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, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah or Washington

About the Role

Vanilla is looking for a curious, resourceful, and technically minded Business Development Representative (BDR) to help generate pipeline and build a smarter, more scalable outbound sales motion.

This is a sales role first - but not a traditional BDR role. You’ll identify and engage target prospects, develop account strategies and messaging, execute outbound campaigns, and create qualified opportunities. You’ll also use AI, agents, automation, and modern GTM technology to make our prospecting more targeted, personalized, and efficient.

You don’t need to be an engineer. We’re looking for an early-career sales professional who is excited about AI, comfortable experimenting with technology, and interested in helping build the next generation of outbound sales at Vanilla.

What You’ll Do

• Generate pipeline: Identify, research, and engage target accounts and prospects through thoughtful, multi-channel outbound outreach.

• Own your goals: Work toward quarterly targets for qualified pipeline, meetings, and outbound activity.

• Develop targeted account strategies: Create Account Plans for priority accounts and tailor outreach based on the company, persona, business need, and relevant buying signals.

• Build better messaging: Develop and test personalized messaging across different segments, personas, and use cases, continuously improving based on results.

• Partner on ABM: Work with Marketing to develop targeted and account-based campaigns and measure what generates engagement and pipeline.

• Use AI for outbound: Leverage AI for prospect research, lead qualification, personalization, messaging, buying-signal identification, and follow-up.

• Build agents and automations: Experiment with lightweight AI agents and automated workflows that eliminate repetitive work and make prospecting more scalable.

• Improve our GTM tech stack: Help connect and optimize tools across Salesforce, prospecting, enrichment, sales engagement, and marketing.

• Manage pipeline and data: Maintain accurate Salesforce account and opportunity data and use reports and dashboards to track performance.

What We’re Looking For

• 2+ years of experience in business development, sales development, B2B sales, growth, or a related role.

• Strong written and verbal communication skills and an ability to create compelling, personalized outreach.

• Curious, analytical, and comfortable researching companies, industries, and prospects.

• Highly interested in AI and how it can improve modern sales and prospecting.

• Comfortable using AI tools such as ChatGPT, Claude, or similar platforms in your everyday work.

• Interested in building AI agents, automated workflows, and repeatable GTM systems

• Comfortable learning and experimenting with new sales and automation technology.

• Self-directed, resourceful, and excited about working in a startup environment where you’ll help build the process, not just follow it.

• Experience with Salesforce, Relevance, Gong, or similar GTM and automation tools is a plus.

What Success Looks Like

Success means creating qualified pipeline while helping Vanilla build a smarter outbound engine. You’ll be measured primarily on pipeline and sales development results, while also helping improve targeting, messaging, conversion, and the AI-powered workflows that make our GTM efforts more effective and scalable.

The salary range for this role is $75,000 to $90,000. 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, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah or Washington

Job Summary

We're hiring a Director of Sales to lead Vanilla's mid-market and HNW/family office sales teams. You'll report to the CRO and own the number, the team, and the operating system behind how we sell.

This is a player-coach role, not an administrative one. The person we hire will be in client and prospect conversations every week, adding real value in the room: framing the estate planning problem, running discovery that surfaces the advisor's actual pain, and positioning against a fast-moving competitive set. You will also own the unglamorous half of the job, which is methodology, pipeline generation, deal inspection, and forecast discipline. We are looking for someone who believes those two things are the same job.

This is a high-velocity motion. Mid-market runs around $7.5K ACV on a 35-day cycle and HNW/family office around $12K on a 70-day cycle, so leverage comes from volume, conversion, and consistency rather than from a handful of large deals. That shapes where your time goes: personally in the room on HNW/family office deals, escalations, and competitive fights, and coaching at scale everywhere else through call review and enablement rather than deal-by-deal involvement.

You'll inherit a fully staffed team of experienced sellers covering Mid-Market East, Mid-Market West, and the HNW/family office segment, an installed base that includes some of the most recognizable names in wealth management, and a set of process gaps we already know about and want fixed. This is not a build-the-team-from-scratch role. The mandate is to get more out of the team and motion we already have.

