Executive Assistant / Virtual Chief of Staff

About Off Leash Construction:
At Off Leash Construction, we are redefining construction management by ensuring transparency, fairness, and efficiency in every project. Founded to stop contractors from taking advantage of investors, our innovative approach drives our work—from managing a multi-property real estate portfolio to executing high-impact construction projects out of Indianapolis. As we continue to set new industry standards, we’re looking for a dedicated professional to streamline our operations and support our dynamic leadership.

Job Summary:
We are seeking a full-time Executive Assistant / Virtual Chief of Staff to serve as a strategic partner to our executive team. This pivotal role is responsible for managing a team of virtual assistants, coordinating complex scheduling for field technicians, mastering our digital systems, and overseeing budgeting, reporting, and client communications. If you are highly organized, proactive, and thrive in a fast-paced, innovative environment, we invite you to apply.

Key Responsibilities:
• Team Management:
• Oversee and mentor a team of virtual assistants to ensure efficient task delegation and timely follow-ups.
• Develop, document, and enforce standardized operating procedures (SOPs) to maintain high productivity and consistency.
• Scheduling & Coordination:
• Coordinate complex calendars for field technicians and internal meetings, resolving conflicts and ensuring smooth operations.
• Act as the primary point of contact for scheduling challenges, proactively communicating changes and alternatives.
• Digital Systems Mastery:
• Learn and become the subject matter expert on our suite of digital tools (e.g., CRM systems, project management platforms, Google Workspace).
• Train and support team members in using these systems, ensuring seamless adoption and optimal efficiency.
• Budgeting & Reporting:
• Oversee expense tracking and manage budgets for projects, ensuring accuracy and timely reporting.
• Prepare regular operational and financial reports for the executive team, highlighting key metrics and trends.
• Client Communication:
• Serve as a liaison between the executive team and clients by drafting and reviewing professional correspondence and reports.
• Maintain high standards of communication to ensure clarity and consistency in all client interactions.
• Process Improvement:
• Continuously identify inefficiencies within existing workflows and propose actionable process enhancements.
• Manage ad hoc projects that drive overall operational excellence.

Key Tasks:
• Daily Operations:
• Monitor and update team schedules and digital task management tools.
• Ensure deadlines and appointments are met and follow up on outstanding tasks.
• Communication:
• Draft professional emails and client updates.
• Organize and facilitate virtual meetings, ensuring clear agendas and follow-up actions.
• Financial Oversight:
• Track expenses and assist in creating detailed financial reports.
• Ensure budgeting activities are conducted accurately and submitted on schedule.
• System Learning & Implementation:
• Quickly master new software tools and develop training materials or guides for the team.
• Act as the go-to expert for troubleshooting and optimizing digital processes.

Qualifications:
• Experience:
• 3-5+ years in a role such as Executive Assistant, Chief of Staff, or a senior administrative position supporting C-level executives.
• Proven experience in managing teams or virtual assistants is required.
• Technical Skills:
• Proficiency with digital tools such as Google Workspace, Microsoft Office, CRM systems, and scheduling software.
• Demonstrated ability to quickly learn and master new digital systems.
• Communication & Organizational Skills:
• Excellent written and verbal communication skills in English.
• Exceptional organizational abilities with strong time management and attention to detail.
• Financial Acumen:
• Experience with budgeting, expense tracking, and preparing financial reports.
• Personal Attributes:
• Proactive, resourceful, and capable of solving problems independently.
• Adaptable and able to thrive under pressure in a fast-paced, innovative environment.
• High level of discretion and a strong commitment to confidentiality.

Our Offer:
• Competitive salary aligned with top-tier rates in the Philippines.
• Full-time remote work
• A strategic role with significant responsibility and ample opportunities for professional growth.
• A supportive, transparent, and innovative work environment where your contributions directly impact our success.

Hiring Process:
1. Application:
• Submit your resume and a cover letter detailing your relevant experience to nick@offleashconstion.com
2. Video Introduction:
• Record a brief (2–3 minute) video introducing yourself and describing a past experience where you successfully managed a team or resolved a scheduling challenge.
3. Skills Assessment:
• Complete the following multi-part skills assessment (detailed below) within 48 hours of receiving the assignment. Please compile all parts into a single PDF file for submission.
4. Structured Interviews:
• Participate in a series of interviews (an initial screening followed by detailed discussions with leadership) to assess technical and cultural fit.
5. Reference Check:
• Provide professional references to verify your past performance and integrity.

Skills Assessment:

Please complete each part of the following assessment and include your responses, any diagrams or screenshots (if applicable), and a clear explanation of your thought process.

Part A: Scheduling Conflict Resolution

Scenario:
You manage the executive’s calendar and discover the following conflict:
• Meeting 1: A key investor meeting is scheduled for tomorrow at 10:00 AM.
• Meeting 2: A critical operational update meeting with field technicians is also set for tomorrow at 10:00 AM due to an urgent on-site issue.
• Some team members are expected to attend both meetings if possible.

Task:
1. Describe your approach:
• Explain how you would prioritize and resolve this conflict. Include your reasoning for any meeting reassignments or rescheduling.
• Detail how you would communicate the necessary changes to all affected parties.
2. Draft a sample email:
• Write an email to either the investor or the internal team (depending on your chosen resolution) that explains the change, offers alternatives, and maintains a professional tone.

Part B: Digital Systems Mastery

Scenario:
Your company is adopting a new project management tool (choose either Trello or Asana). You need to set up a board for managing a project that involves multiple team members, deadlines, and deliverables.

Task:
1. Outline your setup plan:
• Provide a detailed outline or diagram that includes key lists/columns (e.g., “To Do,” “In Progress,” “Review,” “Completed”), task assignments, deadlines, and any labeling or color-coding strategies.
2. Explain your process:
• Write a short explanation describing how this setup will help maintain accountability, track progress, and align with project management best practices.

Part C: Financial Oversight & Reporting

Scenario:
You have received an expense report for a recent project with the following simplified data:
• Project Budget: $10,000
• Actual Expenses:
• Materials: $3,200
• Labor: $4,000
• Miscellaneous: $1,500
• Total: $8,700

Task:
1. Draft a summary email:
• Write an email to the CEO summarizing the key expense figures.
• Highlight that the project is under budget and provide a brief analysis of any notable variances.
• Suggest one or two steps for improved expense tracking or process enhancements for future projects.

Please submit your resume, cover letter, video introduction (or a link to it), and your completed skills assessment (as a single PDF) tonick@offleashconstruction.com with the subject line “Executive Assistant / Virtual Chief of Staff Application – [Your Name].”