Hey folks! 👋

Here’s what you’ll learn in today’s edition of the Product-Led Geek:

• Why even the most successful product-led companies need sales teams to scale effectively.

• The PLG Complexity/Value Matrix to identify when your product needs a sales-assisted approach for optimal growth.

• The 6 critical triggers that signal it's time to layer sales onto your PLG motion and how to implement it successfully.

Total reading time: 7 minutes

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The PLG Myth: Why Even Product-Led Companies Need a Sales Strategy

"The product sells itself."

That's the dream that's derailed many PLG companies.

While companies like Slack and Calendly are seen as pure PLG success stories, the reality is messier: even these product-led growth poster children eventually built substantial sales operations.

The Pure PLG Myth

Yes, the allure of pure product-led growth is powerful: users discovering, trying, and buying your product without human intervention.

It promises the holy grail of SaaS - true scaling without linear costs.

But as someone who is unapologetically bullish on PLG, allow me to debunk three myths:

Myth #1: If you build it (well), they will pay

The harsh reality?

Even the best PLG products see only 1-5% of free users convert to paid.

Many startups learn this lesson the hard way - an overly generous free tier can lead to rapid user growth but slow revenue growth.

When users can get ~80% of what they need for free, there's little incentive to upgrade.

Only a small percentage who need the extra functionality or usage limits will pay.

And that's okay because those free users will contribute to your growth model in other ways.

Myth #2: Adding sales means you've failed at PLG

Snyk's growth is celebrated for their developer-first, product-led approach.

Less discussed?

Their effective enterprise sales team drives most revenue, though about 50% of those deals come from bottom-up product adoption - see this post on Product Influenced Revenue.

They don't wait for developers to self-serve - they convert qualified organic product usage into enterprise deals.

Myth #3: You can scale purely through viral growth

Even Slack, the poster child for viral growth, hit a ceiling.

Their S-1 filing revealed they spent $233.2M on sales and marketing in fiscal year 2019 - more than doubling their spend from two years prior, representing more than half their total revenue in the same period.

Viral loops eventually saturate, requiring multiple growth engines.

Why Self-Serve Falls Short In Enterprise

Larger companies often have stricter procurement processes and are less inclined to make significant purchasing decisions through self-serve channels. There’s usually a human-in-the-loop.

You’re often challenged with multiple usage pockets of your free plan within the company.

There are many reasons for this, but in most cases, these are teams working independently and unaware of each other.

Multiple teams in a large organisation often onboard and establish habits around the free plan features.

• Marketing team: 15 free seats

• Sales team: 12 free seats

• Product team: 20 free seats

• Total potential value: $50,000/year

• Actual revenue: $0

Each team is happily using your free tier, unaware of other teams' usage.

Without sales intervention, you're leaving significant money on the table.

In these situations, despite adoption and high engagement, that usage is likely distributed across multiple teams/workspaces and self-serve monetisation will be limited to smaller team-level plans.

Then there’s the procurement reality.

Take Figma's journey.

While their self-serve motion is legendary, they built a substantial sales org to support growth.

Why? Because enterprise deals require:

• Security reviews

• Custom contracts

• Procurement processes

• Budget approval across departments

• Legal compliance checks

No "Buy Now" button can navigate this maze.

Expanding Deals with Pure PLG

Even in the ideal scenario, when a company-wide or business-unit-wide deal lands via the product with self-serve checkout, a purely product-led approach to expansion can be inefficient.

As adoption of your product grows organically within a company, so does the usage.

With a pure PLG motion and usage-based pricing, that translates into expansion revenue as customers upgrade to accommodate the increasing number of seats or usage volume.

But you're leaving money on the table if usage expansion is your only monetisation lever.

As companies scale, their needs go beyond just more seats or higher usage limits - there are likely use cases not served by the current product feature they have access to.

And even if your product can support those use cases with additional features in higher-tier plans, or through add-ons/other products, it can be difficult to convert the company with purely product-led mechanisms.

The same is true of another common expansion opportunity: cross-selling or up-selling complimentary products.

Yes, it can be done - but it's difficult.

Here's a real scenario I encountered in a company I advised:

A customer was paying $24,000/year through self-serve, steadily increasing their usage. This looked like a healthy, growing account. But when the sales team engaged, they uncovered a much bigger opportunity:

• Marketing, Sales, and Product teams were running separate accounts with basic features.

• Each department had significant annual software budgets with some unused.

• The CIO wanted to implement company-wide governance and user management.

• The security team required enterprise-grade access controls and audit logs.

• Legal mandated SOC 2 compliance features for sensitive data handling

Within 90 days of sales engagement, this became a $250,000 annual contract.

Why Pure PLG Misses Expansion Opportunities

A strictly bottom-up usage-based expansion play can leave a lot of money on the table. Here's why:

1. Hidden Budget Silos: In large organisations, often departments maintain their own budget and purchasing authority. When Marketing signs up for your $2,000/year plan through self-serve, you might think you've maximised that account's potential. But Sales, Engineering, and other departments are running separate free instances - each with their own $20,000+ software budgets. Without sales engagement, these budget pockets remain hidden and untapped.
   

2. Feature Awareness Gap: Users often don't discover advanced features on their own. Teams stick to basic features that solve their immediate needs, missing out on additional value that could transform their workflows. Sales teams can proactively educate customers about relevant features and use cases they might otherwise overlook.
   

