Craigslist
Trainee General Manager (Remote)
Overview
Our organization is seeking a motivated and entrepreneurial Trainee General Manager (Trainee GM) to work closely with the CEO and senior leadership as they learn the full scope of business operations. The Trainee GM will serve as a junior extension of executive leadership, supporting operational execution, client delivery, internal systems, and business development.
This opportunity is ideally suited to a highly eclectic and ambitious individual — someone with broad exposure to consulting, web and software development, and technology services, who aspires to grow into a senior leadership role and become a key player in running the business. The position emphasizes mentorship, hands-on learning, and progressive responsibility across consulting, technology, web/software development, and organizational management.
Key Responsibilities
Client Engagement & Delivery
Support end-to-end project execution across consulting, digital transformation, data/BI/analytics, and web/software development initiatives
Assist in preparing deliverables that meet the organization’s standards of precision, alignment, and professional polish
Participate in client meetings, helping to brief executives, track action items, and manage follow-ups
Business & Strategic Management
Work with the CEO on corporate strategy, growth planning, and business development pursuits
Assist in preparing proposals, RFP responses, capability statements, and presentations
Research and help advance opportunities in consulting, web/software, data/BI/analytics, digital, and technology services
Operational Support
Contribute to internal systems, processes, and workflows for scalability and efficiency
Support financial operations including budgeting, forecasting, and reporting
Help establish project tracking, governance, and quality assurance processes
Practice Area Exposure
Brand, Creative, Strategy & Development – Branding, creative design, marketing communications, GTM planning
Software, Web & Digital – Website/application design and development, hosting and security, digital strategy
DevOps, DataOps & Analytics – Cloud platforms, agile delivery, data strategy, analytics, and AI
Technology Consulting & Management – IT strategy, compliance, cybersecurity, managed services, emerging tech
Team Leadership Development
Learn to recruit, coordinate, and manage consultants and subcontractors under senior guidance
Participate in building a culture of responsiveness, empowerment, and accountability
Serve as a bridge between leadership and delivery teams, with mentorship from the CEO
Qualifications
4–6+ years of experience in providing consulting and tactical execution/support services in brand/creative, web/software development, data/BI/analytics, technology, or related fields
Broad exposure to multiple practice areas, with particular interest in web and software development
Demonstrated ability to manage projects or workstreams, even if at a smaller scale
Some experience in budgeting, forecasting, or contract support
Strong writing and communication skills — able to prepare professional reports, proposals, and presentations
Entrepreneurial mindset, eager to operate in ambiguity, wear many hats, and grow into higher responsibility
Personal Attributes
Eager learner with strong initiative and ambition
Detail-oriented, organized, and process-driven
Comfortable working across diverse projects and shifting priorities
Collaborative by nature, but able to act independently when needed
Motivated to grow into a leadership role with a fast-moving, multi-disciplinary company
Compensation
The base salary will be modest, reflecting the developmental and entrepreneurial nature of the position. However, the Trainee GM will be eligible to participate directly in the company’s upside through a percentage of new client business they help originate or contribute to bringing in. This structure is designed to reward initiative, encourage business development, and create significant long-term earning potential as the individual grows into the full General Manager role.
This will begin as a 1099 contract position, offering flexibility while allowing the organization and candidate to establish fit and performance alignment.

707 Anderson Ave, Rockville, MD 20850, USA
Negotiable Salary