Design leadership at Tive • 3rd Quarter 2026

Scaling design judgment, not just design output

Evolving a senior product design team from reactive execution toward an autonomous, strategic function.

Tive is a global supply chain visibility platform, growing rapidly as a Series C company.

Web · Mobile · HardwareCross-platform design leadership
4Key product areas
Player / coachManagement + hands-on systems work
1 hr → 10 minPrep time per design review, self-timed
Context

Enterprise software spanning web, native mobile, and connected hardware, while the engineering team was growing quickly and adopting AI.

My role

Product Design Manager and player-coach, partnering with product managers, engineering managers, and the leadership team.

The problem

Product and engineering were increasingly “waiting on design.” A stretched senior team needed a repeatable way to focus on strategic work and let others make good design decisions.

What I changed

A lightweight operating model for visibility and ownership, an AI-assisted review-prep workflow, and a risk-based framework for how much evidence each decision needs.

What happened

We rarely hear “waiting on design” anymore. Designers moved from reactive product partners to proactive design leaders, driving architectural changes like tables and global navigation redesigns, and design review moved from UI critique and context sharing to systemic change and architecture evaluation.

The leadership challenge

“We're waiting on design.” No, you're waiting on design mocks.

That feedback got louder as the engineering team grew and adopted AI to speed through code. We were launching faster, with less design confidence and more pressure on the team, and we were stretched thin trying to do it all.

We were spending our time on tedious, tactical work, and we had no repeatable framework for big-rock design work or for consistently designing at a high level. Engineers had come to expect every flow and edge-case to have a high-fidelity Figma mock.

We needed to be less reactive and more proactive to keep a high bar for UX while reducing design debt.

The goal wasn't to add process for process’s sake or to be a decision gatekeeper; it was to create enough structure and context that designers could consistently operate more independently while raising the quality and consistency of the work.

Before (the waterfall)
Product requirements
Design
Mocks
Engineering
After (moving forward together)
Product strategy
Product
↔
Design
↔
Eng
Shared context
Designer ownership
Evidence + critique
Execution

The question became: how do I scale design judgment without becoming the bottleneck?

Results

What changed

Team

More ownership

Designers engaging earlier, driving alignment, and operating with greater autonomy.

Designers lead large architectural changes freely and with clearer direction.

Quality

Better judgment

More informed critique, intentional validation, and more attention to shared patterns.

Mobile app architecture is now scaled strategically instead of by hunch. Time to launch decreased noticeably and launches are of a higher quality, resulting in fewer “fast-follows.”

Leverage

Less coordination overhead

AI and lightweight operations make context, feedback, and cross-team awareness easier to maintain.

By my own timing, prepping for design critique dropped from about an hour to about ten minutes across roughly 20 reviews.

“Design is finally involved in product roadmap discussions and it’s a great thing!”Senior product designer
How I did it

Three places where better systems created leverage.

01
Scale the team

Autonomy requires visibility, not more approval gates.

Problem

Designers were spending long hours on mocks when what we needed was bigger, systemic changes.

In addition to other forums for design alignment, I introduced Design Triage: a dedicated space to align on our shared work and pull in design system and architectural big-rocks alongside our feature work.

The DS / patterns board, live: design-system work moves from Needs Triage through Designing to Design Done.
Upcoming work
Design triage
Product initiatives
DS / patterns
UX papercuts
Designer ownership
Jam · critique · alignment
Development

Design Triage

Weekly visibility into upcoming work, conflicts, risks, and opportunities.

Async coordination

Less meeting overhead; better awareness of related work, AI-assistance where beneficial.

Design Jam

Earlier collaboration, including PMs. Documented decisions and shared notes.

Product-design-at-Tive Slack Channel

Quicker ideas from anyone into tickets.

Result

1. Designers can now drive bigger architectural changes in support of the product roadmap.

2. I now had visibility into the decisions where my involvement had the most impact.

02
Scale the manager

AI helped me spend less time reconstructing context and more time challenging the work.

Problem

Managing senior designers across many simultaneous initiatives created a problem: high quality feedback required gathering a lot of context before every review.

So I built a review-prep workflow in Claude. Give it a project name, it gathers recent context across Slack, Google Drive, and Figma and structures it around the questions I need answered before a critique.

In a few minutes I can see the problem statement, the decisions made during exploration, the tradeoffs and engineering input, and the open questions. It’s like sitting in the planning meetings for every major project. I stop asking designers to replay all of the decisions made, and spend critique on strategy (“Did you consider the work designer B is doing on product X?” “What persona are you targeting with option C?”) instead of pixel-level feedback.