3. Missing Strategic Alignment: Enterprise needs (compliance, security, governance) aren't front-of-mind for end users. While individual teams might be satisfied with basic features, organisation-wide requirements around security, compliance, and governance require executive-level conversations that self-serve motions can't facilitate.

When Product-Led Hits the Ceiling

The most successful PLG companies know when to augment their self-serve motion with sales.

Here's a framework I like to use 👓.

The PLG Complexity/Value Matrix

Think of it as a simple equation:

• Low complexity + Individual value = Pure PLG works great

• High complexity + Organisational value = Sales becomes critical

But there's an important nuance: Even simple products can shift along this matrix as they scale within an organisation.

Take Calendly as an example:

• Individual use: One person can realise value in 5 minutes through pure self-serve.

• Enterprise use: While still relatively low complexity, organisational adoption introduces new needs:

  • SSO integration

  • User provisioning

  • Admin controls

  • Usage reporting

  • Security compliance

  • Cross-department billing

This is where product-led sales becomes valuable - the core product remains simple, but organisational requirements create complexity that benefits from human guidance.

In contrast, a product like Workday starts in the high complexity quadrant:

• Requires months to implement

• Demands org-wide change management

• Needs extensive configuration and integration

• Involves multiple stakeholders from day one

• Can't be adopted bottom-up - it's an all-or-nothing product

Products can occupy different positions on this matrix depending on the implementation scale.

What works as pure PLG for individual users may benefit from a sales-assisted approach as organisational scope increases.

6 Triggers That Signal It's Time for Sales

So, when should you consider layering on a sales-assisted model?

There's no universal answer; it'll always depend on your product and go-to-market context.

If you don't have PMF yet, focus on building something users love.

Assuming you have PMF, think about what’s constraining your growth:

• Are you struggling to land large deals?
  Larger companies prefer contract billing, price negotiation, custom terms, and human interaction. Few companies will spend big (>$50k ACV) with card checkout.

• Are you seeing multiple usage pockets within larger companies on your free plan?
  Sellers can consolidate those accounts, benefiting the customer (simpler billing, company-wide governance) and you (lower support costs, higher deal sizes).

• Are your sales cycles for larger deals too long or your close rates too low?
  If you're selling high-complexity use cases or your buyers aren't your users, bringing in salespeople earlier can streamline and close deals that might otherwise stall or be lost.

• Are you struggling to expand usage within existing customers?
  Human outreach can better explain additional use cases, cross-sell complementary products, and drive adoption of premium features that deliver more value to customers.

Implementing a Sales-Assisted Model

Once you've decided to augment your PLG motion with a sales-assisted model, ensure several things are in place.

• Identify your ideal customer profile (ICP). A well-defined ICP is essential for a product-led sales model. It focuses on which accounts to target for outreach and informs the playbooks and narratives for seller engagement.

• Instrument your product to capture relevant data. Track and analyse customer behaviour to understand:

  • Why customers make purchasing decisions

  • How they use different features

  • What patterns indicate readiness to buy

  This will help in two ways: to define your PQA (product qualified accounts) scoring model and guide the sales team on where and how to engage with the customer - they can leverage their data about customer product usage to craft their narratives and communications.

• Establish a scoring model for PQAs that integrates firmographic, technographic, and usage data and signals, and predicts monetisation likelihood.

• Develop sales playbooks to operationalise the sales-assisted model. Define them for specific scenarios and align them to different PQA scoring triggers. Don’t rely solely on the PQA score, but ensure plays are relevant to the customer’s usage. For example, if a user has hand-raised in product, they likely need support, not a sales pitch.

• Train your sales team. Equipping sales to operate successfully in this new model may involve hiring new roles like product specialists and sales assist, and changing team structure. Compensation plans need to reflect the sales approach, and training must reinforce when to engage - remember sales engagement should only be with accounts scoring above defined PQA thresholds.

• Review and iterate. Treat the entire PLS process as an iterative experiment. Regularly collect feedback from sales, customers, and performance data (e.g. win/loss, sales cycle time). Incorporate learnings into the preceding steps to evolve the PQA scoring model and playbooks, and adapt your team structure and training.

From Product-Led to Product-Led Sales

Here’s the truth:

The most successful "PLG companies" today run sophisticated hybrid motions.

• Datadog: 80% of revenue comes from customers spending $100k+, driven by a strategic mix of self-service, inside sales, and enterprise teams.

• Atlassian: Despite their PLG reputation, they've built a sophisticated enterprise sales organisation targeting their largest customers.

• GitLab: Invests heavily in sales and marketing (68% of revenue) to drive enterprise adoption.

The question isn't if you'll need sales, but when and how to introduce it.

Winning companies aren't choosing between product-led and sales-led growth - they're combining them strategically:

• Product-led: Drives efficient acquisition and proves value

• Sales-led: Unlocks enterprise value and accelerates growth

• Hybrid: Captures value across the full customer spectrum

I love, live and breathe PLG, but don't let the pure PLG myth hold back your growth.

Even the most successful product-led companies have embraced sales to scale, so start building your product-led sales motion before you hit the ceiling.

GEEK OF THE WEEK

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That’s all for today,

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— Ben

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