Penta Group

• Work collaboratively with creative, media, and production teams developing brand strategy and creative campaign recommendations for clients • Draft planning materials that ensure high-quality, strategically sound creative deliverables, including project proposals, strategy briefs, and creative briefs • Inform strategy and partner with creative and production teams to execute comprehensive creative campaign assets, including TV/video, digital, social, or radio ads; websites; and event activations • Work in collaboration with media/ads management team to report on campaign performance and optimization recommendations for clients • Follow clients' businesses and industries to maintain a current knowledge base and keep the team apprised of new and ongoing developments

Role Description Penta Group is seeking an exceptional Executive Assistant to serve as a strategic partner and force multiplier for our CEO. This is not a traditional administrative role. We're looking for someone who can operate at the speed and altitude of a high-performing executive, anticipate needs before they're voiced, and manage the CEO's time, information, and priorities with total discretion and precision. The right candidate will be a highly polished, sharp, and resourceful professional with a track record of supporting C-suite executives in fast-paced, high-stakes environments. You will be a gatekeeper, a sounding board, a fixer, and a trusted extension of the CEO — equally comfortable managing a complex international travel itinerary, synthesizing a board deck, or navigating a sensitive stakeholder conversation. This role demands exceptional judgment, unflappable composure under pressure, and the ability to represent the CEO's interests and voice with credibility across the firm and with external partners, clients, and board members. We're especially interested in candidates who are fluent with AI tools and know how to use them to work faster and smarter, whether that's drafting and refining communications, synthesizing research and briefing materials, or streamlining scheduling and administrative workflows. This is a role for someone who sees AI as a lever for higher-value work, not a replacement for judgment. The CEO is supported by a Chief of Staff for strategic initiatives and cross-functional priorities. This role is focused on calendar management, logistics, and operational execution for the CEO, along with scheduling support for other members of the C-suite as needed. Duties & Responsibilities - Executive Support & Calendar Command - Own and manage the CEO's calendar with a strategic lens, proactively resolving conflicts, prioritizing high-value activities, and protecting time for deep work. - Coordinate complex domestic and international travel, including detailed itineraries, contingency planning, and real-time adjustments. - Prepare the CEO for every meeting and engagement with day-ahead and week-ahead briefings, background research, and materials. - Manage expense reporting, reimbursements, and budget tracking with complete accuracy. - Serve as the primary gatekeeper for the CEO's time, exercising sound judgment on prioritization and access. - Provide scheduling support to other members of the C-suite as needed, coordinating with their assistants and calendars to ensure smooth cross-executive alignment. - Strategic & Business Support - Act as a partner to the CEO in streamlining decision-making and daily operations. - Assist in the preparation of high-stakes materials, including board presentations, client-facing decks, and executive communications. - Support business development and client management efforts, including research, meeting prep, and follow-up coordination. - Manage CRM (Salesforce) needs to ensure data accuracy and timely updates. - Liaise with the Board, senior leadership, investors, and external partners with professionalism and discretion. - Anticipate the CEO's needs and proactively solve problems before they escalate. - Confidentiality & Discretion - Handle highly sensitive, confidential, and proprietary information with absolute discretion. - Serve as a trusted advisor who can be relied upon in high-pressure, time-sensitive, or sensitive situations. - Exercise excellent judgment in representing the CEO internally and externally. - Cross-Functional & Organizational Leadership - Partner with Operations, IT, Marketing, and other teams to ensure seamless execution of CEO priorities. - Lead coordination of executive-level events, offsites, and high-profile meetings, managing logistics, vendors, and contracts end-to-end. - Serve as a resource and mentor to other administrative staff, setting the standard for executive support across the firm. - Manage ad-hoc, high-priority projects as directed by the CEO. Qualifications - 7+ years of experience supporting C-suite executives, ideally a CEO, Founder, or President, in a fast-paced professional services, consulting, or corporate environment. - Impeccable judgment, discretion, and a demonstrated ability to handle confidential information with the utmost integrity. - Executive presence and polish, with the ability to represent the CEO credibly in high-stakes settings. - Exceptional written and verbal communication skills. - Proven ability to manage complex, competing priorities in a fast-moving environment without dropping details. - A proactive, "no task too big or small" mindset paired with the strategic judgment to know what matters most. - Strong technology fluency, including Microsoft Office Suite, Google Workspace, and Salesforce (or comparable CRM). - Demonstrated fluency with AI tools (e.g., Claude, ChatGPT, Copilot) and a track record of using them to improve speed and quality of work, from drafting and research to scheduling and workflow automation. - Availability and flexibility to accommodate the CEO's schedule, including occasional evenings, weekends, or travel as needed. - Composure and grace under pressure; unflappable in high-stakes or fast-changing situations. Salary Range The base salary range for this position is $90,000 to $120,000 per year, depending on a candidate's experience and qualifications as they relate to the position. Benefits - 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. Location This position is location-agnostic within the United States. Candidates may be based near one of Penta's US offices or work fully remote. The CEO is based in Chicago, so candidates in or near Chicago are welcome, though it is not a requirement. Given the nature of the role, some flexibility for occasional travel or in-person availability may be required.