Slack
Drive
Figma
Claude
review prep
Why this solution?
Alternatives explored?
Tradeoffs?
Open questions?
→ Design critique
From a review-prep brief: the open questions worth challenging, gathered before the critique starts.
Result

1. Faster context and fewer basic questions, so reviews go straight to better feedback. By my own timing, prep dropped from about an hour to about ten minutes across roughly 20 reviews.

2. AI didn't replace design judgment. It created more room for it.

03
Scale judgment

Not every design problem deserves the same process.

System

Four parts that work together.

  • Risk scoring: Rate each decision by impact and uncertainty.
  • Validation library: Pick the right method, from heuristic review and analytics to live in-product validation, surveys, interviews, and usability testing.
  • Design Triage: Talk through risk calls as a team.
  • AI analysis tool: Open to the broader org, not just designers.
Low uncertainty
High uncertainty
Low impact
Evidence: lightShip + observe
Evidence: someSome lightweight validation
High impact
Evidence: focusedFocused, targeted validation
Evidence: deepDeep research + deeper validation
Assess risk→Choose method→Gather evidence→Decide
Validation method examples as listed in the Design Operations Manual
Result

App architecture decisions are now made strategically rather than by hunch. Time to launch dropped from two or more sprints to one for many initiatives, and launches are higher quality.

The people side

A system only works if the designers grow with it.

Ownership

Bigger scope

One designer led the tables redesign end to end, including PM and engineering alignment. They took ownership of systems work beyond a typical product scope and made systemic architectural changes inside product feature work.

Coaching

How I coach

Senior designers need space to do their best work. I meet with them 1:1 every week, focus on growing systems-level and holistic solutions over granular pixel-pushing, and keep improving our shared processes so designers can spend their time on the most valuable work.

Team

Hiring and growth

I hired versatile, senior designers and created individual growth frameworks and a design team leveling rubric.

One experiment that failed

Scaling also meant knowing when to remove process.

Experiment

Design Brief v1

A running artifact meant to preserve design goals and decisions throughout an initiative.

What happened
  • Hard to maintain
  • Poor discoverability
  • Didn't solve a big enough problem
  • Added process when it wasn't needed
DecisionNo Go
Going Forward

Closer PM-designer-EM collaboration and project-specific shared documents served us better.

What I learned

The manager shouldn't be the system.

The biggest shift in my management approach was realizing that scaling a senior team isn't about getting better at keeping track of everything, everywhere. It's about building systems that empower the team to do their most valuable work.

Clear ownership creates autonomy. Shared frameworks build consistency and free up valuable time. AI reduces the cost of context. And good design architecture lets individual decisions compound into something larger.

+
Also: scaling the product

Some design problems shouldn't be solved one feature at a time.

Observation

We kept displaying the same underlying product objects in very different contexts. Solving each instance independently created inconsistency and lengthy, repeated design work.

So we defined each core object once—with shared hierarchy and interaction rules—and let context set the density. Carrier and Driver were the first to be trialed in Pickup Verification and Commodities work.

Explore the five-level object framework
One object · five levels of density
Level 3 · Expanded card

Inline detail without leaving the page

The form-step and accordion state. Only the fields and actions that matter in context—carrier compliance in a shipment form, say. Everything else waits for Level 4 or 5.

AeroTrans ExpressCarrier • Road
✎🗑︎⌃

DOT #USDOT 123456
MC #MC-123456
ModeRoad
Phone(617) 555-0134
Address48 Harbor St, Boston, MA 02210
Edit Carrier ↗
Rebuilt from the Figma object card system · sample data · use ← → to step through levels

Same underlying object. Shared interaction and hierarchy rules. Different information density based on context.

Consistency

The same objects behave predictably everywhere.

Velocity

Designers stop reinventing common presentation problems.

Scale

New objects inherit an established framework.

The platform layer underneath
FIGMA ↔ CODE

Library audits against the codebase

Audited Figma libraries against code; pushed for foundations and components as separate published files, variable names that match code tokens literally, and Code Connect to close the interpretation gap.

WEB ↔ MOBILE

A boundary for the platform

Sorted features into Configure / Monitor / Act / Investigate. Configuration lives on web; lightweight action lives on mobile — a rule for what to standardize and what to differentiate.

AI ↔ SYSTEM

AI-assisted audits & handoff

A reusable AI workflow for auditing component libraries and generating developer handoff documentation — making the system cheaper to keep honest.

Brian Cleveland · Design leadership case studyInternal details generalized for confidentiality