Staff Software Engineer - AI Applications - Remote

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. If you’re excited to tackle hard problems, move quickly, and see your work shape both an industry and a growing startup, we’d love to meet you.

Job Summary

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 here 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

• Machine learning and AI: You are passionate and knowledgeable about the current and future state of AI.

  • You will be utilizing existing Large Language Models to build applied AI applications focused on producing high accuracy rates. Your software engineer skills will come into play here as you'll take ownership in constructing services to ingest results.

  • You will work with product, and engineering teams and build models/services that can ingest data, extract key information and surface insights.

  • You can build tooling to support model training, evaluation, inference serving, monitoring and alerting.

  • You want to use the latest ML frameworks and open source tools to develop new model training pipelines.

• Hands On Coding: You have direct experience with software engineering and are familiar with modern languages like Python, Javascript, Go, Rust

  • You have experience building microservices and understand the tradeoffs of the approach.

• Data handling: You can identify, extract, transform, and load data from disparate sources into a centralized system. You are able to normalize, cleanse, and validate this data.

• Database management: You are able to design and implement schemas, optimize queries, and manage database performance.

• Project management: You must be an effective self-organizer: prioritize tasks, manage resources, and communicate effectively with non-technical stakeholders.

• Collaboration: We are one team. You must be able to collaborate with engineers, subject matter experts, product managers, and designers to ensure the success of projects.

Qualifications

• Bachelor's degree in Computer Science, Engineering, a related field, or equivalent practical experience.

• 8+ years 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 the ability to design, train, and implement machine learning models and use natural language processing techniques for automation.

• Production experience with scalability and best-practices of AI infrastructure.

• Must have experience with AI observability, monitoring, and signaling using tools like LangChain or LangGraph.

• Hands-on experience using RAG and chunking to tune LLM performance.

• Experienced 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.

• Candidates must be legally authorized to work in the United States without the need for sponsorship now or in the future. Vanilla is unable to provide visa sponsorship at this time.

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. You love 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. You should be comfortable building production-ready software, integrating AI models into applications, designing APIs, and working with databases. If your experience is mostly in research, data modeling, or experimentation without deploying AI-driven applications, this may not be the right fit.

• You prefer working in highly structured, slow-moving environments. At Vanilla, we move fast and iterate quickly.

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.

• 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 

Vanilla Technologies Inc. (dba "Vanilla") provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.

Vanilla participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S.