Enterprise Account Executive (Estately by FreeWill)

FreeWill is an award-winning, social-good startup that has partnered with 2,400+ nonprofits who support our mission while generating $12B in gift commitments for nonprofits since we were founded in 2017. We’ve been featured in the New York Times, Forbes, Oprah’s magazine, and our co-CEOs have even been named to Town & Country’s “Top 50 Philanthropists” list.

All of this is because we’ve figured out how to make some powerful (but complicated!) ways to donate much easier and more accessible. Our products make things easier for the donors who want to change the world and for nonprofits doing heroic work around the planet.

In the last 8 years, we’ve grown from 5 people to 200+ (all smart, tenacious, and kind), and continue to grow. We’d love to have you be a part of this adventure. We were named a "Most Loved Workplace" by both Newsweek and Best Practice Institute and in 2025, we were named as one of Forbes' Best Startup Employers and the 2025 Most Loved Workplaces® for Diversity; you can also check us out on Glassdoor! Curious about company culture and management at FreeWill? Check out the 2025 Best Manager Ever podcast featuring Anthony Sottile, FreeWill's VP of Partner Success on either Spotify or Apple.

Full-time •  Excellent Benefits • Work from Anywhere in the US (except AL, CO, or LA) Overview:

Estately is FreeWill’s fast-growing B2B arm, driving estate planning via for-profit collaborations with financial advisory firms, legal firms, benefit providers, mortgage providers, and hospital systems.

We have a strong Mid-Market and SMB practice, and recently signed several large enterprise deals with some of the largest names in the financial advisory space. We’re looking for a strategic, high-performing Enterprise Account Executive to join our team and lead our work driving enterprise deals across sectors.

• Effectively prospect, develop, and close new enterprise sales opportunities; create strategic territory plan and drive revenue within that territory
• Drive new business with net new logos
• Meet and exceed all quarterly and annual sales quotas
• Accurately forecast quarterly and monthly sales
• Use in-depth knowledge of industry trends to consult and support prospective customers
• Be the voice of Estately’s clients, sharing customer-driven insights across the organization, including product, engineering, business development, and legal

• 5+ years of enterprise SaaS sales experience
• Strong written and verbal communication skills, strong analytical and creative problem solving abilities, and excellent interpersonal, organizational, operational, and negotiation skills
• Entrepreneurial drive and ability to work autonomously in fast moving, quickly-changing environments
• Ability to hold your own in meetings with senior executives from prospective partners
• Proven success in achieving sales commits and accurately forecasting targets
• Ability to travel 20% of the time to customer meetings, trade shows, and events as needed

• History of continually exceeding sales quotas of $1M or more
• A zero to one leader that loves building a business from the ground up, and thrives under opportunity
• Experience selling into CHROs, financial advisory firms, mortgage providers, or hospital systems, and/or multi-sector expertise
• History of speaking as a thought leader in high-level engagements across sectors

Candidates should be able to demonstrate actual performance against past quotas. We expect the responsibilities to sometimes shift and aim to hire an individual who is comfortable moving quickly in a fast-paced and/or start-up environment. The right candidate will be an energetic person with passion and an innate drive to excel at any task.

FreeWill has set compensation and a non-negotiation policy for fairness reasons (we don't think an individual's pay should be determined by how comfortable they are negotiating). As a result, we would like to be transparent and upfront about the compensation. The compensation for this role will be a base salary of $125,000 and a potential commission of $125,000 for a total OTE of $250,000.

• Recruiter Phone Screen (30 minutes)
• Hiring Manager Interview (30 minutes)
• Mock Presentation (45 minutes)
• Final interviews with 2 FreeWill team members (2 separate 30 minute interviews)
• Offer (contingent on positive references)

Please note that steps in the hiring process can and may change and the Recruiter will be your point of contact in sharing about any updates in terms of the process. If you are selected to move forward in this process, the Recruiter will share more details about the hiring process and interviewers. However, this is a good estimate of what you can expect. For most roles, our hiring processes take an average of 4-6 weeks.

In addition to the immense personal and professional satisfaction you’ll gain from helping to raise $1T for high impact nonprofits in a kind and joyful work environment, full time employees at FreeWill are eligible for the following benefits:

• Work from home 
• Unlimited PTO
• Flexible hours
• Competitive salary
• Commuter benefits
• Company stock options
• 401k
• Medical/Dental/Vision (some single coverage medical plans are 100% employer paid, subsidized rates for spousal, parent-child, and family coverage)
• Short-term and long-term disability insurance
• Life and AD&D insurance
• Free One Medical membership
• Paid parental leave for all parents

• Regular (virtual) team events
• $250 monthly co-working budget which can be used for local co-working spaces
• $300 annual budget to outfit your home office or cover utility bills
• $1,000 referral bonuses for growing our FreeWill community
• $1,000 annual professional development budget

FreeWill is an equal opportunity employer and we value diversity. We are committed to finding talent that is not determined on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law.

We are a remote-first company that’s able to hire in 47 states and D.C. Unfortunately, we are unable to hire in Colorado, Alabama, or Louisiana at this time. We also can’t sponsor working visas, so all applicants will need to have work authorization in the US.

Don’t check off every box in the requirements listed above? Please apply anyway! Studies have shown that marginalized communities - such as women, LGBTQ+ and people of color - are less likely to apply to jobs unless they meet every single qualification. FreeWill is dedicated to building an inclusive, diverse, equitable, and accessible workplace that fosters a sense of belonging – so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!

We are excited to engage with candidates who can demonstrate their experience and skills through their own words and work, not through AI-generated content. We want to understand your genuine interest in the company and your unique perspectives, not simply AI-driven responses. We ask that you refrain from use of AI-generated content during the hiring process which includes phone screens, video interviews, tech screens, or other assessment stages except as otherwise indicated to you by the Recruiter.

For example: Using ChatGPT to generate scripted answers to application questions or during phone screens and video interviews is strongly discouraged and will result in not moving forward in the hiring process. However, the use of an AI design tool to enhance the design of a presentation deck is permitted.

The Recruiter will be able to provide additional guidance during the hiring process if needed. If hired at FreeWill, we do encourage the use of AI in your role to build upon or enhance your skill set.