Executive Assistant to the CEO

About Us

Founded in 1932, Ashland Addison Florist is a fourth-generation, family-owned business that has proudly been Chicago’s favorite florist for over 90 years. With a dedicated team of 90 employees and 6 locations, we continue to grow while maintaining the same commitment to quality and service that has made us a trusted name in the floral industry.

We take great pride in our deep roots and strong values, which have shaped our reputation for excellence. As we expand, we remain committed to fostering a family-oriented and inclusive culture where employees from all walks of life can thrive, feel valued, and make meaningful contributions to our legacy.

At Ashland Addison Florist, we believe that our success is driven by the people who make up our team. We are passionate about providing a supportive, welcoming environment where each individual is empowered to grow and succeed alongside us. If you are looking to be part of a dynamic, growing company with a rich history, Ashland Addison Florist is the place for you.

Overview

We are seeking a highly capable, discreet, and commercially minded Executive Assistant to the CEO & Owner to serve as a strategic partner to our leadership team. This is not a traditional calendar-management role — it's a position built for someone who can protect the CEO's time, filter what truly requires his attention, and help drive the business forward.

The ideal candidate is an experienced executive assistant who understands the difference between urgent and important, operates with strong business judgment, and is comfortable working in a fast-paced, entrepreneurial environment with constantly shifting priorities.

What You'll Do

Protect the CEO's Time

• Monitor, triage, and prioritize all inbound communications
• Determine what requires the CEO's direct attention vs. what should be redirected to the General Manager, another leader, or resolved independently
• Draft responses and ensure every communication receives a clear, professional, and timely reply

Manage a Strategic Calendar

• Build and maintain a highly organized calendar that reflects business priorities, not just incoming request volume
• Create protected focus time for strategic thinking
• Prepare agendas, objectives, and materials ahead of meetings; confirm decisions and follow up on action items afterward
• Continually evaluate whether a meeting needs to happen, can be shortened, combined, or delegated

Coordinate Travel & Events

• Arrange flights, hotels, ground transportation, and detailed itineraries for business and personal travel
• Plan and coordinate leadership meetings, vendor and client events, and other CEO-related commitments

Track Priorities & Follow-Through

• Maintain visibility into the company's most important CEO-level initiatives, owners, and deadlines
• Create a system for tracking commitments so nothing falls through the cracks after meetings
• Deliver a concise weekly executive brief covering top priorities, key decisions needed, risks, and outstanding follow-ups

Support Financial & Relationship Awareness

• Track expenses, coordinate invoices, and flag potential savings opportunities
• Maintain and nurture important professional relationships and networking opportunities on the CEO's behalf

Anticipate & Solve Problems

• Identify potential issues before they escalate
• When bringing a problem forward, come prepared with context, options, and a recommended next step — not just the problem itself

Maintain Confidentiality

• Handle sensitive information related to finances, personnel, compensation, and strategic initiatives with the utmost discretion

What We're Looking For

• 5 years of experience as an Executive Assistant, ideally supporting a CEO, owner, founder, or senior executive
• Experience in a fast-paced, entrepreneurial, or family-owned business environment
• Excellent written and verbal communication skills
• Exceptional organizational, calendar, and prioritization skills
• Strong business judgment and financial/commercial awareness
• High emotional intelligence and absolute discretion
• Comfort pushing back professionally when needed
• Ability to manage ambiguity and shifting priorities with a proactive, low-ego attitude
• Strong follow-through and accountability

Most important trait: Judgment. We're looking for someone who can tell the difference between a meeting that needs the CEO in the room and one that doesn't — not just someone who can schedule it.

How Success Is Measured

This role is evaluated on outcomes, not just task volume:

• Increased CEO capacity for high-value work
• Fewer unnecessary meetings and better-prepared ones
• Timely follow-through on commitments and action items
• Professional, responsive communication with all stakeholders
• Issues caught and addressed before they become emergencies
• Matters routed to the right owner instead of unnecessarily escalating

Why Join Us

This role offers a rare opportunity to work directly alongside the CEO & Owner as a true strategic partner — not just an administrative support function. You'll have real influence over how leadership time is spent and where the business focuses its energy.

To apply, please submit your resume along with a brief note on why you're a strong fit for this role.

Pay: $65,000.00 - $80,000.00 per year

Benefits:

• Dental insurance
• Employee discount
• Health insurance
• Life insurance
• Retirement plan
• Vision insurance

Education:

• Bachelor's (Required)

Experience:

• Executive administrative support: 5 years (Required)
• Calendar management: 5 years (Required)

Ability to Commute:

• Chicago, IL 60608 (Required)

Work Location: In person

Salary : $65,000 - $80,000