, 3, even 4 in 100 users becoming paid customers. That’s a huge change in a business at our scale.

Chris Seidell | 00:40:00–00:52:00
Why freemium instead of classic time-based trials?

Our users are often not professional researchers. They don’t always know exactly what they need when they first sign up. They might have a vague idea — “I need to run a quick survey” — but they learn what they really need only by building.

If we forced them into a 7- or 14-day trial, where they have to pick a plan upfront and then a countdown starts, they may never reach that “aha” moment in time. Or they might choose the wrong plan, feel like it’s overkill or too expensive, and abandon.

Freemium gives them time and flexibility to discover features as they go, without that artificial time pressure. Then we trigger the paywall at the moment they’ve configured something important and are ready to use it.

Trials can be powerful. We still use them in places. But for our core “build a survey” flow, freemium with contextual paywalls fits our users’ behavior better than a generic time-limited trial.

Free Trial vs Freemium: Framework & Funneling

Kyle Poyar | 00:52:00–01:00:00
Let’s zoom out and talk about freemium vs free trial vs hybrid as a framework.

When we work with companies at OpenView, we see two core models:

• Freemium — a free-forever edition with some limitations
• Free trial — a time-boxed access to the full product (e.g., 7, 14, 30 days)

In our benchmark data, we looked at the funnels:

• For every 1,000 website visitors, freemium tends to drive more sign-ups into the product. It removes decision friction because users don’t have to wait until they’re “ready” to start a trial.
• Free trials, on the other hand, tend to have roughly double the conversion rate from free to paid — per user — compared to freemium.

Why?

• Trials create urgency. The countdown motivates people to engage deeply while they have full access.
• Trials also usually expose more of the product’s capabilities, so users discover value they didn’t even know to look for.

Once you combine sign-ups and conversion rates, the overall funnel ends up surprisingly similar: both freemium and trial can perform well.

That’s why I don’t think the real question is “Which one is universally better?” It’s more: “What fits your product and buying motion — and can you combine the two?”

Kyle Poyar | 00:52:00–01:00:00
Take Calendly — one of our portfolio companies — as a great example of a hybrid model.

When you sign up:

• You get 14 days of full access to all premium features.
• After the trial ends, if you don’t upgrade, you’re automatically downgraded to a freemium tier.

That freemium tier is still genuinely useful, but there’s one crucial constraint: you can only have one active event type. If you’re serious about using Calendly — for different meeting lengths, contexts, or teams — that one-type limit becomes painful quickly.

So:

• The trial gives you full exposure to capabilities and drives urgency.
• The freemium plan keeps you in the ecosystem and creates ongoing opportunities for upgrades as your usage grows.

In many cases, this hybrid approach is the best of both worlds.

COVID-Era Case Studies: Adding Free Later

Kyle Poyar | 01:00:00–01:08:00
I also want to highlight that PLG and “free” are not just for born-PLG startups. Many established, more “traditional” SaaS companies have successfully added free motions later and seen big benefits.

A few quick examples from the last year:

• Pluralsight – an enterprise learning platform. During the pandemic, they ran a “Free April” campaign where the full platform was open to everyone for a month. They pulled in over a million new sign-ups, and it was one of their best campaigns ever.
• Atlassian – known for Jira, Confluence, and other tools. They introduced freemium editions across their product line, even though they were originally more trial / sales-driven. One key reason was to let existing Atlassian users self-serve into other Atlassian products without going through centralized admin approval upfront.
• GoDaddy – known for domains and hosting. They started testing a freemium experience for their website and marketing tools, beginning as an A/B test on a small slice of traffic. The results were strong enough that they rolled it out to 100% of traffic, and it’s now part of their standard growth stack.
• Zipwhip – a portfolio company offering business text messaging tied to landline numbers. Historically they used a sales-led motion, partly because onboarding can be complex. But when they introduced a self-service free trial, they tripled the number of new customers they added per day, without hurting their average selling price.

The common theme: even if you were not born PLG, you can still add a free motion — trial, freemium, or both — and get real upside in pipeline, adoption, and conversion.

Q&A: Regulated Industries, Enterprise Buyers, Non-SaaS, and Data-Informed PMs

Roger Snyder | 01:08:00–01:15:00
Let’s take some of the questions that have been coming in. We won’t get to all of them, but we’ll cover a few big themes.

