Strategic Operations Lead, Office of the CEO

Pluralsight•Chicago, IL

1d•Hybrid

About The Position

We are looking for a skilled communicator and operator to join the Office of the CEO. Reporting to the Chief of Staff, this role focuses on two critical areas: crafting our Strategic Narrative and supporting the operational excellence of the executive team. In this role, you will be the "content engine" behind the Chief of Staff. While the CoS drives the strategy and rhythm of the business, you will ensure key meetings and moments are fueled by high-impact content, seamless logistics, and clear storytelling. You will act as the bridge between the Executive Office and our cross-functional partners across the company, ensuring that our story aligns perfectly with our strategy.

Requirements

Expert in Information Design—knowing how to visualize hierarchy, process flow, and data.
Strong organizational skills with the ability to manage multiple priorities.
Comfortable handling the logistics of high-pressure meetings.
High level of professionalism and confidentiality; comfortable working with C-Suite leadership and handling sensitive information.
Ability to take the complex (strategy/technical details) and make it simple and human (communications).
Familiarity with the software development life cycle (SDLC).
4–6 years in Executive Operations, Strategy, Management Consulting, Business Operations, or Chief of Staff support roles.

Nice To Haves

You are not afraid to be yourself, experiment, make mistakes and learn from them, ask questions, or voice your concerns.
When communicating you are self-aware, insightful, and proactive.
You are a team member first and individual contributor second.
You are aware that high-performing teams are only as strong as their weakest link.
You believe in continuous improvement and request frequent feedback from others.
You can sit in a meeting about product roadmaps and understand the context well enough to translate it into a business story.

Responsibilities

Support the Strategy team in translating company strategy into clear, executive-ready materials.
Serve as the lead information designer for high-stakes moments.
Draft scripts and talking points in partnership with the Chief of Staff and Internal Communications team for Town Halls, All-Hands, and Keynotes, ensuring the "voice" of the leadership team is consistent and authentic.
Partner with the Chief of Staff to execute key leadership forums (ELT meetings, CEO Forums, Town Halls).
Act as operational support during these forums, tracking action items and following up with stakeholders to ensure decisions made in the room are executed outside the room.
Support the Strategy team with ad-hoc research, benchmarking, and data analysis—often focused on technology, HR, and learning trends—to help prepare the executive team for critical discussions.
Proactively partner with internal stakeholders across functions to gather inputs, align on deliverables, and drive assignments through completion.