Chief of Staff to the Founder/CEO

Description

Fieldcrest Ventures is the personal investment and operating platform of a serial entrepreneur and early-stage venture investor. We are not a firm, a fund, or a holding company in the traditional sense. We're building real businesses, solving hard problems, and compounding capital across sectors — and we're doing it with intensity.
We're hiring a Chief of Staff to serve as the founder's right hand. You will operate across companies, people, and capital, tackling the high-leverage problems that drive enterprise value while helping the founder refocus from talent firefighting to long-term strategy.
Fair warning: This role is not for the lightly committed. This is an intense, intellectually demanding role. You must thrive in ambiguity, execute with extreme ownership, and find energy in complexity. If you've ever dreamed of being at the nerve center of a small but mighty entrepreneurial engine, this is your shot.

What You'll Actually Do

Portfolio Operations (40%)
- Parachute into portfolio companies to solve critical challenges - from operational bottlenecks to GTM strategy
- Turn vision into execution by transforming vague directives into executed results (Example: "We should implement OKRs at that company" becomes a thoughtfully implemented OKR program within 30 days with full buy-in from the company management team)
- Lead cross-portfolio initiatives that create real enterprise value
- Represent the founder in meetings, negotiations, and strategic discussions.

Executive Talent Development (40%)
- Own the identification, recruitment, and development of executive talent across all companies and initiatives
- Build systems to identify, assess, and develop A+ talent at scale
- Serve as coach, challenger, and accountability partner to portfolio executives
- Create the playbook for turning high-potential operators into successful founders

Strategic Partnership (20%)
- Act as a true thought partner to the founder across new ventures, market research, and strategic planning
- Draft board materials, investment memos, and high-stakes communications
- Dive deep on diligence, capital allocation models, and white-space opportunity assessments
- Switch fluidly between intellectual work and operational triage

Recent Wins You Would Have Owned
- Restructured a seed stage startup's management team
- Recruited a new CRO for a company in under 45 days
- Helped design and launch a new AI product within a portfolio company
- Identified and executed the operational improvements that doubled EBITDA in one of our service businesses
- Built the financial model that justified our passing on an investment opportunity
- Coached an underperforming executive to become a top performer

What Success Looks Like

30 Days: You've mapped the portfolio, earned trust, and are already owning key deliverables.
90 Days: Talent pipelines are active, operators are aligned, and fires are getting solved before they reach the founder.
1 year: The portfolio is staffed with A-players, major systems are running smoothly, and the Founder spends 80% of his time on strategy — because you handle everything else

A Note from the Founder

I'm an entrepreneur with a deep love for systems thinking, problem-solving, and helping smart people do their best work. I've built multiple companies across tech and traditional industries, and I approach each new venture from first principles.
I am at my best when focusing on strategy, investing, and company-building — but too much of my time is lost to operational firefighting and talent challenges. I need a true partner who can bring order to the chaos, excellence to our talent strategy, and execution to our biggest ideas.
I'm looking for someone who shares my curiosity and intensity, but brings complementary strengths in people leadership and operational excellence. This isn't just a job — it's a chance to learn the craft of company building while making a real impact across multiple ventures.

Requirements

Who Thrives in This Role

Must-haves:
- 5-10 years in consulting, VC/PE, or high-growth operations
- Track record of translating vision into measurable results
- Natural ability to assess and develop talent (you can spot future founders in unexpected places)
- Operator-generalist with range: you can build a model, write a memo, lead a meeting, and fix a hiring funnel
- Broad intellectual range - comfortable discussing everything management philosophy and human psychology to emerging technologies and economic risk-factors
- Fluent in ambiguity and allergic to politics
- You don't need a playbook. You're the person who builds the playbook.

Critical capabilities:
- Understand how to motivate, align, and persuade people
- Able to work quickly, effectively, and confidently with insufficient information
- Comfortable and effective in managing conflict, able to facilitate consensus and move the team forward
- Active listener, able to quickly understand what's important, synthesize complexity, and act quickly
- Proactive, clear communicator who takes ownership for setting and managing expectations up, down, and across stakeholder groups
- Fluent in and energized by leveraging data, tech, and AI to accelerate outcomes and performance
- Able to move between big picture strategy and detailed execution seamlessly
- Able to lead by influence, not dependent on hierarchical authority to get things done

You'll thrive here if you:
- Get energized by solving hard problems
- Read widely, think critically, and learn obsessively
- Can disagree respectfully in the morning and fully commit by afternoon
- See developing others as leverage, not overhead
- Find yourself naturally taking ownership of underperforming projects
- Are more interested in impact than credit
- Left your last role because the learning curve flattened
- Have an unwavering commitment to excellence and enjoy working with others who share that commitment
- Thrive in a culture of feedback and continuous improvement
- Are as scrappy as you are competent and believe in progress over perfection

Who shouldn't apply:

• You need work-life balance more than you need challenge
• You get frustrated without structure or predictability
• You prefer optimizing what exists over building from zero
• You're looking for a corporate environment with shared services, formal processes, and Fortune 1000 resources
• You expect 9-to-5 hours
  Note: If your only experience comes from consulting or PE but you've never worked in a true entrepreneurial environment, make sure you REALLY understand the difference. This isn't theory or strategy decks — it's hands-on building with limited resources and infinite ambiguity.

Benefits

Why This Role Is Special

Ideally, we view this as a 2-4 year tour of duty with a clear path to becoming a portfolio company CEO or launching your own venture with our backing.
- True ownership: Within 6 months, you'll run entire workstreams independently. Within 2 years, you’ll be ready to consider taking over an executive role within a portfolio company or launching a startup with our backing and support.
- Accelerated learning: See every aspect of building, scaling, and exiting businesses
- Intellectual growth: Work with someone who thinks in systems and challenges conventional wisdom

Compensation: $200,000 base + up to $100,000 performance bonus