Scaling ARR from $4.5M to $13M by redesigning activation and trust
Head of Product Design (Player-Coach)
Led redesign across Chrome Extension, Search Portal, and company-wide rebrand. 4 core SaaS products across acquisition, activation, and retention.
Led and mentored product designers. Worked cross-functionally with PMs, engineers, growth, and leadership (2x Co-CEOs). Fully remote team across 6 countries.
~3.5 years (Dec 2021 – Jul 2025). Continuous iteration across product and growth experiments.
Users: 400K → 4M. ARR: $4.5M → $13M.
Despite strong acquisition through SEO and Chrome installs, conversion remained low because trust was not established early.
I introduced a value-first activation system across the Chrome extension, search portal, and brand, enabling users to verify data quickly and build confidence through repeated success.
Result:
- 13× increase in organic conversion (0.5% → 6.5%)
- +21.5% onboarding conversion
- +90% directory conversion
- ARR scaled from $4.5M → $13M
- Users grew from 400K → 4M
High-intent users dropped off because the product required commitment before proving value
ContactOut attracted high-intent users:
- Recruiters and sales professionals
- Searching for emails and phone numbers
- Sign up before seeing meaningful results
- Navigate fragmented flows across web and extension
- Trust a product that felt generic
This pointed to a deeper issue: users weren't just dropping off. They were unable to trust the product quickly enough to continue.
Users only trust the product after verifying data accuracy themselves through repeated success
Users:
- Search their own profile
- Check colleagues
- Validate accuracy through repetition
This meant the core problem was not onboarding friction, but a failure to design for trust-building behavior.
Even with a simpler onboarding flow:
- Users would still hesitate
- Trust would still be unproven
- Gated value too early
- Did not encourage repeated validation
- Treated surfaces as separate experiences
I reframed onboarding into a trust-building system driven by repeated value
→ I redefined success as time-to-value + repeated success
I introduced a value-first activation model:
- Deliver value earlier
- Reduce reliance on full onboarding
- Guide users toward meaningful actions
- Product → faster access to value
- UX → repeated validation loops
- Brand → reinforce credibility
I reframed onboarding into a trust-building system driven by repeated value
Translating a trust-first strategy into tangible changes across the product
Chrome Extension — Reducing time-to-value to drive first success
This mattered because without an early success moment, users had no reason to trust the product or continue using it.
I redefined the goal: → Guide users to their first successful contact reveal as quickly as possible.
Led redesign to:
- Simplify onboarding
- Remove unnecessary steps
- Increase information density within constrained UI
- Guide next-best actions
Search Portal — Converting intent into immediate value
This mattered because it represented the highest leverage entry point — users were already expressing intent, but the product was not capitalizing on it.
I repositioned it as: → Primary activation surface, not a passive tool.
Changes:
- Search-first interaction
- Pre-filled intent
- Streamlined reveal flow
- Guided actions
Rebrand — Strengthening perceived trust and differentiation
The existing brand weakened credibility and made the product feel interchangeable despite strong data quality.
This mattered because in a data-driven product, perceived trust directly influences whether users are willing to engage and convert.
I repositioned brand as: → A conversion lever, not visual polish.
Led:
- Full visual identity system
- Mascot + personality
- Product + marketing consistency
- Aligned 2 Co-CEOs + leadership
- Rolled out across remote org
Activation Loop — Designing a repeatable trust-building system
This mattered because trust is built cumulatively — not in a single interaction, but through repeated successful outcomes.
I unified the experience into a single loop:
→ Search → Reveal → Verify → Repeat → Trust → Convert
Reinforced through:
- Nudges
- Incentives
- Consistent flows
Growth accelerated when product, behavior, and perception were designed as one system
Search Portal captured high-intent demand
Chrome Extension delivered immediate value and first success
Brand reduced hesitation and increased perceived credibility
This mattered because each layer removed a different form of friction:
- Search removed effort
- Product removed uncertainty
- Brand removed doubt
→ Users entered with intent
→ Experienced value quickly
→ Built trust through repeated success
→ Converted with higher confidence
→ Returned and reinforced the loop
Growth accelerated not because each part improved, but because they worked together.
Once these elements were aligned, the impact became visible across the entire funnel.
System-level redesign unlocked conversion, activation, and sustained revenue growth
Conversion and Activation: Trust unlocked progression across the funnel
- Organic conversion increased 13x (0.5% to 6.5%)
- Onboarding conversion improved +21.5%
- Directory conversion increased +90%
Users no longer needed to take a leap of faith. They could verify value before committing.
Usage Growth: Faster time-to-value increased repeat behavior
- Chrome Extension DAU: ~27K (+45% YoY)
- Search Portal DAU: ~6.7K (+76% YoY)
Activation was no longer a one-time event, but a repeatable behavior loop.
Business Impact: Trust-driven activation translated directly into revenue
- ARR grew from $4.5M to $13M
- Users scaled from 400K to 4M
- NPS of 88 and employee satisfaction scores of 95%
Fixing activation unlocked monetization across the entire funnel.
What I took away
I initially approached this as a usability problem. But the real constraint was trust. Users don't convert because flows are smoother. They convert when they believe the product is reliable.
Design must enable users to prove value to themselves, not just understand it.
The rebrand was not cosmetic. It changed how users evaluated the product. A stronger brand reduced perceived risk, increased willingness to engage, and made the product feel credible before interaction.
Perception shapes behavior before interaction even begins.
The biggest gains did not come from improving individual features. They came from aligning how users enter (Search), how they experience value (Extension), and how they perceive trust (Brand).
When product, behavior, and perception reinforce each other, growth compounds.
"Bar none the best UX/product/design person I've ever worked with. Activation and conversion rates improved 3-4x. A WEAPON."
"Smart, thoughtful approach to work. Great at coaching and motivating his staff. A secret weapon to any high growth team."
"The most versatile and dedicated person I've had the pleasure of working with. His impact extended far beyond his direct responsibilities."
"The best coach, mentor, and leader I've ever had. He actually listens when you talk and brings out your thoughts in a way that makes it super clear."
"Exceptional as a designer and exceptional as a design leader. He taught me how to think, not just how to design."
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Whether you're scaling a startup, transforming an enterprise, or building a design team, I'd love to hear about it.