Executive Assistant

About OutreachFounded in 2014, Outreach has established itself as the premier AI Revenue Workflow Platform, empowering sales teams with connected account visibility, performance insights, and enhanced forecasting accuracy across all go-to-market functions. The platform leverages agentic AI to automate and optimize a wide range of sales processes—from prospecting new clients to renewals and expansion—allowing sales professionals to focus on strategic, high-value interactions. Outreach’s innovative solutions are trusted by global organizations such as SAP, Siemens, Snowflake, ZoomInfo, and Verizon, among others. The company’s commitment to technological excellence and customer success positions it as a leader in the AI-driven sales enablement space.About The RoleWe are seeking an exceptional Lead Executive Assistant to serve as a strategic partner and trusted advisor to our Chief Executive Officer (CEO). This role requires a highly organized, proactive, and discreet professional capable of managing complex operations at the highest organizational levels. As the Lead EA, you will be instrumental in streamlining executive workflows, facilitating communication across departments and external stakeholders, and ensuring the CEO’s time is optimized for maximum impact. You will be responsible for managing a dynamic calendar, preparing high-level briefing materials, coordinating sensitive communications with board members, investors, and strategic partners, and overseeing key projects and events such as board meetings and executive offsites. This position offers an exciting opportunity to influence the company’s strategic direction while working in a fast-paced, innovative environment. The role may be based in Seattle, WA with a hybrid model, or remotely in San Francisco, CA.Qualifications7+ years of executive support experience, with at least 3+ years supporting a CEO in a high-growth or fast-paced organizationProven ability to manage complex calendars and travel logistics, including international arrangementsExceptional written and verbal communication skillsStrong organizational and multitasking abilities with meticulous attention to detailExperience working with board members, investors, and senior leadershipProficiency in Microsoft Office Suite, Google Workspace, and modern communication tools such as Slack and ZoomDemonstrated ability to build and maintain confidential relationshipsProactive problem-solving skills and ability to anticipate needsSelf-starter with high initiative and influence without authorityBA/BS degree or equivalent professional experienceExperience utilizing AI tools to enhance productivity is a plusResponsibilitiesOperate as a trusted partner to the CEO, anticipating needs and streamlining prioritiesManage and optimize the CEO’s complex and dynamic calendar with discretion and efficiencyPrepare briefing documents, agendas, presentations, and follow-up materials for meetingsCoordinate internal and external communications, including with board members, investors, and strategic partnersFacilitate and support high-level meetings, including board meetings, executive offsites, and internal planning sessionsLead and oversee high-impact projects and events on behalf of the CEOMentor and coordinate with other Executive Assistants, establishing best practices and scalable support systemsServe as a gatekeeper and problem solver, triaging urgent issues and opportunitiesHandle sensitive information with the utmost confidentiality and professionalismManage complex domestic and international travel arrangements, including visas and itinerariesSupport expense reporting, vendor relationships, and budget tracking as neededIdentify operational efficiencies and streamline workflows within the executive support functionBuild and maintain strong relationships with internal teams and external stakeholdersAddress conflicts and prioritize competing demands to ensure smooth executive operationsBenefitsFlexible time off policy to support work-life balance401(k) retirement plan to help save for the futureComprehensive medical, dental, and vision insurance coverage for employees and dependentsParental leave programs, including options for paid night nurses and gradual return to workBenefits for infertility and assisted reproductive servicesEmployee referral bonuses to attract top talentOffice snacks, beverages, and social events to foster a vibrant company cultureParticipation in diversity and inclusion initiatives, including Employee Resource Groups such as Outreach Women’s Network, Latinx Community, Outreach Black Connection, AAPI, Pride/LGBTQIA+, Gender+, Disability Community, and Veterans/MilitaryEqual OpportunityOutreach is an equal opportunity employer. We are committed to creating a diverse and inclusive workplace where all individuals are valued and respected. All applicants will be considered for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran status, or disability. We believe that diverse teams foster innovation and growth, and we actively seek to build a workforce that reflects our global community. We encourage applicants from all backgrounds, including those from historically marginalized groups, to apply. Our success depends on the unique perspectives and experiences each individual brings to our organization.