HaaS on SaaS

Jonathan Haas

I'm a product manager at Vanta with a passion for security and privacy. I write about SaaS, startups, and security.

Ship to Learn: Why Iteration Beats Perfection

10/8/2024

Understanding why shipping early and often is the key to building better products and stronger customer relationships

Written by: Jonathan Haas

The metallic framework of an unfinished building, with construction workers visible in the background

The most valuable product development insight I’ve gained over my career isn’t about frameworks, methodologies, or technical decisions. It’s simpler and more fundamental: the fastest way to learn is to ship. Not to plan, not to perfect, but to ship.

The Paradox of Perfection

We’ve all been there: caught in the loop of “just one more feature” or “just one more refinement” before release. This pursuit of perfection feels responsible, even necessary. After all, shouldn’t we put our best foot forward? But this mindset contains a dangerous assumption: that we know what “perfect” looks like before we put our product in users’ hands.

The reality is that our understanding of user needs is always imperfect, and sometimes flat-out wrong. The only way to improve that understanding is through real-world feedback—and you can’t get that feedback without shipping something.

The Power of the First Ship

Breaking Through Analysis Paralysis

The first version of anything you ship will be imperfect. It might even be embarrassing. But it serves a crucial purpose: it transforms abstract discussions into concrete learning opportunities. Consider two scenarios:

Scenario A: The Perfect Plan

  • Spend 6 months planning the perfect feature
  • Get stakeholder buy-in on comprehensive specifications
  • Build for 3 months
  • Ship and discover fundamental misunderstandings about user needs
  • Start over

Scenario B: The Quick Ship

  • Spend 2 weeks building a basic version
  • Ship to a small user group
  • Learn immediately that your assumptions were wrong
  • Adjust course while you still have resources and time

The second scenario might feel uncomfortable—even risky—but it’s actually the more conservative approach. It risks less time, less money, and less organizational capital.

The Continuous Discovery Cycle

Iterative shipping isn’t just about getting features out the door faster—it’s about creating a continuous feedback loop that improves your understanding of user needs. Here’s how it works:

1. Ship Small, Learn Big

Each release is an opportunity to test hypotheses about user needs:

  • What problems are users actually trying to solve?
  • How do they interact with our solution?
  • What unexpected use cases emerge?
  • What assumptions did we get wrong?

2. Listen Actively

The key to making iteration valuable is having robust feedback mechanisms:

  • Usage analytics that tell you what users do
  • Direct feedback channels that tell you what users think
  • Support tickets that tell you where users struggle
  • Sales conversations that tell you what prospects care about

3. Adjust Quickly

The value of iterative shipping comes not just from learning, but from being able to act on that learning quickly:

  • Course-correct before investing too heavily in the wrong direction
  • Amplify what’s working while it’s still relevant
  • Address pain points while users are still engaged

Building Trust Through Consistency

Perhaps the most underappreciated benefit of iterative shipping is how it affects your relationship with customers. Here’s what happens when you ship frequently and responsively:

1. Demonstrated Listening

When customers see their feedback reflected in quick iterations, they learn that you’re truly listening. This creates a virtuous cycle:

  • Customers provide more detailed feedback
  • They become more invested in your success
  • They’re more forgiving of initial limitations
  • They become partners in your development process

2. The Compound Interest of Trust

Each successful iteration builds upon the last:

  • Small wins accumulate into strong relationships
  • Users learn to expect regular improvements
  • Feature requests turn into collaborative discussions
  • Support burden decreases as users trust your process

3. Predictable Progress

Regular shipping creates a rhythm that benefits everyone:

  • Teams develop sustainable delivery patterns
  • Customers can plan around your release cycle
  • Stakeholders see consistent progress
  • Market momentum builds naturally

Making Iteration Work

To make iterative shipping successful, you need to build the right foundations:

1. Technical Infrastructure

  • Robust deployment processes
  • Feature flagging capabilities
  • Strong monitoring and analytics
  • Quick rollback capabilities

2. Cultural Elements

  • Comfort with imperfection
  • Focus on learning over perfection
  • Clear communication about iteration plans
  • Shared understanding of “good enough”

3. Process Components

  • Regular release schedules
  • Clear feedback collection methods
  • Defined success metrics
  • Quick decision-making mechanisms

The Art of the MVP

A crucial skill in iterative shipping is defining the right Minimum Viable Product (MVP). The key questions to ask:

  • What’s the core hypothesis we need to test?
  • What’s the smallest thing we can ship to test it?
  • What can we learn from this version?
  • How quickly can we iterate based on what we learn?

Iteration as a Mindset

Iterative shipping isn’t just a development methodology—it’s a fundamental approach to product development that acknowledges our limitations and turns them into advantages. By shipping quickly and often, we:

  • Learn faster than our competitors
  • Build stronger relationships with our customers
  • Reduce our risk of major missteps
  • Create sustainable momentum

The next time you find yourself tempted to perfect something before shipping it, remember: the perfect product isn’t the one that ships without flaws—it’s the one that evolves in response to real user needs, guided by real user feedback.

Start shipping. Start learning. Start improving. The rest will follow.