Lead Executive Assistant (to CEO)
Outreach
Administration
Seattle, WA, USA
Posted on Oct 24, 2025
About Outreach
Outreach, founded in 2014, is the only complete AI Revenue Workflow Platform that helps sales leaders benefit from connected account visibility, performance insights, and higher forecasting accuracy across every GTM team. Outreach infuses agentic AI to power 100s of use cases across sales motions. From new logo prospecting to renewal and expansion, Outreach AI automates workflows and frees sellers to focus on more strategic conversations and actions. Global organizations use Outreach to power their revenue teams, including SAP, Siemens, Snowflake, ZoomInfo, and Verizon to name a few. To learn more, please visit www.outreach.io.
The Role
We are seeking an exceptional Lead Executive Assistant to be a trusted partner to our Chief Executive Officer (CEO). As the Lead EA, you'll work at the highest level of the organization, managing complex operations, building relationships across internal and external stakeholders and providing critical support in our fast-paced environment. As the Lead Executive Assistant to our CEO, you will play a vital role in supporting the direction of the company. You'll be the unseen force behind major initiatives, ensuring that time and focus are aligned with our most strategic priorities. You will also partner closely with the other Executive Assistants to help in problem solving and creating a high bar for executive support across the company.
Location: We are looking to hire this role in Seattle, WA (hybrid office model), or remotely in San Francisco, CA.
Your Daily Adventures Will Include
- Executive Partnership: Operate as a trusted partner to the CEO - anticipating needs, streamlining priorities and protecting the CEO's time and energy.
- Calendar Management: Own and optimize a complex and dynamic calendar, prioritizing meetings and engagements with speed, precision and discretion.
- Meeting and Communication Support: Preparing briefing documents, agendas, talking points presentations and detailed follow-ups for internal and external meetings. Work closely with the Chief Business Officer to organize and facilitate key business meetings and initiatives.
- Cross-Functional Leadership: Act as the connective tissue between the CEO and teams across the organization, helping to align communication and track key initiatives.
- High-Level Stakeholder Engagement: Coordinate communications with board members, investors, strategic partners and executive leadership.
- Operational Support: Communicate directly and on behalf of the CEO’s office, both internally and externally (VIP stakeholders including customers, executive staff, vendors, and company-wide communications).
- Project and Event Oversight: Lead and manage high-impact projects and events on behalf of the CEO, including executive offsites, board meetings and internal planning sessions, with appropriate follow-up communication.
- Team EA Leadership: Serve as a mentor and point of coordination for other Executive Assistants within the company, establishing best practices and scalable systems.
- Triage and Prioritization: Serve as a gatekeeper and problem solver, helping the CEO triage urgent issues and respond to time-sensitive opportunities.
- Confidentiality and Discretion: Handle sensitive information with the utmost confidentiality and professionalism at all times, including maintenance of records, files and confidential information.
- Travel and Logistics: Manage complex domestic and International travel, including itineraries, visa documentation and 24/7 support as needed.
- Expense and Budget Management: Manage accurate expense reporting, vendor relationships and support high-level budget tracking or procurement efforts as needed.
- Operational Support:Anticipating the CEO's needs, streamlining workflows, and identifying opportunities for improvement.
- Conflict resolution: Prioritize conflicting needs while handling matters expeditiously with proactive follow-through
- Relationship Management: Build strong relationships to establish and maintain credibility, trust, and confidence with executive staff and peers
Our Vision Of You
- 7+ years of Executive Experience, with at least 3+ years directly supporting a CEO, preferably at a high-growth or fast-paced company.
- Comfortable interfacing with board members, investors and senior leadership. Ability to represent the CEO with professionalism and poise.
- We are an organization that values professionalism and collaboration, especially within our EA team. Previous leadership and/or team building within an EA organization is highly desired. This role is expected to setthe example and encourage other EAs to work together to find solutions.
- Proven ability to build strong, confidential relationships with executives.
- Proactive problem solver - you don't wait for instructions but rather anticipate, act and adapt.
- Ability to manage ambiguity with confidence, along with staying calm under pressure.
- Self-starter with the ability to influence without authority. You naturally take on initiatives and set high standards for others around you.
- Exceptional written and verbal communication skills, including the ability to draft executive-level correspondence, talking points and presentations.
- Proficient in Microsoft Office Suite, Google Workspace and modern productivity tools (e.g. Slack, Zoom, etc.).
- Meticulous attention to detail, top-tier organizational skills and ability to juggle multiple priorities seamlessly.
- Fast learner. You love solving puzzles and take pride in your work. You have a strong sense of urgency, the ability to anticipate needs, and exceptional follow-through at all times. You thrive in a fast-paced environment.
- Utilize the latest AI tools to make your work as efficient as possible. You have a natural curiosity for the tech industry and want to be part of a highly energetic and passionate team about to make history.
- BA/BS degree or equivalent experience
#LI-SC1
#LI-Hybrid
#LI-Remote
Why You’ll Love It Here
• Flexible time off
• 401k to help you save for the future
• Generous medical, dental, and vision coverage for full-time employees and their dependents
• A parental leave program that includes options for a paid night nurse, and a gradual return to work
• Infertility/ assisted reproductive services benefit
• Employee referral bonuses to encourage the addition of great new people to the team
• Snacks and beverages in the Office, along with fun events to celebrate
• Diversity and inclusion programs that promote employee resource groups like Outreach Women's Network, Latinx community, Outreach Black Connection, AAPI community, Pride/LGBTQIA+, Gender+, Disability Community, and Veterans/Military
Outreach is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.
Our success is reliant on building teams that include people from different backgrounds and experiences who can elevate assumptions and ideas with fresh perspectives. We're dedicated to hiring the whole human, not just a resume. To that end, we look for a diverse pool of applicants-including those from historically marginalized groups. We would like to invite you to apply even if you don't think you meet all of the requirements listed below. We don't want a few lines in a job description to get between us and the opportunity to meet you.
