Vice President, All-Star/Rep Baseball Operations

Vice-President – All-Star / Rep Baseball Operations

Board of Directors Position

Oakville Little League (OLL)
Oakville, Ontario
425 Cornwall Road

Time Commitment: Minimum 10 hours per month
Schedule: Year-round, with significant increases in workload during peak periods of the baseball season

Position Overview

Oakville Little League is seeking a committed, organized, and strategic volunteer to serve as Vice-President – All-Star / Rep Baseball Operations. This Board of Directors position is responsible for the planning, development, implementation, and oversight of OLL’s All-Star and Select baseball programs.

Reporting to the Board of Directors, the Vice-President will work collaboratively with team managers, coaches, the Coach & Player Development Coordinator, and other league volunteers to establish a structured, competitive, and development-focused program that supports the growth of players and the success of each team.

The successful candidate will provide leadership across the Summer All-Star program, Fall Travel All-Star program, and Fall/Winter High Performance training programs. This includes manager and coach recruitment, player selection processes, seasonal planning, budgeting, performance evaluation, and ongoing program oversight.

As a member of the Board of Directors, the Vice-President will also contribute to the overall governance, strategic direction, and continued development of Oakville Little League.

Key Responsibilities

1. Program Leadership and Development

• Develop and oversee the annual All-Star and Select baseball program structure.
• Establish program objectives, operating plans, timelines, and expectations for each team.
• Coordinate seasonal planning with team managers, including off-season training, conditioning, and summer and fall schedules.
• Work with the Coach & Player Development Coordinator to support player development and program quality.
• Review program outcomes annually and identify opportunities for improvement.

2. Team Manager and Coaching Staff Management

• Recruit, select, and appoint qualified team managers and coaches within established timelines.
• Work with team managers to develop team plans, schedules, budgets, and seasonal objectives.
• Establish a consistent process for evaluating managers and coaching staff.
• Provide constructive feedback and support ongoing coaching development.
• Address performance concerns and make difficult decisions when required, in the best interests of the players and the league.

3. Player Selection and Evaluation

• Develop and oversee fair, consistent, and transparent player selection processes for Summer and Fall teams.
• Ensure player evaluations and selection procedures are appropriately planned and communicated.
• Establish an annual player evaluation framework to support development and future program planning.
• Monitor player and team performance through periodic attendance at practices, games, and tournaments.

4. Budgeting and Resource Management

• Prepare annual budgets for All-Star and Select teams, including Summer and Fall programs.
• Monitor team expenditures and program financial performance in accordance with OLL policies and approved budgets.
• Secure field permits, practice times, and indoor training facilities to support program requirements.
• Coordinate the allocation of facilities and other resources to meet seasonal operational needs.

5. Board Governance and Committee Participation

• Attend monthly Board of Directors meetings throughout the year.
• Provide regular updates on program activities, planning, budgets, and operational matters.
• Support and oversee relevant committees as assigned.
• Collaborate with other Board members and league volunteers on initiatives that contribute to OLL’s overall success.
• Ensure program operations align with league policies, governance requirements, and established expectations.

Qualifications and Desired Experience

The ideal candidate will demonstrate:

• Strong leadership, interpersonal, and communication skills.
• Excellent organizational, strategic planning, and decision-making abilities.
• The ability to manage competing priorities and varying seasonal workloads.
• Confidence in addressing difficult situations professionally and objectively.
• A commitment to fair, consistent, and development-focused player and coach evaluation.
• A collaborative approach to working with volunteers, coaches, players, parents, and fellow Board members.
• Knowledge of baseball, competitive youth sports, or sports program administration.

Previous experience in a similar role within baseball or another sporting organization is an asset. Playing experience at an advanced or competitive level is beneficial but not required. Familiarity with Little League Baseball is an advantage but is not essential.

Above all, the successful candidate will be committed to providing a positive, well-organized, and competitive baseball experience for OLL players while supporting the values of community-based youth sports.

Volunteer Commitment

This is an unpaid volunteer position with Oakville Little League.

The minimum expected commitment is 10 hours per month; however, the workload will vary throughout the year and may be significantly higher during team selection, pre-season planning, training periods, and tournament play.

The position requires a year-round commitment, including attendance at monthly Board meetings and ongoing communication with team managers and league leadership.

Application Process

Interested candidates are asked to complete the Volunteer Position Application Form and submit it by email to the designated contact below.

Application email: president@oakvillelittleleague.com

Contact Information

For questions regarding this position, please contact:

Oakville Little League
Email:president@oakvillelittleleague.com

Oakville Little League appreciates the dedication of its volunteers and welcomes individuals who are passionate about youth baseball, player development, and building a strong, sustainable community sports program.