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Vanilla is an AI-powered estate advisory platform transforming wealth transfer and estate planning through modern, visual, intelligent technology. The company unifies scenario modeling, client visualization, and document creation into a seamless digital experience, serving advisors, attorneys, and wealth managers.
As Director of Sales, you will lead Vanilla's mid-market and high-net-worth (HNW) family office sales teams, reporting to the Chief Revenue Officer. This is a player-coach role requiring active client and prospect engagement weekly—not an administrative position. You will frame estate planning problems, conduct discovery to surface advisor pain points, and position against competitors while owning sales methodology, pipeline generation, deal inspection, and forecast discipline.
The sales motion is high-velocity: mid-market operates at ~$7.5K ACV on a 35-day cycle; HNW/family office at ~$12K on a 70-day cycle. Leverage comes from volume, conversion, and consistency rather than large individual deals. You will spend time personally in HNW/family office deals, escalations, and competitive situations, while coaching at scale through call review and enablement.
You will inherit a fully staffed team of experienced sellers covering Mid-Market East, Mid-Market West, and HNW/family office segments, an installed base including recognizable wealth management names, and known process gaps to fix. This is not a build-from-scratch role; the mandate is to extract more from the existing team and motion.
Key responsibilities include: personally engaging as senior sales voice on HNW deals and escalations; becoming fluent in estate planning to be credible with advisors and attorneys; owning competitive positioning; selecting and enforcing a single sales methodology; defining qualification and stage exit criteria; running deal and call reviews using conversation intelligence; owning pipeline creation (currently no SDR layer); evaluating AI-driven pipeline tools; making recommendations on BDR function rebuilding; fixing lead management execution; ensuring forecast accuracy and CRM hygiene; running weekly business reviews and monthly pipeline reviews; designing territory and coverage models; leading and developing the existing team; building enablement and ramp plans; managing performance directly; and partnering with Customer Success on expansion/renewal and Marketing on demand generation.
The role requires fluency in estate planning, credibility with wealth advisors and attorneys, sales methodology expertise, pipeline generation capability, and strong team leadership. You will be distributed across the US with flexibility while maintaining close team connection.
