Sr Executive Assistant to the CEOManaging PartnerPreston Design and Construction Consulting

Steele Recruiting; Chicago (IL); On-site; USD 115,000 - 180,000; Full time

Benefits offered by this job

Health Insurance

Vision & Dental Insurance

401K with company match

Bonus Opportunity 10-20%

Paid Time Off

Job summary

Steele Recruiting LLC is seeking a Senior Executive Assistant to support the CEO/Managing Principal of Preston Design & Construction Consulting. The role emphasizes strategic calendar management, proactive coordination, and confidentiality to enable executive leadership to focus on high-impact priorities.

The ideal candidate will have 3–7 years in senior EA roles, strong MS Office skills, and a proven record in fast-paced environments.

Qualifications

• Minimum three to seven years of experience as a Senior Executive Administrative Assistant.
• Supporting a CEO, C-Suite, or President in a high-growth environment is ideal.
• High attention to detail, proactiveness, and organizational skills are required.
• Strong communication and professional representation of the team are essential.
• Experience with complex travel, calendar management, and scheduling is needed.
• Proficiency with Microsoft Office and related tools is expected.

Responsibilities

• Manage the CEO/Managing Principal’s calendar and prioritize requests.
• Coordinate meetings, agendas, minutes, and action items.
• Handle email inbox and follow-ups with minimal direction.
• Anticipate needs and improve workflows to support priorities.
• Coordinate heavy travel arrangements and itineraries.
• Maintain confidential information with discretion and professionalism.
• Lead team-building activities and support culture initiatives.
• Protect time and manage competing priorities effectively.

Skills

Calendar management

Executive support

Communication

Organizational skills

Discretion

Travel coordination

CRM experience

Microsoft Office

Adaptability

Team coordination

Education

High School Diploma

College Degree preferred

Tools

Microsoft Office Suite

Microsoft Copilot

Adobe Suite

Canva

DocuSign

CRM (Salesforce)

Job description

Steele Recruiting LLC is a Retained Search firm located in Minneapolis, Minnesota, with national reach, specializing in permanent placements of Executive Administrative Assistants, Personal Assistants, and Chiefs of Staff for C-Suite and Senior Leadership Executives across the United States.

With over 20 years in recruitment, we have a solid reputation for quality placements, professionalism, and maintaining confidentiality for every client and candidate.

We are thrilled to partner with our trusted client, Preston Design & Construction Consulting, for a Senior
Executive Assistant to the CEO/Managing Principal, located in their beautiful office in downtown Chicago, Illinois.

Preston Design & Construction Consulting is a 100% woman-owned, WBENC-certified project management and development advisory firm specializing in representing owners, operators, developers, and tenants on complex, high-end construction and development projects. The firm provides comprehensive development advisory, owner's representation, and project management services for first-class core and shell developments, redevelopments, and interior spaces across country clubs, nonprofit organizations, educational institutions, hospitality, and commercial office environments.

Founded by Amy Preston and supported by a team of experienced project managers and trusted industry partners, Preston Design & Construction Consulting has built a reputation for delivering strategic leadership, exceptional client service, and innovative design and construction solutions tailored to each client's unique vision.

Their services include: Planning & Budgeting, Land Planning & Due Diligence, Entitlements, Permitting, RFP Development, General Contractor Bid & Award Selection, Contract Negotiation, Construction Oversight, Pre-Development, Consultant Onboarding, & Design Management.

They take pride in involving M/WBE business partners in the work they do, and are intentionally thoughtful in this process. They work alongside their partners and vendors to achieve these diversity goals together, proactively recommending proven strategies with a strong track record of success in reaching these goals.

Most importantly, this ensures that the teams they put together are representative of the communities in which their projects are built, and inclusive of minorities, women, veterans, and other historically excluded populations.

What makes this opportunity exceptional?

This Senior Executive Assistant role offers the opportunity to build and define a newly created, high-impact position supporting the CEO/Managing Principal. Serving as a trusted executive administrative thought partner, this role goes beyond traditional administrative support. It requires precision, adaptability, and proactive coordination across complex priorities and confidential initiatives.

Beyond providing exceptional executive support, this role offers the opportunity to serve as the driving force behind the CEO's efficiency, effectiveness, and long-term success, as you work alongside the CEO/Managing Principal in a fast-paced role and a company experiencing tremendous growth and expansion in the US.

