UX Writing2024

Dempsey UX Writing

Designed a handout that turned a startup pitch into an emotional conversation — capturing judge attention and investment at the Dempsey Startup Competition 2024.

Best marketing handoutJudges drawn to boothTangible UX strategy
UX WritingContent StrategyUser TestingStartup

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TL;DR

Crafted UX writing that turned a startup pitch into an emotional story — using attention, empathy, and clarity to convince judges to invest at Dempsey Startup Competition 2024.

Overview

Role

UX Writer & Strategist

Context

Dempsey Startup Competition, UW

Team

Team Tale

The Need

Standing out in a sea of startups

Two weeks before our final exhibition-style showcase for our startup Tale at the Dempsey Startup Competition 2024, we realized we needed something that set us apart. It was easy to get lost in the sea of startups present at the venue.

We knew two things: “Silent Marketing” was allowed and encouraged during the competition, and inviting and capturing the judges' attention was entirely up to the team.

2-week deadline

Final exhibition showcase approaching fast — no time for lengthy iteration cycles

Silent marketing

No verbal pitching to judges — materials had to speak entirely for themselves

Attention scarcity

Judges spend mere seconds on each startup's materials before moving on

Research

Learning from those who came before

We looked at all previous startups and images we could find across the internet, the Buerk Center for Entrepreneurship archives, and resources provided by the Foster School of Business.

Custom marketing required

Off-the-shelf materials wouldn't cut it — differentiation was the name of the game

Style varies wildly

Every company had a different marketing approach — no single 'right' template existed

Seconds matter

Judges spend less than a few seconds on each material — capturing attention immediately was crucial

Research reference materials — placeholder

Previous competition examples — placeholder

Images from the Buerk Center for Entrepreneurship

Development

What if the handout felt like a conversation?

After looking at all previous teams and startups, one thing was clear: it was very easy to have your marketing material get lost or undervalued in the fast-paced and messy environment of the venue. We decided that our material should “shock” the reader at first glance.

Tale is designed to complete sentences and conversations. I believed that the marketing handout should be like a conversation for the reader — I wrote a bunch of phrases that could invoke the emotions and empathy that Tale required.

I love you.I believe in you.What's up?My pet is growing fast.I made a new friend.It was a great day.I am so happy for you.I am proud of you.I am thinking of you.Thank you for everything.I appreciate you.I scored a goal.That was fun.I miss you.I am sorry.My little girl turned three.I'm just chilling.My son just started college.We're moving to a new house.I learned something new today.It's going to be okay.I'm looking forward to it.I need some rest.I made pasta.Long time no see.I'm running late.

A few of the many phrases written to evoke emotion and empathy.

Focus Grouping

Designing beyond our own bias

Through focus grouping within our team, we decided on a few phrases and final designs that worked for us. But this was only half the work — what worked for our Gen-Z and Millennial team might not work for Gen-X and Baby Boomers, whom most of the judges belonged to.

Generational bias

Our Gen-Z/Millennial preferences could misalign with Gen-X/Baby Boomer judges — what resonates emotionally varies across generations

Design for the audience

The phrases and visual style had to transcend generational taste — universally human, not generationally trendy

User Testing

Qualitative feedback, quantified

Once we had a bunch of variations, we showed them around to get quick feedback from our mentors, professors, and as many people as we could find. Based on a lot of qualitative feedback — which was then quantified based on majority consensus — we finally decided on the particular design that would represent Tale.

Design variation — placeholder

Final selected design — placeholder

Competition Day

Strategic placement, not just distribution

We not only handed them out to judges and visitors — we kept these handouts at strategic places. Near and on top of the coffee machine, near the food stalls, on judges' tables, and even in washrooms. The materials were everywhere the judges would be, creating an ambient presence that was impossible to ignore.

Judges' tables

Placed directly in their line of sight before sessions began

Coffee machines

Captured attention during casual break moments

Food stalls

Ambient presence in high-traffic rest areas

Washrooms

Unexpected placement that guaranteed a moment of focused reading

Pamphlet at the water station — placeholder

Handing out pamphlets to judges — placeholder

Pamphlet at the coffee station — placeholder

Feedback

Curiosity, emotion, and a trip to our booth

Our marketing campaign was phenomenal because of this one handout. People were being drawn to our booth with the utmost curiosity and emotions that got them to invest in us.

“This was the best marketing handout across the competition.”

— Competition judges

Judges engaged

Drew judges to the booth through curiosity

Emotional impact

Created genuine emotional connections

Best handout

Recognized as top marketing material

Team Tale at the Sweet 16 Investment Round — placeholder

Team Tale at the Sweet 16 Investment Round of Dempsey Startup Competition 2024

Learnings

What this taught me

01

Strategy over content

It's not just what you say — it's where, when, and how you say it. The distribution strategy was as important as the writing itself.

02

Best UX is invisible

Despite our digital-focused startup, the tangible handout became our most powerful communication tool. This reinforced that UX thinking applies beyond screens — every touchpoint is an opportunity to create meaningful user experiences.

03

Empathy is a two-way street

Writing that connects isn't about broadcasting a message — it's about creating space for the reader's own emotions to surface. The handout worked because it invited people to feel something personal, not just read something clever.