Staff Product Designer

About EasyLlama

EasyLlama is on a mission to end checkbox compliance. We started by reinventing compliance training with engaging, bite-sized, mobile-first learning instead of outdated, one-size-fits-all courses. Today, we're building an AI-powered Human Risk Management platform that helps organizations reduce risk through modern training, policy management, phishing simulations, and intelligent automation. Our goal is to help companies build compliance programs that are effective, measurable, and built for the way people work today.

More than 6,000 organizations, including Shake Shack, WeightWatchers, Sephora, Jiffy Lube, and Y Combinator, trust EasyLlama. We're proudly bootstrapped, profitable, and recognized on the Inc. 5000 list, with a 96% G2 rating and industry-leading NPS and CSAT scores. We move quickly, value ownership and collaboration, and believe the best ideas come from people who are excited to solve meaningful problems and make a real impact.

Our CORE values

DRIVE is how we work at EasyLlama. Weʼre Doers, Resourceful, Impactful, Valued Partners, & Excellence-Focused.

• We are Doers. We proactively make things happen.

• We are Resourceful. We treat time, money, and energy as valuable.

• We are Impactful. We prioritize what matters.

• We are Valued Partners. We put customers & teammates first.

• We are Excellence-Obsessed. We always deliver excellent work.

From CEO to newest hire, DRIVE asks us to take ownership, solve problems, prioritize what matters, support teammates, and deliver high- quality work.

When we live these values, our product choices, customer interactions, hiring, and promotions all help us live out our mission: to build safer and more productive workplaces.

About the Role

As EasyLlama continues to evolve into a multi-product platform, spanning Compliance Training, Security Awareness Training, AI-powered Course Authoring, and emerging AI-native capabilities, our next phase of growth requires an evolution of our multi-product platform experience.

We're hiring a Staff Product Designer to own the design and optimization of EasyLlama's core platform experiences. This is a high-impact, staff-level IC role, reporting to the VP of Product, with a mandate that goes well beyond improving individual screens or flows.

In your first year, you'll regularly workshop and partner with senior stakeholders to own the design function, process, and end-to-end platform experience to identify its most critical friction points, evangelizing contemporary design paradigms while championing innovation. You'll design foundational systems that drive activation, engagement, and expansion - translating complex platform architecture (metadata, automation & agentic AI workflows) into clear, intuitive experiences users genuinely trust.

You'll embed AI-driven recommendations and intelligent automation throughout the platform, while partnering closely with experienced leaders across Product Management, User Research, Engineering, and Data to ship measurable improvements to core growth metrics.

What You'll Do

Platform Experience & Systems Design

• Design the end-to-end systems that drive customer value: onboarding, product and content discovery, training course assignment flows, cross-product expansion, and AI agents that own meaningful tasks and programs.

• Define interaction models for platform-level systems - not just UI layers or “more modals” - covering content metadata, training assignment logic, document and policy management, recertification automation, and cross-product orchestration.

• Translate complex platform architecture into clear, intuitive, and trusted user experiences

• Own the simplification of EasyLlama's most critical UX challenges, such as framing features that are orchestrated into a cohesive, multi-product user experience.

AI-Native Product Development Experience

• Actively practice use of AI tooling within your workflow, such as prototyping with modern AI tools (Lovable, v0, Figma Make, etc.) to create clickable MVPs in a day, rapidly turning rough prototypes into dev-ready specs.

• Design AI-driven systems - recommendation engines, intelligent automation, and AI agents that are usable, trustworthy, and effective.

• Embed AI workflows and actionable guidance into the product in ways users understand and trust.

• Partner with Product Management and Legal experts to design and innovate within defined guardrails for compliance-critical AI experiences.

• Treat AI not as a feature, but as a foundational layer of the systems you are designing.

Cross-Functional Design Leadership

• Act as a Design Leader across platform initiatives, influencing decisions beyond your immediate scope

• Partner closely with Senior Management, Product Management, Engineering, and Data Analytics Leads

• Contribute new patterns to the EasyLlama Design System as required for platform-scale complexity, partnering with the Design System owner to extend capabilities consistently across multi-product experiences

Experimentation & Data-Informed Design

• Workshop with Senior Management and Leaders (CxOs, VPs, PMs) to propose, frame, and design UX experiments and hypotheses.

• Define test variants and success criteria; prototype and iterate rapidly based on results

• Design for measurable impact - not subjective preference - balancing speed of iteration with design system consistency.

• Partner with Data & Analytics to track and improve core metrics such as our course assignment rate, activation, retention, and expansion signals.

Who You Are

• Mandatory 7+ years of product design experience in multi-product, B2B SaaS platforms - this is a hard requirement.

• Proven ability to define, articulate, and drive measurable product outcomes, such as adoption, engagement, retention, and expansion.

• Deep experience workshopping and collaborating with senior stakeholders (CxOs, VPs, PMs, UXR, Engineering Leads, etc.) on platform-level problems

• Experience designing AI-powere