Director of Operations

Director of Operations

Rolling Meadows, IL · 

On-site

Full-time

About the job

This is a rare opportunity to partner directly with the Founder/CEO of a growing insurance and wealth management firm to build the operational infrastructure that will support the company’s next phase of growth.

As the firm’s Integrator, you will lead operations, develop people, implement EOS, and translate vision into execution.

This is a true leadership role and is designed to evolve into a Chief Operating Officer position as the firm grows

As we scale, we’re seeking an experienced and entrepreneurial Director of Operations (Integrator) to turn vision into reality — driving operational excellence, empowering people, and ensuring the firm delivers on its promise of client success.

The Opportunity

This is a high-impact leadership role for someone who loves translating strategy into execution. As our Integrator, you’ll be the central bridge between the CEO (Visionary) and the rest of the organization. You’ll own the firm’s internal operations — ensuring every process, project, and person is aligned with our goals, values, and growth plan.

we are actively implementing the Entrepreneurial Operating System (EOS) framework. You’ll help bring it to life — facilitating leadership rhythms, ensuring accountability, and turning big ideas into tangible results.

Key Responsibilities

Leadership & Strategy

Partner with the CEO to translate long-term vision into actionable strategies, quarterly priorities (“rocks”), and measurable goals.

Lead, coach, and hold accountable department leads in Service, Processing, Scheduling & Events, and Client Experience.

Facilitate weekly leadership meetings, drive scorecard reviews, and maintain firm-wide alignment.

Operations & Systems

Oversee cross-departmental workflows and handoffs to ensure a seamless, high-touch client experience.

Manage and optimize operational systems (CRM, project management, productivity tools, dashboards).

Own data integrity, performance metrics, and reporting across the firm.

Develop, implement, and continually improve Standard Operating Procedures (SOPs).

People & Culture

Support HR functions including onboarding, training, and professional development.

Champion company culture and team engagement consistent with our core values.

Collaborate with Marketing, Finance, and Strategy teams to ensure initiatives align with business metrics and brand standards.

Accountability & Results

Drive execution discipline through consistent communication, scorecards, and project reviews.

Provide weekly performance updates and quarterly business reviews to senior leadership.

Qualifications

Proven leadership in operations, business management, or a similar integrator-type role within a growing organization.

Experience with or strong interest in the EOS/Traction framework.

Bachelor’s degree in business, finance, or related field.

Skilled in project management, CRM and workflow systems, and Microsoft Office Suite.

Strong data-driven mindset with experience implementing KPIs and operational dashboards.

Excellent communication, leadership, and problem-solving abilities.

Background in financial services, wealth management, or professional services preferred.

Benefits & Perks

Paid Vacation (PTO) 80 Hours

Paid Holidays (10)

Paid Birthday Off

401 K Match 100% (for first 1% contribution) and 50% (for up to 6% contribution)

Medical Benefit Reimbursement

Company Paid Meals

Retreat Events

Summer Fridays (1/2-day June 1-September 1)

Office Address: 4190 Euclid Ave, Rolling Meadows, IL 60008

Benefits found in job post

401(k)

Requirements added by the job poster

• Bachelor's Degree

• Accept a background check

• Working in an onsite setting

• Authorized to work in the United States