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!
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What We Do
We believe in the power of technology to create sustained, differentiated advantage. Our firm helps organizational leaders understand and use emerging digital solutions to drive value across their business. Technology has become an accelerating source of competitive divergence – Cuesta helps companies capitalize on this opportunity with a pragmatic, hands-on approach. Our team has scaled and operated companies across several industries, launching technology solutions focused on delivering business value. We believe the truth is in the details and projects are successful when the work is done the right way. At Cuesta, we are building the firm where we always wanted to work. We challenge convention, work efficiently, and seek ongoing personal growth. Our team supports each other and laughs together. We value diversity, creativity, humility, and perseverance.