Responsibilities

In the Room With Clients and Prospects

• Personally engage as the senior sales voice on HNW/family office deals, competitive situations, and escalations: discovery, multi-threading, executive alignment, and negotiation support

• Get fluent in estate planning fast enough to be credible with advisors, attorneys, and firm leadership, and hold your own on substance rather than deferring to product or solutions consulting

• Own competitive positioning in the field and make sure every rep can articulate where we win and where we don't

• Bring the field's voice back to Product with evidence, not anecdotes, particularly on the HNW and multi-generational planning gaps

Sales Methodology and Deal Execution

• Select, install, and enforce a single sales methodology across the team, and hold reps to it in deal reviews rather than letting it live in a slide deck

• Define qualification criteria and stage exit criteria that mean something, so forecast calls are conversations about evidence

• Run deal reviews and call reviews at a cadence that fits a 35-day cycle, using conversation intelligence to coach at volume rather than inspecting deals one at a time

• Improve win rates and shorten cycle time in the segments you own, and be able to explain why the number moved

Pipeline Generation

• Own pipeline creation for your segments. We do not currently have an SDR layer, so self-sourced and marketing-assisted pipeline both sit with you

• Get real output from our AI-driven pipeline engine, including conversation intelligence, agentic outbound, and marketing automation, and tell us honestly where it works and where it doesn't

• Make a recommendation in your first quarter on whether we rebuild a BDR function, at what size, and what it has to produce to justify itself

• Build pipeline from partner and channel motions alongside direct outbound, in coordination with Strategic Partnerships

• Fix lead management execution. Response SLAs, routing, and follow-through on inbound handraisers are non-negotiable

Process and Operating Rhythm

• Own forecast accuracy and CRM hygiene as first-class deliverables, not reporting overhead

• Run a weekly business review with real inspection, plus monthly pipeline reviews and quarterly planning

• Design territory and coverage models as the segments grow, and adjust them when the data says to

• Partner with Revenue Operations on comp design, quota setting, and the reporting the team runs on

Team Leadership

• Lead, coach, and develop a team that is already in seat, and get more production out of it without waiting on headcount

• Build enablement and ramp plans that get new reps to first close faster than our current benchmark, and use them to lift the existing team as much as new hires

• Manage performance directly and early, including the hard conversations

• Partner with Customer Success on expansion and renewal motions, and with Marketing on demand generation and content

First Twelve Months

• Segment pipeline coverage and forecast accuracy inside an agreed tolerance, every quarter

• One methodology installed and demonstrably in use, evidenced in CRM and in deal reviews

• A documented, working answer on pipeline generation without a traditional SDR layer

• Measurable win rate improvement against our primary competitors in the HNW and mid-market segments

• No inbound handraiser without first touch inside SLA

• Higher production per rep from the team as it stands today, before any capacity is added

• The team intact and above quota attainment targets

Qualifications

• 8+ years in software sales with at least 4 years leading quota-carrying reps, including experience selling to wealth management firms, RIAs, family offices, or other financial institutions

• Track record of carrying and hitting a number personally before leading others to it

• Demonstrated fluency in a named sales methodology, and a real example of installing it on a team that was not using it

• Experience leading a high-velocity motion in the $5K to $15K ACV range with cycles measured in weeks, not quarters, where the number is made on volume and conversion

• Experience owning pipeline generation directly rather than inheriting it from a demand gen or SDR function

• Experience building sales process and infrastructure for a scaling team, including forecasting, stage definitions, and CRM discipline

• Strong executive presence with the ability to lead a room of firm principals and CIOs

• Bachelor's degree preferred

What Sets You Apart

• Working knowledge of estate planning, trust, or tax, or a credible track record of learning a technical domain to the point of being useful in front of experts

• Deep network within wealth management, with a track record of opening C-level doors

