Chicago - Senior Manager, Operations Strategy
Winston Taylor
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Job summary
Winston Taylor in Chicago seeks a Senior Manager of Operations Strategy to support executive decision-making across finance, talent, operations, technology and real estate.
You will build KPI frameworks, run analyses, develop business cases, and translate complex data into executive-ready recommendations while advancing AI-enabled workflows.
The role requires strategic problem solving, strong business judgment, and the ability to operate independently in a fast-moving, high-ambiguity environment.
Qualifications
- Bachelor's degree in Business, Finance, Economics, Engineering, Operations or related field required.
- 5+ years of experience in management consulting, corporate strategy, business operations, FP&A, strategic finance, or comparable analytical roles required.
- Must live within a commutable distance to the firm office with the ability to come into the office 3-4 days per week.
Responsibilities
- Executive Decision Support: Partner with COO and senior leadership on high-priority strategic initiatives; conduct analyses to inform decisions; develop business cases and scenarios; translate analyses into executive-ready presentations.
- Enterprise Analytics & Performance Management: Design, develop, and maintain enterprise KPIs; build new performance management disciplines; develop analytical frameworks for workforce planning, capacity, office utilization, and service delivery.
- Strategic Analysis: Conduct analyses across organizational design, headcount, procurement, benchmarking; integrate AI/tools into day-to-day work; develop recommendations balancing financial, operational, and strategic considerations.
- Cross-Functional Partnership: Collaborate with Finance, Talent, Technology, Procurement, Real Estate, Marketing; act as enterprise analytics partner; improve data quality and reporting.
- Strategic Initiative Support: Plan and execute enterprise initiatives; develop workplans, risk assessments, and governance materials; track progress across functions.
- Executive Communications: Produce executive-ready presentations, dashboards, briefings, and memoranda; distill complex information into concise narratives.
Skills
Education
Tools
Job description
At Winston Taylor, we set the standard, together. Winston Taylor is a transatlantic law firm built for the businesses, people, and markets driving capital and innovation. Here, you're in the room. In the action. Sleeves rolled up. You'll work with leading clients. Disruptors. Fast-growth companies. And help them to stay one step ahead of the moment and make critical decisions that shape their future. We're present in the U.S., U.K., Europe, Latin America, and the Middle East, combining the scale and speed that clients demand. You'll be trusted with real responsibility from the outset and build experience through hands-on work. We take your progression personally. We provide the platform. You shape the work around your goals and aspirations. Step into the moments that matter. Join Winston Taylor.
At Winston Taylor, we set the standard, together. Winston Taylor is a transatlantic law firm built for the businesses, people, and markets driving capital and innovation. Here, you're in the room. In the action. Sleeves rolled up. You'll work with leading clients. Disruptors. Fast-growth companies. And help them to stay one step ahead of the moment and make critical decisions that shape their future. We're present in the U.S., U.K., Europe, Latin America, and the Middle East, combining the scale and speed that clients demand. You'll be trusted with real responsibility from the outset and build experience through hands-on work. We take your progression personally. We provide the platform. You shape the work around your goals and aspirations. Step into the moments that matter. Join Winston Taylor.
The Senior Manager, Operations Strategy serves as a key member of the Office of the Chief Operating Officer, providing executive-level analytical, strategic, and operational support across the firm's operations functions. Operating at the intersection of finance, talent, operations, technology, procurement, real estate, and other business services, this role helps senior leadership make informed, data-driven decisions on the firm's most important operational priorities.
With a focus on enterprise problem-solving, this role identifies emerging opportunities, develops new analytical frameworks, establishes operational performance measures, synthesizes complex information into executive-ready recommendations, and supports the successful execution of strategic initiatives.
The role also serves as a catalyst for modernizing how the firm approaches operational decision-making by identifying opportunities to leverage artificial intelligence, automation, advanced analytics, and emerging technologies to improve organizational effectiveness, enhance decision quality, and increase capacity across business functions.
The successful candidate combines the analytical rigor of a management consultant with strong AI fluency, exceptional business judgment, structured problem solving, executive communication skills, and the ability to operate independently in highly ambiguous environments.
