Fail Fast, Pivot Smart with Paul Doerwald
Paul Doerwald set out to solve a problem he knew well. Helping small consultancies manage multiple projects without getting lost in Trello boards and Gantt charts. The idea made sense. It was solving a real issue. But when he brought it to his target audience, the response was clear:
“I wouldn’t use it.”
Instead of defending his idea, Paul listened. The same person, without prompting, brought up a completely different frustration: timesheets. That’s when Clockk was born.
This moment highlights a key lesson in product-market fit: the best business ideas aren’t always the ones you start with. They’re the ones your customers can’t stop complaining about.
Solving an Annoyance vs. Solving a Necessity
Paul’s original idea tackled a legitimate challenge but wasn’t urgent enough to demand a solution. Small consultancies could work around it with makeshift systems. In contrast, timesheets were an ongoing frustration that people wanted to escape.
This is the difference between a nice-to-have and a must-have. Customers won’t always adopt a tool that improves their workflow, but they will actively seek to eliminate something that slows them down.
The Product-Market Fit Shortcut
Many founders enter the market with a vision of the problem they want to solve. The mistake? They try to force customers into their vision instead of adjusting to reality.
Paul avoided this by:
- Paying attention to unsolicited frustrations: Real pain points surface naturally in conversations.
- Recognizing that urgency beats complexity: A product doesn’t need to be revolutionary; it just needs to solve an unavoidable problem.
- Pivoting before building: Instead of wasting time coding a solution no one wanted, he built something customers already requested.
Great products don’t come from founders who best predict what people need. They come from founders who are the best at listening.
Customer Development Isn’t Just About Validation
Paul’s first customer conversation gave him a new direction, but it didn’t automatically mean he had a business. Recognizing a pain point is one thing. Understanding how widespread and painful it really is. That’s where customer development comes in.
Rather than jumping straight into building, Paul talked to 100 people. 80 informally, 20 in structured interviews. Before writing a single line of code.
The Right Questions Lead to the Right Product
Following Cindy Alvarez’s Lean Customer Development framework, Paul focused on open-ended questions rather than leading ones. (Check Cindy’s appearance on the Predictable Revenue Podcast.)
The goal? To let customers surface their frustrations instead of steering them toward pre-defined problems.
The most revealing question: “If you could wave a magic wand and fix something you can’t today, what would it be?”
The answer kept coming back to the same thing: “Make timesheets go away.”
Emotional Pain = Product Opportunity
When customers talk about a problem with frustration, anger, or even tears, it’s a sign they aren’t just annoyed. They desperately want a solution.
For agencies and consultancies, time tracking wasn’t just an inconvenience. It was a barrier to cash flow, an endless source of internal frustration, and a monthly fight between finance teams and employees.
Timesheets weren’t a feature request. They were an unsolved pain point that people would pay to eliminate.
The Key Takeaway
Customer development isn’t about confirming your idea. It’s about digging until you find a problem so painful that customers demand a solution. If people aren’t visibly frustrated, it might not be a big enough problem to build a business around.
The Real Test of Product-Market Fit
Validating an idea is one thing. Getting someone to pay for it is another. Paul Doerwald’s first paying customer wasn’t a random early adopter. It was his own UI/UX designer, who initially hated the idea of Clockk.
At first, the designer refused to use it. But once he installed the trackers, something clicked, literally. Within hours, he found 20 minutes of unbilled work, covering the cost of his first month. A second user had the same experience, realizing she had underbilled by two hours on her very first day.
This is the strongest form of validation: when customers see immediate financial benefit without being convinced. There is no hypothetical ROI or drawn-out sales cycles. Just direct, tangible value.
Early Growth
After landing those first customers, Clockk’s early growth was anything but predictable.
- A year in the AppSumo marketplace brought in a wave of users. Some are valuable, others just deal-hunters.
- SEO became a major lead driver thanks to an early article titled What is AI Time Tracking? A term that later exploded in search volume.
