Executive Assistant to the CEO

HERITAGE HOLDING COMPANY

Position Announcement

Executive Assistant to the CEO

Location: Shelbyville / Crestwood, KY (On-Site)

Reports To: Logan Baker, Founder & CEO

Type: Full-Time

About Heritage Holding Company

Heritage Holding Company is a growing family of businesses spanning signage, LED manufacturing, and related industries, led by Founder & CEO Logan Baker. The environment is fast-paced and entrepreneurial, with a deep commitment to excellence, integrity, and team culture. Logan has been recognized as a Louisville Business First Forty Under 40 honoree and leads multiple companies with high-growth ambitions. This is an opportunity to work alongside a dynamic CEO and make a real impact.

The Opportunity

Logan is a visionary leader who moves fast, manages multiple companies, and operates best when he is focused on relationships, strategy, coaching, and high-leverage communication. He is looking for a true right-hand partner — someone who doesn't just take orders, but proactively runs the systems, clears the noise, and helps him stay locked in on what matters most. This is not a passive support role. It's a high-trust, high-initiative position that demands excellent judgment, strong verbal communication skills, and the confidence to lead up.

What You'll Own

Inbox Management

Own Logan's inboxes end-to-end — triage, sort, respond, archive, unsubscribe, and surface only what truly needs his attention.

Achieve Inbox Zero daily. Logan's goal is to spend fewer than 20 minutes per day in email.

Draft replies, handle routine correspondence independently, and escalate sensitive items (legal, HR, financial) promptly.

Calendar Management

Serve as the sole owner of Logan's work calendar — scheduling, rescheduling, declining, and auditing meetings on a rolling 6-week basis.

Color-code and protect time blocks for Deep Work, Leadership, External, Travel, and Personal commitments.

Build in buffers; eliminate back-to-back marathons; proactively manage OOO periods.

Daily & Weekly Communication Cadence

Lead a daily 5–15 minute morning standup at 8:00 AM ET — you bring the agenda, the decisions, and the owners.

Facilitate a weekly project deep-dive and maintain Logan's accountability structure.

Prefer voice/video communication; minimize long text-based back-and-forth.

Travel Coordination

Manage all travel logistics: flights (nonstop preferred), hotels, ground transport, and itinerary details loaded into the calendar with confirmation numbers.

Apply Logan's travel preferences (aisle seat, front of plane, business class for flights over 5 hours with budget approval).

Always obtain final approval before purchasing tickets.

Project & Task Coordination

Manage follow-up systems — every thread has an owner and a due date.

Use Asana to track tasks, SOPs, and daily reports; keep Logan's project view clean and current.

Identify broken processes, propose fixes, and deliver automation wins (email filters, calendar rules, etc.).

Administrative & Financial Support

Handle receipt management and company card purchases up to $100 within approved SOPs.

Submit receipts via the internal credit card receipt process and keep Logan's expense records clean.

Manage personal scheduling items (barber, family logistics) as needed.

What Success Looks Like

Logan's inbox sorted every day before he starts work.

Logan's calendar reflects his "Core Four" priorities — not reactive clutter.

Logan spends fewer than 20 minutes per day in email.

Every open loop has an owner, a due date, and a follow-up.

Logan is focused, on-time, and rarely surprised by what's coming.

You're proactively flagging issues before they become problems.

Who You Are

Proactive, not reactive — you initiate, don't wait for permission.

A strong, clear verbal communicator who picks up the phone and shows up on camera.

Highly organized, detail-oriented, and relentless about follow-through.

Comfortable leading up — you'll politely push back on Logan when it's in his best interest.

Tech-savvy with Google Workspace (Gmail, Calendar, Drive), Asana, and general productivity tools.

Discreet and trustworthy — you'll have access to sensitive communications and personal information.

Self-managing — you don't need hand-holding to figure out what to do next.

Available to start your day 30–60 minutes before the 8:00 AM sync to get ahead of the inbox and calendar.

This Role Is NOT a Fit If You...

Prefer text-only communication and avoid phone or video calls.

Wait to be told what to do rather than managing up proactively.

Are passive or need consistent hand-holding to stay on task.

Struggle with follow-through or let things fall through the cracks.

Are uncomfortable representing the CEO in external communications.

Your First 90 Days

Days 1–30: Learn & Stabilize

Shadow meetings, document SOPs, and set up the daily standup report.

Take full ownership of inbox and calendar; reach Inbox Zero daily.

Build the template library and implement the autoresponder SOP.

Days 31–60: Own & Optimize

Lead daily and weekly syncs; run the full follow-up system independently.

Reduce Logan's email time to under 30 minutes per day; clean calendar debt.

Identify the top three broken processes and propose fixes.

Days 61–90: Scale & Extend

Introduce weekly metrics tracking (Inbox Zero %, follow-through rate, Core Four calendar %).

Deliver at least two automation wins (filters, rules, or calendar bots).

Present a quarterly "flight plan" showing Logan's Core Four time blocks.

Heritage Holding Company | Shelbyville / Crestwood, KY | An Equal Opportunity Employer

Pay: $48,445.14 - $58,342.53 per year

Benefits:

• 401(k) matching
• Dental insurance
• Employee assistance program
• Health insurance
• Life insurance
• Paid time off
• Relocation assistance
• Vision insurance

Work Location: In person

Salary : $48,445 - $58,343