Enterprise Account Executive

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, Maine, Massachusetts, Minnesota, New Jersey, New York, Ohio, Pennsylvania, Texas, Utah or Washington

As an Enterprise Account Executive, you will grow Vanilla's footprint with the largest wealth management firms in the U.S. That includes RIAs and RIA aggregators, wirehouses and broker-dealers, banks, and trust companies. You'll own a portfolio of existing enterprise customers and new-logo targets, with responsibility for new business, expansion, and renewals.

These are complex, consultative sales with many stakeholders. They include home-office executives, advisor and planner teams, technology and architecture groups, and compliance, security, and vendor-risk reviewers. The ideal candidate has sold to more than one type of wealth firm and understands how each one buys. They are equally comfortable in a C-suite meeting, a vendor-risk review, and a room full of advisors.

You'll work closely with customer success, product, and a Vanilla executive sponsor on each strategic account. You'll play a key role in shaping how we go to market with enterprise firms.

• Own and grow a portfolio of enterprise customers and prospects, winning new logos while expanding and renewing existing relationships.

• Build and execute account plans that map each firm's structure, decision-makers, and buying process, from home office to field.

• Lead complex evaluations across executive, advisor, technology, compliance, InfoSec, vendor-risk, and AI governance stakeholders.

• Build advocacy with advisors and planning teams early, alongside executive sponsorship, so that field demand supports home-office decisions.

• Win competitive evaluations by clearly articulating Vanilla's differentiation, particularly for complex high-net-worth and ultra-high-net-worth planning.

• Structure enterprise agreements that fit how each firm wants to buy, including enterprise license agreements and usage-based models.

• Partner with customer success and executive sponsors on business reviews, ROI checkpoints, and renewal strategy.

• Bring customer and market feedback to product, and close the loop with customers on what's coming.

• Maintain accurate pipeline, forecast, and account activity in Salesforce to drive cross-functional alignment.

• Contribute to Vanilla's enterprise go-to-market strategy, messaging, and playbooks.

• 8+ years of full-cycle B2B sales experience, including 5+ years in enterprise sales to financial services firms with annual quotas exceeding $2M.

• Experience selling into more than one type of wealth management firm (RIAs and aggregators, wirehouses and broker-dealers, banks, trust companies), with a clear understanding of how their buying processes differ.

• Consistent top performer with 100%+ quota attainment across multiple years.

• Proven ability to close deals ranging from mid five figures to seven figures, including both new-logo wins and expansions within existing customers.

• Experience managing 6–18 month sales cycles with senior and C-suite stakeholders.

• Track record of navigating security, compliance, and vendor-risk reviews at regulated institutions.

• History of winning competitive evaluations and displacing incumbent solutions.

• Skilled in building ROI-based business cases that drive executive buy-in.

• Strong executive presence and excellent written and verbal communication, adept at tailoring the message to technical and non-technical audiences.

• Self-starter who thrives in ambiguous, high-growth environments.

• Experience selling AI-enabled software to regulated financial institutions.

• Familiarity with estate planning, trusts and estates, or advanced planning workflows.

• Established relationships with executives across wealth management firms.

• Experience structuring enterprise license agreements or multi-year enterprise contracts.

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 $280,000 to $330,000. 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.