Director of Sales

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.

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

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.

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

• 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

• 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

• 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

• 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.

• 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.