Lead Executive Assistant (to CEO) at Outreach

San Francisco, California, United States

Apply Now

Not SpecifiedCompensation

Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, SaaSIndustries

Requirements

Ability to operate in a fast-paced environment with speed, precision, and discretion
Exceptional skills in anticipating needs, prioritizing, and protecting executive time and energy
High level of confidentiality and professionalism in handling sensitive information
Strong organizational and problem-solving abilities for complex calendars, triage, and urgent issues
Experience managing high-stakes stakeholder communications (board members, investors, partners, executives)
Proficiency in project management, event coordination (e.g., offsites, board meetings), and follow-ups
Leadership and mentoring skills for other Executive Assistants, establishing best practices
Expertise in travel logistics (domestic/international, visas, 24/7 support)
Financial acumen for expense reporting, budget tracking, and vendor management
Location: Seattle, WA (hybrid) or remote in San Francisco, CA

Responsibilities

Operate as a trusted partner to the CEO, anticipating needs and streamlining priorities
Own and optimize a complex, dynamic calendar
Prepare briefing documents, agendas, talking points, presentations, and detailed follow-ups for meetings
Work closely with the Chief Business Officer to organize key business meetings and initiatives
Act as connective tissue between CEO and organization teams, aligning communication and tracking initiatives
Coordinate communications with board members, investors, strategic partners, and executive leadership
Communicate on behalf of the CEO’s office internally and externally with VIP stakeholders
Lead and manage high-impact projects and events (executive offsites, board meetings, planning sessions) with follow-up
Mentor and coordinate other Executive Assistants, establishing best practices and scalable systems
Serve as gatekeeper, triaging urgent issues and time-sensitive opportunities
Manage complex domestic and international travel, including itineraries and 24/7 support
Handle expense reporting, vendor relationships, and high-level budget tracking
Anticipate CEO's needs, streamline workflows, and identify improvement opportunities

Skills

Executive Assistance

Calendar Management

Stakeholder Management

Prioritization

Discretion

Operations Management

Relationship Building

Outreach

Sales engagement platform for B2B clients

About Outreach

Outreach.io offers a sales engagement platform that helps businesses enhance their sales processes through automation of email campaigns, phone calls, and social media interactions. The platform is designed for B2B clients, ranging from small startups to large enterprises, allowing sales teams to track customer interactions and close more deals. Operating on a subscription model, Outreach.io provides various pricing tiers to meet the needs of different clients while ensuring a steady revenue stream. The company stands out by focusing on automation and data-driven insights, making it particularly beneficial for optimizing sales workflows.

Seattle, WashingtonHeadquarters

2014Year Founded

$512.9MTotal Funding

SERIES_GCompany Stage

Consumer Software, Enterprise SoftwareIndustries

1,001-5,000Employees

Benefits

Parental Leave: Extended PTO for both parents, plus unique perks to ease the transition of returning to work.

Full Medical Benefits: Majority of employer paid medical, dental and vision coverage.

401k: A competitive plan to help you save for retirement.

Flexible Time Off: We believe in a healthy work/life balance, and in our employees to make practical time off arrangements.

Risks

Leadership transition with Manny Medina stepping down may cause strategic shifts.

AI Prospecting Agent's public BETA could face user adoption and technical challenges.

Partnership with Harte Hanks may lead to integration challenges affecting effectiveness.

Differentiation

Outreach leverages AI to optimize sales interactions across email, voice, and social.

The platform offers a subscription model with premium add-ons and integrations.

Outreach serves diverse B2B clients, from startups to large enterprises.

Upsides

AI-driven sales tools are projected to increase productivity by 30% by 2025.

The demand for personalized customer experiences is rising, boosting Outreach's relevance.

Remote work trends accelerate the adoption of digital sales tools like Outreach.

Land your dream remote job 3x faster with AI

Try Jobo Free