- Partner closely with the COO and senior leadership on high-priority strategic and operational initiatives.
- Conduct quantitative and qualitative analyses to inform executive decision-making.
- Develop business cases, options analyses, scenario models, and recommendations for complex organizational issues.
- Translate complex analyses into clear, concise, executive-level presentations and recommendations.
- Prepare materials for senior leadership meetings, steering committees, and other governance forums.
- Design, develop, and maintain enterprise operational KPIs that support executive oversight and strategic decision-making.
- Build new performance management disciplines where metrics do not currently exist.
- Develop analytical frameworks for topics such as workforce planning, organizational capacity, span of control, support staff ratios, office utilization, space planning, service demand, productivity, operational effectiveness, and service delivery.
- Continuously evaluate opportunities to improve operational effectiveness through AI-enabled workflows, intelligent automation, and process redesign.
- Continuously refine reporting and measurement approaches as business needs evolve.
- Conduct analyses across organizational design, headcount planning, procurement, survey data, benchmarking, resource allocation, capacity planning, and operational performance.
- Incorporate AI and advanced analytical tools into day-to-day work to improve the speed, quality, and depth of analysis while maintaining appropriate professional judgment and governance.
- Develop recommendations balancing financial, operational, organizational, and strategic considerations.
- Collaborate with Finance, Talent, Technology, Procurement, Real Estate, Marketing, and other administrative functions.
- Serve as an enterprise analytical partner while respecting functional ownership of source data.
- Identify opportunities to improve data quality, reporting consistency, and analytical capabilities.
- Support planning and execution of enterprise strategic initiatives.
- Develop workplans, issue logs, risk assessments, executive updates, and implementation materials.
- Track initiative progress and coordinate activities across multiple functions.
- Produce executive-ready presentations, dashboards, briefing materials, and memoranda.
- Distill complex information into concise, compelling narratives for senior leadership.
- Bachelor's degree in Business, Finance, Economics, Engineering, Operations, or related field required.
- 5+ years of experience in management consulting, corporate strategy, business operations, FP&A, strategic finance, or comparable analytical roles required.
- Must live within a commutable distance to the firm office with the ability to come into the office 3-4 days per week.
- Experience with a top-tier management consulting firm.
- MBA or other relevant graduate degree.
- Professional services or law firm experience.
- Experience building KPI frameworks and performance management disciplines.
- Experience with Power BI, Tableau, or similar business intelligence tools.
- Exceptional quantitative and qualitative analytical skills.
- Advanced proficiency in Microsoft Excel and PowerPoint.
- Excellent written, verbal, and presentation communication skills.
- Experience supporting senior executives and preparing executive-level materials.
- Demonstrated fluency with generative AI and emerging productivity technologies, with the ability to thoughtfully integrate AI into research, analysis, problem solving, presentation development, and operational improvement.
- Strategic problem solving and business judgment.
- Analytical excellence with the ability to translate complex data into actionable insights.
- Executive communication and presentation skills.
- Cross-functional collaboration and influence.
- AI and digital fluency.
- Project and change leadership.
- Continuous improvement mindset.
- Thinks like a management consultant while operating as a trusted advisor and member of the executive team.
- Is comfortable developing sophisticated analyses and presenting recommendations to senior leadership.
- Thrives in ambiguity, proactively defining problems before solving them.
- Demonstrates intellectual curiosity, sound judgment, and strong commercial acumen.
- Produces executive-ready work that requires minimal revision.
- Balances strategic thinking with hands-on execution.
- Challenges traditional ways of working by identifying opportunities to simplify, automate, and redesign processes.
- Leverages AI to enhance critical thinking, accelerate analysis, and improve strategic decision-making while exercising sound judgment.
Winston offers comprehensive benefits that provide a full spectrum of coverage and support for our full-time employees and their families. Additional information about benefits and rewards can be found here.
The target annual salary range for this role is currently $170,000-$190,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.
The target annual salary range for this role is currently $182,000-$210,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.
We are an equal opportunity employer and welcome applicants from all backgrounds and experiences.
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