SurePeople — building self-awareness across an organization
0→1 Startup · Culture-tech SaaS

Building a startup from employee #1.

Joined with no team, product, or brand — and shipped a SaaS platform that landed Comcast, US Cellular, and Boston Children's Hospital, reached 400+ learning modules, and helped secure Series B.

RoleProduct Design Lead · Creative Director · Brand Strategist
ContextFirst employee · culture-tech startup
Team I led1 UX · 1 Visual · 5 offshore engineers
OutcomeSeries B · marquee enterprise clients

The problem

The leadership-development market ran on dated tools — static assessments, generic curriculum, low engagement. SurePeople's bet: raise each employee's self-awareness, then prescribe personalized learning against the gaps. I had to turn that thesis into a product three very different people would trust — the executive who buys it, the manager who acts on it, the employee who lives in it — as employee #1, with no product, team, or brand yet.

My role

I owned design end to end — product, UX, the visual system, and the brand — building the function from scratch and leading a small team as the company scaled to ~22.

Approach

I designed for three users, not one — a chain with conflicting needs:

  • Learning Leader — the buyer and admin; controls budget, needs to measure learning and justify the spend.
  • Manager — needs concrete insight into each report, and their own blind spots.
  • Employee — wants to feel understood and grow specific skills.
The platform

One assessment, every feature

Three personas feed one shared assessment that drives every surface — from the Culture Board to personalized learning.

Relationship diagram — Learning Leader, Manager, and Employees feeding a shared assessment that powers the product surfaces

Map the year, not the screen.

A service-design blueprint orchestrated the entire first year — rollout, onboarding, and the ongoing loop of people data, community, and content — phased against real touchpoints, not a one-time setup.

Design for novices and experts at once.

Two paths through one product — a guided, wizard-like flow for people who don't know where to start, and fast, faceted navigation for power users.

The work

From a blank page, the team shipped an integrated learning ecosystem:

  • A proprietary assessment — the data spine — surfacing each person's strengths and gaps.
  • 400+ personalized learning modules with video, mapped to those gaps.
  • A Relationship Manager helping two people work better together, in their primary and under-pressure states.
  • A Culture Board and new brand — a social layer for community, and a position as the modern alternative.

Reflection

The lesson that stuck: in a 0-to-1 company, design is strategy. Making the year-one experience visible aligned founders, engineers, and a sales team that didn't exist yet — once everyone could see the journey, the roadmap argued itself. Next time I'd instrument engagement sooner, to prove the learning loop with numbers, not just logos.

"A unicorn leader that would be a tremendous value to any team. His rich experience across product strategy, design, marketing, and customer management comes together into a highly creative and efficient approach to solving any complicated problem."

Elaine Zhao · Lead Designer, Rippling