Job Description Overview:
We're seeking an exceptional Chief of Staff with a strong foundation in M&A, investment analysis, private equity, and finance operations to support the founder of a fast-growing, diversified portfolio of companies. This is a hands-on role for someone who thrives in both the strategic and tactical trenches—a proven operator who's comfortable managing high-value projects while executing rapidly with precision and accountability.
You'll work directly with the founder of a diverse and growing business portfolio. You will lead daily operations, drive initiatives across companies, identify gaps, implement solutions, and ensure the entire system runs smoothly. Financial literacy is required, but your core value will come from how well you operationalize and follow through on ideas, initiatives, and deliverables.
About The Business Portfolio
The founder operates a lean and dynamic portfolio of seven (and growing) companies spanning e-commerce, operations, entertainment, and virtual staffing. The businesses are distributed globally with hybrid team setups. Your role will be to bring structure, systems, and strong execution across a dynamic and entrepreneurial environment.
Role Classification: Independent Contractor, 1099
Requirements
Who We're Looking For
You're not a consultant or a career executive. You're an operator who's lived inside the financial engine room of a company. You've spent at least 3 years doing the real work in environments like private equity, venture-backed startups, investment banking, or corporate M&A.
You're deeply strategic but grounded in action. You can lead a diligence process, build processes from scratch, negotiate with vendors, and chase down a task list—all in the same day. You're fast, clear, curious, and decisive.
To be clear, this is an operational role. Someone with a bias towards action, with some financial and M&A acumen, will succeed.
Required Availability:
- 45-55+ hours/week on average, fully remote (can fluctuate depending on portfolio demands)
- Flexible, on-call nature; must be responsive during the founder's waking hours (approx. 8am-10pm EST)
- Requires weekday evening and some weekend availability, with some flexibility depending on workload
- Must be responsive and reliable, especially during US business hours
- Time off is flexible—but continuity and accountability are non-negotiable
- Occasional travel support and availability during international travel is required
Education & Experience:
- Bachelor's degree in business, finance, economics, or related field (MBA not required but a plus)
- 3+ years in a finance-led operations role (e.g. PE firm operations, investment-backed startup ops, portfolio management, strategic ops within investment banking, etc.)
- Experience in operational execution, project management, and systems building
- Strong understanding of financial workflows, investment operations, reporting, and deal flow tracking
- Clear history of owning day-to-day operations and managing multiple business streams
- Strong written and spoken English; you may represent the founder in meetings and correspondence
- Proficiency with modern tools (Google Suite, Notion, Slack, Zapier, QBO, project management platforms)
Core Responsibilities:
Founder & Business Portfolio Support
- Act as an extension of the founder — owning follow-ups, driving decisions, and filling gaps
- Track follow-ups, drive decisions, and ensure clear accountability across the portfolio
- Sit in on key meetings, take action points, and follow through
- Manage founder's calendar, inbox, and communications as needed
M&A & Financial Oversight
- Monitor and evaluate new business, acquisition, or partnership opportunities across the portfolio
- Conduct initial due diligence and research to assess potential fit and viability
- Coordinate with legal, finance, and external advisors to support transactions and business structuring
- Support post-deal integration by aligning operations, systems, and team execution
- Flag operational or compliance risks early and ensure consistent process oversight
Operational Execution & Systems Building
- Manage and optimize cross-functional projects across various business units
- Build, document, and iterate on SOPs to create scalable operations
- Oversee vendors, contractors, and new hires on a project-by-project basis
- Build dashboards to track KPIs and enable decision-making
Special Projects
- Execute high-priority, time-sensitive initiatives—from research to rollout
- Jump into urgent business challenges to problem-solve and deliver results
- Coordinate with internal and external stakeholders to move things forward
Personal Life Support (As needed)
- Travel booking, gift sourcing, personal appointments, helping family with coordination
- Personal assistance with EA like activities as needed
Desired Traits & Skills:
- Organized, precise, steady, and takes pride in doing things right
- High conscientiousness and follow-through—you don't drop balls
- Strong problem-solving, decision-making, and execution skills
- Capable of working independently while staying tightly aligned
- Exceptional communicator—both in writing and in person
- Discreet, trustworthy, and ethically grounded
- Tech-forward and resourceful—able to build workflows and automate where possible
Benefits
- Monthly contractor rate of $4,000-$6,500 USD, depending on experience
- Includes a probationary period during the first 3 months at a slightly reduced rate
- Unlimited vacation, with the expectation of full continuity and accountability
- Role can scale with the business—this is a potential long-term, growing opportunity
If you're looking for a role where you can make a real impact, move fast, learn across industries, and act as a true business partner—this could be the perfect opportunity. We're looking for someone exceptional. If that's you, apply now.