Senior AI Engineer

About Sybill:

At Sybill.ai, we're building the next evolution in B2B sales – an AI-first platform that transforms how sellers work. Think of it as your intelligent sales IDE (Integrated Deal Environment), empowering sellers to focus on what truly matters: building relationships and closing deals.

Today, sellers spend 70% of their time on non-revenue activities. We're flipping this paradigm on its head. Sybill's AI lets sellers become super-performers who guide AI systems and focus on high-impact customer interactions.

Our proprietary AI technology, developed by a small but mighty team from Stanford, Harvard, and the IITs, and backed by leading investors in Silicon Valley, is not just another tool; it serves as the foundation of a groundbreaking sales workflow that delivers exceptional outcomes for our users. With 99%+ retention and 20x growth to $1.2M ARR last year, our customers' enthusiasm speaks for itself.

Who Thrives at Sybill?

We're looking for ambitious individuals who:

• Are excited to create a new way of working for today’s top sellers

• Can run with projects independently - you won't have someone looking over your shoulder

• Aren’t afraid to try new approaches; are candid about wins and own mistakes, and learn from both

• Get excited about big goals, but also know how to break them down and execute

• Understand that some weeks are intense - we're building something ambitious and that takes real work

Our commitment to you: We believe Sybill should be your biggest career accelerant yet. We'll deliver on this by tackling hard problems together, giving you real ownership, and pushing you to grow beyond your comfort zone. If you're ready to match this ambition with your own drive, we should talk.

The Opportunity:

At Sybill, we're building an AI co-pilot that's transforming how B2B sales is done. As a Senior AI Engineer, you'll architect and implement sophisticated retrieval-augmented generation (RAG) systems that power our sales co-pilot, making it feel like every seller has a seasoned sales mentor by their side. You'll drive continuous innovation by incorporating cutting-edge AI advancements, running rapid experiments, and iterating based on real user feedback to create truly magical experiences for our users.

What You'll Be Doing:

• Design and implement end-to-end RAG systems that power our deals knowledge database and co-pilot features

• Architect an agentic system that autonomously plans and orchestrates multi-tool workflows

• Architect sophisticated retrieval systems that surface contextually relevant sales information in near real-time

• Build robust evaluation frameworks to continuously measure and improve our AI system performance

• Design and optimize vector databases and embedding systems for efficient information retrieval

• Collaborate with product and engineering teams to design AI features that solve real sales pain points

• Drive technical decisions around model selection, deployment strategies, and AI feature implementation

• Stay on top of the latest developments in AI and rapidly prototype new capabilities

• Build monitoring systems to track model performance, costs, and reliability metrics

• Use modern developer tools like Cursor and CoPilot to maximize productivity

Who You Are:

• Deep experience architecting end-to-end AI systems that combine multiple components; LLMs, hybrid search indexes (lexical, vector, and knowledge graphs)

• Track record of optimizing retrieval systems for both accuracy and performance at scale

• Strong software engineering foundation with expertise in Python and modern AI/ML infrastructure

• Proven track record in prompt engineering for complex use cases

• Data-driven mindset with experience in designing metrics and evaluation frameworks for AI systems

• Bias for action and ability to move fast while maintaining high-quality standards

• Strong user empathy and collaboration skills with the ability to work across product, engineering, and customer-facing teams

Qualifications:

• 5+ years of software engineering experience, with at least 2 years focused on RAG and AI copilot systems

• Strong experience with vector databases (e.g., Pinecone, Weaviate) and embedding models

• Strong proficiency in Python and modern AI infrastructure

• Advanced degree (MS/PhD) in Computer Science or related fields strongly preferred

• Proven track record of delivering multiple complex backend systems or features as an individual contributor.

• Proven ability to architect real-time AI systems that combine multiple data sources and models

• Experience with fine-tuning language models is a nice-to-have

• Experience with cloud platforms (AWS preferred) and scalable AI service deployment

• Exposure to or experience with B2B products is highly preferred.

• A proven track record of thriving in early-stage startup environments, showing resilience and flexibility in the face of uncertainty.

What We Offer:

• Competitive compensation: $180,000 - $210,000 + comprehensive Health/Dental/Vision insurance + equity in a rapidly growing startup

• AI Innovation Playground: Create magical experiences that make sellers feel like they have a secret superpower

• Direct Impact at Scale: Your AI systems will transform how thousands of sellers work, directly driving our 20x growth

• Rapid Innovation Cycles: See your AI experiments go from idea to production in days, not months

• Customer-Driven AI: Work directly with users to understand their needs and create "wow" moments through AI

• Research to Reality: Transform cutting-edge AI concepts into features that sellers can't live without

• Engineering Excellence: Build on our battle-tested AI infrastructure while pushing the boundaries of what's possible

If you're energized by executing ambitious technical projects and seeing your code transform how sales teams operate, join us in building the future of B2B sales.