Executive Assistant to the CEO

*PLEASE NOTE: this role will be required to be located in Seattle, WA and work in-office at least 3 days per week.* 

ABOUT LENDINGTREE

LendingTree is the nation’s leading online lending marketplace. We connect consumers with multiple lenders so they can easily compare options and find the right fit. Our story began in 1996, when our founder, Doug Lebda, set out to make the home-buying process easier after his own frustrating house-hunting experience. What started as a simple idea to help people find better mortgage options has grown into a platform that empowers millions of consumers to compare and choose the financial products that fit their lives best — including loans, credit, savings, and insurance products.

Position Overview

As the Executive Assistant to the CEO, you will play a critical role in optimizing the CEO’s effectiveness, ensuring smooth day-to-day operations, and serving as a trusted partner and gatekeeper. This position requires exceptional judgment, discretion, organizational skills, and the ability to operate in a fast-paced, highly innovative environment. The Executive Assistant will manage daily communication with LendingTree leadership, external stakeholders, board members, and other key partners.

Key Responsibilities

• Executive Support
• Manage complex calendar and scheduling needs, ensuring optimal time management and alignment with strategic priorities.
• Coordinate and prepare materials for meetings, including agendas, briefs, presentations, and follow-ups.
• Act as the primary liaison between the CEO and internal/external stakeholders.
• Handle sensitive and confidential information with absolute discretion.
• Manage domestic travel arrangements, including itineraries and logistics.
• Serve as a proxy to the CEO in various types of communications.

• Strategic and Operational Support
  • Track and help drive key initiatives and projects, ensuring timely follow-up and accountability.
  • Assist with board communications, materials, and meeting scheduling and logistics.
  • Prepare detailed written communications, reports, and executive summaries.
  • Organize and support meetings, including timely distribution of pre- and post- meeting materials, and ensure CEO is adequately prepared for meetings.
  • Follow up on action items, including interaction with internal staff as well as external partners
  • Act as liaison with LendingTree leadership to help align executive priorities.

• Office of the CEO Operations
  • Identify opportunities to streamline and improve executive processes and systems.
  • Own special projects, as assigned by the CEO.
  • Support occasional personal and administrative needs to allow the CEO to focus on strategic leadership.

Qualifications

• 7 years of experience as an Executive Assistant supporting C-level executives, preferably in a high-growth tech, fintech, or startup environment.
• Proven ability to manage complex calendars, projects, and priorities with minimal oversight
• Experience planning board meeting, such as scheduling, preparing materials, and follow-up communications.
• Exceptional written and verbal communication skills.
• Familiarity with FinTech companies, startup operations, or financial services.
• High level of professionalism, integrity, and discretion in handling confidential information.
• Ability to deal professionally with internal and external partners at all levels as friendly facilitator.
• Self-motivated; able to work with little or no guidance and make sound decisions under pressure.
• Strong organizational and project management skills, with a keen attention to detail.
• Tech-savvy, with proficiency in Microsoft Office, Slack, and other modern productivity tools such as Confluence and SharePoint.
• Ability to thrive in a fast-paced, ambiguous, and innovative environment.
• Experience working in Public company.
• Ability to travel occasionally. 
• Flexibility to be available after hours/on weekends to support meetings and handle urgent issues.
• Bachelor's degree or equivalent work experience.  

OUR CULTURE

We’re a collaborative, entrepreneurial team that values curiosity, creativity, and getting things done together. Our teammates are some of the brightest, most driven people you’ll meet — and we celebrate innovation, inclusion, and ownership. At LendingTree, you’ll find an inclusive culture where diverse perspectives make us stronger. We believe in working hard and supporting one another — with the flexibility and trust that help you thrive both personally and professionally.

We’re proud to offer generous benefits, wellness programs, and time-off policies designed to help you recharge, stay healthy, and bring your best self to work every day. And yes — we still have fun doing it (our “GSD – Get Stuff Done” award is a fan favorite!)

Come grow with us, make an impact, and be part of a company that truly cares about its people and its community.

COMPENSATION

The base pay for this position is $150,000, however, base pay offered may vary depending on internal factors, job-related knowledge, and candidate experience.

INCENTIVE COMPENSATION

Eligible for annual performance bonus

BENEFITS

Medical, dental, and vision insurance and 401(k) matching

LendingTree is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We do not discriminate based on race, color, religion (or creed), gender, gender expression, age, national origin, disability, marital status, sexual orientation, or military status.