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Director Chicago Bears Jobs (NOW HIRING)

... bears a rugged look. This territory belongs to the loon, the bear, and most of all, the lordly ... SW, Delta, American, United, Republic, Direct to: Atlanta, Baltimore, Charlotte, Chicago) THE ...

... bears a rugged look. This territory belongs to the loon, the bear, and most of all, the lordly ... SW, Delta, American, United, Republic, Direct to: Atlanta, Baltimore, Charlotte, Chicago ) THE ...

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Director Chicago Bears information

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$57K

$186.4K

$331K

How much do director chicago bears jobs pay per year?

As of Aug 23, 2026, the average yearly pay for director chicago bears in the United States is $186,382.00, according to ZipRecruiter salary data. Most workers in this role earn between $115,500.00 and $249,500.00 per year, depending on experience, location, and employer.

What does a director for the Chicago Bears do?

A Director for the Chicago Bears is a high-level executive responsible for overseeing specific departments or operations within the organization, such as marketing, player personnel, or community relations. Their duties include strategic planning, managing staff, ensuring departmental goals align with the team's overall objectives, and working closely with other executives to support the team's success on and off the field. Directors play a key role in decision-making and are integral to the smooth operation and growth of the Chicago Bears franchise.

What are the key skills and qualifications needed to thrive as a director for the Chicago Bears?

To thrive as a Director for the Chicago Bears, you need extensive leadership experience in sports management, a deep understanding of NFL operations, and a relevant degree such as business administration or sports management. Familiarity with sports analytics systems, league compliance platforms, and budget management tools is typically required. Strong strategic thinking, communication, and relationship-building skills set outstanding candidates apart. These abilities are essential for driving organizational success, maintaining compliance, and fostering a winning culture within a professional football organization.

What are some common challenges faced by a director at the Chicago Bears, and how can they be navigated?

A Director at the Chicago Bears often faces the challenge of balancing organizational objectives with the fast-paced demands of the NFL season. This includes coordinating between various departments, managing high-profile projects under tight deadlines, and maintaining effective communication with both executive leadership and operational teams. Navigating these challenges requires strong leadership, adaptability, and a collaborative mindset. Building relationships across the organization and staying proactive in problem-solving are key to success in this role.

What is the difference between Director Chicago Bears vs Coach Chicago Bears?

AspectDirector Chicago BearsCoach Chicago Bears
Primary RoleOversees team operations, management, and strategic planningDevelops game strategies, trains players, and manages on-field performance
Required CredentialsBusiness, management, or sports administration degree; leadership experiencePlaying experience, coaching certifications, and sports-specific training
Work EnvironmentOffice-based, administrative, and organizational settingsOn-field, training facilities, and game days
Industry UsageCommonly used in sports organizations for leadership rolesCommonly used for on-field coaching and team strategy roles

The main difference is that the Director Chicago Bears focuses on overall team management and strategic planning, often in an administrative capacity, while the Coach Chicago Bears is responsible for on-field performance, training, and game tactics. Both roles are essential but serve different functions within the team structure.

What cities are hiring for Director Chicago Bears jobs?

Cities with the most Director Chicago Bears job openings:

What are the most commonly searched types of Chicago Bears jobs?

The most popular types of Chicago Bears jobs are:

What states have the most Director Chicago Bears jobs?

States with the most job openings for Director Chicago Bears jobs include:

What job categories do people searching Director Chicago Bears jobs look for?

The top searched job categories for Director Chicago Bears jobs are:

Infographic showing various Director Chicago Bears job openings in the United States as of August 2026, with employment types broken down into 2% As Needed, 83% Full Time, 12% Part Time, 1% Temporary, and 2% Contract. Highlights an 91% Physical, 3% Hybrid, and 6% Remote job distribution, with an average salary of $186,382 per year, or $89.6 per hour.

Insurance Agent with Training

Glosson Region - Modern Woodmen of America

Fort Myers, FL • On-site

$67K - $124K/yr

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 10 days ago


Job description

Benefits:
  • 401(k)
  • 401(k) matching
  • Company parties
  • Dental insurance
  • Flexible schedule
  • Health insurance
  • Opportunity for advancement
  • Training & development
  • Vision insurance

