Two Chicks With A Side Hustle

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. 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.

We are a team that collaborates, asks hard questions, ships quickly, and has fun. Our team cares deeply about crafting the highest quality member experiences, and each team member has a profound impact on the vision and direction of what we deliver.

We’re looking for someone who’s eager to lead and strategically grow our Member Support team. With a holistic approach in mind, you’ll have a direct impact on shaping the trajectory of our member support offering and contribute to the growth and success of our company. As a strategic leader, you’ll be responsible for leading a team of support specialists, developing and executing on innovative member support enhancements, and optimizing support processes to ensure efficient operations. You and your team are subject matter experts around all Trust & Will products and distribution channels, from estate planning and probate to advisors and partnerships.

About you

You are a strong, effective, and resolution-driven communicator who has a proven track record in building relationships and collaborating across all functional areas of the business. You are skilled in developing a strong team and influencing change through process improvement, operational management practices, and innovation. You think outside of the box and aren’t afraid to take risks. You are detail and goal-oriented, flexible, and have the ability to run fast while constantly striving to improve an already excellent member experience. 

While support itself can be reactive, you have a proactive mindset and can effectively prevent issues from arising before they are presented. You can plan long-term with your strategic mindset and are constantly thinking through the long-term vision of where support is going as our business grows.

You will

  • Lead, build, and grow a culture of top-performing team players to deliver a best-in-class member experience.
  • Develop and execute a comprehensive member support strategy aligned with overall business objectives.
  • Provide strategic direction and set clear goals to optimize for an incredible member experience, operational efficiencies, and employee engagement.
  • Develop support capacity forecasts and targets in collaboration with senior management. Monitor SLA performance, analyze variances, and take corrective actions to ensure success goals are achieved.
  • Think critically about the member experience and how it is executed. Evaluate, implement, and improve systems and processes to help the team be successful and operate more efficiently.
  • Analyze user and agent performance data to make informed decisions about team management.
  • Set clear quarterly and ongoing goals/KPIs with team alignment to business goals with operational efficiencies to increase member experience.
  • Drive thoughtful and effective communication with both Trust & Will Members and Trust & Will internal stakeholders.
  • Act as the voice of the member in presenting qualitative and quantitative feedback to internal stakeholders on improvements to enhance member experience.


  • 5+ years of experience in managing and scaling customer support teams
  • Strong experience in developing and implementing quarterly team goals and strategies
  • Possess natural curiosity and has an affinity for creative problem-solving for both our members + internal teams 
  • Maintain high standards, drives results, and has a bias for action in a dynamic and collaborative environment
  • Understand customer service and communication, technical issue resolution, incident management (e.g. outages), and customer support best practices
  • Data-driven with strong experience identifying, baselining, and tracking KPIs 
  • Strong understanding of team capacity planning and workforce management principles
  • Building procedures and standardization; e.g. quality assurance programs, learning management systems, community platforms, etc.
  • Self-motivated, eager to learn, and thrive in a collaborative environment
  • Experience with tools: Zendesk, G-Suite, ClickUp
  • We are looking for someone who can work Pacific Time Zone hours

Bonus Points for

  • Startup experience 
  • Experience with BPOs
  • Experience working in a B2C organization
  • Knowledge and understanding of Estate Planning and Probate
  • Bilingual in English/Spanish (speaking and writing)

Full-time Employee Benefits & Perks:

  • Our salary range for this position is $95k – $125k, 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.
  • Unlimited time off that you are encouraged to use
  • Quarterly company-wide breaks (think Winter, Spring, Summer, and Fall break)
  • 1 PTO day a month to spend with friends, family, or however you choose
  • 4 days/year to volunteer in your community
  • 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)
  • An informal mentorship program, guest speakers & reimbursement for learning opportunities
  • 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 + mac & Apple accessories
  • Join an Inc. Magazine Best Workplace & Inc. 5000 winner! 

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.

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.