Staff Engineer – Conversational AI

About Grayscale:

At Grayscale, we believe the best frontline experience is powered by conversation—not forms or clunky software, but a simple text or WhatsApp message from your phone. Our conversational software automates critical hiring tasks like screening, interview scheduling, and onboarding, delivering a seamless frontline experience throughout the employee lifecycle. Trusted by leading brands like Hershey's, DICK'S Sporting Goods, and Walgreens, Grayscale is revolutionizing the way companies engage with their frontline teams.

About the Role:

We’re hiring a Staff Engineer to lead development of AI-powered product features built on large language models (LLMs). This is not a machine learning research role — it’s a hands-on engineering position focused on building production-grade applications powered by LLMs via services like AWS Bedrock.You’ll be responsible for designing and implementing new capabilities from the ground up, including conversational workflows, retrieval-augmented generation (RAG), and real-time AI interactions that deliver measurable value to our customers in HR tech. You’ll also guide architecture decisions, mentor engineers, and help shape the future of our AI roadmap.

• AI-Powered Feature Development: Build new end-user features leveraging LLMs (via AWS Bedrock), prompt engineering, and retrieval-augmented generation (RAG) patterns.
• System Design & Architecture: Lead architectural planning for scalable AI-backed systems and APIs, with attention to performance, cost-efficiency, and reliability.
• Rapid Prototyping: Translate product ideas into working prototypes quickly, iterating alongside product and design.
• Cross-Functional Collaboration: Partner with Product, Design, and Support to define requirements, shape user experiences, and ship impactful AI features.
• Mentorship: Provide technical guidance and mentorship to engineers across the team.
• Operational Support: Contribute to system reliability through well-instrumented code, thoughtful monitoring, and on-call participation when needed.

• 7+ years of software engineering experience building complex, user-facing products.
• Experience building and deploying LLM-powered features using services like AWS Bedrock, OpenAI, or similar.
• Familiarity with retrieval-augmented generation (RAG), vector databases, and embedding techniques. Experience with orchestration frameworks like Langchain is a plus.
• Strong backend experience (Ruby on Rails preferred) and API design (REST, GraphQL).Strong product sense and a track record of building features from 0 to 1.
• Comfort working in a fast-paced startup environment and balancing short-term execution with long-term thinking.
• Experience mentoring engineers and driving cross-functional technical initiatives.

• Backend: Ruby on Rails, PostgreSQL, Redis, Sidekiq, Shoryuken, Protobuf
• Frontend: React, Tailwind CSS
• LLM & AI Tools: AWS Bedrock, Claude
• Infrastructure: AWS ECS, EC2, S3, Kinesis, CloudWatch, Route 53, Elasticsearch
• Messaging & Pipelines: AWS SQS, AWS Kinesis
• Tooling: GraphQL (Apollo), Semaphore, GitHub, Datadog, Zoom, Slack

• Driven By Our Values: Our core values shape everything we do. We strive to Make Each Other Better by cultivating a growth mindset and practicing radical candor, ensuring that both our team and our customers continually level up. We’re committed to Trailblazing, finding the right balance between optimism and reality, and embracing the challenges ahead with a can-do attitude. And we strive to take Ownership of our work, acting with integrity, urgency, and a deep sense of personal responsibility.
• Capital-Efficient Growth: Grayscale is a capital-efficient business with a clear line of sight to becoming cash flow positive. We’re growing in a fast-paced, healthy, and sustainable manner, supported by a board and investors who believe in our vision and approach. Our lean and agile structure allows us to make impactful decisions quickly, driving the business forward without unnecessary bureaucracy.
• Balanced and Supportive Environment: We value family, balance, and personal growth. At Grayscale, you’ll find a culture that supports your professional development while also respecting your time and commitments outside of work. We believe that when our team members thrive personally, they bring their best selves to work.
• Impactful Work with Leading Brands: Join a team that is revolutionizing the frontline experience for some of the world’s most recognized brands like QuikTrip, Northrop Grumman, and Chewy. Your work will directly impact how these companies engage with their frontline teams, creating more meaningful and effective interactions.

Does this sound like you? If so, drop us a line and say hello! 👋

Every voice, every perspective matters. That’s why Grayscale is proud to be an equal opportunity employer. We do not discriminate on the basis of race, color, ethnicity, religion, national origin, sexual orientation, age, citizenship status, marital status, disability, gender identity, gender expression, or veteran status.