Are you a former athlete or someone who has always had a relentless competitive spirit? Do you thrive on challenges and achieving greatness in your career and beyond? The Glosson Region at Modern Woodmen of America is ready to add a new Associate Financial Representative (future Financial Representative once licensing is achieved) to our team. We are a dedicated group of driven, ambitious professionals, eager to impact people’s lives as we rapidly expand our offices across the region.
About The Glosson Region - Modern Woodmen of America:
At the Glosson Region, our mission is to grow membership by protecting legacies for families and businesses through wise financial planning. Our vision is to build a Legacy Region that grows beyond our generation, creating lasting impact for years to come. We are guided by unwavering faith, working diligently today to shape a better future tomorrow. With relentless grit, we fight for our goals and never quit. We foster a winning attitude, learning and helping others along the way, while embracing a growth mindset that drives both personal and professional development. We believe in the power of collaboration – when two or more work together, our growth multiplies. Join us in building a legacy that will stand the test of time.
Watch this short video to see how sharing meaningful moments—both personal and professional—can transform perspectives on a career in financial services with Modern Woodmen of America: https://youtu.be/-qWeFzHB-ck
About Modern Woodmen:
Modern Woodmen is about people. Created for our members. Owned and operated by them too. Together, we’re here for each other, for our families and for the communities we love. We are a member-owned fraternal financial services organization. Together with over 700,000 members, we’ve been touching lives and securing futures since 1883. Modern Woodmen's financial strength is anchored in a robust asset base of $17.14 billion. Guided by a prudent investment philosophy, the organization focuses on high-quality, diversified investments with high industry ratings from A.M. Best and KBRA. With a surplus of $2.42 billion and a solvency ratio of 116.41%, Modern Woodmen is committed to ensuring additional protection for its members, affirming its dedication to long-term financial stability.
Check out the varying backgrounds of some of our local leaders:
Jarrett Glosson, Regional Director:
  • Year Started with MWA: March of 2007
  • Prior to MWA: Jarrett worked in media sales for Charter Media (now Spectrum), focusing on B2B and selling airtime.
  • Passionate About: Outside of business, Jarrett is dedicated to his church and enjoys spending time with his wife, Autumn (married for 22 years), and their dog, Benson (a miniature Bernedoodle). He loves to travel, having visited 16 countries, with Italy being his favorite. Jarrett also has a strong passion for self-development and is a fan of the Tennessee Titans.
Christopher Schults, Financial Representative:
  • Year Started with MWA: February of 2016
  • Prior to MWA: Chris previously ran his own cabinet business and was a volunteer firefighter.
  • Passionate About: Chris is deeply involved with his church and enjoys spending time with his wife, Alicia, and their three daughters. He combines his love for golf with fraternal work to give back to his community. Chris is a Tampa Bay Buccaneers fan and enjoys working out. Born and raised in Florida, he values his family and community.
Lenny Cannova, Financial Representative:
  • Year Started with MWA: February of 2014
  • Prior to MWA: Lenny was a pizza shop owner before deciding to transition into the Modern Woodmen role.
  • Passionate About: Lenny enjoys spending time with his wife, Lynn, their two daughters, and their grandchildren. He is passionate about golf, boating, and working on motorized projects such as motorcycles, ATVs, and jet skis. Lenny is a member of a boat club and loves spending time on the water. He is also a Chicago Bears fan.
Kristina Ribali, Managing Partner:
  • Year Started with MWA: March of 2020
  • Prior to MWA: Kristina worked in non-profit and donor relations before joining Modern Woodmen.
  • Passionate About: Kristina and her husband, JD, were instrumental in starting a campus of their church and are passionate about serving their community. They are dedicated to helping children become leaders through JD’s BizKidz program, which provides coaching and opportunities for kids to sell products and compete for cash prizes. Kristina loves to mentor the children involved in these events.
Our thriving offices are located across several locations:
  • The Regional Office can be found at 8981 Daniels Center Dr. Ste 210, Fort Myers, FL 33912.
  • Our Naples Office is located at Ste 302, 3435 10th St N, Naples, FL 34103.
  • The Punta Gorda Office is at Unit 116, 265 E Marion Ave, Punta Gorda, FL 33950.
  • Our Cape Coral Office is located at NBR 1b4, 3046 Del Prado Blvd S, Cape Coral, FL 33904.
Role Responsibilities:
  • Member Consultation: Meet with client members to assess their insurance needs and recommend appropriate coverage.
  • Customer Service: Provide exceptional customer service, addressing client inquiries and resolving issues promptly.
  • Networking: Build and maintain a network of client members through referrals, networking events, and community engagement.
  • Training and Development: Participate in ongoing training and professional development to stay current with industry changes and enhance sales skills.
  • Target Achievement: Meet or exceed business development goals.
Perks/Benefits:
  • Strong Income Opportunity. 
  • Potential to earn client/member leads. 
  • Advancement Opportunity to become a Managing Partner
  • Exclusive training/development locally and nationally.
  • An environment and culture of mutual support and growth.
  • Attainment of prestigious credentials and recognition.
  • Consistent opportunities for growing your income and character.
  • Strong benefits and retirement package.
  • Dental, health, and vision insurance
  • Flexible schedule
  • Reward Travel
  • Life insurance
  • Professional development assistance
  • Referral program
Qualifications:
  • Team-Oriented
  • Enthusiastic
  • Positive Attitude
  • Self-Starter
  • Community-Focused
  • Coachable
  • Athletic Background (bonus)
  • Military Background (bonus)
  • Goal-Driven
  • Willingness to Obtain State Insurance License
  • Willingness to Obtain Series 6 or 7 Finra License
  • College Degree (preferred, not required)
If you're ready to unleash your competitive drive and embark on a career that changes lives, join our team. 

Flexible work from home options available.