Chief of Staff — Physician-Entrepreneur C Systems Old Greenwich, CT Job Details Part-time | Internship $40 - $60 an hour 6 hours ago Qualifications Microsoft Excel Spreadsheets Writing skills Research Business development Bachelor's degree Management consulting Project management software Master of Business Administration Full Job Description Chief of Staff — Physician-Entrepreneur | Fairfield County, CT I am a triple board-certified physician, founder of an ancillary healthcare company, and MBA building two parallel platforms alongside an active clinical enterprise: an ancillary services real estate investment group focused on the Fairfield County transit corridor, and an early-stage healthcare venture. I am a few years from transitioning out of daily operations and into chairman role and near full-time platform management I need a Chief of Staff. Before the role description, here is the honest test of whether you're the person. Read this first — six questions Answer these for yourself. If the honest answer to any of them is no, this role will frustrate both of us. 1. Can you build the tracking system, not just maintain one? There is no existing project management office. You will design the master tracker across real estate acquisitions, operating businesses, fund formation, and business development — decide what gets tracked, at what granularity, and how status rolls up to me. If you have only ever updated someone else's system, this isn't the role. 2. Can you read a term sheet, an operating statement, and a pro forma — and know what's wrong with them? You will not build the models. You will be the person who reads the attorney's redline, the lender's term sheet, and the broker's offering memo before I do, and tells me in five lines what matters. If you can't spot an aggressive exit cap rate or an unusual indemnification clause or understand what it is the first time you read it. Good. 3. Can you write a one-page briefing that leads with the recommendation? Not minutes. Not a summary of what was said.
A document that says:
here's the decision, here's what I'd do, here's why, here's what I'm unsure about. You will write in my voice for my signature, to attorneys, bankers, investors, and partners. If your writing samples are meeting notes and scheduling emails, this isn't the role. 4. Can you drive a deadline through people who don't report to you? Outside counsel, lenders, brokers, contractors, and co-investors will not do what they said they'd do, when they said they'd do it. Your job is to notice first and close the gap — by calling, by escalating, by proposing a workaround — without waiting for me to ask. If your instinct when something stalls is to flag it and wait, this isn't the role. 5. Can you hold multiple unrelated workstreams in your head at once and know which one is drifting? On a given
Tuesday:
a property under contract with a due diligence deadline, a fund formation document with the attorney, a business development conversation with a potential partner, a vendor contract renewal, and a hiring decision. None of them related to each other. Your value is the pattern recognition across all of them — which one is quietly going sideways. If you need one domain to go deep on, this isn't the role. 6. Can you tell me I'm wrong? I move fast and think broadly. That means I'm sometimes wrong, and a Chief of Staff who agrees with me all the time is worth nothing. If pushing back on a principal is uncomfortable for you, this isn't the role. What this role is not If you've been searching for personal assistant, executive assistant, or project coordinator roles, you may be reading this posting because the title sounds adjacent. It isn't. This role does not involve managing my calendar, arranging travel, screening calls, taking dictation, sourcing supplies, maintaining filing systems, or providing secretarial support. Those are real skills; they are not these skills. Applicants whose experience is primarily in those areas will not be advanced, and I'd rather save you the time. What you will do Design and own the master project tracker across real estate, operating businesses, fund formation, and business development Prepare one-page briefing notes before key meetings — decision, recommendation, open questions Drive open items to closure with attorneys, bankers, brokers, vendors, and partners Draft correspondence, memos, and investor-facing communications for my review Research and synthesize information into decision-ready summaries Identify drift early and pull projects back on track — without being asked Background that typically produces these skills 2-5+ years in management consulting, investment banking office, private equity office, real estate finance, or a founder's/principal's office Direct exposure to transaction documents and financial statements as part of your actual work A track record of written work product that went to senior decision-makers Nice to have: real estate private equity or healthcare services exposure; MBA or in progress These are the backgrounds that usually build the six skills above. If you built them a different way, tell me how in your note.
Job Types:
Part-time, Internship, Commission Pay:
$40.00 - $60.00 per hour Expected hours: No more than 25.0 per week
Education:
Bachelor's (Required)
Experience:
Microsoft Excel:
5 years (Required) Project management software: 5 years (Required)