• Experience selling into the HNW and family office segment, where the buyer and the sales cycle look different from mid-market RIAs

• Experience launching new products or entering new market segments

• Track record of using AI tooling to produce actual pipeline or forecast improvement, with numbers you can defend

• Understanding of regulatory and compliance requirements in wealth management, including third-party technology risk review

• Track record of leading through varied market conditions, including a quarter that missed and how you recovered it

Key Performance Indicators

• New business revenue against plan, by segment

• Self-sourced pipeline creation and pipeline coverage ratio

• Stage-to-stage conversion and forecast accuracy

• Win rate against named competitors

• Sales cycle length

• Lead response SLA compliance

• Rep quota attainment, ramp time to first close, and team retention

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 around $350-380k annually. Pay is based on a number of factors 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, 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, 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.

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, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah or Washington

Job Summary

Integrations are how our product works inside customers' real environments, and where our delivery risk concentrates. We're hiring a senior PM to own that surface end to end: someone who writes specs precise enough to prevent late stage rework, and who has the credibility to sit across from a partner's product and engineering leads and change their approach when it doesn't fit our use case. This is a senior IC role with minimal direction.

What you’ll own

• The integrations roadmap and its sequencing: which systems we connect to, in what order, at what depth, and why.

• The requirements and specification quality for every integration we ship.

• The technical relationship with partner product and engineering teams, jointly with our engineering leads.

• The internal definition of "done" for an integration: not "the connection works," but "the customer's workflow works."

• Reusable integration patterns and platform primitives, so the tenth integration is meaningfully cheaper than the third.

What you’ll do

Get the requirements right the first time

• Validate assumptions against real data and real customer environments, through discovery calls and hands on sandbox testing, before committing engineering time.

• Define the best-in-class user experience making the ease of importing data into Vanilla systems incredibly intuitive.

• Translate business context and customer workflows into specifications engineering can build against without needing to guess, covering data models, sync behavior, auth, rate limits, and failure handling.

• Hunt down edge cases early, conflicting writes, permission changes, schema drift, failed syncs, before they surface in build.

• Serve as the product-side counterpart to partner product and engineering teams, scoping joint work and negotiating technical approaches when our needs and their constraints don't align.

• Push partners to adapt their approach where the better solution sits on their side, and know when to concede and design around a constraint instead.

• Maintain a clear view of each partner's roadmap, deprecation timelines, and reliability posture, and factor it into our own planning.

Operate as a senior PM

• Have an AI mindset where user effort is replaced by agentic workflows.

• Influence the direction of the roadmap instead of being an order taker bringing a point of view on where integrations should go and defend it with evidence.

• Prioritize across competing customer, partner, and internal demands and be able to say no with a reason.

• Communicate crisply to executives, engineering, GTM, support, and external partners, adjusting depth to the audience.

• Define the success metrics for integrations, activation, sync reliability, time-to-connect, support load, rework rate, and manage against them.

• Raise the bar on how the wider product team handles requirements and technical discovery.

What we’re looking for

Required

• 6+ years in product management, with at least 3 years owning integrations, APIs, platform, or partner-facing products.

• A demonstrable track record of shipping non-trivial third-party integrations — ideally several — where you personally owned the requirements.

• Real technical depth: you read API documentation effortlessly, can test endpoints yourself, reason about data models and sync architecture, and hold your own in an engineering design discussion without being the engineer.

• Written specification skills strong enough that engineers reference your docs rather than re-interview you.

• Direct experience negotiating technical approach with external partners or vendors, including at least one case where you changed their plan.

• Strong customer-workflow instinct: you frame integration work in terms of the job the user is trying to complete, not the systems being connected.

Nice to Have

• Experience integrating with portfolio management or financial planning platforms (e.g., Addepar, eMoney), CRM systems used by advisors, or AI meeting/notetaking tools.

• Background in wealth management or fintech, or prior work in a domain with comparable data sensitivity and compliance constraints.

• Experience building an integration platform or framework, not only point-to-point connections.

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.