Overview
About the Role:
We're seeking an exceptional Executive Assistant to support the CEO of a dual-enterprise operation: a thriving financial planning practice and a financial services software development company with 40+ applications. This role demands someone who doesn't just manage a calendar—they orchestrate efficiency, anticipate needs, and solve problems before they reach the CEO's desk.
Primary Responsibilities:
Calendar & Meeting Management
- Own and optimize the CEO's calendar with ruthless efficiency
- Schedule and coordinate meetings across financial planning practice and software company
- Prepare meeting agendas, materials, and briefing documents
- Ensure proper time blocking for production work, client meetings, and strategic planning
Production & Project Coordination
- Monitor and maintain alignment with production schedules across both businesses
- Interface with software development team to ensure CEO involvement is timely and purposeful
- Track deliverables and deadlines, proactively flagging potential conflicts
- Coordinate between financial planning operations and software company activities
Proactive Problem-Solving
- Identify and resolve scheduling conflicts, operational bottlenecks, and coordination issues independently
- Research and present solutions, not just problems
- Anticipate needs based on patterns and upcoming priorities
- Filter communications and requests, handling what you can and escalating only what requires CEO decision-making
Administrative Excellence
- Manage travel arrangements and logistics
- Maintain organized documentation and filing systems
- Handle confidential information with discretion
- Coordinate with team members across both organizations
Required Qualifications:
- Type A Personality: Driven, organized, and thrives on getting things done right
- Exceptional attention to detail: Nothing falls through the cracks on your watch
- Proactive mindset: You see three steps ahead and solve problems before they become problems
- Strong judgment: You know when to handle something yourself and when to escalate
- Tech-savvy: Comfortable with calendar systems, project management tools, CRM platforms, and communication software
- Financial services experience preferred: Understanding of financial planning, compliance considerations, or fintech environment is a strong plus
- Availability for travel: Occasional travel required to support in-person meetings and events
What Makes You Successful:
- You understand that the CEO's time is the most valuable asset and you guard it fierciously
- You think "How can I make this easier?" before "I need to ask about this"
- You're comfortable making decisions within your scope of authority
- You can juggle multiple priorities without dropping balls
- You communicate clearly and concisely
- You're self-motivated and don't need hand-holding
Work Environment:
- Remote position with flexibility
- Must be available during business hours with some flexibility for cross-time-zone coordination
- Occasional travel for in-person meetings, events, or strategic planning sessions
- Fast-paced environment supporting dual business operations
Compensation: Competitive salary commensurate with experience, plus benefits
IDEAL CANDIDATE AVATAR
Background:
- 7-10 years of executive assistant or chief of staff experience
- Previous experience supporting C-level executives in either financial services, professional services, or tech startups
- Bachelor's degree (business administration, finance, or related field preferred)
- Has worked remotely successfully for at least 3 years
Personality Traits:
- Type A+++: Gets a dopamine hit from checking things off lists
- Low ego: Success means making the CEO successful, not being in the spotlight
- Naturally proactive: Sees problems as puzzles to solve, not obstacles to report
- Calm under pressure: Thrives in fast-paced environments with competing priorities
- Detail-obsessed: Would rather spend 10 minutes getting something perfect than 2 minutes getting it "good enough"
Working Style:
- Starts each day reviewing the CEO's calendar for the week ahead, identifying potential conflicts or preparation needs
- Maintains a running list of items handled vs. items that need escalation
- Uses time-blocking and prioritization frameworks naturally
- Communicates in bullet points and action items, not paragraphs
- Asks "What's the desired outcome?" before diving into execution
Technical Competencies:
- Expert in calendar management systems (Google Calendar, Outlook, etc.)
- Proficient with project management tools (Asana, Monday, Notion, etc.)
- Comfortable learning new software quickly (will need to understand your financial and CRM systems)
- Strong with document creation and organization
- Can create simple spreadsheets and reports
Pay: $60,000.00 - $70,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Flexible schedule
- Paid time off
- Parental leave
- Professional development assistance
Application Question(s):
- This role is subject to criminal background and credit history checks due to regulatory obligations and firm policies. Are you able to successfully pass these checks, as permitted by law?
- This position supports a CEO across two fast-moving businesses and requires anticipating needs, resolving conflicts, and managing competing priorities independently. Do you have experience successfully operating at this level of autonomy?
- How many years have you supported C-level executives, and how many of those years were in a fully remote role? Briefly describe the type of business(es) you supported.
- List the calendar, project management, and communication tools you have used regularly. Which system did you have to learn quickly, and how did you manage that while still supporting a busy executive?
- You notice the CEO’s calendar has back-to-back meetings across two businesses, overlapping prep work, and a last-minute “urgent” request. What steps would you take to assess, prioritize, and resolve this before involving the CEO?
Education:
Experience:
- Executive administrative support: 7 years (Required)
Work Location: Remote
