Executive Sales Assistant (CEO Support) - Microsoft 365 Expert

Job Title: Executive Sales Assistant (CEO Support) – Microsoft 365 Expert

Employment Type: Part-time (20 hrs/week), targeted transition to Full-time (40 hrs/week) within 30 days based on performance

About the Role:
I’m Paul Swider, CEO of RealActivity. I’m looking for a highly skilled, tech-savvy assistant to help manage my personal sales pipeline, executive operations, and strategic initiatives. You’ll be my right hand in staying organized, maximizing opportunities, and driving results.
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Core Responsibilities

Lead Management & Sales Support
• Own and organize my personal leads/opportunities in Dynamics 365 (separate from the SDR pipeline)
• Plan outreach and follow-up sequences; draft emails from my account for review
• Set and track follow-up reminders; research prospects and prepare briefs
• Conduct company and competitive research; find/validate contact details
Meeting Management
• Prepare agendas and briefing docs
• Take call notes; create action-item summaries
• Send concise follow-up emails with recaps and next steps
• Track action items to completion
Executive Support & Coordination
• Manage my calendar and schedule via Microsoft Bookings (transitioning from Calendly)
• Coordinate with the team in Microsoft Teams
• Organize information on MS Teams and collaborate in Microsoft Loop
Project & Task Management
• Track ongoing initiatives and projects I’m involved in
• Follow up with owners for status updates
• Manage cross-functional coordination so nothing slips
CRM Hygiene & Automation
• Maintain accurate, de-duplicated data in Dynamics 365 with proper tagging and consistency
• Build and optimize simple workflows using Power Automate
Document Creation
• Format/polish presentations, proposals, and sales materials
• Create templates for common communications
• Manage contracts, NDAs, and key documents
Reporting & Analytics
• Produce weekly/monthly pipeline and activity reports
• Build quick insights in Excel or Power BI
• Provide data-driven recommendations
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Required Skills (Non-Negotiable)
• Expert-level Microsoft 365 (Power Automate, Excel, Outlook, Teams)
• Strong automation skills (build/maintain Power Automate flows)
• Advanced Excel (formulas, pivots, analysis, reporting)
• AI-proficient (ChatGPT, Copilot, Grok, ClaudeAI, etc.)
• Excellent written English for CEO-level communications
• Proactive, strategic problem-solver; highly organized and reliable

Preferred (or Must Learn Quickly)
• Dynamics 365 CRM (or ability to become productive within 2 weeks)
• Microsoft Bookings
• Sales/lead management experience
• Power BI or data visualization
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What Makes You the Perfect Candidate
• Microsoft 365 power user who automates repetitive work
• Strategic thinker who improves processes and anticipates needs
• Learns new systems quickly and works independently
• Organized, detail-oriented, and dependable in a fast-paced environment
• Takes ownership and follows through to completion

What to Expect
• Direct collaboration with the CEO and high visibility
• Part-time start with planned transition to full-time within ~30 days based on clear KPIs (CRM hygiene, useful automations shipped, consistent reporting/follow-ups)
• Opportunity to grow as we scale

To Apply (please include)
• Your experience with Microsoft 365 tools (especially Power Automate and Dynamics 365)
• Examples of how you’ve used AI to improve efficiency
• A brief description of how you would manage a CEO’s lead pipeline
• Your availability and hourly rate