Chapter 10: When Users Sell For You

The clearest signal your onboarding works: users upgrade without being pushed.

Here's the moment that validates everything you've built.

A user who was successfully onboarded, who reached their Same-Day Win, who progressed through the journey milestones, who built habits around your product, starts doing something you didn't explicitly ask them to do.

They upgrade to a paid plan. They invite teammates. They champion your product in a meeting. They ask about enterprise pricing. They recommend you to a peer at another company.

This isn't magic. It's the natural result of the activation and retention loops doing their job. When users get real, compounding value from your product, expansion becomes the logical next step, not a hard sell.

This is the expansion loop. And it's where onboarding pays for itself.

Product Qualified Leads

Traditional sales qualifies leads based on marketing activity: downloaded a whitepaper, attended a webinar, filled out a form. These are Marketing Qualified Leads (MQLs), and they tell you who's interested. They don't tell you who's ready.

Product Qualified Leads (PQLs) are different. A PQL is a user who has demonstrated, through their actual usage of the product, that they're likely to buy or expand.

The key distinction: PQLs are qualified by what they've done, not by what they've consumed.

A user who has sent 50 invoices, connected their bank account, and invited two teammates is a stronger buying signal than a VP who downloaded your pricing PDF. The first user has proven the product works for them. The second might just be comparison shopping.

Defining your PQL criteria is one of the most valuable exercises a product-led company can do. It connects your onboarding success metrics directly to your revenue engine.

The Product Adoption Indicator

Inside your product, there's almost always one key engagement action that predicts long-term success better than any other. I call this the Product Adoption Indicator (PAI).

For Slack, it might be teams that send 2,000+ messages in their first month. For a CRM, it might be users who log 10+ activities in their first two weeks. For a project management tool, it might be teams where 3+ members update tasks daily.

The PAI isn't a vanity metric. It's the behavior that, when it happens, reliably predicts that the user or team will stick around, expand, and eventually pay more.

Finding your PAI requires looking at your retention data and working backwards. Take your best customers, the ones who renewed, expanded, and stayed for years, and ask: what did they do in their first 30 days that churned customers didn't?

The answer is your PAI. And your onboarding should be designed to drive users toward it.

The Product-Led Qualification Matrix

Not every engaged user is a good fit for your product, and not every good-fit company has engaged users. You need both dimensions to qualify effectively.

Picture a 2x2 matrix:

High product engagement, high customer fit. These are your best PQLs. They're using the product actively and they match your ideal customer profile. Priority: sales-assisted expansion. Reach out, offer help, discuss upgraded plans.

High product engagement, low customer fit. They love the product but they're not your target customer. Maybe they're too small, in the wrong industry, or using it for something you don't support well. Priority: serve them through self-serve channels, but don't invest heavy sales resources.

Low product engagement, high customer fit. They match your ICP perfectly, but they're not using the product. This is the most dangerous quadrant: these are the accounts most likely to churn despite being exactly who you want. Priority: re-engage. Human outreach, onboarding support, understand what's blocking them.

Low product engagement, low customer fit. Neither engaged nor a good fit. Priority: automated nurture, low investment. Focus your energy elsewhere.

This matrix tells your sales team where to spend their time. Instead of chasing every trial user or waiting for inbound requests, they can focus on the accounts most likely to convert and expand.

Sales-assisted onboarding: the hybrid model

There's a persistent myth in product-led growth that sales is the enemy. That truly PLG companies don't need salespeople. That the product should sell itself entirely.

This is rarely true in B2B. The reality is a continuum:

On one end: fully self-serve. The user signs up, onboards themselves, and upgrades with a credit card. No human involvement. This works for low-ACV products with simple use cases.

On the other end: fully sales-led. The user can't do anything without talking to a salesperson first. This works for high-ACV products with complex implementation requirements.

In the middle: sales-assisted. The user onboards themselves to a point (reaching the Same-Day Win, hitting some journey milestones), and then a salesperson steps in to help them expand. This is where most successful B2B SaaS companies land.

The salesperson's role in a product-led model is fundamentally different from traditional sales. They're not pitching. They're not cold-calling. They're coaching.

They direct users to value: "I see you've been using X; have you tried Y? It solves the same problem for teams at your scale."

They land and expand: "Your team of 5 is seeing great results. Have you thought about rolling this out to the rest of the department?"

They guide buying decisions: "Based on how you're using the product, the Pro plan would unlock the features you're already bumping into."

The best sales-assisted motions feel like customer success, not sales. The user doesn't feel sold to. They feel helped.

Going deeper vs. going wider

There are two directions for user expansion, and your onboarding journey should create paths for both:

Going deeper means the same user discovers more advanced features for the same job. They started with basic reporting, now they're building custom dashboards. They started with simple project tracking, now they're using automations. The user's original job hasn't changed; they're just getting better at it.

Going wider means the same user (or their team) starts using the product for new jobs. They started with invoicing, now they're using accounting. They started with email campaigns, now they're using the CRM. The product serves a broader set of needs for the same customer.

Both types of upgrade are expansion loop wins. Both are signals that onboarding worked. And both should be designed into the journey, not left to chance.

The retention loop naturally creates paths for going deeper: each milestone introduces slightly more advanced capabilities. The expansion loop creates paths for going wider: once users are confident with one use case, they're open to exploring others.

The expansion loop

This is the third and final loop of The Onboarding Loop, and it's the one that turns onboarding from a cost center into a growth engine.

The expansion loop works like this: a successfully onboarded user reaches the point of independent value. They don't need help anymore; they're getting results on their own. That independence creates confidence, which makes them willing to explore new use cases, which creates new value, which drives expansion (more seats, higher tier, more features), which creates new users (teammates who get invited), who start their own activation loop.

The expansion loop is what makes product-led growth compounding. Each successfully onboarded user potentially creates multiple new users, each of whom can go through their own activation and retention loops.

This is why onboarding isn't just a product feature or a CS function. It's the engine that drives compounding growth. Every user who reaches their Ultimate Win is a potential catalyst for the next wave of activation.

Putting it together

The upgrade loop is the payoff. Everything you've built in Parts Two and Three, the activation, the retention, the psychology, all of it leads here: users who find so much value that growth happens organically.