• 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.

• Serve as the business owner of Salesforce by configuring and creating fields, stages, workflows, and reports to match how the business actually operates • Own the revenue tech stack, including CRM, marketing automation, and sales engagement tools • Lead the evaluation, implementation, and integration of tools that improve team productivity and data quality • Ensure systems are configured to support reporting needs and operational workflows • Run the recurring forecasting process, including a weekly pipeline review with commercial leadership, a bi-weekly forecast submission to Finance, and a monthly close-out summary that compares forecast to actuals and identifies sources of variance • Establish clear deal inspection criteria so forecast calls are grounded in data to drive meaningful improvements in forecast accuracy as a tracked, reported metric • Build and maintain bottom-up and top-down forecasting models that translate accurate CRM pipeline data into reliable near-term and long-term revenue projections for Finance and the CGO; proactively identify, flag, and correct forecast errors in real time • Partner with Finance and commercial leadership on GTM planning and revenue performance analysis • Develop the reporting infrastructure end-to-end, ensuring accurate, real-time data across all deal stages to provide leadership with a clear, trusted view of pipeline health, stage progression, and conversion trends • Lead the development of sales enablement materials, process documentation, and training to support global GTM initiatives • Implement scalable sales processes across the customer lifecycle, from lead generation and pipeline management through to renewal and expansion • Continuously evaluate and improve existing workflows to reduce friction and improve conversion rates at each stage of the funnel; support territory planning, capacity modeling, quota setting, and compensation plan design • Own data management practices including field standardization, record hygiene, deduplication, and data governance policies • Drive CRM adoption and behavior change across the commercial team — enforce data entry standards not just through system rules but through manager accountability, rep enablement, and demonstrating the value of clean data in deal reviews

Penta Group is a global company providing data-driven solutions to help clients achieve their objectives in an increasingly complex stakeholder environment. We provide cutting-edge intelligence products to help clients understand what their stakeholders think, see, and hear, and then leverage that intelligence to develop and execute effective, measurable strategies. Our global team brings decades of experience in business, government, communications, research, data science, and media. Our clients include companies across a variety of industries, including technology, financial services, energy, healthcare, and more. Penta has offices in New York, London, Washington, DC, San Francisco, Dublin, London, Brussels, Singapore, and Hong Kong. Role Summary: As a Monitoring & Insights Intern, you will support Penta’s Intelligence division across both our proprietary insights and real-time monitoring services, helping global clients understand stakeholder sentiment, media coverage, and emerging risks. You will work with large volumes of news, media, and proprietary data to produce both real-time outputs and longer-form analysis, contributing to alerts, briefings, and client and industry facing reports on reputation, topic trends, and stakeholder views. Your work will involve tracking developments as they unfold, identifying key drivers behind trends, creating visualizations, and translating data into clear, actionable insights. Working alongside our analysts, you will use industry-leading media aggregation and analytics tools to monitor coverage in real time while building structured analyses. You will support the delivery of alerts, briefings, and reports, helping clients respond to media developments as they happen while also contributing to deeper insights that inform planning, strategy, and decision-making. This role is ideal for an ambitious and analytically minded early-career professional interested in media analysis, business intelligence, and stakeholder insights, and offers training, mentorship, and professional development within a fast-paced and dynamic team. This role is expected to: - Monitor news and events across outlets and platforms, including print, digital, television, radio, and social media - Collaborate with a team of analysts to alert the news to clients in a timely and effective manner - Collect and prepare data to support media analysis and scheduled report deliveries - Assist with long-term research projects - Create pivot tables from Excel report data - Update report graphics and charts for review - Write descriptive text to tell the stories behind data - Validate and interpret automated scoring from Penta’s proprietary platform on reputation risk, and stakeholder views The ideal candidate will have: - A bachelor's degree in any discipline, where a focus on communications, journalism, economics, history, or another social science is preferred - Experience writing analytical reports & creating engaging presentations using Microsoft office, or Google Suite products - A solid understanding of leveraging Excel for exploratory data analysis & visualization purposes - A strong interest in media, the 24/7 news cycle, and the intersection of culture, business, and politics - Excellent communication, organizational, and writing skills - Intellectual curiosity and a desire to understand the deeper meaning behind content or data - Meticulous attention to detail and a strong ownership mentality - Coachability and possess a learning & growth oriented mindset - The ability to prioritize multiple, competing priorities - Experience working in teams with a collaborative mindset Compensation: This is a non-exempt position eligible for overtime. The hourly pay for this internship will be $20 per hour. Any pre-approved hours worked over 40 hours per week will be paid at time and a half. Benefits: - Dynamic and supportive environment for learning and growth - Access to ongoing training to help develop a strong understanding of the technology and methods used to monitor the news - Mentoring opportunities and support in the development of long-term career goals Location, Work Hours, and Remote Schedule: For this position, we are only considering applicants located on the west coast of the United States who are able to work remotely 35-40 hours per week during a 11 am - 7 pm PT shift. Occasional afternoon shifts (2 pm - 5 pm PT) on both Saturday and Sunday will be required on a rotational basis every six weeks throughout the internship. The internship’s duration will be 3 months with the possibility of extension, and have anticipated start date of mid-May through early June 2026. 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.

