Head of Operations

OpenTrack; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Job summary

OpenTrack is seeking a Head of Operations in Chicago to act as an extension of the CEO, driving strategic initiatives and cross-functional execution. You will own end-to-end projects, filter and delegate CEO requests, and formalize scalable processes to improve efficiency while maintaining close alignment with company goals.

The role requires 3–6 years in high-growth startups or similar environments, exceptional communication, analytical skills, and a bias toward action.

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.

Responsibilities

• 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.

Skills

Analytical skills

Written communication

Project management

Decision making

Cross-functional collaboration

Job description

At OpenTrack, we’re tackling the fragmented data and workflows of the trillion dollar logistics industry. Using data collected in real time from hundreds of sources, we help customers keep their cargo moving efficiently, on time and at a cost savings.

The OpenTrack platform includes an AI logistics workflow builder, enterprise web application, API service, and customer white label portal which gives companies the ability to use best-in-industry freight visibility, performance metrics and predictive insights to fully automate logistics workflows.

Our customers are some of the most iconic brands and logistics companies in the world, and we have already transformed the way they work.

We are an international team (Nashville, Chicago, Europe) with a growing presence at our Nashville HQ.

We value autonomy, curiosity, and having a good time. We’re seeking a qualified candidate to join our team in the Head of Operations role.

Responsibilities

• 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

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 insightsli>
• 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