Chief of Staff, Internal AI Optimization

About the COOL company

At the COOL company, we believe in creating a win-win environment where everyone benefits. We are committed to ensuring users, publishers, franchisees, and advertisers all have a better experience and achieve more than they ever thought possible through our innovation, advanced AI, groundbreaking advertising technology, and teams of inspired experts. Our every move, expansion, acquisition, and upgrade is done to provide that better experience for an ever-growing list of satisfied clients and users all over the world.  

COOL Media products under the COOL company include DCO & Creative Automation, a data-driven, creative ad server capable of personalizing, automating, measuring, and optimizing digital ads and placements for advertisers; Franchise & Multi-Location, a complete advertising management platform for franchise and network businesses; Media & Attribution, a managed service solution for agencies and brands to reach and measure audiences; Publisher Experiences, a premier SSP and engagement platform for publishers; and Supply-Side Platform, delivering website and app publishers everything they need to maximize their ad revenue.

Coming soon in 2026, COOL AI is a next-generation advertising platform that builds, buys, and optimizes digital ad campaigns faster and smarter using AI. It automates every step of the media journey—from generating ad creatives to launching campaigns and optimizing performance across channels like Google and Facebook. With no agency fees or waiting, COOL AI helps brands maximize ROI through data-driven strategy, automated creative generation, and real-time performance measurement.

Collectively, the COOL company reaches over 350 million consumers monthly across their network of premium publishers and advertisers, including Disney, Hyundai, Air France, Kohler, Suzuki, Acer, Pearle Vision, Trek, Brita, Viking Cruises, MLB, Playmaker, Blitz, Evolve Media, and more.  Under the former umbrella of Insticator, the COOL company is a proud 7x recipient of the Inc 5000 list of America's fastest-growing private companies, a 2x recipient of Deloitte's Fast 500, recognized on Crain's New York Fast 50 list, recognized by Digiday's Digiday Media Awards as a company working to modernize digital media, and awarded as one of AdWeek's Top 10 Fastest Growing Solution Providers globally.

Our Core Values

At the COOL company, we believe in being C.O.O.L.:

Creative - we look to find solutions that others can’t and new ways of doing things that are smarter, faster, better and more efficient.

Open-minded - we’re always evolving and keep an open mind as to new ways of doing things, new solutions and new processes that can help us.

Optimistic - The glass is always half full :) as a growing tech startup we’re always faced with new challenges, we overcome them because we see them as opportunities.

Leaders - We look for drivers, people who like to set the pace of the organization, who don’t simply go with the flow, you’re setting a fast impact pace and holding others to it.  We look for speed, impact, and setting the industry benchmark.

We creatively integrate new elements in innovative combinations, fueled by our optimism to drive success. Our open-mindedness allows us to embrace new ideas and approaches, empowering us to lead our industry through bold initiatives. That’s the attitude we bring to work with us every day, and it’s what we expect from everyone who works here.

That’s just part of the values that drive us to greatness. We also believe in this trio of truths that inform every decision we make and everything we do:

• Sleeves Up: At the COOL company, we provide you with the autonomy and creativity needed to own your role. We encourage iteration where necessary so that you can drive massive impact.
• 100% Viewability: the COOL company is passionate about open feedback at all levels of the company. This allows us to fail fast, create in real-time, and build an open company culture.
• Be Defiantly Great: We're defiant, and that's in our blood. Challenging the status quo is a central part of who we are. We're capable of much more than what others deem impossible.
  

Description

The COOL company is looking for a Chief of Staff to support the CEO and the rest of the executive team. This role consists of leading special projects, assisting in the development of various areas of business, and acting as a liaison for the CEO as needed. A key focus of this role is driving the company’s AI-forward strategy including owning CRM systems powered by AI, integrating all Firefly company videos into an AI knowledge base to generate coaching outputs, and championing AI adoption across the organization.

About the Role

• Serve as truest advisor to Zack and the executive team, providing strategic guidance and supporting key initiatives
• Lead special projects across business development, operations, and strategic growth initiatives
• Efficiently manage key processes and systems, including email inbox, Slack, and other tools, resulting in increased productivity and operational efficiency
• Execute strategic projects and tasks for the CEO such as decks, business plans, and longer-term initiatives
• Communicate daily with the CEO to optimize the planning and execution of his various commitments and responsibilities
• Manage all administrative duties for the CEO, including owning the calendar and scheduling all meetings and events
• Serve as a key representative of the executive team both inside and outside of the company
• Handle confidential information, write correspondence, and support the CEO and teams across global time zones
• Coordinate travel and related logistics on behalf of the CEO
• Lead & organize quarterly team onsites
• Act as a liaison between the CEO and other key stakeholders, both internal and external
• Own and manage the company CRM with AI integration, ensuring the system is continuously optimized, data is clean and actionable, and AI-driven insights are surfaced to the executive team
• Lead the initiative to ingest all Firefly company videos into an AI knowledge base, enabling intelligent coaching and insights to be automatically surfaced to the team
• Oversee the pipeline that transforms Firefly video content into personalized coaching outputs delivered via email and broader team communications
• Champion AI adoption across the organization from identifying opportunities to automating workflows, enhancing productivity, and embedding AI tooling into day-to-day operations
• Lead projects do internal AI optimizations across the company
• Effectively integrate subsidiaries
  

Competencies

• 8–10 years in a role supporting executives and/or C-suites
• Very high EQ and people skills
• Creativity and open-mindedness
• Great project management skills
• Excellent written and verbal communication skills
• Ability to synthesize various viewpoints 
• High empathy and ability to make team members feel heard and acknowledged
• Great listener and ability to absorb information
• Strategic thinking and problem-solving abilities
• Comfort with ambiguity and flexibility to adapt to changing priorities and deadlines
• Demonstrated experience with AI tools, CRM platforms, and emerging technology (strongly preferred)
• Ability to manage and implement AI-driven workflows and communications systems

Cultural Competencies

• Must be able to work primarily between the hours of 9:30 AM - 6:30 PM ET
• Must have a player/coach mentality, willing to both execute and lead
• Ability to juggle multiple projects concurrently and set and meet deadlines
• Skilled at receiving and providing direct feedback
• Collaborative mindset and great teamwork skills
• Entrepreneurial & adaptable; great learning skills
• Curious, research-minded, data-informed
• Able to search for possible solutions and apply them
• Creative confidence
• Proactive communicator
• A sense of humor and a love of online culture
• Thrives in a start-up culture

Benefits

• Competitive Salary
• Health, Dental and Vision Insurance
• Annual Performance Bonus
• Paid Time Off
• Company Holidays
• Flexible work schedule
• 401k