DIGITAL & AI STRATEGY LEAD

DIGITAL & AI STRATEGY LEAD

Thresh Consulting — Strategy in Action for the AI Era

Salary: $165,000 – $195,000 + up to 25% annual bonus

Location: Hybrid Chicago

ABOUT THRESH

Thresh Consulting is a modern digital consulting firm built for the AI era—where strategy, execution, and craft come together to deliver real outcomes with speed. Our specialty is helping organizations design, build, and scale AI-native digital products that create exceptional customer experiences and drive measurable value. We equip clients to separate signal from noise, moving from AI experimentation to operational adoption.

At Thresh, our strategy teams connect executive-level vision to actionable product growth. We help client leaders navigate ambiguity, define market opportunities, and build the business case for digital innovation.

ROLE OVERVIEW

The Digital & AI Strategy Lead is a project leader responsible for defining the 'why' and 'how' behind AI-accelerated digital products and strategic business-model transformation. This role operates with significant autonomy, serving as a key advisor to client leadership on proactively leveraging Generative AI, machine learning, and automation to redefine market positioning, accelerate growth projections, and shape long-term digital strategy.

You are accountable for translating complex data into compelling narratives and creating actionable roadmaps that drive executive alignment and measurable business value. You will look across multiple industries to find innovative solutions our clients can bring to their busines

WHAT YOU'LL DO

SHAPE STRATEGIC DIRECTION

• Conduct AI-driven market and competitive research to identify opportunities, assess the competitive threat of new AI models, and define new value chains affecting our client’s businesses
• Build growth models and business cases that quantify the ROI and impact of digital product investments and implications of AI to operations
• Create strategic roadmaps that prioritize initiatives based on business objectives, technical feasibility, and market timing always with a focus on acceleration
• Telco Knowledge (Preferred): Apply expertise in Telecommunications and Media sectors to guide clients through an increasingly competitive marketplace.

DRIVE EXECUTIVE ALIGNMENT

• Translate complex strategy into compelling narratives that influence C-suite stakeholders and drive consensus across business units
• Create executive-ready presentations and materials that distill ambiguity into clarity and confidence using the latest AI tools (Claude, Lovable, Gamma, etc.)
• Serve as a primary point of accountability on client engagements, accountable for strategic outcomes and vision alignment

VALIDATE STRATEGY THROUGH EXECUTION

• Partner with engineering and design teams to ensure strategic recommendations are technically feasible, user-centered and aligned to corporate strategy
• Champion product acceleration and prototyping to pressure-test strategic assumptions, validate core design decisions and begin testing integrations
• Leverage AI tools to accelerate research and synthesis , integrating AI into the research and strategy development process to accelerate delivery and enhance insight depth

LEAD AND COLLABORATE

• Mentor junior strategists and analysts , establishing best practices for strategy development and presentation craft leveraging AI.
• Work across disciplines —you'll collaborate closely with product managers, designers, and engineers to ensure strategy translates to reality

WHAT YOU BRING

• 4–6+ years in digital strategy, product strategy, or management consulting —ideally at a leading consulting firm, tech company or high-performing startup. You understand how to manage stakeholder expectations, navigate ambiguity, and delivery quickly under pressure
• AI Strategy & Technical Fluency: Experience defining, leading, or contributing to AI-centric product or business strategy engagements. Deep understanding of the strategic and commercial implications of Generative AI, LLMs, and emerging ML technologies on various business models
• Track record of leading strategic projects that resulted in real business outcomes (launched products, validated new markets, influenced investment decisions)
• Experience working directly with senior executives (C-suite, VP-level) and driving alignment in complex, political environments
• Exceptional storytelling and presentation skills —you can distill complexity into clarity and make compelling cases for action
• Proficiency with financial modeling and growth projections —comfortable building complex models from scratch
• Industry Expertise: Deep knowledge of Telecom industry and strategic trends preferred, knowledge of the broader TME landscape required

WHY THRESH

• Competitive compensation with high performance bonus upside
• Healthcare benefits and 401(k) with company matching
• High ownership and the opportunity to shape Thresh’s growing AI and digital product strategy practice
• A culture built on clarity, craft, and outcomes, with a commitment to human competency amplified by AI tools

AN EQUAL OPPORTUNITY EMPLOYER

Individual salaries that are offered to a candidate are determined after consideration of numerous factors including internal equity, market data, the candidate’s qualifications- including but not limited to specialty skills, prior relevant industry experience, relevant degrees or certifications. The salary range estimate below is inclusive of all departments, and offered salaries may vary within the given range between departments. A reasonable estimate of the base salary range for this level is $165,000 to $195,000 annualized and other competitive benefits.