Job Description

About the Job

The Chief of Staff to the Chief Operating Officer serves as a strategic partner and operational leader responsible for driving execution, alignment, and accountability across the organization. Reporting directly to the COO, this role operates with delegated authority to move priorities forward, monitor performance, and ensure strategic initiatives translate into measurable business outcomes. Acting as an extension of the COO, the Chief of Staff partners closely with senior leaders to lead cross-functional initiatives, strengthen operating discipline, and guide organizational transformation as the business evolves and scales.

The Chief of Staff shapes how strategy becomes action, clarifying priorities, building accountability, and improving the structures, processes, and leadership practices that enable sustained performance. The role requires a leader who can navigate complex business dynamics, influence outcomes, and help drive meaningful change while reinforcing a high-performing culture and ensuring the organization executes effectively against its strategic priorities.

DATTCO is a successful, well-established provider of transportation and related services throughout New England. We operate through three divisions: Motorcoach (supply buses/drivers to tour operators), School Bus (operate school bus routes for local school districts), and Sales & Service (dealerships for bus and truck sales, collision repair, maintenance service, and other related support). Learn more about us at www.dattco.com.

Primary Responsibilities

• Partner with the COO to translate organizational strategy into clear priorities, initiatives, and measurable outcomes across the team.
• Drive execution of key business initiatives, ensuring alignment, momentum, and accountability across departments.
• Develop and manage operating rhythms that monitor performance, track progress on priorities, and ensure leadership alignment.
• Develop, implement, and manage enterprise KPIs in partnership with leadership.
• Establish systems for tracking progress against strategic and operational goals.
• Hold teams accountable for delivering results while proactively identifying and addressing risks or barriers to execution.
• Lead and manage high-impact projects on behalf of the COO, including cross-functional initiatives and acquisitions.
• Ensure strategic initiatives move from concept to implementation with clear ownership and measurable outcomes.
• Act as a proxy for the COO when needed, helping reinforce expectations, priorities, and standards of leadership across the organization.
• Support the development of leaders and teams by strengthening accountability, collaboration, and leadership effectiveness.
• Help shape and reinforce the organization’s culture and leadership norms during periods of growth and transformation.
• Navigate complex team dynamics and organizational challenges to maintain alignment and momentum across the leadership team.
• Facilitate communication, decision-making, and coordination across functions to ensure clarity and shared ownership of outcomes.
• Provide candid insights and recommendations to the COO and executive leadership to support informed decision-making.
• Support organizational transformation efforts that improve performance, operating discipline, and cultural alignment.
• Identify opportunities to improve processes, structures, and leadership practices that enable the organization to scale effectively.
• Interface in-person with customers and other stakeholders on an as needed basis across DATTCO’s expanding geographic footprint.

Minimum Requirements

• Bachelor’s degree in business, organizational leadership, or a related field required.
• MBA or Master’s degree in Industrial and Organizational Psychology, Organizational Leadership, Organizational Development, or a related discipline strongly preferred.
• 8–12+ years of strategic leadership experience, preferably within complex or multi-site organizations.
• Demonstrated ability to drive execution of strategic initiatives and lead cross-functional projects from concept through implementation.
• Experience working closely with senior executives and influencing outcomes across leadership teams.
• Strong capability in performance management, KPI development, and building a culture of accountability.
• Proven ability to navigate complex organizational dynamics and build alignment among diverse stakeholders.
• Experience leading organizational transformation, change initiatives, or large-scale operational improvements.
• Strong analytical thinking, problem-solving, and decision-making skills.
• Excellent communication, facilitation, and executive presence.
• Experience in the transportation industry is preferred.

Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, protected veteran status and any other protected classes.