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 Pooled Customer Success Manager (CSM) at Vanilla, you’ll be part of a shared Customer Success team supporting a large portfolio of lower-ACV or smaller-license clients. You’ll manage customer outcomes across multiple accounts rather than owning a dedicated book of business.

Reporting to the Senior Director of Customer Success, you’ll focus on efficient onboarding, scalable adoption, proactive retention, and operational excellence. This role is well-suited for a Customer Success professional who excels in structured, team-based environments and enjoys influencing customer retention, adoption, and overall satisfaction at scale.

Responsibilities:

• Manage a shared portfolio of customers, focusing on engagement, adoption, and retention through standardized playbooks.

• Execute automated and trigger-based success plays — including onboarding workflows, adoption nudges, and renewal reminders.

• Monitor account health scores and usage data to identify at-risk customers and drive proactive outreach.

• Support the renewal motion by managing assigned renewal pods or time-based cohorts, ensuring timely communication and coordination with Sales.

• Collaborate cross-functionally with Support, Product, and Marketing to improve the customer experience and surface product insights.

• Contribute to the development and improvement of CS processes, templates, and automation tools for scalable success delivery.

• Document customer interactions and health indicators in CRM systems to maintain full visibility and accountability within the team.

• Track and report portfolio metrics (health, retention, engagement) to drive continuous improvement.

• Act as the voice of the customer, advocating for needs and sharing patterns with leadership to inform strategy.

Required Qualifications:

• 2+ 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.

• Demonstrated ability to manage a high volume of customer accounts with strong attention to detail and prioritization.

• Solid understanding of customer retention principles and how to influence renewal outcomes at scale.

• 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:

• 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 $90,000 to $120,000. 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, 4 weeks for all full-time employees and up to 12 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

We’re looking for a Senior Product Manager to lead and evolve VAI, the intelligence layer that powers our AI-driven experiences. This is a uniquely impactful role: you’ll define how advisors interact with AI, how the system handles uncertainty, and how we build trust in an industry where accuracy truly matters.

This is a high-ambiguity environment. You’ll be building new capabilities across our abstraction workflows, document experiences, and AI-powered inputs. 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 VAI workflows and contribute to architectural cleanup

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

• 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 AI or ML-enabled products, 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)

• Confident using 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, RAG architectures, or prompt engineering at a working level

• Experience in fintech, wealthtech, or regulated industries

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

• You've worked on trust and accuracy problems—where getting it wrong matters

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, 4 weeks for all full-time employees and up to 12 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

As the Sr. Engineering Manager at Vanilla, you will lead a dynamic team of engineers, provide technical direction, foster collaboration across various teams within the company and support the professional growth of your team members. This role demands a leader with a solid technical foundation, outstanding leadership abilities, and a passion for nurturing innovation in a fast-paced, start-up environment.

Responsibilities

• Drive technical and product strategy by aligning engineering execution with the company's broader business goals and customer needs. You’ll help architect solutions that scale both technically and operationally.

• Lead end-to-end delivery, balancing speed with technical quality. You bring clarity to complexity and champion scalable design principles.

• Act as a key operational leader, implementing systems, tools, and processes that improve development velocity, quality, and collaboration across teams.

• Mentor and grow high-performing engineers, supporting their professional development and creating a culture of accountability, autonomy, and learning.

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

• Support pre-sales conversations and customer onboarding, helping technical stakeholders understand product capabilities and ensuring feedback loops from the field inform our roadmap.

• Coordinate external integrations and platform partnerships, managing stakeholder expectations and ensuring secure, seamless implementation.

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

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

Qualifications

• 8+ years of professional engineering experience, with 3+ years in an engineering management role or technical program management role.

• A track record of building and scaling complex software systems at high-growth SaaS companies or startups.

• 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, 4 weeks for all full-time employees and up to 12 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, 4 weeks for all full-time employees and up to 12 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 Senior 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 Senior 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 drive technical vision and leverage open source technologies and cloud services to build an AI/ML platform.

  • 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.

• 6+ years relevant work experience.

• Proficiency in, at least, one modern programming language such as Python or Javascript.

• Experience building commercial SaaS solutions.

• Experience integrating with backend services, and APIs.

• 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.

• Experience with tuning AI performance and scalability of AI infrastructure.

• Preferred experience with AI observability, monitoring, and signaling with tools such as LangChain or LangGraph.

• Experienced with LLM orchestration tooling and decision frameworks.

• Experience or exposure building agentic capabilities and workflows.

• Experience or exposure to evaluation testing frameworks.

• Exceptional candidates will have direct experience with RAG for tuning LLMs.

• Experience with API design and accessing data from external sources.

• 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 $160,000 to $190,000. 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, 4 weeks for all full-time employees and up to 12 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 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 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.

• 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.

• 4+ years relevant work experience.

• Proficiency in, at least, one modern programming language such as Python or Javascript.