- ChatGPT unexpectedly became a referral source, ranking Clockk among its recommended tools for project-based professionals.
Make Your Product Sell Itself
The easiest products to sell are the ones that instantly make users feel the pain of not using them. Clockk didn’t need aggressive marketing. Its best selling point was when customers realized they were leaving money on the table.
Key Lessons for Founders
- Customer objections don’t mean rejection. Paul’s first user hated the idea until he tried it.
- ROI must be obvious. If customers need an explanation to see the value, the product isn’t solving the right problem.
- Content marketing takes time but compounds. A well-written SEO article from years ago is now a major growth engine.
- New channels emerge unexpectedly. ChatGPT recommendations weren’t planned but became an organic lead source.
AppSumo: A Growth Lever or a Risk?
Platforms like AppSumo can be tempting for early-stage startups. They offer instant exposure, a surge of users, and a boost in feedback. But Paul Doerwald learned that success on AppSumo depends on preparation, strategy, and knowing what you’re signing up for.
Key Lessons from AppSumo
- Read the Fine Print
- AppSumo deals often involve lifetime licenses, which can become a liability.
- You could be on the hook financially if you need to cancel deals later.
- Paul’s advice: Read every detail in the license agreement before committing.
- Offer Something That’s Cheap to Deliver
- If your product has high per-user costs, AppSumo may not be sustainable.
- Clockk worked well because its core value didn’t come with heavy operational costs.
- Understand the AppSumo User Base
- AppSumo attracts hustlers, consultants, and deal-seekers. Not long-term enterprise clients.
- Many users have deep software knowledge but little loyalty.
- It might be a great fit if your product serves agile, cost-conscious professionals. However, the audience may not be aligned if you target larger companies.
- Leverage the Review System
- AppSumo’s internal review system boosts visibility, creating a feedback loop that helps drive more signups.
- Incentivizing honest reviews (through extra features, not payments) helps gather valuable feedback and improve ranking.
Product-Market Fit Isn’t a Moment. It’s a Process
For Paul, product-market fit wasn’t a single event. It was a slow, steady grind. A long road of iteration, feedback, and refinement.
Early users loved Clockk, but sales weren’t taking off. Something wasn’t clicking. The Sean Ellis test (a common product-market fit survey) showed over 40% of respondents would be “very disappointed” if they lost access to Clockk. A strong indicator of fit. Yet, the business metrics didn’t match up:
- Poor lead flow
- Low conversion rates
- High churn
Why “Loving the Product” Isn’t Enough
Through dozens of customer interviews, Paul discovered a disconnect:
✔️ For the right users, Clockk was perfect. They loved it and couldn’t imagine working without it.
❌ For everyone else, it had blockers. The UI was frustrating. Tracking wasn’t as seamless as expected. Missing integrations forced some users to competitors.
Clockk wasn’t a bad product. It just needed refinements to reduce friction for more users.
The Moment It All Clicked
Paul’s biggest realization came not from happy customers, but from churned ones.
Two former users told him:
- “Clockk is the best time tracker I’ve ever used, but I need it to integrate with my project management tool.”
- “I love the accuracy, but sometimes I need a faster way to get things done.”
These weren’t fundamental product flaws. They were fixable issues keeping users from sticking around. And more importantly. They weren’t asking for a complete overhaul. They wanted to keep using Clockk if just a few things improved.
Finding Fit Is About Closing the Gaps
Clockk didn’t need to change its core value proposition. It just needed to remove barriers to adoption.
Paul’s approach to PMF is a masterclass in persistence:
- Customer development doesn’t stop at validation. It’s ongoing.
- A great product isn’t enough. You have to refine the experience.
- The best insights come from churned users. Their feedback shows where the gaps are.
After six years of iteration, Clockk truly resonates with its market. The next step? Scaling the go-to-market motion to match the product’s strength. Check them out!
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