Senior Product Designer, Gladly
AI Platform
$150-185k
+ Equity
Customer experience AI built for LTV
Be an early applicant
Customer experience AI built for LTV
201-500 employees
Be an early applicant
$150-185k
+ Equity
201-500 employees
Company mission
To make customer service radically personal.
Role
Who you are
- 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 the job involves
- 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
- 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
- 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
- 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
Our take
Gladly is a cloud-based platform integrating multiple customer service channels into a single UI. It helps companies cater to the upward trend in personalized service by allowing them to communicate with their customers seamlessly across any channel from voice, email, messaging, chat and social media.
The rise in eCommerce has meant demand for services like Gladly is growing. To stand out, the company has focussed on building out its platform with new features. Most lately, this has included an AI and automation-driven customer service platform.
As a certified app partner to Shopify, Gladly benefits from the ability of Shopify merchants to integrate directly with its platform. The company has raised considerable funding, the latest of which supports accelerated growth on the back of releasing its unified customer service platform.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
15% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Sep 2024
$40m
LATE VC
Dec 2022
$55m
LATE VC
Total funding: $208m
Company benefits
- Stock options
- Medical, Dental, Vision and Life insurance
- Generous paid time off
- Generous paid Parental Leave
- 401K
- Flexible Spending Accounts
- Home office stipends
Company HQ
Bernal Heights, San Francisco, CA
Leadership
Charlie Besecker
(CEO)Charlie joined Gladly in 2024 as a President, moving into the role of CEO in 2025. Prior to this, he was a CRO at GRIN and Route.
Joseph Ansanelli
(Co-Founder & Executive Chairman)After co-founding Gladly in 2015, Joseph served as the CEO until 2025. He has also been at Greylock since 2012, spending 5 years as a General Partner before becoming a Venture Partner.
Andy D'Amato
(CRO)Prior to joining Gladly in 2022, Andy spent nearly 9 years at PTC. While there he held a number of roles, including Senior VP of Sales, Americas IoT & Augmented Reality and Senior VP of Global IoT Sales.
Todd Rakow
(CFO)Todd joined Gladly in 2019 as a VP of FInance & Operations before moving into the role of CFO in 2022. Previously, he co-founded Kanjoya and served as the CFO for nearly 6 years. He also spent some time at PayPal as a Senior Operations & Strategy Manager.
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