One question from Virginia:

“I work in a heavily regulated industry, and our products use client data, which makes it difficult to offer free offerings. Any suggestions?”

Think banking or healthcare — B2B customers, sensitive data.

Kyle Poyar | 01:08:00–01:15:00
We see this a lot in our portfolio. One pattern is to start with free trials that are sales- or support-assisted, rather than purely self-service.

You still bring the product to the forefront — you let prospects use it — but you wrap it with:

• A more controlled onboarding,
• Strong security assurances,
• And explicit conversations about compliance and data handling.

In other words, “free” doesn’t have to mean “anonymous, self-serve, no human involved.” You can still be product-led and have a guided trial motion, especially in regulated spaces.

Over time, as you and your customers gain confidence in your security model, you can gradually make more of that experience self-service.

Chris Seidell | 01:08:00–01:15:00
I’d add: technically, there’s no reason you can’t offer some version of free in a regulated industry. The key is understanding what your customers need to feel safe:

• Maybe they need a dedicated environment
• Maybe data needs to be anonymized in trial
• Maybe you need a “sandbox” with synthetic data

If you know those requirements and design your free experience around them, you can still leverage PLG.

Roger Snyder | 01:08:00–01:15:00
Another question is about selling into enterprises with C-level buyers:

“Appeal to end users sounds great, but in B2B we still need consultative sales and C-level approval. How do we reconcile that with freemium or free trials?”

Kyle Poyar | 01:08:00–01:15:00
In mid-market or enterprise, your free motion is typically not aimed at the CEO or CIO. They don’t have time to do a trial themselves.

Your free product is aimed at the end users and teams:

• Sales reps
• Developers
• Marketers
• Support agents

When they adopt the product, customize it, and invite colleagues, you now have a strong internal constituency.

Then you go to the executive buyer with data and insights:

• “You already have 80 people using our free edition.”
• “Here are the use cases they’ve built.”
• “Here’s how this usage compares to your peers.”

At that point, you’re not just pitching a vision; you’re showing actual value already being created. That’s a much more compelling enterprise sale.

David Nash | 01:08:00–01:15:00
We also had a question from Drew:

“I’m not a SaaS provider. How do I use these free techniques?”

PLG definitely emerged in SaaS, but the principles show up elsewhere. Two quick examples:

• Warby Parker – with eyewear, they let you try multiple frames at home. It’s a tangible “freemium” experience. If you love them, you buy.
• The Black Tux – for tuxedo rentals, they radically simplified the experience: sizing kits, home try-ons, clear timelines, easy returns. That’s product-led thinking applied to a physical service.

Even if your product is physical, you can still:

• Lower initial friction
• Provide a “try-before-you-buy” experience
• Make onboarding delightful
• And instrument what you can (e.g., digital touchpoints around a physical product)

Closing, Feedback Poll & Upcoming Webinars

Roger Snyder | 01:15:00–01:18:00
We’re almost at time, so let’s wrap up.

First, we’d love your feedback. There’s a quick poll:

“Was this webinar helpful?”

Please take a moment to answer. Being good product folks, we want to continuously improve.

Roger Snyder | 01:15:00–01:18:00
Second, a quick plug: we have online courses coming up in:

• Optimal Product Management
• Digital Product Management

If you’re looking to go deeper into PLG — including pricing, PQLs, analytics, and digital roadmapping — our digital product management courses are a great fit.

We’ve also got an upcoming webinar on “Writing Product Requirements That Amplify Customer Needs” with Colleen O’Rourke, and other sessions in partnership with AIPMM.

Nicole will paste links to our courses and upcoming webinars into the chat, and all of this will be in the follow-up email as well.

Roger Snyder | 01:15:00–01:18:00
Thank you so much, Chris and Kyle, for sharing your experience and insights. And thanks to all of you for your questions and engagement.

Have a wonderful rest of your day, and we look forward to seeing you at the next webinar.

Chris Seidell | 01:15:00–01:18:00
Thanks everyone, this was fun.

Kyle Poyar | 01:15:00–01:18:00
Thanks all, great being here.

David Nash | 01:15:00–01:18:00
Thank you everyone, and happy building.