[Hiring] Executive & Business Operations Virtual Assistant @VA Desk

Role Description

Our client is a managed IT, cybersecurity, compliance, and AI automation provider serving accounting firms, law offices, dental practices, and manufacturers since 2005. They run on AI and automation every day, and we expect this role to as well.

The Virtual Executive Assistant protects the founder's time and attention. You will own the inbox, the calendar, and the daily plan, so the Client spends his day on the work that only he can do. You will also keep client relationships warm, coordinate events and speaking engagements, prepare the Client for every meeting, and keep his personal commitments from colliding with work. This is a high-trust role. You will see client information, financial details, and personal matters, and you will handle all of it with discretion.

SCOPE OF WORK

• Executive & Personal Schedule Management
• Meeting Preparation, Team Coordination & Follow-Through
• Event & Speaking Engagement Coordination
• Marketing, Podcast & AI-Assisted Productivity Support
• Client Relations & Relationship Management
• Administrative Operations, Documentation & Confidentiality

Key Responsibilities

• Inbox management
  • Triage Client's inbox at least twice daily: respond, delegate, file, or flag for his decision
  • Draft replies in Client's voice for his review, and send routine replies on his behalf once approved
  • Unsubscribe, filter, and keep the inbox near zero
  • Flag time-sensitive client, sales, and vendor items the same day
• Daily planning and calendar
  • Build Client's day each morning based on task priority, deadlines, and energy, with focus blocks for deep work
  • Send a short morning brief: today's meetings, top three priorities, open decisions, and anything overdue
  • Send an end-of-day wrap: what got done, what moved, and what is on deck for tomorrow
  • Manage scheduling, rescheduling, travel time, and buffers between meetings
  • Run a weekly planning review with Client to set the coming week's priorities
• Meeting preparation
  • Prepare a brief for every internal, client, and vendor meeting: who is attending, purpose, history, open items, and the outcome Client wants
  • For client meetings, pull account context such as open tickets, recent projects, renewals, and past notes
  • Use our meeting task dashboard, which pulls action items from meetings automatically, to confirm owners and follow up until each item closes
  • Prepare agendas for recurring internal meetings such as the weekly L10
• Events and speaking engagements
  • Research and track speaking opportunities, association events, and networking events that fit our target verticals
  • Handle logistics for speaking events: submissions, deadlines, bios, headshots, slide delivery, travel bookings, and follow-up with organizers
  • Coordinate customer events remotely: venue booking, invitations, RSVPs, vendors, and post-event follow-up, with our local team handling anything on site
  • Plan in-person networking for Client: pick the right events, register, prep a short attendee target list, and log new contacts afterward
• Client relations
  • Keep a calendar of client milestones: anniversaries, renewals, birthdays, and key wins
  • Order gifts through online services that ship directly to clients, and send e-cards and thank-you emails
  • Hand off anything that needs to be physically mailed, such as handwritten cards, to our local team with clear instructions
  • Draft check-in emails and follow-ups so no client goes quiet for too long
  • Keep contact records current after every touchpoint
• Team coordination
  • Act as the link between Client and the team: relay decisions, chase updates, and keep projects moving
  • Track commitments Client makes to staff and make sure they get done
  • Coordinate schedules for internal meetings, reviews, and team events
• Marketing support
  • Assist with our AI marketing workflows for blog posts, social content, podcast promotion, and email campaigns
  • Work with our external marketing agency: share requests, track deliverables and deadlines, and route drafts to Client for approval
  • Review content for accuracy and brand voice before it goes to Client
  • Support the "Off the Stack" podcast: guest outreach, scheduling, and prep notes
• Personal assistance
  • Manage personal appointments, family commitments, and reminders alongside the work calendar
  • Handle personal errands that can be done online: bookings, renewals, orders, and reservations
  • Protect personal time blocks and flag conflicts early
• Admin and operations
  • Track expenses, collect receipts, and submit reports
  • Manage subscriptions and renewals for tools Client uses
  • Keep files, SOPs, and shared folders organized
  • Write and update SOPs for any recurring task you take over, so the work is repeatable

How you will use AI

• Use Claude and other AI assistants to draft emails, summarize threads, build meeting briefs, and plan the day
• Use our meeting task dashboard to track action items pulled from meetings
• Suggest ways AI could take over repetitive tasks, and share them with our automation team
• Check AI output before it goes out. You are responsible for accuracy, tone, and anything sent in Client's name
• Follow our security and data handling rules for client information, since we are a SOC 2 certified company

Tools you will work in

• Microsoft 365 (Outlook, Teams, OneDrive, SharePoint)
• Claude
• Meeting task dashboard

Requirements

• 3+ years supporting a founder, CEO, or senior executive, ideally a US-based one
• Comfortable using AI tools such as Claude or ChatGPT every day, with examples of how you used them to save time
• Excellent written and spoken English, with the ability to match someone else's voice
• Experience managing a busy inbox and calendar in Microsoft 365
• Highly organized, with a track record of following up until things close
• Sound judgment on what needs Client's attention and what does not
• Proven discretion with confidential business and personal information
• Able to work US Eastern time business hours
• Reliable internet and a quiet, private workspace

Nice to have

• Experience in an MSP, IT services, or professional services firm
• Experience coordinating events remotely with venues and vendors
• Experience working with a marketing agency or outside vendors
• Background supporting marketing or podcast production

Traits we hire for

• Anticipates needs instead of waiting to be asked
• Comfortable making decisions and owning the result
• Curious about new tools and quick to try them
• Calm under pressure when priorities shift mid-day

Success Metrics

• First 30 Days: You own inbox triage and the calendar. Morning brief and end-of-day wrap go out every workday.
• Within 60 Days: Every meeting has a prep brief. Client touchpoint calendar is built and notes and gifts go out on time.
• Within 90 Days: You run event logistics end to end, support the marketing workflows with our agency, and have suggested at least two ways AI could save time.
• Ongoing Success: Client gets back 10+ hours a week, nothing falls through the cracks, and their clients feel remembered.