• Experience integrating with backend services, and APIs.

• Experience with OpenAI, Anthropic, or similar for both chat and API interfaces.

• 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.

• Experience with tuning AI performance and scalability of AI infrastructure.

• Bonus experience with AI observability, monitoring, and signaling with tools such as LangChain or LangGraph, or experience with RAG for tuning LLMs.

• Experience with API design and accessing data from external sources.

• 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 $130,000 to $160,000. 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, 4 weeks for all full-time employees and up to 12 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

We're looking for a Security GRC Program Manager to own our customer trust, security compliance, and assurance programs. As our first hire in this role, you'll build the operational backbone that lets us ship reliably while maintaining the trust of customers who depend on us with their most sensitive financial and estate planning data.

You’ll own our customer trust program, assist with coordination of our SOC 2 program and audits, coordinate customer security diligence responses, and enable our enterprise sales motion through customer-facing security conversations and documentation. You’ll run point on customer DDQ and RFP responses, establishing scalable processes that enable fast, accurate, and consistent turnarounds.

This means spending your time running SOC 2 audit cycles, building and scaling trust and compliance processes, responding to customer security questionnaires, and translating between engineering teams, auditors, customers, and leadership. You’ll work closely with the CTO, Chief Legal Officer, Security Engineer, and Revenue teams to make compliance and customer trust strategic advantages rather than overhead.

This role is ideal for someone who thrives at the intersection of technical program management and security compliance, enjoys building foundational programs, and wants high-impact visibility at a Series B company where customer trust is a competitive differentiator.

Responsibilities

• Lead customer due diligence questionnaire (DDQ) and RFP response process and third-party risk management process; track and manage high volume of DDQ and RFP requests. Coordinate and collaborate with internal teams to meet tight deadlines. Handle a high volume of requests and interactions in a fast-paced environment

• Support enterprise sales with technical customer security discussions

• Lead SOC 2 Type II audit preparation, evidence collection, and remediation

• Conduct third party vendor security assessments, collaborate on third party risk management processes

• Implement and manage third party tool and new processes to create efficiencies

• Develop the security narrative and conduct security reviews for new product functionality to enable GTM

• Review and negotiate security and compliance language in customer contracts in collaboration with Legal team

• Build and manage Trust Center integrations and public-facing security documentation in collaboration with Legal team

• Build customer-facing compliance artifacts (security whitepapers, certifications)

Skills

• Minimum of 5 years in a technical and/or security role with customer facing experience

• Minimum of 3 years experience in program management, customer trust, or DDQ/RFP management within the tech industry with highly regulated customers

• Proven track record in driving security processes and operational plans

• Requires strong attention to detail, organizational skills, good judgement, and the ability to prioritize tasks, manage timelines, and meet tight deadlines

• Strong contract review and negotiation skills related to security and compliance

• Knowledge of security risks, vulnerabilities, and threat management

• Background in supporting customer audits and engagements

Nice to Have:

• Experience in fintech, healthtech, or regulated industries

• Prior experience at Series B-D companies scaling security compliance programs

• Demonstrable experience implementing tools to drive and streamline DDQ processes

The salary range for this role is $135,000 to $150,000. 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, 4 weeks for all full-time employees and up to 12 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, Rhode Island, South Carolina, South Dakota, Texas, Utah, Virginia, Washington

Job Summary

We’re looking for a Senior Product Marketing Manager to own how our products are positioned, launched, and adopted in the market. You’ll sit at the intersection of Product, Sales, Customer Success, and Marketing—shaping our narrative, enabling revenue teams, and ensuring we build and sell what customers truly need. This is a highly visible role with significant ownership, combining strategic leadership with hands-on execution in a lean, collaborative environment, and includes direct management and mentorship of a product marketing team member.

Responsibilities

Product Positioning & Messaging

• Own product positioning, messaging, and value propositions across key personas and segments

• Translate complex product capabilities into clear, compelling customer-facing narratives

• Maintain and evolve messaging frameworks as the product and market advance
  

Go-To-Market & Launches

• Lead end-to-end go-to-market planning for new products, features, and recurring releases

• Partner with product management and design to influence roadmap based on market and customer insights

• Own cross-functional launches across Marketing, Sales, and Customer Success
  

Sales & Revenue Enablement

• Create and maintain sales enablement assets (pitch decks, one-pagers, battlecards, FAQs)

• Train Sales, Customer Success, and Customer Care teams on product value, competitive differentiation, and use cases

• Support key deals with tailored messaging and competitive insights
  

Market, Customer & Competitive Insights

• Develop deep understanding of customer needs through research, interviews, and feedback loops

• Own competitive analysis and win/loss insights to inform strategy and enable teams

• Identify new market opportunities, segments, and ICP refinements
  

Content & Campaign Strategy

• Partner with Demand Gen and Content teams to inform campaigns, thought leadership, and product content

• Contribute to the production of content for presentations, events, sales enablement, website, and communications alongside internal stakeholders.
  

