Business Development Representative, AI Enabled

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.

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.

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• 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.

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.