Overview of Episode 837: How Do You Learn Product? and Optimizing Your Trial Funnel
Rob Walling and Ruben Gamez dig into two deep listener questions: how to optimize SaaS trial funnels with the right amount of friction, and how founders actually learn “product sense.” The discussion centers on how different businesses need different onboarding approaches, why product decisions are part intuition and part customer understanding, and how founders can build that skill over time through repetition, customer exposure, and deliberate learning.
Optimizing a SaaS Trial Funnel
The core idea: friction can help, but only in the right business
Ruben explains that friction works differently across his two SaaS products:
-
BidSketch (proposal software): some friction helps
- Users are often anxious and uncertain about pricing, positioning, and proposal structure.
- The product has a longer time-to-value.
- Education and lead nurturing before the trial can improve conversion.
-
SignWell (e-signature software): less friction is better
- Users are usually already past the “thinking/learning” stage and want to move fast.
- Time-to-value is very short.
- Adding steps usually reduces paid conversions.
What worked for SignWell
- A very low-friction sign-up flow:
- Click Sign in with Google
- Choose an account
- Immediately enter the product
- Some lightweight qualifying questions are used, but only where they help route users to the right experience.
- A higher-friction onboarding path exists for certain larger-company users, but it’s still being tested.
A cautionary test: forcing business emails
They tried adding friction by discouraging Gmail signups and pushing users toward business email addresses.
- Result: about 30% fewer signups
- Paid conversions also dropped by about 30%
- Conclusion: the added friction did not help in this case
Key lesson
Ruben and Rob both stress:
- Don’t over-optimize early.
- If you have enough volume, test changes carefully.
- If you don’t have the data, use judgment and product understanding.
- Focus on the core problem, not just the symptom.
Example takeaway for a project management SaaS
If users need more than a two-week trial to get value, the real question is:
- Are they struggling because of onboarding?
- Is the product too complex?
- Are expectations unclear?
- Is the customer segment wrong?
The answer is usually in the underlying reason, not just “make the trial longer.”
How to Learn Product Sense
Product is really two different skills
Rob and Ruben split “product” into two major disciplines:
1. Product management: what to build
This includes:
- Prioritizing feature requests
- Building a roadmap
- Deciding what matters most for the business
- Understanding customer segments and market direction
2. UX / product design: how to build it well
This includes:
- Making features intuitive
- Creating elegant workflows
- Avoiding bloated, literal implementations
- Designing features people can use without heavy documentation
How Ruben learned product
He didn’t learn it from a single course. He learned it gradually through:
- Working in environments where no one else really owned product
- Having to make decisions repeatedly over time
- Reading UX and design books
- Hiring and learning from designers and UX people
- Watching how experienced builders approached feature design
- Developing stronger opinions about customers and market direction over time
The role of intuition
Both hosts emphasize that product sense is partly:
- Experience
- Pattern recognition
- Customer empathy
- Taste
- Gut feel
Rob notes that you can’t really teach this only with theory. You build it by repeatedly asking:
- Who is this for?
- How many customers will use it?
- What problem are we actually solving?
- Is this feature elegant, or just technically possible?
A practical framework for founders
When evaluating feature requests, ask:
- How many users will actually need this?
- Does this solve one problem or several?
- Does it fit the product’s positioning?
- Is this the right use of our time right now?
Ruben’s team often estimated feature usefulness by rough percentage:
- 5% of customers?
- 50%?
- Something in between?
Even if the answer was a guess, it was usually informed enough to guide the decision.
Key Takeaways
- Friction is not universally bad — it can improve conversion if it builds trust, filters poor fits, or matches user psychology.
- Speed matters for products with short time-to-value, like e-signature tools.
- Product sense is learnable, but it develops through repetition and customer immersion, not just reading.
- Separate product from product management if you’re a founder:
- Focus less on corporate stakeholder management
- Focus more on roadmap decisions, positioning, and UX
- Good product decisions are usually customer-informed, not purely analytical.
- Avoid obsessing over small tests if your volume is too low to give meaningful results.
Notable Recommendations
- For founders wanting to improve product thinking:
- Study customer use cases closely
- Read UX/design fundamentals
- Learn from experienced product people
- Practice prioritizing features repeatedly
- Rob specifically recommends exploring content from Shreyas Doshi, including his Product Sense material and free content.
Note on the Transcript
The provided transcript also contains an unrelated post-show UFC trivia segment that appears to be extraneous or from another recording. It does not relate to the main SaaS/product discussion above.