Director of Sales

This is a fully remote position, open to applicants in Arizona, +17 more states.

📋 Description

• Lead Vanilla's mid-market and high net worth/family office sales teams, reporting directly to the Chief Revenue Officer (CRO).

• Own the revenue stream, the sales team, and the operating framework that supports the sales process.

• Serve as the senior sales representative for high net worth/family office deals, competitive scenarios, and escalations.

• Conduct discovery sessions, engage multiple stakeholders, ensure executive alignment, and provide negotiation support.

• Achieve fluency in estate planning to engage effectively with advisors, attorneys, and firm leadership.

• Manage competitive positioning and enablement initiatives.

• Gather field feedback for Product using data-driven insights.

• Implement and uphold a unified sales methodology.

• Establish qualification criteria and stage exit standards.

• Conduct deal reviews and call evaluations utilizing conversation intelligence tools.

• Enhance win rates and shorten sales cycles.

• Drive pipeline creation through self-sourced, marketing-assisted, partner, channel, and direct outbound efforts.

• Assess the AI-driven pipeline engine to determine the need for rebuilding a Business Development Representative (BDR) function.

• Optimize lead management, response SLAs, routing, and follow-through on inbound leads.

• Ensure forecast accuracy and maintain CRM hygiene.

• Oversee weekly business reviews, monthly pipeline evaluations, and quarterly strategic planning.

• Design territory and coverage models.

• Collaborate with Revenue Operations on compensation structures, quotas, and reporting.

• Lead, mentor, and develop the existing sales team.

• Create enablement and ramp-up plans.

• Manage performance proactively and promptly.

• Partner with Customer Success on expansion and renewal efforts, and Marketing on demand generation and content initiatives.

• Deliver on segment pipeline coverage, forecast accuracy, methodology adoption, pipeline-generation strategies, improvement in competitive win rates, SLA compliance, increased representative productivity, and team quota achievement.

⛳️ Requirements

• 8+ years of experience in software sales, with at least 4 years in a leadership role overseeing quota-carrying representatives.

• Proven experience selling to wealth management firms, Registered Investment Advisors (RIAs), family offices, or other financial institutions.

• A successful history of meeting personal sales targets prior to leading others towards achieving similar goals.

• Demonstrated expertise in a recognized sales methodology, with experience implementing it within a team that previously did not utilize it.

• Experience in managing a high-velocity sales process within the $5K to $15K ACV range, with sales cycles measured in weeks.

• Proven track record of owning pipeline generation directly.

• Experience in developing sales processes and infrastructure for a scaling team, including forecasting, stage definitions, and CRM discipline.

• Strong executive presence, capable of leading discussions with firm principals and Chief Investment Officers (CIOs).

• A bachelor's degree is preferred.

• Familiarity with estate planning, trust, or tax, or a solid history of swiftly learning a technical domain.

• A well-established network within wealth management, with a history of engaging C-level executives.

• Experience in selling to the high net worth and family office segments.

• Proven experience launching new products or penetrating new market segments.

• A record of utilizing AI tools to achieve tangible improvements in pipeline or forecasts.

• Understanding of regulatory and compliance requirements within wealth management, including third-party technology risk assessments.

• A history of effective leadership through various market conditions.

• Must reside in 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.

• Must possess legal authorization to work in the United States.

🏝️ Benefits

• Flexible paid time off policy along with 10 company-wide paid holidays.

• Parental leave of 6 weeks for all full-time employees, extending up to 14 weeks for birthing parents.

• Comprehensive medical, dental, and vision benefits for employees and their families.

• Eligibility for 401K after one month of employment.

• Complimentary estate planning documents.

• Budget allocated for learning & development as well as home office setup.

• Paid parking or transit for hybrid and in-office employees.

• Variable compensation through a sales incentive plan.

• Equity share in the company.