Associate / Sr Associate - Chicago

Cuesta Partners is looking for a highly motivated Associate or Senior Associate with technology and business experience to work with our broad base of clients on technology-focused engagements.

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 an Senior Associate to help our clients design and execute technology strategies to solve their biggest challenges. Cuesta project teams work across all levels of our clients’ organizations and provide expertise and analysis on topics such as:

• Technology, Data, and AI Strategy

• Software Research and Suitability Assessments

• 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

This role will be responsible for:

• Executing workplan components and developing quality client deliverables

• Managing project plans to ensure timely delivery of project elements

• Translating project efforts into client value they produce

• Engaging technical and non-technical team members to support communication to client

• Mapping business objectives into technological capabilities

• Processing extensive, diverse information into concise, professional client deliverables

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

• Leveraging company and industry frameworks to glean strategic insights and formulate recommendations

• Using logic and reasoning to solve ambiguous problems

• Distilling complex business operations

• Conducting research and analysis to assimilate information and develop perspectives

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

Requirements

• 3-8 years management consulting or technology experience

• Strong interest in technology, including how it is used to drive business performance

• Exceptional analytical and quantitative problem-solving skills

• Systems thinking to understand complex business and technological ecosystems

• High attention to detail and ability to document business processes, systems, and summarize detailed analysis

• Project management experience – ability to manage multiple tasks concurrently and execute against client timelines

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

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

• Ability to navigate multiple levels of an organization, with comfort presenting to leaders, including C-Suite

• Ability to communicate effectively with clients across multiple mediums (email, phone, video, etc.)

• Agile, adaptive, and learning mindset

• Ability to work independently with confidence and adaptability, effectively navigating ambiguous situations and making sound decisions in evolving environments

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

• Proficiency in Microsoft PowerPoint and Excel

Nice-to-haves

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

• MBA/MS in Business, Computer Science, or related field

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

• Experience working with vendors and technology partners

• Understanding of change management risks and requirements

• Previous exposure to automation or artificial intelligence / machine learning

• Experience with data analysis and/or data engineering

• Experience with Private Equity, including an understanding of the Private Equity lifecycle, why companies raise money, and how a PE firm build and executes upon an investment thesis

About Cuesta

At Cuesta we challenge convention, move quickly, and seek personal growth in tandem with that of the firm. All of us possess agency in building Cuesta into the company at which we’ve always wanted to work. Sound like you?

Benefits: What you’ll gain

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

• Constant opportunities for exposure & learning

• Regular off-sites to meet and connect with your teammates

• 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, flexible paid time-off and more!

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