Senior AI Engineer, Gladly
$134-167k
+ Equity
Customer service platform
Posted today
Customer service platform
201-500 employees
Posted today
$134-167k
+ Equity
201-500 employees
Company mission
To make customer service radically personal.
Role
Who you are
- 5+ years of experience developing data-powered products, ideally as an AI engineer, data scientist, or applied ML specialist
- Proven ability to design, prototype, and iterate on algorithms that deliver customer or business value
- Strong fluency in Python and SQL, with hands-on experience in data manipulation, modeling, and visualization
- Deep understanding of machine learning techniques and their practical tradeoffs, with a growing knowledge of emerging GenAI capabilities
- A track record of influencing product direction with your insights and solutions
- A product mindset—you view technology as a tool to improve experience, not an end in itself
- Experience working closely with product managers, designers, and engineers to shape roadmaps and ship impactful features
- A growth-oriented approach to learning new domains, technologies, and tools
What the job involves
- At Gladly, the AI Research team is at the heart of designing intelligent systems that transform how customer service is delivered
- We combine data, experimentation, and algorithmic thinking to power innovative AI solutions and help shape product direction through deep analytical insights
- We're looking for an AI Engineer—someone who thrives at the intersection of data science, product thinking, and engineering
- You’re curious, hands-on, and driven to create practical solutions that address real customer problems
- You don’t stop at analysis—you prototype, experiment, and iterate with purpose, always guided by business impact and customer experience
- Lead with insights: Partner with product, engineering, and design to frame problems, define success metrics, and identify data-driven opportunities for innovation
- Explore with intent: Conduct robust exploratory data analysis and experiments to uncover patterns, validate hypotheses, and guide strategic decisions
- Prototype with purpose: Design and prototype novel algorithms—including GenAI-driven features—that improve automation, customer experience, and agent productivity, taking ideas from concept to production
- Drive algorithm development and iteration: Collaborate closely with engineers to translate prototypes into production-ready systems, and refine models based on real-world performance and feedback
- Promote best practices through collaboration and mentorship: Share insights, lead code and research reviews, and guide others in adopting scalable, repeatable approaches to building AI-powered solutions across the product lifecycle
- Champion the customer: Ensure every solution delivers measurable value to our users and aligns with our business goals
- You’ll be successful by
- Thinking like a builder: You treat every analysis, model, and algorithm as part of a larger product system with real users and business stakes
- Working autonomously with impact in mind: You self-organize and prioritize your work based on what drives the most value for customers and the business—not just what’s technically interesting
- Being deeply curious: You dive into product code, data pipelines, and behavioral data to understand the "why" behind the numbers
- Balancing rigor and velocity: You know when to explore, when to iterate, and when to ship
- Leading with clarity: You can distill complex findings into compelling stories that drive decisions
- 30 Days: Get hands-on with the data and our platform; deliver an impactful analysis in one product area
- 60 Days: Lead exploratory initiatives and start prototyping algorithms for customer-facing features
- 90 Days: Ship production-ready components for AI products, backed by experiments and performance validation
Application process
- 2 hour timed case study
- Basic SQL (45min)
- Programming screen (45 min)
- Discussion of a past data science project (60 min)
- Experimental design and data interpretation interview (60 min)
- Gladly product demo and discussion (45 minutes)
- Presentation and Q&A (30 min)
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 6 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
- Wellness and home office stipends
Company HQ
Bernal Heights, San Francisco, CA
Leadership
Dirk Kessler
(Co-Founder)They were a Senior Software Engineer at Claris and Architect for 4 years at FileMaker. They also were the Principal Engineer at Vontu. Worked at Symantec for 7 years, leaving as Distinguished Engineer. They were also an Entrepreneur in Residence at Greylock Partners.
Michael Wolfe
(Co-Founder & CPO)Current Portfolio Advisor at Point Nine Capital. They worked as a Developer at Goldman Sachs and as Director of Engineering at iPro+. Previously a VP of Engineering at Kana Communications. Co-founded Vontu and was CEO of Pipewise.
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