Job Description Overview:
Have you got what it takes to succeed The following information should be read carefully by all candidates.
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.
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Remote working/work at home options are available for this role.