What You'll Own:

Calendar & time:

Own the founder's calendar end to end — schedule, defend, and re-sequence it against stated priorities
Protect deep-work blocks and Sabbath observance; treat them as immovable unless explicitly released
Prepare the founder for every meeting: agenda, background, desired outcome, and what he needs to decide Communication & gatekeeping:
Manage inbox triage — sort, respond on his behalf where appropriate, escalate what actually needs him
Draft and send correspondence in his voice: emails, letters, follow-ups, thank-yous
Serve as first point of contact for advisors, lenders, attorneys, brokers, and acquisition targets Follow-through & accountability:
Capture every commitment made in meetings and track it to closure
Run the weekly and quarterly meeting rhythm: agendas, notes, action items, owner, due date
Chase down deliverables from internal team members and outside vendors — politely, persistently, and without needing to be reminded Deal & project support
Maintain acquisition pipeline trackers, data rooms, LOI and diligence checklists
Coordinate with attorneys, CPAs, bookkeepers, lenders, and insurance
Organize and maintain the document vault — entity records, licenses, contracts, notes, filings Travel & events:
Book and manage travel, conferences, and mastermind commitments
Build trip itineraries with everything needed already handled before departure Personal & household logistics
A limited amount of personal coordination that keeps the founder's week clear Marketing (Strongly Preferred): Cooleys runs an active content operation, and marketing support is a meaningful part of this seat for the right candidate:
Coordinate the content calendar across LinkedIn and Facebook
Schedule, format, and publish posts; manage the videographer and any outside vendors
Capture raw material — photos, clips, customer stories, five-star reviews — and route it into content
Track campaign and challenge progress and keep the marketing scorecard current
Help build simple decks, one-pagers, and marketing collateral If you have marketing chops, this role gets bigger and more interesting fast.

Manage Up —

What We Actually Mean:

Most people say they can manage up. Here's the specific behavior we're hiring for:

You bring solutions, not questions . \"Here's the issue, here are two options, I recommend the first — say the word.\"
You tell the founder no . When something conflicts with a stated priority, you say so before it's on the calendar.
You chase him . If he owes you a decision, you follow up until you get it. You don't wait, and you don't take silence as an answer.
You catch what he drops . You notice the commitment he made in passing three weeks ago and surface it before it becomes a problem.
You protect him from himself . You flag when the week is overbooked, when the travel doesn't work, when he's about to say yes to something that doesn't serve the plan.
You anticipate . You see two steps ahead and have the document, the number, or the contact ready before he asks. You will get direct feedback here, and you're expected to give it. Success Metrics First 30 days
Full command of the calendar, inbox, and key contacts
Meeting rhythm documented and running with agendas and notes
Nothing scheduled without prep materials attached First 90 days
Founder's inbox triaged daily; response time on external requests under 24 hours
Zero dropped commitments — every action item tracked with an owner and a due date
Travel and events handled without founder involvement beyond approval
Marketing content calendar built and publishing on schedule First 12 months
Founder's time measurably reallocated toward acquisitions, leadership, and strategy
Advisors, lenders, and vendors route through you by default
You are trusted to make decisions in his absence within defined limits Who You Are Required
3+ years supporting a senior executive, business owner, or entrepreneur
Exceptional written communication — you can write in someone else's voice
Relentlessly organized; you run a system, not a memory
Comfortable with ambiguity and rapid change; priorities shift and you shift with them
High discretion with confidential financial, legal, and personal information
Proficient with Google Workspace; quick to learn new software
Direct, confident, and unintimidated by strong personalities Preferred
Marketing, social media, or content coordination experience
Exposure to home services, construction, or the trades
Experience with M&A, commercial lending, or transaction support
Familiarity with EOS, Scaling Up, or similar operating systems
ServiceTitan or comparable field service software Culture fit — non-negotiable
Gratitude — you see what's good and say it
Respect — for the team, the customer, and the work
Integrity — you do what you said you'd do, especially when it's inconvenient
Trust — you earn it, and you extend it Why This Seat Matters
Cooleys grew from nothing in 2020 to a company with a new 4,500 sq ft headquarters, a dedicated training facility, and a plan to become the dominant home services platform on the Western Slope. That plan requires the founder operating at the top of his ability — not buried in scheduling, follow-up, and paperwork. You are the reason that's possible. To Apply
Send a resume and a short note answering one question: Tell us about a time you told your boss no — and what happened.

Applications without an answer to that question will not be reviewed .

Pay:

$50,000.00

$85,000.

00 per year

Benefits:

401(k) Dental insurance Paid time off Ability to

Commute:

Delta, CO 81416 (Required)

Work Location:

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