Chief Transformation and AI Officer

Penta is a leading corporate affairs advisory firm that helps organizations predict what matters and shape outcomes. By combining proprietary intelligence, stakeholder insights, and strategic counsel, we help CEOs and leadership teams navigate the increasingly complex intersection of business, policy, culture, and reputation. Our clients turn to us when the stakes are high, the signals are difficult to interpret, and the consequences of getting it wrong are significant. We are building a new model for corporate affairs advisory and are seeking leaders who want to help define the future of the industry.

Penta’s global team brings decades of experience in business, government, communications, research, data science, and media. Our clients include many of the world's most influential organizations across technology, financial services, energy, healthcare, and other sectors, including over 25% of the Fortune 100. Penta has offices in New York, Washington DC, San Francisco, London, Brussels, Dublin, and Singapore.

Role Summary

We are seeking a visionary leader to build and lead Penta's industry-leading AI and Intelligence capabilities, including the firm’s platform, product and intelligence teams that power all of our client work. Working closely with senior leaders across the firm, this individual will define the strategy, team, products, and platforms that transform stakeholder intelligence into actionable insights, enabling clients to better understand emerging risks, stakeholder dynamics, and opportunities to shape outcomes. The ideal candidate brings deep expertise in analytics, product development, AI transformation, and technology-enabled advisory services, along with a demonstrated track record of building and scaling commercially successful businesses, products, and capabilities. This leader will play a critical role in advancing Penta's differentiated market position, building innovative capabilities, and ensuring our partners and consultants are equipped with the active intelligence needed to deliver exceptional client outcomes.

Key Responsibilities

• Lead Penta's Intelligence platform, working with functional leaders to define the vision, strategy, operating model, talent, and roadmap for the firm's platform, product and intelligence team capabilities.
• Lead the firm's AI transformation efforts, in partnership with other functional leaders, identifying opportunities to enhance client delivery, improve operational effectiveness, and create innovative products and services that strengthen Penta's competitive advantage.
• Elevate Penta's profile as a leader in intelligence and stakeholder analytics through thought leadership, industry engagement, strategic partnerships, and the development of innovative approaches to understanding and influencing stakeholder behavior.
• Develop, scale, and commercialize proprietary intelligence products, platforms, and methodologies that help clients anticipate emerging risks, understand stakeholder dynamics, and shape outcomes.
• Embed data-driven insights and intelligence capabilities across the firm's advisory services, ensuring partners and consultants are equipped to deliver differentiated, evidence-based counsel to clients.
• Evaluate emerging technologies, data sources, and AI capabilities, identifying opportunities to develop new offerings, expand intelligence capabilities, and position Penta at the forefront of innovation in corporate affairs advisory.
• Serve as a market-facing leader and trusted advisor, contributing to business development efforts, and translating complex data into actionable strategic recommendations for senior decision-makers.

Candidate Attributes

• Proven experience building, scaling, and leading multidisciplinary organizations spanning product management, data science, analytics, engineering, research, and intelligence functions.
• Significant business leadership experience, including ownership of a substantial P&L—ideally in the range of $50 million or greater—and a track record of driving revenue growth, managing investments, and delivering strong financial performance.
• Deep expertise in AI transformation, analytics, and emerging technologies, with a demonstrated track record of applying these capabilities to transform business models, create new products, and generate measurable commercial value.
• Demonstrated success translating emerging technologies, data assets, and market insights into scalable products, services, and revenue-generating capabilities.
• Strategic vision and the ability to anticipate market shifts, identify emerging opportunities, and execute enterprise-wide roadmaps that align intelligence, technology, product innovation, and business growth objectives.
• Strong understanding of how AI and data-driven insights can be embedded within advisory, consulting, communications, or professional services environments to enhance client outcomes and create competitive advantage.
• Proven ability to lead enterprise transformation initiatives, including the adoption of AI-enabled tools, new operating models, and technology-driven approaches to client delivery and organizational effectiveness.
• Strong executive advisory skills, with the ability to engage CEOs and senior leadership teams, translate complex analytical concepts into actionable business recommendations, and influence decision-making at the highest levels.
• Recognized market credibility and thought leadership in areas such as AI, intelligence and analytics, product innovation, and stakeholder insights, demonstrated through industry engagement, speaking, publishing, media visibility, or strategic partnerships.
• Entrepreneurial and collaborative leadership style, with a track record of building high-performing teams, identifying new market opportunities, and bringing together technologists, researchers, consultants, and business leaders to drive growth and innovation.

Location:

We have global offices in the US, Europe, and Asia and are open to candidates in these locations. Candidates can either be local to one of our offices or remote, as long as frequent business travel and working hour flexibility across time zones is not an issue.

Benefits:

Penta Group is committed to providing a comprehensive and competitive benefits package to support the well-being and financial security of our employees. For US employees, our benefits include:

• Healthcare Coverage: Excellent medical, vision, and dental insurance through Cigna and UNUM, with the company covering the majority of individual employee premiums and 50% of dependent premiums​
• Retirement Benefits: A 401(k) plan with a generous employer match, contributing 100% on the first 3% of salary deferred and 50% on the next 2%, helping employees maximize their retirement savings​
• Income Protection: Employer-paid short-term disability (STD), long-term disability (LTD), and life insurance
• Paid Parental Leave: 12 weeks of paid parental leave​ for birthing and non-birthing parents
• Flexible Paid Time Off: Flexible Paid Time Off (PTO) policy and a generous holiday schedule​

Additional Perks & Support:

• A monthly cell phone reimbursement
• Frequent firm-wide social events and team-building activities​
• Access to Employee Assistance Programs (EAP), including confidential counseling and resources for personal and work-related issues​
• Wellness benefits including a gym membership discount program, mental health resources, and access to virtual health consultations
• Discounted employee-paid pet insurance coverage through Nationwide

Penta Group, LLC values diversity and inclusion, is committed to equal employment opportunity, and to compliance with federal anti-discrimination laws. We also comply with District of Columbia law, which prohibits discrimination and harassment against employees, applicants for employment and interns based on race, color, religion, sex (including pregnancy, childbirth or related medical conditions, reproductive health decisions and breastfeeding), national origin, disability, age (18 and over), personal appearance, sexual orientation, gender identity or expression, marital status, family responsibilities, matriculation (e.g., being enrolled in a college or university or in a business, nursing, professional, secretarial, technical or vocational school), political affiliation, genetic information (including family medical history), lawful use of tobacco products, unemployment status and status as a victim or the family member of a victim of domestic violence, a sexual offense or stalking.

Penta Group, LLC is committed to providing reasonable accommodations to qualified individuals with disabilities throughout the application and hiring process. If you require an accommodation to complete your application, participate in an interview, or otherwise engage in the recruitment process, please contact us at careers@pentagroup.com. We will work with you to ensure appropriate arrangements are made.