Why Learning Velocity Will Define the Next Decade of SaaS: Insights from Rupon Anandanadarajah

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The last ten years of SaaS growth were dominated by acquisition tactics, viral loops, and product led growth playbooks. The next ten years, according to product strategist Rupon Anandanadarajah, will be defined by something far more fundamental.

Learning velocity.

Learning velocity is the speed at which a company can identify a signal, understand it, test a solution, and update direction. It is a simple idea with profound consequences.

“Companies do not lose because they ship slowly,” Rupon explains. “They lose because they learn slowly. They make decisions based on outdated assumptions, stale data, or unclear reasoning. That is what kills momentum.”

The Three Layers of Learning Velocity

Rupon breaks learning velocity into three layers.

Layer 1: Individual insight

How quickly a product manager or analyst can interpret a metric or user behavior.

Layer 2: Team alignment

How quickly a cross functional team can turn insight into a shared understanding.

Layer 3: Organizational action

How quickly the entire company can shift direction based on new evidence.

Most SaaS companies only operate effectively at layer 1. A few operate well at layer 2. Very few excel at layer 3. Those that do often become category leaders.

The Hidden Cost of Slow Learning

Slow learning is expensive. It shows up as:

  • quarter long projects that solve the wrong problem
  • experiments that validate nothing
  • duplicated analysis across teams
  • roadmap churn
  • endless stakeholder escalations

Rupon argues that many SaaS issues that appear technical are actually learning problems in disguise. When teams lack clarity or evidence, they fill the gaps with assumptions. And assumptions, no matter how well intentioned, accumulate until they steer the product off course.

One SaaS company Rupon worked with had been chasing the wrong activation metric for an entire year. They believed a specific action predicted success. After re checking with proper cohorts and discovery, they realized the action was irrelevant. Their entire onboarding flow had been optimized around a false signal.

“Most waste is not engineering waste or design waste,” Rupon says. “It is learning waste.”

The Cross Functional Advantage

Companies often treat product, marketing, engineering, and sales as separate domains. Rupon sees them as parts of a single system. Learning velocity increases dramatically when information flows freely between them.

In his work, he introduces shared metrics across teams, not separate ones. If product measures activation, marketing should too. If sales measures conversion intent, product should understand it. When teams share metrics, they share understanding. When they share understanding, they move together.

One B2B platform saw a major uplift in retention when Rupon implemented a weekly cross functional evidence session. The session lasted 30 minutes. Each team brought one insight or data point. Over time, patterns emerged. Decisions that used to take weeks began taking days.

“When teams see evidence together, they create direction together.”

The Emotional Component of Retention

Many SaaS teams focus heavily on functional value. Does the product work, does it solve a problem, does the feature do what it should. But Rupon argues that the emotional component is equally important.

“Retention often comes down to confidence,” he says. “Confident users return. Confused users churn.”

Early emotional signals matter. If a user feels overwhelmed in minute five, or stuck in minute ten, or uncertain in minute fifteen, they may never come back.

Rupon encourages teams to track emotional friction the same way they track conversion friction. This means:

  • where users hesitate
  • where they feel unsure
  • where cognitive load spikes
  • where motivation drops

He has found that solving emotional friction often produces faster gains than adding new features.

Why Strategy Must Become More Fluid

The traditional model of annual strategy is breaking down. Markets shift too quickly, customer behavior evolves too fast, and new competitors emerge constantly. Rupon predicts that strategy will become a continuous process, not a seasonal one.

Instead of fixed long term plans, he expects SaaS companies to adopt:

  • quarterly themes
  • monthly learning targets
  • weekly recalibration
  • flexible opportunity scoring

This fluid approach allows teams to respond to insights without waiting for the next planning cycle. It also increases accountability because strategy becomes something the team touches often, not something written once and forgotten.

“Strategy should be a living document, not a ceremonial one.”

The Rise of the Evidence Oriented Team

In the same way that design thinking reshaped the last decade of product development, Rupon believes that evidence orientation will define the next decade. Evidence oriented teams use insight as their primary currency. They gather it consistently, interpret it collectively, and apply it decisively.

Evidence oriented teams:

  • embrace uncertainty
  • test assumptions early
  • treat learning as progress
  • avoid overconfidence
  • challenge comfortable beliefs

These teams evolve faster because they are less attached to being right and more attached to learning the truth.

Why AI Will Not Replace Judgment

Artificial intelligence is transforming analytics, research, and experimentation. But Rupon sees limits.

“AI can accelerate analysis. It can summarize interviews. It can simulate scenarios. But it cannot make the judgment call. Strategy depends on judgment, timing, and context. AI does not have that.”

He expects AI to increase learning velocity by automating the slowest parts of discovery and analysis. But human leadership will remain essential because product strategy is still a values driven discipline.

A Final Insight

When asked what separates successful SaaS companies from the rest, Rupon pauses before answering.

“The winners are the ones that commit to learning as a competitive advantage.”

Not speed.
Not features.
Not marketing spend.
Learning.

Learning velocity determines whether a product remains relevant, whether a team remains aligned, and whether a company can adapt faster than the market around it.

Rupon’s work, at its core, is about helping companies learn better and learn faster. Because in a world where customer expectations shift weekly, learning is the only durable advantage that remains.

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