Caddie AI
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UX Designer
role at
Caddie AI
Caddie is hiring for a
UX Designer Role
on behalf of
LetterAI .
About Letter AI
Letter AI is the world’s first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Lenovo and Redpanda to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry’s first AI Sales Room. We’ve raised almost $15M in seed and series A funding from top-tier VC firms, including Y Combinator, Stage 2 Capital, Formus Capital, Soma, Pioneer Fund, and TechNexus. We are now scaling to $4M ARR and looking for someone motivated and passionate to join us on this adventure.
The Role
We are looking for a UX Designer to join our team in San Francisco as our first design hire. You’ll play a pivotal role in shaping the user experience of our platform; helping define how sellers, managers, and buyers interact with our AI-powered workflows. You’ll work closely with product and engineering to turn complex problems into elegant, intuitive experiences that drive adoption and delight. This is a high-impact, ground-floor opportunity to set the bar for design at Letter AI.
What You’ll Do
Own the end-to-end design process for core platform features: from research and user flows to wireframes, prototypes, and polished UI.
Collaborate with product managers and engineers to translate business goals and technical constraints into seamless user experiences.
Conduct user research and usability testing to uncover pain points and inform design decisions.
Build scalable design systems and components that keep our product cohesive as we grow.
Champion the voice of the user, balancing simplicity and power in every interaction.
Work with leadership to shape the overall product vision and design culture at Letter AI.
What We’re Looking For
3+ years of professional UX/UI or product design experience.
Strong portfolio showcasing user-centered design work across web or SaaS products.
Proficiency with Figma and other modern design/prototyping tools.
Experience running user interviews, usability tests, and synthesizing findings into actionable insights.
Ability to thrive in a fast-paced startup environment with evolving priorities.
Strong collaboration and communication skills, with the ability to influence across teams.
Bonus: experience designing AI-powered or multi-modal (text, video, audio) interfaces.
How We Operate
At Letter AI, we want you to be unapologetically you while operating with our core principles in mind.
Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place
Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization
Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
Driven yet humble: Push for excellence and deliver fast, but keep your humility
Why Join
At this early stage, you’ll not only receive competitive salary and benefits, but also a meaningful equity stake in the company. You’ll have a direct hand in shaping both our product and our design culture from the ground up.
Seniority level
Mid-Senior level
Employment type
Full-time
Job function
Design, Art/Creative, and Information Technology
Industries
Technology, Information and Internet
#J-18808-Ljbffr
UX Designer
role at
Caddie AI
Caddie is hiring for a
UX Designer Role
on behalf of
LetterAI .
About Letter AI
Letter AI is the world’s first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Lenovo and Redpanda to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry’s first AI Sales Room. We’ve raised almost $15M in seed and series A funding from top-tier VC firms, including Y Combinator, Stage 2 Capital, Formus Capital, Soma, Pioneer Fund, and TechNexus. We are now scaling to $4M ARR and looking for someone motivated and passionate to join us on this adventure.
The Role
We are looking for a UX Designer to join our team in San Francisco as our first design hire. You’ll play a pivotal role in shaping the user experience of our platform; helping define how sellers, managers, and buyers interact with our AI-powered workflows. You’ll work closely with product and engineering to turn complex problems into elegant, intuitive experiences that drive adoption and delight. This is a high-impact, ground-floor opportunity to set the bar for design at Letter AI.
What You’ll Do
Own the end-to-end design process for core platform features: from research and user flows to wireframes, prototypes, and polished UI.
Collaborate with product managers and engineers to translate business goals and technical constraints into seamless user experiences.
Conduct user research and usability testing to uncover pain points and inform design decisions.
Build scalable design systems and components that keep our product cohesive as we grow.
Champion the voice of the user, balancing simplicity and power in every interaction.
Work with leadership to shape the overall product vision and design culture at Letter AI.
What We’re Looking For
3+ years of professional UX/UI or product design experience.
Strong portfolio showcasing user-centered design work across web or SaaS products.
Proficiency with Figma and other modern design/prototyping tools.
Experience running user interviews, usability tests, and synthesizing findings into actionable insights.
Ability to thrive in a fast-paced startup environment with evolving priorities.
Strong collaboration and communication skills, with the ability to influence across teams.
Bonus: experience designing AI-powered or multi-modal (text, video, audio) interfaces.
How We Operate
At Letter AI, we want you to be unapologetically you while operating with our core principles in mind.
Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place
Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization
Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues
Driven yet humble: Push for excellence and deliver fast, but keep your humility
Why Join
At this early stage, you’ll not only receive competitive salary and benefits, but also a meaningful equity stake in the company. You’ll have a direct hand in shaping both our product and our design culture from the ground up.
Seniority level
Mid-Senior level
Employment type
Full-time
Job function
Design, Art/Creative, and Information Technology
Industries
Technology, Information and Internet
#J-18808-Ljbffr