Business Development Representative, AI Enabled

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 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.