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. 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.

Working Location

This role is a remote position, you must be based out of one of the following states: Arizona,California, Colorado, Connecticut, Florida, Georgia, Idaho, Illinois, Kentucky, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah or Washington

Job Summary

We’re looking for a Senior Product Manager to lead and evolve our estate planning platform. This is a uniquely impactful role: you’ll define how advisors interact with the estate platform in order to service their customers.

This is a high-ambiguity environment. You’ll be building new capabilities across our AI powered product, document creation, platform and core application. Success requires balancing user needs, model behavior, legal constraints, and business priorities—often with incomplete information.

Responsibilities

• Translate high-level direction into clear, buildable scopes without waiting for perfect inputs

• Partner with product leadership on priorities, then own the execution end-to-end

• Write crisp, detailed requirements and user stories that anticipate edge cases, failure states, and dependencies

• Work closely with engineering to break work down, remove blockers, and keep momentum high

• Define success metrics and build lightweight dashboards or queries to monitor them

• Lead discovery yourself—interviews, workflow mapping, quick validation loops

• Collaborate with design to rapidly prototype, test, and refine interaction patterns

• Identify opportunities for simplification across the product workflows and contribute to architectural cleanup

• Champion AI internally by using it in your workflow and helping teammates adopt AI-first processes

• Find valuable ways to embed AI into the product experience to delight our customers.

• Drive alignment across engineering, design, and GTM so shipped work stays coherent and connected

• Ship quickly, measure, learn, and iterate

Required Qualifications

• 5+ years in product management, with direct ownership of shipping features

• Experience working with commercial SaaS products, including embedded AI - ideally with hands-on familiarity (prompting, testing models, using AI tools to validate assumptions)

• Comfortable turning messy, ambiguous problem spaces into structured, incremental delivery plans

• Demonstrated ability to work closely with engineering and understand tradeoffs (latency, accuracy, model behavior, retrieval constraints)

• Demonstrable use of AI tools in your own workflow (analysis, spec writing, research, QA)

• Strong analytical skills and comfort working directly with data (SQL, Mixpanel, Looker, or similar is a plus)

• Excellent written communication—you can write fast, clearly, and with enough precision for engineers to execute

• Experience at startups, scale-ups, or any environment where velocity and autonomy matter

• Experience in a SaaS company shipping commercial grade software

Preferred Qualifications

• Familiarity with LLMs, associated architectures, or prompt engineering at a working level

• Exposure to or experience in fintech, wealthtech, or regulated industries

• Background in B2B SaaS serving professional users (advisors, attorneys, accountants)

• You've worked in high demand and velocity environments

✅ You Might Be a Great Fit If

• Curious by default. You dig into how things work, especially when they're new.

• Comfortable with "we don't know yet" as a starting point.

• Direct. You say what you think, ask hard questions, and don't hide behind process.

• Bias toward action. You'd rather ship and learn than wait for perfect information.

• Grounded. You care about users, not just features

The salary range for this role is $170,000 to $180,000. Our compensation packages also include a performance based bonus and equity. Compensation is based on a number of factors 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 

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.

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. 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.

Working Location

This role is a remote position, you must be based out of one of the following states: Arizona, California, Colorado, Connecticut, Florida, Georgia, Idaho, Illinois, Kentucky, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah or Washington

Job Summary

As the Sr. Engineering Manager at Vanilla, you’ll be a true player/coach — a hands-on technical leader who spends a meaningful share of each week in the codebase alongside your team. You’ll write and review code, design and debug systems, and set the technical bar by example, while also leading a small team of engineers, providing direction, and supporting their growth. This is not a hands-off, manager-of-managers role: you’ll pair with engineers, pick up meaningful work in critical or ambiguous areas, and stay close enough to the details to make sharp technical calls. It demands a leader with deep, current technical skills, strong leadership instincts, and a passion for building great software in a fast-paced, start-up environment.

Responsibilities

• Stay hands-on in the code contribute directly to the codebase—writing production code, reviewing PRs, and picking up meaningful work in critical, complex, or ambiguous areas. You lead by doing, not just directing.

• Set the technical bar by example architect and implement scalable solutions, drive strong engineering practices, and raise quality through the work you personally ship and the reviews you give.

• Coach and grow engineers through the work pair, mentor, and unblock your team in the moment. Support their professional development while creating a culture of accountability, autonomy, and learning.

• Lead end-to-end delivery balance speed with technical quality, bring clarity to complexity, and champion scalable design principles across your team’s work.

• Drive technical and product strategy align engineering execution with the company’s broader business goals and customer needs, and help architect solutions that scale both technically and operationally.

• Improve how the team builds implement systems, tools, and processes that improve development velocity, quality, and collaboration—often by prototyping the improvement yourself.

