👓 6 Critical Lessons from SLG to PLG/PLS Transitions

Welcome folks! 👋

This edition of The Product-Led Geek will take 4 minutes to read and you’ll learn:

• Why most companies fail at transitioning from sales-led to product-led growth/sales by approaching it backwards.

• How to identify the perfect moments for sales intervention when users have high intent but low confidence.

• The critical components of a successful pilot team and why cultural resistance is often the biggest challenge.

Let’s go!

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6 Critical Lessons from SLG to PLG/PLS Transitions

I've helped numerous B2B SaaS companies through successful sales-led to product-led growth/sales transitions.

The key is understanding and being prepared for the implication - rewiring your entire go-to-market DNA

Here's a few of the most important lessons I’ve learned leading and advising teams in this area.

1. Sometimes your sales-led product just can't go self-serve

I’ve seen a lot of companies approach this backwards.

They take their existing sales-led product and try to make it self-serve by improving onboarding flows and adding tooltips.

Lipsticks and pigs.

Even with the best onboarding, what’s next?

How will you retain users and teams?

Ask yourself: Can someone who's never heard of your company sign up, understand what you do, get value within their first session, AND want to keep coming back?

If the answer is no, you're not ready for product-led sales. You’ll need to work on at least one - and probably several - of these:

1. Find a simpler use case that delivers immediate value

2. Build a different entry point to your product

3. Invest heavily and continuously in a core UX overhaul - not a one time project

And sometimes you’ll just have to accept that your product is fundamentally enterprise-sales-driven

There's no shame in that - not every product should be product-led.

2. Sales Helps Where Users Have Intent But Lack Confidence

It’s easy to focus on the obvious places to add sales: enterprise procurement, security reviews, complex implementations.

All of those are important.

But the more overlooked opportunity is in moments of high intent combined with low confidence.

Look for users who are:

• Actively using your product but haven't converted

• Asking detailed questions in support

• Showing usage patterns that suggest they're evaluating alternatives

These users want to buy, but they need confidence that they're making the right decision.

A well-timed human interaction can provide that confidence in ways your product can't.

Sales in a product-led motion isn't about convincing people to buy.

You need to instead think how you can help people who already want to buy feel confident about their decision.

3. Why Most Tiger Teams Fail

Most PLS tiger teams fail because companies staff them with whoever is available, not whoever is right for the job.

Product-led sales requires a completely different skill set than traditional enterprise sales.

You need people who are:

• Comfortable with ambiguity and experimentation

• Data-driven in their approach

• Genuinely curious about user behaviour

• Able to have consultative conversations, not just pitch meetings

Start with 2-3 people maximum.

Give them complete freedom to experiment with messaging, timing, and channels.

Remove all the normal sales constraints - no quotas, no call scripts, no required fields in Salesforce.

Their job isn't to hit numbers.

Their job is to figure out what works so you can eventually scale it.

4. Measure What Matters

Don't just track conversion rates. Track leading indicators that predict success:

Response rates to outreach: If fewer than 20% of people respond to your messages (even to say "not interested"), your targeting or messaging is off.

Time from first touch to meeting: In product-led sales, interested users move fast. If it takes more than a week to get a meeting, you're probably reaching out too early or too late in their journey.

Account expansion after sales assist: The real test isn't whether sales helps with initial conversion - it's whether those accounts grow faster than pure self-serve accounts.

Most importantly, track team learning velocity.

How quickly is your pilot team identifying what works and what doesn't?

If they're not generating new insights weekly, something's wrong.

5. When and How to Scale

The biggest scaling mistake is trying to accelerate your way out of an unproven playbook.

Don't scale until you can clearly answer:

• What specific user behaviours trigger outreach?

• What messaging gets responses?

• How do you hand off between self-serve and sales-assist?

• What does success look like for a sales-assisted account?

When you do scale, do so gradually.

Each new person should be able to follow a documented playbook that your tiger team created.

Segment accounts based on behaviour

• Usage patterns (behavioural signals, key product milestones of users/teams)

• Intent signals (responding to emails, visiting ToS and pricing pages)

Further segment to focus on ICP accounts

6. The Cultural Challenge

The hardest part of this transition is cultural.

Old-school sales teams will resist because product-led sales feels like it devalues their skills.

Your product team might become overly focused on self-serve.

Be explicit about what you're doing and why.

Make it clear that both motions are valuable and that you're not replacing traditional sales.

You're adding a net new capability.

Some people won't adapt, and that's okay.

The people who do adapt will be your strongest advocates for the new model.

Most importantly, don't try to force your entire sales team to adopt product-led sales immediately.

Let the tiger team prove the model, then let natural selection determine who wants to learn the new approach.

THAT’S A WRAP

Before you go, here are 3 ways I can help:

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That’s all for today,

If there are any product, growth or leadership topics that you’d like me to write about, just hit reply to this email or leave a comment and let me know!

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Until next time!

— Ben

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