Gladly · 2 months ago
Staff Software Engineer, AI & Automation
United States
Full-time
Remote
Senior Level, Lead/Staff
$183K/yr - $215K/yr
5+ years expGladly is a customer experience platform powered by Customer AI, focusing on delivering personalized and efficient customer service solutions. The Staff Software Engineer will play a crucial role in defining the future of customer service through the application of generative AI, leading high-impact projects, and collaborating with product teams to create innovative systems.
Artificial Intelligence (AI)Customer ServiceInformation TechnologySaaSSoftwareTechnical Support
Responsibilities
Lead Major AI & Automation Initiatives Architect and drive high-impact projects involving LLMs, embeddings, RAG, agentic workflows, and more
Ship Real Products Build features that move from idea to production quickly—often with direct input from leading customers like Crate & Barrel and REI
Design Foundational Systems Create scalable infrastructure and reusable components that power teams across Gladly
Collaborate Closely Work shoulder-to-shoulder with product managers, designers, and customer-facing teams to solve meaningful problems
Drive Innovation Stay on the cutting edge of AI, evaluate new tools and models, and continually introduce new best practices at Gladly
Qualification
Required
5-10+ years of full-stack engineering experience, including large-scale product development and team leadership
A proven ability to turn ambiguous ideas into shipped product, especially in early-stage, 0-to-1 settings
A passion for AI and automation—you stay current on the latest trends and are eager to apply them creatively
Deep experience, or willingness to learn, TypeScript, React, Go, and PostgreSQL
Strong communication and collaboration skills—you're as comfortable mentoring as you are coding
A customer-centric mindset—you care about what you're building and who you're building it for
A data-driven approach—you use metrics and insights to guide decisions and measure impact
Preferred
Hands-on experience with LLMs (OpenAI, Claude, etc.), embeddings, vector search, RAG pipelines
Familiarity with operational monitoring tools like DataDog, SumoLogic, and LangSmith
Open-source work, public talks, or thought leadership in AI or engineering
Benefits
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
Company
Gladly
SaaS Customer Service AI Platform
Founded in 2015San Francisco, California, USA
51-200 employees
H1B Sponsorship
Gladly has a track record of offering H1B sponsorships. Please note that this does not
guarantee sponsorship for this specific role. Below presents additional info for your
reference. (Data Powered by US Department of Labor)
Distribution of Different Job Fields Receiving Sponsorship
Represents job field similar to this job
Trends of Total Sponsorships
2025 (3)
2023 (1)
2022 (2)
2021 (2)
2020 (2)
Funding
Current Stage
Late StageTotal Funding
$208MKey Investors
AVPRiverwood CapitalNotable Capital
2024-09-26Series Unknown· $40M
2022-12-14Series Unknown· $55M
2019-01-29Series D· $50M
Leadership Team
Dirk Kessler
Co-Founder
Todd Rakow
Chief Financial Officer
Recent News
Greylock
2025-12-03
2025-12-03
2025-10-24
Company data provided by crunchbase