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Director of Learning & Development

Cooper's Hawk Winery and Restaurants
Downers Grove, IL Full Time
POSTED ON 11/23/2025
AVAILABLE BEFORE 11/29/2025
Cooper’s Hawk Winery and Restaurants continues to expand its restaurant presence, innovate winery capabilities and build its Lifestyle Brand. The Director of Learning and Development will play a critical role in advancing leadership capability across our restaurants and at the Restaurant Support Center. This leader will design and deliver impactful leadership training programs that build a strong pipeline of talent, strengthen culture and enable operations excellence. By equipping current and future leaders with the skills, confidence, and mindset to grow their careers, this role will drive long-term success and support Cooper’s Hawk Vision – We Create Community.

What You’ll Do:

  • Lead the design, implementation, and sustainment of learning programs that align with company strategy, operational priorities, and growth objectives.
  • Lead, design and evolve the Operations Management Training programs including Manager-in-Development and Areas of Responsibility, to build well-rounded and competent leaders by integrating leadership capabilities and skills along with operational expertise.
  • Partner with business leaders to assess needs, identify skill gaps and deliver innovative and effective training solutions for both Operations and Restaurant Support Center (RSC) leaders.
  • Design and deliver Leadership Development experiences that strengthen belonging, collaboration and engagement across all levels.
  • Facilitate leadership training sessions to both Operations and the RSC.
  • Partner with Operations and HR leaders to build a strong pipeline of future leaders by supporting development plans for high-potential leaders and emerging talent.
  • Create and lead a scalable assessment program that evaluates internal managers’ readiness for their next role, ensuring objective insights to guide promotions, succession planning, and targeted development.
  • Evaluate effectiveness of leadership development programs by leveraging business analytics, feedback, performance outcomes, and competitive insights to measure impact and continuously refine program design and delivery.
  • Leverage learning technology not only to deliver engaging leadership training programs, but also to capture data and insights that inform program effectiveness and enhancements.
  • Support the planning and execution of the annual Leadership Conference as well as targeted development sessions including Area Team development throughout the year.

What You’ll Need:

Ideal candidates will have the following:

  • Must represent Cooper’s Hawk values
  • Minimum of 10 years of experience in learning and development with at least 5 years in a leadership role in a multi-unit restaurant or hospitality environment
  • Bachelor’s degree in Human Resources, Organizational Development/Organizational Behavior, Business Administration, Education or related field
  • Experience in leading and developing a high-performing team
  • Ability to assess training needs and develop and implement programs to support company growth objectives, operational excellence and workforce and succession planning initiatives
  • Excellent, effective and professional verbal and written communication skills; ability to manage a productive flow of communication in a variety of settings
  • Ability to partner with key stakeholders at all levels of the organization
  • Desire and flexibility to assume the roles of individual contributor, team player and leader simultaneously as the organization evolves
  • Sound understanding of adult learning principles
  • Strong learning design skills including eLearning and instructional design, AI experience a plus
  • Ability to travel, as needed

Competencies

  • Manage Talent
  • Communicate Effectively
  • Collaborate
  • Develop Others
  • Plans and Aligns
  • Drive Results
  • Business Acumen
  • Drive Engagement

Compensation Range: $140,000-170,000/year bonus potential. The final offered salary will be based on several factors, including but not limited to the candidate’s depth of experience, skill set, qualifications, and internal pay equity.

What You’ll Get:

  • Incredible Discounts:
    • Monthly Dining Allowance
    • 50% Dining and Carryout
    • 40% Retail Wine
    • 20% Retail and Private Events
  • Monthly Complimentary Wine Tasting for Two
  • Medical, Prescription, Dental, Vision Insurance plus Telemedicine and Wellness Program
  • Company Matching 401(k) Retirement Savings Plan
  • Flexible Savings Accounts- Health and Dependent Care
  • Health Savings Account
  • Long-Term Disability; Voluntary Short-Term Disability
  • Basic Life and AD&D Insurance (with option to purchase additional coverage)
  • Paid Parental Leave
  • Highly Competitive Pay plus Team Member Incentives & Rewards
  • Paid Time Off
  • Milestones Recognition Program
  • Complimentary Gym Membership in RSC Building
  • Hybrid Work Week (3 days in office, 2 days remote, depending on role)

Cooper’s Hawk is an equal opportunity employer. All qualified applicants are considered for employment without regard to the persons race, color, religion, national origin, sex, sexual orientation, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Coopers Hawk makes reasonable accommodations during all aspects of the employment process, including during the interview process.

The information provided above indicates the general nature and level of work required of the position and is not a comprehensive list of all responsibilities or qualifications. The Benefits list is only a highlight of some of the benefits offered to team members; eligibility for certain benefits apply.

About Us

Cooper's Hawk Winery & Restaurants was created with the inspiration of bringing the Napa Valley experience to all of America, by combining an elegant tasting room with a polished casual restaurant and scratch kitchen. Cooper's Hawk wines have won hundreds of awards and are the Official Wines of the Screen Actors Guild® Awards. We are built upon the belief that food and wine hold the power to forge a COMMUNITY, and with the world's largest wine club membership, we are paving the way to democratizing the good life!

Salary : $140,000 - $170,000

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