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
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.