Strategic Executive Assistant & Program Lead

Full-Time | Bainbridge Island, WA

Compensation

• Hourly Rate: $35–$40 per hour
• Performance Bonus: Eligible for an annual bonus of up to one month’s base pay, tied to execution quality, program milestones, and overall performance impact.

About the Organization

This role supports a mission-driven organization based in Bainbridge Island, WA that operates at the intersection of hospitality, workforce development, and inclusive employment. The organization manages a venue-based operation while also developing technology solutions that expand access to structured job training, career pathways, and employer-facing tools that support inclusive hiring.

The team is small, fast-moving, and ambitious, focused on building operational systems and scalable digital tools that drive measurable impact.

About the Program

This role also supports a technology-enabled initiative currently in active development. The program includes an online workspace designed to help job seekers organize and present skills, collaborate with support networks, and engage with employers through structured tools and processes.

The Program Lead will coordinate execution across product development, user engagement, partnerships, and internal operations—while also serving as a strategic support partner to the CEO.

Role Overview

This position blends execution, coordination, and strategic support in a dynamic startup environment. With a separate team managing on-site operations, this role focuses primarily on:

• Program coordination
• Business development support
• Data reporting and analysis
• Executive-level administrative and strategic support

This is not a traditional assistant role. It is designed for someone who excels at building systems, organizing moving pieces, and turning strategic ideas into measurable progress.

Key Responsibilities

Program Coordination

• Coordinate tasks between leadership and external partners
• Support user testing, customer interviews, and structured feedback processes
• Assist with product demos and stakeholder presentations
• Manage partner outreach and follow-up
• Organize documentation, workflows, and project information

Strategic & Administrative Executive Support

• Prepare presentations, board materials, and structured reports
• Conduct research supporting business development initiatives
• Build spreadsheets, dashboards, and data-tracking tools
• Support budgeting visibility and data organization
• Track timelines and maintain accountability for cross-functional projects

Seasonal Event Support

• Provide occasional weekend support during peak seasons
• Offer operational backup when necessary
• Receive compensatory time off for weekend work

Technical & Skill Requirements

• 5–8 years experience in SaaS, tech-enabled, or growth-stage environments
• Strong proficiency in Google Workspace (Docs, Sheets, Slides, Drive)
• Advanced spreadsheet skills, including reporting and analytics
• Familiarity with AI tools for workflow automation and productivity
• Basic knowledge of keyword research, SEO fundamentals, and AI-assisted content optimization
• Experience with project management platforms such as ClickUp, Asana, or Notion
• Skilled in Canva for presentations and marketing collateral
• Strong written and verbal communication skills
• Highly organized, structured, and execution-driven

Preferred Skills

• Strong executor who thrives on bringing structure to evolving concepts
• Comfortable with technology and AI tools
• Confident assisting with demos, presentations, and external communication
• Adaptable and effective in small, fast-moving teams
• Passion for inclusive employment and workforce development
• Hungry to grow with an expanding program and take on more ownership over time

Why This Role Is Unique

This is not a narrow administrative role. You will work directly with organizational leadership to help scale a mission-driven, tech-enabled initiative from development into growth. Your work will directly influence product evolution, strategic decisions, operational systems, and partnership development.

If you prefer a rigid, highly structured corporate environment, this role may not be the right fit. If you’re excited to help shape an evolving ecosystem, contribute meaningfully to social impact, and grow within an innovative startup, this opportunity offers a rare blend of purpose, ownership, and career development.