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Manager - Chicago

Cuesta Partners

Chicago, Illinois, United States Remote permanent

Posted: December 2, 2025

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Quick Summary

A high-potential, creative problem solver with experience managing technology programs for a mid-senior level strategy consultant position.

Job Description

Cuesta Partners is looking for a high-potential, creative problem solver with experience managing technology programs for a mid-senior level strategy consultant position.

At Cuesta we believe in the power of technology to create sustained, differentiated advantage for our clients. We support companies and private equity firms throughout their technology journey, from pre-close diligence through strategy definition and hands-on execution. We are a unique, energetic firm that believes in challenging convention, moving quickly, and seeking ongoing personal growth.

Job Description: What you’ll do

We’re looking for a Manager to help our clients design and execute technology strategies to solve their biggest challenges. This includes working across all levels of our clients’ organizations and providing individual expertise and team leadership on topics such as:

• Technology, Data, and AI Strategy

• Software Research and Suitability Assessment

• Architecture Design and Tech Stack Evaluation

• Analytics Enablement and Business Intelligence

• AI Acceleration & Execution

• Project and Program Delivery

• Business Case Development

• Product Roadmap Design and Implementation Planning

• Due Diligence

New York and Chicago metros preferred, but please note there is no need to apply to both roles.

The role will be responsible for:

• Leading workstreams as a part of a larger project; planning work according to project scope and timelines

• Managing stakeholder relationships and expectations across client teams, including at the executive level

• Owning deliverable story line development and ensuring the flow and level of detail is appropriately tailored to the audience

• Prioritizing work across multiple teams and facilitating trade-off discussions

• Identifying critical strategic gaps and designing solutions

• Processing extensive, diverse information and distilling that information into clear, concise, professional client deliverables

• Interpreting information and translating insights into optionality and / or pathways

• Assigning and delegating ownership of work to project team members

• Taking a proactive approach to identifying and managing issues

• Communicating updates, progress, and upcoming plans for the project to internal and client stakeholders

• Managing and mentoring junior team members

• Identifying, escalating, and addressing gaps in client and Cuesta team skills, capacity, or capabilities

• Using professional concepts and project objectives to resolve complex issues

• Generating insights and devising plans to address issues identified

• Supporting sales and account expansion efforts

Requirements

• Bachelor’s Degree

• 5-10 years of experience in management consulting, technology, or business management

• Experience managing or leading teams

• Exceptional analytical and qualitative problem-solving skills

• High degree of organization and ability to manage competing priorities, driving results across multiple projects, exercising influence without authority

• Ability to work at all levels of an organization, from C-Suite to front-line worker

• Flexibility and comfort bringing structure to ambiguity, with project or program leadership experience

• Systems thinking to understand complex business and technological ecosystems

• Value working in a fast-paced, iterative, high-energy environment

• Comfort presenting, teaching/workshopping, sharing ideas, and synthesizing information to inform direction

• High attention to detail and ability to move quickly from tactical to strategic thinking

• Exposure to various delivery models in both the traditional and Agile landscape

• Collaborative working-style, with ability to self-motivate and execute

• Track record of delivering large-scale complex programs

Nice-to-haves

• Exposure to start-up or initial launch of software development

• Experience working with Private Equity

• BS or MS in Computer Science or related field

• MBA or master's degree in a related field

• Hands-on experience building technology applications, whether for work or as a hobby

• Background in automation or artificial intelligence/machine learning

Benefits: What you’ll gain

• At Cuesta, we value entrepreneurship, humility, diversity, learning, speed, and balance. We provide our managers with:

• Constant opportunities for exposure & learning

• Flexible working location and enabling personal-life harmony with work

• Agency and influence in the company’s total strategy and direction

• Collaboration with a high-performing team

• Competitive base salary (outlined in this listing) and target bonus of 20-25%

• 401k, healthcare benefits, paid time-off, and more!

• Please apply at cuestapartners.com/careers

#Chicago #ChicagoRemote #ChicagoConsulting #PE #ManagementConsulting

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