Rebuilding Trust at the Point of Purchase: FreshBooks

Overview

Role: Lead Product Designer
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Timeline: 12 Weeks
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Responsibilities: User Research, UX/UI Design, Prototyping, Stakeholder Alignment
Tools: Figma, Miro, User Interviews, Sketch

The Challenge:

FreshBooks' pricing page was creating a crisis of trust at the most critical moment in the customer journey. User interviews revealed widespread confusion, pricing shock, and frustration that threatened conversion rates and customer retention.

The Impact:

  • 12% increase in conversion rates within 3 weeks of launch
  • 18% improvement in customer satisfaction (CSAT scores)
  • Significant reduction in support calls about pricing confusion

The Breaking Point: "It will charge me $58, with conversion it will be more"

That quote from a user interview wasn't just feedback. It was a symptom of a fundamental breakdown.

FreshBooks is built for solopreneurs and small businesses every dollar counts. An unexpected $100 charge due to currency conversion isn't an inconvenience. it's a betrayal of trust that loses a customer for life.

My discovery process revealed the pricing page wasn't just outdated. It was actively hostile.

  • 5/5 users experienced "pricing shock" from hidden team member costs ($10/user)
  • Canadian users faced unexpected 30% price increases due to USD conversion
  • Internal jargon like "1% ACH" and "award winning support" meant nothing to a social media consultant just trying to invoice their client.
  • Critical features like credit card processing were buried until higher-tier plans
  • Support was flooded with repetitive calls about basic pricing questions

This wasn't a cosmetic problem. It was a crisis of clarity eroding trust at the point of purchase.

My Process: Autopsy of a Broken Experience

I moved beyond standard usability testing to conduct a full autopsy, correlating data from three sources:

  • User Interviews (The "Why"): I heard the frustration in their voices when they hit the "$10 per team member" add-on page. "I didn't expect that," they said. Unexpected is the antithesis of good UX.
  • Stakeholder Sessions (The "Cost"): I sat with Support and learned the immense operational cost of a confusing page. I learned from Sales that we were failing to sell the value of our highest-tier plan.
  • Interface Audit (The "How"): I cataloged every point of failure: the disappearing "Pay Now" button, the data loss when adding a 51st client, the plan comparison that broke your flow. Benchmarking against industry leaders showed how transparent pricing builds trust rather than eroding it.

The synthesis was clear: we were not being the respectful, transparent partner we promised to be.

The Strategy: From "Gotcha" to "Welcome"

The goal wasn't a new layout. The goal was to rebuild trust. Every design decision was tested against one question: "Does this make the user feel informed and in control?"

The old design operated on a "reveal-as-you-go" model that prioritized short-term conversions over long-term trust. Our research showed this backfired users who felt tricked either abandoned or churned quickly.

  • I fought for total price transparency. The new design featured a running tally that calculated the total cost in their local currency live, as they made selections. No more surprises on the payment page.
  • I became an advocate for plain language. I replaced "ACH" with "bank payment (1% fee)" and turned "award winning support" into "24/7 support via chat and phone." Clarity over marketing fluff.
  • I treated bugs as trust-breaking emergencies. Fixing the broken payment button wasn't a "dev task", it was the highest priority trust building exercise we could do.

I facilitated a charrette (design workshop) with stakeholders, not to present solutions, but to align everyone on this new principle: The pricing page must be the most transparent, helpful, and trustworthy page in our product.

We shifted from asking "How can we maximize immediate conversions?" to "How can we build lasting customer relationships through transparency?"