PDCC’s unique culture and small and mighty team of professionals

creates a stable yet growth-oriented team environment where they respect each other, are kind, and work as a team. This is a unique opportunity to contribute and shape how executive support is delivered to a high-profile executive, within a dynamic and values-driven company.

Your days will include working with a team that jumps in to help wherever they can, celebrating the big and little wins. There is a true sense of camaraderie that puts people first.

The Role

The Senior Executive Assistant serves as a trusted partner to the CEO/Managing Principal, providing high-level administrative and strategic support that maximizes her effectiveness. This role goes beyond traditional administrative tasks by proactively managing priorities, protecting her time, coordinating communication, anticipating needs, and ensuring projects, meetings, and commitments move forward efficiently.

The Senior Executive Assistant acts as the central point of coordination, exercising sound judgment, maintaining confidentiality, and creating the organization and structure that allows the CEO/Managing Principal to focus on leadership and high-impact responsibilities.

Primary Responsibilities

• Manage and protect the
  CEO/Managing Principal’s calendar, ensuring priorities, focus time, and strategic scheduling.

• Serve as the primary gatekeeper by prioritizing requests and determining what requires the executive's attention.

• Manage the CEO/Managing Principal’s email inbox, organize correspondence, prepare responses, and track follow-up items.

• Develop weekly priorities, task lists, and action plans to keep projects and responsibilities organized.

• Coordinate meetings, prepare agendas, attend meetings, document minutes, and track action items.

• Learn the CEO/Managing Principal’s business, projects, systems, contacts, and preferred ways of working.

• Research information, solve problems, and proactively move projects forward with minimal direction.

• Coordinate heavy business and personal travel, including itineraries, lodging, transportation, and schedule changes.

• Schedule meetings, lunches, calls, and appointments while balancing travel time and competing priorities.

• Monitor voicemail and communications, ensuring timely follow-up and organized callback management.

• Communicate professionally with the team, clients, consultants, and external partners on behalf of the executive.

• Hold the executive and team members accountable for commitments, deadlines, and agreed-upon priorities.

• Reinforce boundaries surrounding the CEO/Managing Principal’'s calendar, availability, and use of time.

• Maintain highly organized filing systems, documentation, and administrative processes.

• Handle sensitive information with professionalism, discretion, confidentiality, and sound judgment.

• Adapt quickly to changing priorities while maintaining organization, accuracy, and attention to detail.

• Learn and utilize new technology, software, and administrative systems to improve efficiency.

• Anticipate needs, identify opportunities to improve workflows, and take initiative before being asked.

• Lead firm team building activities, enhancing culture of fun and cohesiveness, golf, dinners, lunches, etc.

Required Background

• Minimum three to seven years of experience as a Senior Executive Administrative Assistant supporting a CEO, C-Suite, or President, or similar

• High School Diploma, College Degree preferred.

• High level of attention to detail, proactiveness, and organizational skills required.

• Capable of representing Preston and the team professionally, with strong communication skills and a deep appreciation for the experiences they create for those around them.

• Complex travel arrangement and calendar management experience required.

• High proficiency with Microsoft Office Suite, with the ability to learn new or updated software, including Microsoft Copilot, Adobe Suite, Canva, DocuSign, and CRM such as Salesforce

• Ability to execute all tasks in a fast-paced and dynamic environment, with a high-level of adaptability, confidentiality, and discretion.

• Experience operating in a high-profile Executive Assistant position, interacting with team members, clients, and affiliates of the firm.

Preferred Qualifications:

• Industry Experience in real estate, property management, office buildout, construction, desirable but not necessary

• Experience with AI Claude, ChatGpt, Anthropic

• Experience supporting a CEO, Founder, President, or Managing Partner within an entrepreneurial or high-growth organization.

Compensation

• Senior Executive Assistant Salary target range $115,000 to $180,000

• Health Insurance - Blue Cross Blue Shield

• Vision, Dental

• Long Term / Short Term Disability

• Accidental Death & Life Insurance

• 401K with company match

• Discount parking/commuter benefits

• Vacation Time / Personal Days

• Sick Leave

• Expense account

• Bonus Opportunity 10-20% target

• Casual Office Attire

• This is an in office position with flexibility as needed, 9-5 pm hours

• Priority application deadline: August 28, 2026

Preston Design and Construction Consulting is committed to complying with all laws prohibiting discrimination in employment and is proud to provide equal employment opportunities to applicants and employees without discrimination based on race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability status, or any other applicable characteristics protected by local, state, and federal law.