Principal Strategist, Digital Strategy (Contract)

Bounteous; Northern (KY); Hybrid; USD 140,000 - 200,000; Full time

Job summary

Bounteous is a global AI Services firm where strategy and human experience converge to deliver transformative outcomes for the enterprise. The Principal Strategist, Digital Strategy (Contract) partners with senior clients to define digital strategies, roadmaps, and AI-enabled opportunities across channels and touchpoints.

The role requires leadership in advisory settings, strong executive storytelling, and collaboration with multidisciplinary teams to translate challenges into actionable

Qualifications

• Ten-plus years delivering digital strategy and transformation engagements for enterprises.
• Experience with C-suite and senior stakeholder workshops and advisory sessions.
• Strong understanding of customer experience, platforms, data, and digital marketing ecosystems.

Responsibilities

• Lead development of comprehensive digital strategies and transformation roadmaps aligned with client goals.
• Assess clients' digital capabilities, experiences, operating models, and technology ecosystems.
• Identify opportunities to improve engagement, operations, and performance through digital programs.
• Translate objectives into actionable strategic initiatives and investment roadmaps.
• Present clear, compelling business cases to executives and drive alignment across functions.
• Collaborate with Strategy, Experience Design, Product, Data & Analytics, Technology, and Marketing teams.

Skills

Digital strategy

Executive advisory

Transformation roadmaps

Customer experience

Stakeholder management

Presentation skills

Education

Bachelor's degree in Business/Strategy/Tech

Job description

Bounteous is a global AI Services firm where agentic engineering and human experience converge to deliver transformative business outcomes for the enterprise. We help organizations design, build, and scale AI-driven products, platforms, and processes. With more than 5,000 team members worldwide, Bounteous delivers AI that sticks, powering adoption and outcomes that move organizations from experimentation to true transformation. Bounteous is backed by New Mountain Capital, a New York-based growth-oriented investment firm that emphasizes business building.

We are seeking an accomplished Principal Strategist, Digital Strategy (Contract) to lead strategic engagements and help enterprise clients define and execute transformative digital experiences.

The ideal candidate will combinebusiness strategy, customer experience, digital transformation, technology understanding, and strong executive advisory skills. This role will partner closely with senior client stakeholders to identify business opportunities, define digital strategies and roadmaps, and translate complex business challenges into actionable transformation initiatives.

The Principal Strategist will serve as a trusted advisor to clients while collaborating with multidisciplinary teams acrossStrategy, Experience Design, Product, Data & Analytics, Technology, and Digital Marketing.

Information Security Responsibilities

• Promote and enforce awareness of key information security practices, including acceptable use of information assets, malware protection, and password security protocols
• Identify, assess, and report security risks, focusing on how these risks impact the confidentiality, integrity, and availability of information assets
• Understand and evaluate how data is stored, processed, or transmitted, ensuring compliance with data privacy and protection standards (GDPR, CCPA, etc.)
• Ensure data protection measures are integrated throughout the information lifecycle to safeguard sensitive information

Key Responsibilities

• Lead the development of comprehensivedigital strategies and transformation roadmapsaligned with client business objectives.
• Assess clients' current digital capabilities, customer experiences, operating models, and technology ecosystems.
• Identify opportunities to improve customer engagement, operational effectiveness, and business performance through digital transformation.
• Translate business objectives and customer needs into actionable strategic initiatives.
• Develop prioritized recommendations, investment roadmaps, and implementation strategies.
• Define future-state digital experiences and capabilities across channels and customer touchpoints.
• Evaluate emerging technologies and market trends to identify opportunities for innovation and competitive differentiation.
• Serve as atrusted strategic advisorto senior client stakeholders and executive leadership.
• Facilitate executive workshops, discovery sessions, stakeholder interviews, and strategy discussions.
• Effectively communicate complex strategic recommendations to both business and technology audiences.
• Build compelling executive-level presentations, business cases, and strategic narratives.
• Influence senior stakeholders and drive alignment across diverse business functions.
• Establish strong, trusted relationships with client executives and key decision-makers.
• Develop customer-centric strategies based on customer insights, business objectives, and market opportunities.
• Partner with research and experience teams to understand customer behaviors, needs, pain points, and expectations.
• Define customer journey improvement opportunities across digital and physical touchpoints.
• Support customer journey mapping, experience strategy, personalization, and omnichannel initiatives.
• Identify opportunities to improve customer acquisition, engagement, retention, and loyalty.
• Identify opportunities to leveragedata, analytics, AI, and Generative AIto improve customer experiences and business outcomes.
• Help clients define practical AI-enabled transformation opportunities and strategic use cases.
• Partner with Data, AI, and Technology teams to ensure strategic recommendations are technically achievable and commercially viable.
• Evaluate emerging digital trends and their potential impact on client organizations.
• Support the development of AI-enabled customer experience and operating-model strategies.

Preferred Qualifications

• 10+ yearsof experience in Digital Strategy, Management Consulting, Digital Transformation, Customer Experience Strategy, Product Strategy, or a related discipline.
• Demonstrated experience leading complex digital strategy and transformation engagements for enterprise organizations.
• Strong experience working directly withC-suite and senior executive stakeholders.
• Proven ability to translate complex business challenges into actionable digital strategies and roadmaps.
• Strong understanding of customer experience, digital platforms, data, technology, and digital marketing ecosystems.
• Experience facilitating executive workshops and strategic planning sessions.
• Strong analytical and structured problem-solving capabilities.
• Excellent storytelling, presentation, and executive communication skills.
• Demonstrated ability to lead multidisciplinary teams and influence stakeholders without direct authority.
• Bachelor's degree in Business, Strategy, Marketing, Technology, or a related field; MBA or advanced degree preferred.

Bounteous is proud to be an equal opportunity employer. Bounteous does not discriminate on the basis of race, religion, color, sex, gender identity, sexual orientation, age, physical or mental disability, national origin, veteran status, or any other status protected under federal, state, or local law.Bounteous is willing to sponsor eligible candidates for employment visas.

Individual pay is determined by many factors, including experience, relevant education or training, and organizational needs. The mid-range to maximum of the salary range is generally reserved for individuals who are highly experienced in the role.

I joined Bounteous largely because of the organization’s innate passion to drive meaningful change, impact, and growth - for employees, customers, and partners. That mission remains a guiding principle for the company today and why I am so honored to be a part of the organization. With a focus on co-innovation and a commitment to doing things better and doing better things, I am constantly learning, growing, and being challenged – all while feeling like I am making a real impact at the end of the day.