Develop and execute executive communications and PR strategies, including messaging, thought leadership, media pitches, journalist relationships, podcast and speaking opportunities, interview preparation, and reputation management. Track outreach and outcomes while advising senior stakeholders. The role supports a high-profile executive in expanding media presence and positioning them as a recognized voice across business, leadership, investment, and industry media.
We are seeking an experienced Senior PR Strategist (Freelance, Remote) to support a high-profile business executive and entrepreneur in strengthening their media presence, executive brand, and thought leadership.
This role is ideal for a strategic and hands-on PR professional who can independently manage media relations, identify opportunities, develop compelling pitches, and execute outreach campaigns across business, leadership, investment, and industry-focused media.
The successful candidate will work directly with senior stakeholders to build upon existing PR momentum, expand media opportunities, and position the executive as a recognised voice within relevant industries.
Requirements
Key Responsibilities
- Develop and execute executive communications strategies aligned with business and brand objectives.
- Create and refine executive messaging, narratives, and positioning.
- Identify opportunities for thought leadership, media appearances, interviews, podcasts, speaking engagements, and industry recognition.
- Build relationships with journalists, media outlets, podcast hosts, and relevant industry communities.
- Develop communications materials including media pitches, briefing documents, articles, and executive content.
- Support preparation for interviews, public appearances, and external engagements.
- Monitor relevant industry conversations and identify opportunities for executive commentary.
- Track communications activities, opportunities, and outcomes while providing recommendations to stakeholders.
Qualifications
- 5+ years of experience in executive communications, public relations, corporate communications, or a related field.
- Proven experience supporting senior executives, founders, entrepreneurs, investors, or other public-facing leaders.
- Strong writing, storytelling, and message development skills.
- Experience developing thought leadership content and external communications strategies.
- Strong understanding of media relations and executive reputation management.
- Ability to work independently, manage priorities, and communicate effectively with senior stakeholders.
Preferred Experience
- Experience supporting CEOs, C-suite executives, authors, or industry experts.
- Background in business, finance, investment, technology, leadership, or professional services.
- Experience securing media coverage, podcast appearances, speaking opportunities, or executive profiles.
- Agency, consultancy, or senior in-house communications experience.
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What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
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