Penta Group is a global company providing data-driven solutions to help clients achieve their objectives in an increasingly complex stakeholder environment. We provide cutting-edge intelligence products to help clients understand what their stakeholders think, see, and hear, and then leverage that intelligence to develop and execute effective, measurable strategies. Our global team brings decades of experience in business, government, communications, research, data science, and media. Our clients include companies across a variety of industries, including technology, financial services, energy, healthcare, and more. Penta has offices in New York, London, Washington, DC, San Francisco, Dublin, London, Brussels, Singapore, and Hong Kong. Role Summary: As a Monitoring & Insights Intern, you will support Penta’s Intelligence division across both our proprietary insights and real-time monitoring services, helping global clients understand stakeholder sentiment, media coverage, and emerging risks. You will work with large volumes of news, media, and proprietary data to produce both real-time outputs and longer-form analysis, contributing to alerts, briefings, and client and industry facing reports on reputation, topic trends, and stakeholder views. Your work will involve tracking developments as they unfold, identifying key drivers behind trends, creating visualizations, and translating data into clear, actionable insights. Working alongside our analysts, you will use industry-leading media aggregation and analytics tools to monitor coverage in real time while building structured analyses. You will support the delivery of alerts, briefings, and reports, helping clients respond to media developments as they happen while also contributing to deeper insights that inform planning, strategy, and decision-making. This role is ideal for an ambitious and analytically minded early-career professional interested in media analysis, business intelligence, and stakeholder insights, and offers training, mentorship, and professional development within a fast-paced and dynamic team. This role is expected to: - Monitor news and events across outlets and platforms, including print, digital, television, radio, and social media - Collaborate with a team of analysts to alert the news to clients in a timely and effective manner - Collect and prepare data to support media analysis and scheduled report deliveries - Assist with long-term research projects - Create pivot tables from Excel report data - Update report graphics and charts for review - Write descriptive text to tell the stories behind data - Validate and interpret automated scoring from Penta’s proprietary platform on reputation risk, and stakeholder views The ideal candidate will have: - A bachelor's degree in any discipline, where a focus on communications, journalism, economics, history, or another social science is preferred - Experience writing analytical reports & creating engaging presentations using Microsoft office, or Google Suite products - A solid understanding of leveraging Excel for exploratory data analysis & visualization purposes - A strong interest in media, the 24/7 news cycle, and the intersection of culture, business, and politics - Excellent communication, organizational, and writing skills - Intellectual curiosity and a desire to understand the deeper meaning behind content or data - Meticulous attention to detail and a strong ownership mentality - Coachability and possess a learning & growth oriented mindset - The ability to prioritize multiple, competing priorities - Experience working in teams with a collaborative mindset Compensation: This is a non-exempt position eligible for overtime. The hourly pay for this internship will be $20 per hour. Any pre-approved hours worked over 40 hours per week will be paid at time and a half. Benefits: - Dynamic and supportive environment for learning and growth - Access to ongoing training to help develop a strong understanding of the technology and methods used to monitor the news - Mentoring opportunities and support in the development of long-term career goals Location, Work Hours, and Remote Schedule: For this position, we are only considering applicants located in the United States who are able to work remotely 35-40 hours per week during a morning shift (6 am - 2 pm ET) or afternoon shift (2 pm - 10 pm ET). Occasional evening shifts (5pm - 8 pm ET) on both Saturday and Sunday will be required on a rotational basis every six weeks throughout the internship. The internship’s duration will be 6 months with an anticipated start date of mid-May 2026. 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.