Senior Account Executive II, Advisors

Founded in 2017, Trust & Will is the leading digital estate planning platform, trusted by over one million users. We provide modern, accessible solutions to help families protect their legacies with attorney-approved, legally valid documents tailored to individual state requirements. Our seamless online platform simplifies the estate planning and settlement process, empowering individuals to create wills and trusts while also partnering with financial advisors, attorneys, and institutions to make legacy planning more inclusive and affordable.

Trust & Will is seeking a Senior Account Executive II, Advisors to own and scale our enterprise revenue motion within the advisor channel. This is a senior individual‑contributor role designed for a proven enterprise seller with deep experience in the advisor ecosystem. You will be responsible for selling into mid‑to‑large RIAs and key Broker‑Dealers, managing complex, multi‑stakeholder sales cycles, and closing high‑value strategic partnerships that materially impact company growth.

Reporting to executive leadership, this role will play a critical role in shaping enterprise sales strategy, refining our go‑to‑market motion, and serving as a senior voice of the customer across the organization. While this role does not initially carry direct people management responsibilities, it is expected to operate with executive presence, leadership influence, and ownership typical of a Head‑of‑function level seller.

About You:

You are a seasoned enterprise sales professional with 7–10+ years of experience, preferably selling SaaS or technology solutions into RIAs, broker‑dealers, wealth management firms, or adjacent regulated financial services organizations. You have a strong track record of closing large, consultative deals, navigating long sales cycles, and building trusted relationships with executive‑level decision makers.

You are comfortable operating autonomously, building enterprise pipeline from both outbound and strategic relationships, and partnering cross‑functionally to ensure successful launches and long‑term account expansion. You think strategically about territory, accounts, and partnerships, while still executing with urgency and precision.

About the Role:

• Own the enterprise sales motion for mid‑to‑large RIAs and broker‑dealers, with accountability for new logo acquisition and revenue growth
• Develop and execute account‑based sales strategies targeting high‑value advisory firms and institutional partners
• Manage the full enterprise sales cycle from initial engagement through contract negotiation, close, and launch
• Engage senior and executive stakeholders (C‑suite, Partners, Heads of Wealth, Compliance, and Operations) in complex buying environments
• Lead highly consultative discovery to uncover business, compliance, and operational needs, positioning Trust & Will as a strategic long‑term partner
• Deliver executive‑level presentations and product demonstrations aligned to business outcomes and ROI
• Partner closely with Marketing, Product, Legal/Compliance, and Member Success to ensure alignment and deal success
• Accurately forecast enterprise pipeline and revenue, maintaining disciplined CRM hygiene and reporting
• Represent Trust & Will at industry conferences, events, and key partner meetings (up to ~20% travel)
• Serve as a senior sales leader and role model, sharing best practices and influencing the broader advisor sales organization

Qualifications:

• 7–10+ years of quota‑carrying sales experience, with a strong emphasis on enterprise or strategic accounts
• Demonstrated success selling into RIAs, broker‑dealers, wealth management firms, or regulated financial services organizations
• Proven ability to close complex, high‑ACV deals with multiple stakeholders and long sales cycles
• Strong consultative and value‑based selling skills, with the ability to tie solutions to business outcomes
• Experience with enterprise contract negotiation, pricing strategy, and procurement processes
• History of consistently meeting or exceeding annual revenue targets
• High level of executive presence, communication, and professionalism
• Comfortable operating in a fast‑paced, high‑growth SaaS environment
• This position is available to candidates residing in the following states only: California (CA), Colorado (CO), Florida (FL), Georgia (GA), Idaho (ID), Illinois (IL), Maryland (MD), New Jersey (NJ), New York (NY), North Carolina (NC), South Carolina (SC), Nevada (NV), Utah (UT), Pennsylvania (PA), Texas (TX), Vermont (VT)

Bonus Points for:

• Prior experience in WealthTech, FinTech, or LegalTech
• Existing relationships within the RIA or broker‑dealer ecosystem
• Experience influencing go‑to‑market strategy or mentoring senior sellers

Full-time Employee Benefits & Perks:

• Compensation: Salary + Equity
  • Our OTE range for this position is  $250,000 - $300,000, in addition to compensation we also include an employee equity package as a component of our offer along with other benefits and perks outlined below. 
• PTO
  • Flexible time off that you are encouraged to use
  • Generous paid company holidays and breaks throughout the year 
  • Monthly friends & family day
  • Paid time off to volunteer in your community
• Health and Wellness Benefits
  • Fantastic health benefits including medical, dental, vision, life insurance, and generous parental leave 
  • Financial wellness benefits (Financial coach support, and employer-sponsored 401k with an employer match)
  • Guest speakers & reimbursement for learning opportunities
• Extra
• Flexible work schedule + hours
• Family-friendly work environment. We support the complexity of a remote world with the needs of families
• Optional company-sponsored events and travel throughout the year
• $500 Work from home stipend + Apple accessories 

About Trust & Will: 

• We are a remote-first company, giving our employees the flexibility they need to work in an environment that best suits their needs. Our hiring process is also conducted virtually unless otherwise noted. We are a company that was founded in San Diego, CA, and offer a collaborative co-working space that is available for you to use if you'd like but not required. #LI-Remote
• We are proud to be a certified B Corporation, using business as a force for good. We are committed to building a healthy, sustainable, and engaging working environment for all employees, their families, and communities. We publish an annual impact report to outline our positive contributions to our world and set an example for all employers.
• Trust & Will's mission is to help every family leave their legacy through affordable, accessible estate planning. That starts with the people we hire and the ways in which we support the development of their unique talents and capabilities. We are committed to prioritizing ways to make our company and industry more inclusive. This means we must be revolutionary in the way we value diversity to revolutionize our business sector. At Trust & Will, everyone has a seat at the table and space to be their authentic selves because only in a company that is inclusive and diverse can we truly stand in our members' shoes.

California Privacy Notice: Trust & Will collects personal information from applicants including identifiers, professional/employment history, and education information to evaluate qualifications and communicate about your application. California residents have the right to know what information we collect, request a copy, correct inaccuracies, or request deletion (subject to exceptions). To exercise these rights, contact legal@trustandwill.com. For more information, visit our privacy policy.

Trust & Will may use AI tools to assist with administrative recruiting tasks. All final hiring decisions are made by people. For accommodations, contact people-ops@trustandwill.com.