The Transformation - Evidence Based Redesign

Before & After: A Visual Comparison

Old Pricing Page before Re-design
Re-designed Pricing page

Key Design Solutions

1. Transparent Pricing Architecture

  • Before: Temporary discounts hiding true costs ("$15/month*")
  • After: Clear monthly pricing with any promotions explained simply
  • Impact: Users could make decisions based on actual long-term costs

2. Add-On Visibility

  • Before: Team member costs hidden until final checkout
  • After: "$13/team member" displayed directly on main pricing page
  • Impact: Eliminated the major source of "pricing shock"

3. Plain Language Conversion

  • Before: "1% ACH" without explanation
  • After: "Bank payments (1% fee)" with contextual help
  • Impact: Reduced cognitive load and support queries

4. Intelligent Plan Comparison

  • Before: "+more" links that broke user flow
  • After: Inline expansion that maintained context
  • Impact: Users could actually compare plans effectively

5. Trust Building Elements

  • Prominent reassurance: "Your card won't be charged until after your trial"
  • Security badges and guarantee information where relevant
  • Clear contact information for support questions

The Detailed User Flow

Step 1: Plan Selection

  • Clean, scannable layout with clear value propositions
  • All add-on costs visible upfront
  • Annual/monthly toggle with savings clearly calculated

Step 2: Customization

  • Live-updating total cost calculator as users add features
  • Clear explanations of each feature's business value
  • Visual confirmation of selections

Step 3: Checkout

  • Final review with complete cost breakdown
  • Reassurance about trial period and billing timing
  • Streamlined payment process with error prevention

Measuring Impact

Quantitative Results

  • 12% increase in conversion rates within 3 weeks of launch
  • 18% improvement in CSAT scores for paying customers
  • 23% reduction in support tickets related to pricing confusion
  • 15% increase in annual plan selection due to clearer savings communication

Qualitative Feedback

"Finally I understand what I'm paying for!" - User feedback

"My calls are now about real problems, not explaining basic pricing" - Support team member

"We're attracting better fit customers who understand our value" - Sales lead

Business Impact

  • Improved customer lifetime value through better plan matching
  • Reduced churn from billing confusion
  • Higher-quality leads who understood the product's value
  • Operational efficiency gains in support and sales

My Role & Leadership

Beyond Design Execution

  • Conducting rigorous qualitative and quantitative analysis
  • Synthesizing complex feedback into actionable insights
  • Creating compelling data visualizations to drive stakeholder buy in

This project required me to operate at multiple levels:

As a Researcher

  • Facilitating cross-functional alignment on design principles
  • Balancing user needs with business constraints
  • Developing a phased rollout plan to mitigate risk

As a Strategist

  • Presenting to executive leadership with confidence
  • Building consensus across sometimes competing priorities

As a Lead Designer

Key Decisions I Championed

  • Fighting for upfront pricing transparency against concerns about conversion impact
  • Investing in plain language documentation instead of technical jargon
  • Prioritizing trust building elements over "dark pattern" optimization tactics
  • Advocating for comprehensive user testing rather than rapid assumption based iteration

Reflection & Learnings

What I Learned

Trust is Your Most Vurable Metric

The biggest insight was that trust isn't a "soft" metric it directly impacts hard business numbers. When users trust you, they convert better, stay longer, and require less support.

Stakeholder Management is Design Work

The most challenging part wasn't the UX design it was aligning multiple departments with different goals and metrics. Learning to speak each stakeholder's language was crucial.

Data Tells the Story

Having concrete user quotes alongside analytics data made arguments undeniable. "5/5 users were confused by..." is more powerful than "I think this is confusing."

What I Would Do Differently

  • Earlier stakeholder involvement in the research process to build buy in faster
  • More robust A/B testing framework to measure individual changes' impact
  • Earlier collaboration with content writers to ensure language consistency

The Ripple Effects

  • Established new standards for transparency across the product
  • Created a reusable framework for pricing page evaluations
  • Demonstrated the ROI of user research to skeptical stakeholders

This project changed how FreshBooks approaches pricing beyond just this page:

Conclusion

The FreshBooks pricing redesign proved that the most transactional moments in a product journey are also the biggest opportunities to build lasting trust. By combining deep user empathy with business acumen and design excellence, we transformed a point of friction into a competitive advantage.

This approach doesn't just create better conversions it builds better customer relationships. And in the competitive SaaS landscape, that's the ultimate differentiator.