• Serve as a critical cross-functional partner work with product, design, marketing, sales, and support to align roadmaps, unblock execution, and ensure customer-centric outcomes.

• Support pre-sales and customer onboarding help technical stakeholders understand product capabilities, dig into integration details when needed, and ensure feedback from the field informs the roadmap.

• Coordinate external integrations and platform partnerships manage stakeholder expectations and, where it counts, get hands-on to ensure secure, seamless implementation.

• Define and own engineering metrics and KPIs drive continuous improvement in product quality, team performance, and operational efficiency.

• Collaborate with Legal and Security teams uphold compliance, privacy, and regulatory standards across all systems.

• Adopt the vanilla AI SDLC and scale it throughout the team and organization. Continually evolve use of AI for product delivery as capabilities become available.

Qualifications

• 8+ years of professional engineering experience, including recent, current hands-on coding, with 3+ years leading engineers as a hands-on technical lead or player/coach engineering manager.

• Demonstrated ability to operate as a player/coach—comfortable splitting your time between shipping code and leading people, and energized by both.

• A track record of building and scaling complex software systems at high-growth SaaS companies or startups, as a direct contributor and not only as an overseer.

• Deep, current technical skills—you can jump into the codebase, reason about architecture, and debug hard problems yourself.

• Strong operational instincts; you’re process-oriented, data-driven, and focused on systems that enable high-leverage execution.

• Experience influencing product architecture and engineering strategy through a systems-thinking lens.

• Comfort navigating ambiguity and working autonomously in a fast-paced environment.

• Strong communication and leadership skills; you excel at guiding technical discussions and aligning diverse stakeholders.

• Prior experience in pre-sales engineering roles is highly valued.

• Project management experience, particularly in fast-paced or cross-functional environments, is a strong plus.

• Bachelor’s degree in Computer Science, Engineering, or equivalent practical experience.

The salary range for this role is $180,000 to $210,000. Our compensation packages also include a performance based bonus and equity. Compensation is based on a number of factors 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 

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.

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. 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.

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 

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.

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. 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.

Working Location

This role is a remote position, you must be based out of one of the following states: Arizona, California, Colorado, Connecticut, Florida, Georgia, Idaho, Illinois, Kentucky, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah or Washington

Job Summary

As a Customer Success Manager (CSM) at Vanilla, you will be the primary point of contact for our customers, helping them maximize the value of our products and services. You will play a key role in onboarding new clients, driving meaningful product adoption, and identifying opportunities for growth.

We’re looking for a customer-centric, proactive, and strategic thinker who thrives in a fast-paced environment and is passionate about building lasting client relationships. Your insights and collaboration with internal teams will directly contribute to improving customer experiences and enhancing our products.

Responsibilities:

• Guide customers from onboarding through long-term adoption, ensuring they achieve their business goals with Vanilla’s solutions.

• Create and manage Customer Success Plans (for simple accounts) and Strategic Customer Account Plans (for complex accounts) that outline customer goals, key metrics, and opportunities for growth.

• Own the renewal process, identifying expansion opportunities and mitigating potential churn.

• Act as the voice of the customer, gathering insights and collaborating with Product, Sales, and Support teams to improve customer experiences.

• Implement and refine tools and processes that enhance customer engagement, track client health scores, and improve overall satisfaction.

• Work closely with Sales, Product, and Leadership to align customer needs with company strategies.

• Contribute to a company-wide mindset that prioritizes customer obsession and long-term relationships.

Required Qualifications:

• 5+ years of experience in Customer Success, Account Management, or related B2B SaaS roles.

• Proven track record of driving customer retention, renewals, and account growth through consultative engagement.

• Experience developing success plans and customer-facing resources that align with business objectives.

• Strong understanding of the customer lifecycle with demonstrated ability to meet or exceed revenue targets.

• Proficiency with CRM and customer success tools (e.g., Salesforce, Totango, Gainsight, or equivalent).

• Analytical and problem-solving skills: able to use data to measure customer health, identify risks/opportunities, and resolve escalations effectively.

• Cross-functional collaboration experience: skilled at being the voice of the customer and influencing product, sales, and support initiatives.

• Process improvement mindset with experience optimizing tools and workflows for scalability.

• Excellent communication and relationship-building skills with high emotional intelligence and empathy.

• Adaptability and tech-savviness: comfortable learning new tools quickly and thriving in a fast-paced, high-growth environment.

Preferred Qualifications:

• 3+ years of experience in financial services or wealth management, with a strong understanding of industry-specific client needs.

• Familiarity with regulatory and compliance considerations relevant to financial services clients.

• Background in managing high-value or complex client relationships in a regulated industry.

The salary range for this role is $110,000 to $130,000. Our compensation packages also include a performance based bonus and equity.  Compensation is based on a number of factors 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 

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.