Demo

Head Of Sales

Trust & Will
California, MO Full Time
POSTED ON 4/12/2025
AVAILABLE BEFORE 5/11/2025

We’re on a mission to help every family leave their legacy with a fast, easy, and secure way to create, manage, and distribute their estate plan online. Since 2017, we’ve helped hundreds of thousands of families plan for their future with a streamlined and intuitive approach that makes estate planning simple, affordable, and accessible – in addition to 13,000 financial advisors who love our platform. We’re backed by leading names in venture capital including Jackson Square Ventures, Link Ventures, Revolution’s Rise of the Rest, Halogen Ventures, and more.

If you would like to join us, we are looking for a Head of Sales that will lead our advisor sales team to continue to scale our best-in-class advisor platform to thousands of advisory firms nationwide. We’re looking for a dynamic, experienced sales manager to drive our sales strategy, build and lead a high-performing sales team, and help us scale our growth via this distribution channel. Winning in the Financial Advisory market is crucial to our success at Trust & Will, and you will be a critical piece to our success. Our Financial Advisory sales are mostly focused on SMB’s, so we are looking for an experienced manager in the SMB to mid-market space.

Position Overview :

  • The Head of Sales will be responsible for leading and growing the advisor sales organization, developing and executing sales strategies, and building a culture of excellence within the sales team. In this role, you will work closely with the executive team to drive revenue growth and build scalable sales processes that align with the company‘s overall objectives. Additionally, you will leverage your experience in building and optimizing a CRM and our sales operations processes to ensure efficiency and scalability while managing a team of Account Executives and Business Development Reps. This is a high-impact leadership role with the opportunity to shape the future of Trust & Will as we expand our Advisory market presence.

About You :

  • You have a strong background in SMB sales and a passion for sales operations, empowering you to make strategic decisions based on data. Your experience building outbound and inbound sales strategies while managing a strong sales team will help the company grow and exceed its goals. You will also work closely with the General Manager of Advisors and other key leaders, including cross-functional collaboration with marketing, product, and others.
  • About the Role :

  • Sales Strategy Planning : Define and execute a comprehensive sales strategy to drive customer acquisition, retention, and market penetration.
  • Identify and prioritize key verticals, target accounts, and sales initiatives.
  • Develop territory maps to support the sales team to have an organized and strategic sales strategy.
  • Leverage data, analytics, and customer feedback to continue to enhance the sales processes.
  • Continue to enhance our strategy for inbound, outbound, and existing customer sales strategy.
  • Team Leadership and Development : Build, lead, and inspire a high-performing sales team which includes :
  • Hire, train, and mentor sales leaders and individual contributors.
  • Foster a culture of high performance, collaboration, accountability, and results-driven.
  • Set clear goals, performance metrics, and KPIs to ensure team alignment and accountability.
  • Invest in our team members to help them grow professionally and deliver performance reviews.
  • Build trust with team members and lead with empathy to help drive results.
  • Sales Operations Management : Implement sales processes, tools, and technologies to increase efficiency and effectiveness (ex : CRM, sales enablement tools).
  • Utilize data to make proactive decisions regarding our sales process.
  • Set goals for the sales team and drive accountability.
  • Forecast sales performance and pipeline growth accurately.
  • Revenue Growth : Lead the sales team to achieve and exceed quarterly and annual revenue targets while optimizing the sales funnel to increase conversion rates and shorten the sales cycle.
  • Develop acquisition strategy for both new and existing clients within the advisor market.
  • Partner closely with leadership to help execute on sales strategies for any new partner launches that unlock our ability to sell into that firm.
  • Cross-Functional Collaboration : Work closely with marketing to align on messaging, content, and lead generation strategies that help you meet goals.
  • Partner closely with product and customer success teams to ensure feedback loops, product improvements, and top-notch customer experience.
  • Qualifications :

  • 5 years of proven sales management experience in an SMB sales leadership role, preferably in the SaaS industry.
  • Deep understanding of SaaS sales cycles, pricing models, and acquisition strategies.
  • Ability to thrive in a fast-paced, dynamic environment.
  • Strong emotional intelligence that helps you get the most out of a sales team.
  • Experience in CRM and sales tools; HubSpot a plus.
  • Strong communication, presentation, and negotiation skills.
  • Strong background in Sales Operations.
  • Bonus Points for :

  • Experience working in a tech company and / or high-growth startup.
  • Have experience selling into the advisory market (familiar with RIA and BD space).
  • Employee Benefits & Perks :

  • Compensation : Salary Equity
  • Our OTE range for this position is $220,000 - $250,000, 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.
  • 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 (Equity & tax advisory support, savings options, and employee-sponsored 401k).
  • Guest speakers & reimbursement for learning opportunities.
  • Extra
  • 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 reimbursements 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.
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    Salary : $220,000 - $250,000

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