Senior Manager | Technology & AI Consultant

Cuesta Partners

Chicago or New York

Cuesta Partners is seeking a high-potential, creative problem solver with a proven track record of leading both consulting engagements and technology initiatives to join us as a senior-level consultant.

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.

What You’ll Do

You will lead clients through complex technology decisions—from strategy to execution—helping them unlock value from data, AI, and modern architectures. You’ll operate as both a trusted advisor to senior executives and a hands-on leader guiding teams to deliver measurable outcomes.

Your work will span:

* Technology, data, and AI strategy

* Architecture design and tech stack evaluation

* Analytics and business intelligence enablement

* AI use case development and execution

* Product strategy, roadmaps, and implementation planning

* Technology due diligence and investment support

Location: New York or Chicago metros preferred (Eastern or Central time zones)

Role & Responsibilities

Client Leadership & Delivery

* Lead engagements end-to-end, from scoping through delivery, ensuring high-quality outcomes and client impact

* Serve as a trusted advisor to senior stakeholders, including C-level executives

* Translate ambiguous business challenges into clear strategies, actionable plans, and measurable results

* Drive alignment across stakeholders and facilitate key trade-off decisions

Team Leadership

* Lead and mentor cross-functional teams, balancing hands-on contribution with strategic oversight

* Provide coaching on problem structuring, storytelling, and client communication

* Ensure teams are operating effectively, prioritizing the right work, and meeting deadlines

Strategic Thinking & Problem Solving

* Identify critical business and technology gaps and design practical, scalable solutions

* Synthesize complex, diverse inputs into clear insights and executive-ready deliverables

* Develop compelling recommendations and business cases that drive decision-making

Growth & Firm Development

* Lead proposals, scoping, and business development efforts

* Build lasting client relationships and identify follow-on opportunities

* Capture and scale intellectual property from engagements (frameworks, thought leadership, training content)

Qualifications

Required

* 8–15 years of experience in management consulting, technology, or related fields

* Proven track record leading complex, large-scale programs

* Experience managing teams and delivering client-facing work

* Strong analytical and problem-solving capabilities (both quantitative and qualitative)

* Excellent communication skills, with the ability to influence senior stakeholders

* Ability to operate in ambiguity and bring structure to complex problems

* Systems thinking across business processes and technology ecosystems

* Experience with AI/ML, data platforms, or modern software architectures

Preferred

* Background in software development or hands-on technical work

* Experience working with private equity or transaction environments

* Exposure to early-stage products or startup environments

* Advanced degree (MBA, MS, or similar)

What Sets You Apart

* You combine strategic thinking with execution focus—you don’t just design solutions, you make them happen

* You can move fluidly between executive conversations and detailed problem-solving

* You elevate the people around you, improving both team performance and client capability

Benefits: What you’ll gain

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

* Constant opportunities for exposure & learning

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

* Agency and influence in the company’s strategy and direction

* Collaboration with a high-performing team

* Competitive base salary (outlined in this listing) and target bonus of up to 25%

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

Compensation Range: $175K - $210K