Head of Operations

Skokie, IL, USA|Remote

Job Overview

Compensation

Salary

Range $77,800.00 - $139,700.00

Benefits

Health Insurance

Paid Time Off

flexible schedule

Professional Development

remote work options

Retirement Plan

team events

Job Description

OpenTrack is a cutting-edge technology company revolutionizing the trillion-dollar logistics industry by addressing its long-standing issues of fragmented data and inefficient workflows. Based out of Nashville with additional teams in Chicago and Europe, OpenTrack specializes in harnessing real-time data from hundreds of sources to empower businesses to keep their cargo moving efficiently and on schedule while achieving significant cost savings. The company’s pioneering platform combines an AI-driven logistics workflow builder, an enterprise web application, a robust API service, and a customizable white label portal, providing customers with best-in-industry freight visibility, actionable performance metrics, and predictive insights. These tools enable businesses to fully automate their logistics processes, dramatically improving operational efficiency and delivering a transformative experience to some of the world’s most iconic brands and logistics companies.

OpenTrack is seeking a strategic and capable Head of Operations to join its dynamic and rapidly expanding team. This is a pivotal leadership role that acts as an extension of the CEO by managing communications, critical decisions, and workstreams on the CEO’s behalf. The ideal candidate will partner closely with the CEO and senior leadership to drive essential strategic initiatives, focusing on high-impact projects while freeing the CEO to concentrate on major priorities. The Head of Operations will have ownership over cross-functional project management, handling initiatives from planning through execution to keep the CEO informed without needing their direct involvement in day-to-day details. This role requires a proactive approach to filtering and resolving incoming requests and delegating matters to appropriate teams, reducing the CEO’s operational load.

In addition, the successful candidate will help define and implement company-wide processes that increase alignment and efficiency, act as a central communication hub across diverse teams, and identify operational bottlenecks with solutions ownership rather than escalation. Tracking progress against company goals, KPIs, and strategic priorities is a core responsibility, with an emphasis on driving accountability and surfacing risks with minimal CEO involvement. The Head of Operations will also perform in-depth analysis and research to inform decision-making around business strategy, partnerships, and growth, delivering actionable recommendations instead of raw data. Acting as a trusted advisor to the CEO, this role demands a blend of strategic insight, operational excellence, strong judgment, and excellent interpersonal skills. The candidate must thrive in a fast-paced, dynamic startup environment, demonstrating high levels of business judgment, independence, and the ability to adapt quickly to evolving priorities. Autonomy, curiosity, and a positive team culture are highly valued at OpenTrack, making this an exciting opportunity for a motivated professional ready to make a significant impact in logistics innovation.

Job Requirements

Bachelor's degree or equivalent experience
3-6 years of relevant experience in operations, strategy, consulting, or startup environments
Strong communication skills
Proven project management capability
Ability to work independently and make decisions in ambiguous situations
Demonstrated leadership skills
Analytical mindset
High level of organizational skills
Strategic and operational experience
Flexibility to adapt in a fast-paced environment

Job Qualifications

Proven experience (3-6 years) in a high-growth startup environment, consulting, operations, or strategy
Excellent written communication and organizational skills
Strong analytical and problem-solving skills, with the ability to synthesize complex information into clear insights
Exceptional project management skills, with the ability to manage multiple priorities simultaneously
High level of business judgment and ability to operate independently in ambiguous environments, comfortable making decisions without full information
Demonstrated ability to act as a trusted representative of senior leadership, owning outcomes rather than just supporting them
Excellent communication and interpersonal skills, with a demonstrated ability to collaborate across teams and levels
Strategic thinker with a strong bias toward action and execution, removing problems rather than surfacing them
Detail-oriented, with a commitment to accuracy and operational excellence
Ability to thrive in a fast-paced, dynamic startup environment and adapt quickly to evolving priorities

Job Duties

Serve as an extension of the CEO, owning decisions, communications, and workstreams on the CEO's behalf so they can focus on the highest-leverage priorities
Partner directly with the CEO and leadership team to drive strategic initiatives and ensure company priorities are executed effectively, often stepping in to lead directly when the CEO's bandwidth is needed elsewhere
Own cross-functional project management for high-impact initiatives end-to-end, from planning through execution, so the CEO is informed without being in the weeds
Triage and manage incoming requests, decisions, and open items directed at the CEO, filtering, delegating, and resolving the majority independently
Help define, document, and operationalize company-wide processes to improve efficiency and alignment, reducing the need for CEO involvement in recurring decisions
Act as a central hub for communication, ensuring clarity and coordination across teams and serving as the first point of contact so that only the most critical matters reach the CEO
Identify operational bottlenecks and proactively implement solutions, owning the fix rather than escalating
Drive accountability by tracking progress against company goals, KPIs, and strategic priorities, surfacing risks and course-correcting with minimal CEO involvement
Conduct analysis and research to inform decision-making on business strategy, partnerships, and growth opportunities, delivering clear recommendations rather than raw information
Serve as a trusted advisor and sounding board to the CEO on both strategic and operational matters, and proactively flag what the CEO needs to know before they have to ask