Chief of Staff

Position Title: Chief of Staff

Location: Remote

Employment Type: Full-Time

Position Overview

The Chief of Staff will be a trusted advisor and “right hand” to senior leadership (CEO, COO, or other C-suite executive). This role acts as both an operator and strategist, ensuring effective execution of high-priority initiatives, streamlining business operations, and fostering alignment across functions. The ideal candidate combines strong organizational skills with an ability to see the big picture, excels at relationship management, and can adapt to the evolving needs of a dynamic business.

Key Responsibilities:

Strategic Planning & Alignment

• Collaborate with executive leadership to set organizational goals, craft business strategies, and define key performance indicators (KPIs).
• Organize and lead cross-functional planning sessions, ensuring each department aligns on objectives, milestones, and deadlines.
• Provide data-driven recommendations and decision support; identify and mitigate risks to strategic initiatives.

Project & Program Management

• Drive complex, multi-disciplinary projects from conception to completion, ensuring timelines, budgets, and deliverables are met.
• Implement and refine project management frameworks—providing structure, accountability, and visibility to all stakeholders.
• Proactively remove bottlenecks, anticipate challenges, and propose solutions to maintain momentum.

Operational Excellence

• Oversee the development and optimization of operational processes, identifying areas for improvement and ensuring smooth day-to-day execution.
• Coordinate cross-departmental workflows, fostering collaboration and efficient communication.
• Standardize reporting procedures and maintain dashboards for real-time insights into operational health.

Executive Support & Coordination

• Serve as a key liaison between senior leadership and internal/external stakeholders; communicate directives and maintain priority alignment.
• Manage leadership’s calendar, orchestrate key meetings, and prepare agendas, ensuring time is spent on the highest-impact activities.
• Track, document, and follow up on action items arising from leadership meetings, guaranteeing accountability and progress.

Stakeholder Engagement & Communication

• Coordinate and facilitate communication among executives, board members, investors, and/or external partners.
• Assist in preparing presentations, reports, and briefs for executive-level discussions, client meetings, or investor updates.
• Present recommendations, provide status updates, and advocate for the leadership team’s vision to internal and external audiences.

Organizational Culture & Team Development

• Uphold and promote the company’s values, ensuring they’re woven into all processes and touchpoints.
• Collaborate with HR or People Operations teams on talent acquisition, onboarding, and professional development initiatives.
• Foster a transparent, inclusive environment where cross-functional teams can innovate and execute effectively.

Business Performance Monitoring

• Establish metrics to measure progress on key strategic and operational goals; track performance and identify trends.
• Conduct market research, competitor analysis, and financial modeling to inform executive decision-making.
• Continuously iterate on reporting mechanisms to ensure real-time data is available to leadership.

Special Projects & Innovation

• Serve as a thought partner to the CEO/COO on emerging opportunities—whether that’s product expansion, new market entry, or organizational restructuring.
• Take the lead on confidential or high-impact “special projects” that require swift, discreet execution.
• Identify and drive new initiatives to enhance efficiency, reduce costs, or bolster revenue.

Qualifications:

Education: Bachelor’s degree in Business, Finance, or related field (advanced degree a plus).

Experience:

• 3+ years in operations, consulting, project management, or a similar role.
• Experience working closely with senior leadership in a high-growth environment (e.g., technology/SaaS startups).
• Proven track record of scaling businesses, orchestrating cross-functional teams, or leading significant organizational initiatives.

Technical & Analytical Skills:

• Proficiency in standard project management tools (Asana, Trello, Monday.com, etc.).
• Strong command of data analysis, reporting, and presentation tools (Excel, Google Sheets, BI dashboards).
• Ability to adapt to new technologies quickly and optimize processes accordingly.

Soft Skills:

• Strategic Mindset: Ability to connect daily tasks to the broader organizational vision and long-term objectives.
• Communication: Excellent written and verbal communication skills; able to distill complex information into concise, clear presentations.
• Leadership & Influence: Skilled at building trust, influencing without direct authority, and rallying teams around shared goals.
• Problem-Solving & Adaptability: Demonstrated success in navigating ambiguity and managing competing priorities in fast-paced settings.
• Emotional Intelligence: Ability to read the room, resolve conflicts, and maintain strong relationships across various teams and stakeholders.

What We Offer:

• Competitive compensation and benefits package (including health, dental, vision, 401(k) with match, etc.).
• Opportunity to collaborate directly with executive leadership, gaining unique insights into strategic decision-making.
• A dynamic, mission-driven environment where your contributions have immediate impact.
• Professional growth opportunities through regular mentorship, training, and exposure to diverse projects.
• Flexible work arrangements (on-site, hybrid, or remote as applicable).

How to Apply:

Interested candidates should submit their résumé and a brief cover letter detailing their relevant experience to info@oggment.ai. Please include “Chief of Staff Application” in the subject line.

Requirements

• Experience with budget management
• Consulting experience with a focus on operations management
• Proven success in a project coordination role
• Nimble business mind with a focus on developing creative solutions
• Strong project reporting skills, with a focus on interdepartmental communication