Required Qualifications

• 6+ years of experience in B2B SaaS Product Marketing, ideally within the financial services industry

• Experience in a growth-stage or mid-sized company

• Proven ownership of product launches, positioning, and sales enablement

• Strong storytelling and messaging skills—clear, concise, and customer-focused

• Ability to synthesize technical concepts into business value

• Strategic thinker with a bias toward execution

• Excellent cross-functional communication and stakeholder management
  

Nice to Have

• Experience marketing to RIAs, broker-dealers, banks, and financial institutions.

• Prior exposure to PLG, usage-based pricing, or complex SaaS products

• Experience working closely with Sales in a quota-carrying environment
  

The salary range for this role is $165,000 to $175,000. 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, 4 weeks for all full-time employees and up to 12 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, Rhode Island, South Carolina, South Dakota, Texas, Utah, Virginia, Washington

Job Summary

As an Account Executive, you are responsible for identifying and developing new opportunities within our core market with a focus on private wealth / family offices. This includes managing the full sales cycle for Vanilla's prospects from lead management to closing new sales. You will work closely with prospective customers as a trusted advisor who deeply understands the unique challenges and goals of wealth management professionals. Reporting to the Vice President of Sales, the team will work cross functionally with marketing, customer success and product to ensure Vanilla is well positioned to meet its revenue targets and grow the business.

Responsibilities

• Identify high-potential prospective customers from inbound leads and outbound prospecting.

• Develop and implement full sales cycle strategies for driving product adoption and expansion within existing Vanilla customers.

• Utilize Salesforce to track the full lifecycle of opportunities to ensure monthly and quarterly forecasts are up-to-date on a weekly basis.

• Craft engagement strategies to build, grow and expand Vanilla’s footprint within RIAs and independent broker / dealers.

• Responsible for meeting quarterly sales quota in Vanilla's middle market segment.

• Respond to all inbound inquiries in a manner that is consistent with Vanilla’s brand and reputation.

• Deliver polished presentations and product demonstrations that clearly articulate the value proposition of Vanilla to our target market.

• Collaborate with and maintain strong working relationships across multiple internal teams including sales, marketing, product and operations.

• Provide input for new marketing collateral that enables the sales process, including presentation decks, factsheets, client case studies and more.

• Willing to travel up to once per month (approximately twice per quarter) for prospect events and in-person meetings.

Qualifications

• 5+ years total working experience with a combination of 1+ years of experience in full cycle software or SaaS sales combined with 3+ years of experience in wealth management as a wealth manager, financial advisor, portfolio manager or analyst/associate.

• Experience working in or selling to wealth management firms.

• Entrepreneurial spirit and ability to wear multiple hats / operate in a high-pace environment.

• Bring a sense of creativity in finding solutions for prospective clients, including creativity in pricing structure, press release or joint marketing, in-person presentations.

• Experience managing annual quotas with a record of quota over-achievement.

• Experience building strategic and creative territory plans in order to meet targets.

• Ability to lead a full-cycle sales engagement from initial outreach/discovery all the way through to execution and close of contract.

• Strong written and interpersonal communication skills to maintain many relationships throughout the sales process.

• Ability to understand complex customer needs and communicate concise, impactful solutions.

• Can operate joint mandates and increasing workloads while maintaining a high level customer experience.

Preferred Qualifications:

• Experience in full cycle selling of fintech or wealthtech SaaS products.

• Experience in scaling start up environments.

• Exposure and/or high level understanding of estate planning.

• Experience with Salesforce.

You Might Be a Great Fit If:

• You have a strong track record in SaaS, fintech, or wealth tech sales in a start up, successfully managing the entire sales process.

• You have had success in wealth management working as an advisor, planner, or associate and understand why a product like Vanilla would add value to that type of buyer because you have been in their shoes.

You May Not Be a Great Fit If:

• You don’t have experience in full-cycle software sales, if you haven’t worked in SaaS, fintech, or wealthtech sales, this role may be challenging.

• If you don’t have a background as an advisor, planner, or associate, it may be difficult to identify and connect with Vanilla’s target customers.

• You have experience in financial services but not in advisory roles - if you’ve worked in financial services or banking but haven’t been an advisor or similar type role, you may lack the necessary perspective for this role.

The compensation range for this role is a 50/50 split between base salary and variable compensation, for a total OTE (On-Target-Earnings) of $200,000-$240,000. Pay is based on a number of factors including market location and may vary depending on job-related knowledge, skills, and experience. This position is eligible for variable pay via a sales compensation plan and equity in the company. These plans pay according to achievement level against sales targets and/or business objectives.

Benefits:

• Flexible paid time off policy and 10 company-wide paid holidays 

• Parental leave, 4 weeks for all full-time employees and up to 12 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.