Staff Software Engineer - AI Applications - Remote

About Us

We’re a startup with big ambitions: to make estate planning modern, visual, and intelligent. Vanilla is the first AI-powered estate advisory platform, built by advisors, planners, and attorneys to transform how wealth is transferred across generations. Our technology unifies scenario modeling, client visualization, and document creation into one seamless, digital experience. Our team brings together diverse subject matter expertise across estate planning, wealth management, and scaling SaaS startups. We’re distributed across the U.S., with a mix of fully remote and hybrid roles, and we embrace flexibility while staying closely connected. At Vanilla, you’ll join curious builders and problem-solvers who thrive on speed, autonomy, and impact. Here, you won’t just join a company, you’ll help create it.

About the Role

Vanilla is seeking a Staff Software Engineer - AI Applications with a strong background in software development, data science, machine learning, and artificial intelligence. You will be utilizing existing Large Language Models to build applied AI applications focused on producing high accuracy rates. Your software engineering skills will come into play as you’ll take ownership in constructing services to ingest structured results. If you’re a proactive problem-solver who lives to disrupt archaic processes with cutting-edge technology, this is the job for you. As a Staff Software Engineer, you will work collaboratively with engineering and subject matter experts to find innovative and disruptive uses of AI to streamline (or replace) workflows.

Responsibilities

• Utilize existing Large Language Models to build applied AI applications focused on producing high accuracy rates, constructing services to ingest results.
• Work with product and engineering teams to build models/services that can ingest data, extract key information, and surface insights.
• Build tooling to support model training, evaluation, inference serving, monitoring, and alerting using the latest ML frameworks and open-source tools.
• Develop new model training pipelines and maintain hands-on coding experience with modern languages like Python, JavaScript, Go, or Rust.
• Build and maintain scalable microservices, understanding the tradeoffs of this architecture.
• Identify, extract, transform, and load data from disparate sources into a centralized system, normalizing, cleansing, and validating this data.
• Design and implement database schemas, optimize queries, and manage database performance.
• Prioritize tasks, manage resources, and communicate effectively with non-technical stakeholders as an effective self-organizer.
• Collaborate with engineers, subject matter experts, product managers, and designers to ensure project success.

Requirements

• Bachelor's degree in Computer Science, Engineering, a related field, or equivalent practical experience.
• 8+ years of relevant work experience.
• Proficiency in modern programming languages such as Python or JavaScript.
• Experience with OpenAI, Anthropic, or similar for both chat and API interfaces.
• Deep understanding of machine learning and AI technologies, including designing, training, and implementing machine learning models and using natural language processing techniques for automation.
• Production experience with scalability and best practices of AI infrastructure.
• Experience with AI observability, monitoring, and signaling using tools like LangChain or LangGraph.
• Hands-on experience using RAG and chunking to tune LLM performance.
• Experience with LLM orchestration tooling and decision frameworks.
• Experience or exposure building agentic capabilities and workflows.
• Experience or exposure to evaluation testing frameworks.
• Ability to effectively articulate technical challenges and solutions.
• Deal well with ambiguous/undefined problems; ability to think abstractly.
• Knowledge of professional software engineering practices & best practices for the full software development life cycle, including coding standards, code reviews, source control management, build processes, testing, and operations.
• Legally authorized to work in the United States without the need for sponsorship now or in the future.

You Might Be a Great Fit If:

• You have hands-on experience with AI and Large Language Models (LLMs).
• You’ve worked with OpenAI, GPT models, or other similar technologies and have integrated them into real-world applications.
• You are a critically thinking software engineer.
• You have built and maintained scalable microservices and understand the tradeoffs of this architecture.
• You can build AI-powered applications with high accuracy.
• You understand the challenges of AI implementation and know how to optimize models, fine-tune them, and create efficient pipelines for training, evaluation, and deployment.
• You are a problem-solver and innovator who loves tackling undefined, ambiguous problems and applying AI to disrupt outdated processes.
• You’re excited about revolutionizing estate planning with cutting-edge technology.

You May Not Be a Great Fit If:

• You are primarily a data scientist or ML researcher, rather than a software engineer. While AI and machine learning are key components of this role, we need a strong application developer first.
• Your experience is mostly in research, data modeling, or experimentation without deploying AI-driven applications.
• You prefer working in highly structured, slow-moving environments. At Vanilla, we move fast and iterate quickly.

Pay

The salary range for this role is $190,000 to $210,000. Our compensation packages also include a performance-based bonus and equity. Compensation is based on a number of factors including market location and may vary depending on job-related knowledge, skills, and experience.

Benefits

• Flexible paid time off policy and 10 company-wide paid holidays.
• Parental leave: 6 weeks for all full-time employees and up to 14 weeks for birthing parents.
• Medical, dental, and vision benefits coverage for employees and their families.
• 401K eligibility after one month of employment.
• Free estate planning documents.
• Budget for learning & development and home office setup.
• Paid parking or transit for hybrid and in-office employees.