Senior Product Designer, AI Platform

Cacheflow; Northern (KY); Hybrid; USD 155,000 - 185,000; Full time

Benefits offered by this job

Fully remote work environment

Stock options

Competitive benefits

Job summary

Gladly is hiring a senior product designer to lead the Agent Harness workstream, shaping how AI agents are configured, steered, and evaluated across channels. You will partner with engineers and PMs to raise the quality bar for AI-enabled interfaces and contribute to the design system and consistency across the platform.

You will prototype rapidly with AI-assisted tooling, review the work of others, and help teams ship high-quality experiences.

Qualifications

• Strong generalist portfolio featuring complex workflow tools and polished visual craft.
• Experience with AI-native product surfaces including configurables and dashboards.
• Fluency with AI-assisted prototyping and design tooling as part of daily workflow.

Responsibilities

• Own end-to-end product design for the Agent Harness, including design of flows, interactions, and visuals for configuring and steering AI agents.
• Lead the shared design library and ensure quality across teams, including tooling shipped without a designer.
• Define direction on undefined problems and shape implementation through prototyping and design systems.

Skills

AI prototyping

Design systems

UI design

Portfolio

Senior IC judgment

Tools

AI tooling

Job description

About Gladly

For business leaders who want to get AI right, Gladly is the only customer experience AI that delivers the cost savings they need AND the customer devotion that drives lasting business value. With over a decade of singular CX focus and trusted by the world's most customer-centric brands including Crate & Barrel, Breeze Airways, and Ulta Beauty, Gladly was designed for devotion, not deflection: purpose-built to engage customers and turn every conversation into lasting relationship equity. The result is experiences that are radically personal and effortlessly scalable, emotionally intelligent and operationally efficient.

At the heart of our simply powerful platform, Gladly maintains one continuous conversation across all channels while striking the perfect balance of AI and human connection. With 450M+ conversations powered globally, $510M+ cumulative cost savings delivered for customers, and a 65% increase in CSAT, this is a team where your work has real impact at scale. Learn more at www.gladly.ai.

About the role

You will own product design for the Agent Harness, the part of Gladly AI where teams build, test, launch, monitor, and improve AI agents. Your surface spans both sides of the harness.

1. On the side Gladly controls, the agent itself and the channels it works across, your job is helping AI handle more conversations end to end without a human.
2. On the side our customers control, the reporting, simulations, and configuration tools brands use to improve their own agents, your job is making every change a customer ships drive more revenue and resolutions.

This is a generalist role where range matters more than depth in any single discipline. In a given week, you might design an eval review workflow, prototype an agent-steering interaction, tighten the design system components that every team consumes, and review UI that shipped without a designer touching it. Much of the product surface at Gladly is now built with AI-assisted tools by engineers and PMs, so a core part of this job is setting and elevating the quality bar for interfaces you didn't author: through the design system, through review, and through taste.
Thoughtful problem-solvers do well here. They dig into the problem before the fix, make their case clearly, and hold strong opinions loosely. The best work usually has more than one mind in it, so we look for designers who seek out other people's ideas and treat them as well as their own.

What you'll own

• End-to-end product design for the Agent Harness: research, flows, interaction design, and visual design for the tools teams use to configure, steer, and evaluate AI agents.
• The shared design library: components, patterns, and guidelines that keep quality high across every team, including teams shipping UI without a dedicated designer.
• Direction on the undefined problems: taking a product area where the direction is still ambiguous, finding the real problem in it, and giving the team something concrete to build toward.
• Design quality across your product areas, including reviewing and elevating AI-generated and engineer-built UI rather than personally producing every screen.
• Prototyping as a first-class design tool: working prototypes, built fast with AI-assisted tooling, used to test ideas with users and align teams before a line of production code is written.
• Designers here shape the practice as well as the product. You'll have real say in the critique rituals, review norms, and craft standards we already run on, and in where they go next.

What we're looking for

• A strong generalist portfolio spanning complex workflow tools, systems thinking, and polished visual craft, ideally including AI product surfaces such as conversational interfaces, agent configuration and oversight tools, or evaluation/observability dashboards.
• Fluency with AI-assisted prototyping and design tooling as part of your daily workflow (going from idea to working prototype in a matter of hours) and a clear point of view on where AI accelerates design work and where human judgment is non-negotiable.
• Experience designing for AI-native products: interfaces where the system's behavior is probabilistic, where trust and steering matter, and where the design problem is as much about legibility and control as about pixels.
• Comfort operating as the design owner for surfaces you didn't personally build: giving crisp, actionable feedback, encoding standards into reusable systems, and raising the bar without being a bottleneck.
• Demonstrated senior-IC judgment: you scope your own work, make progress before the problem is fully defined, carry multiple product areas at once, and operate with minimal oversight.

What this role is not

• This is not a people-management role; it is a senior individual contributor position reporting to the Head of Product.
• This is not a specialist role in a single discipline (pure UX research, pure visual design, or pure design systems); it deliberately spans all of them.
• This is not a brand or marketing design role; it is product design for our AI platform.

Compensation:

$150,000 to $185,000 annual salary + equity + benefits

For cash compensation, we set standard ranges for all U.S.-based roles based on function, level, and geographic location, benchmarked against similar-stage growth companies. In order to be compliant with local legislation, as well as to provide greater transparency to candidates, we share salary ranges on all job postings regardless of desired hiring location. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise, and may vary from the amounts listed above.

Why Join Gladly?

Gladly is redefining customer experience AI; we're designed for devotion, not deflection. We put people at the center of everything we build, from our platform to our culture. When you join us, you'll enjoy:

• Competitive salaries, stock options, and comprehensive benefits
• Generous paid time off, parental leave, and home office stipends
• A fully remote work environment with opportunities for in-person team gatherings
• A strong commitment to professional growth and an inclusive workplace where diverse perspectives thrive
• A company where AI is not a buzzword. We build AI products and we expect our team to use AI tools daily

We're a team that believes in transparency, collaboration, and the idea that the best work happens when talented people genuinely enjoy working together. Top talent, good vibes, no politics. If this role excites you but you don't meet every qualification, we still encourage you to apply. The perspectives and experiences you bring matter more than checking every box.