Manager of Strategic Initiatives & Business Operations (Chief of Staff)

Cloverpop; Chicago (IL); On-site; USD 90,000 - 120,000; Full time

Job summary

Cloverpop seeks a Manager of Strategic Initiatives & Business Operations to optimize business processes and support commercial execution. This role blends strategic planning with operational excellence in a fast-growing AI-driven company. Ideal for analytical thinkers with relevant experience, the position involves collaboration with executive leadership and managing high-impact projects.

Qualifications

• 3-5 years of experience in management consulting, business operations, or strategy roles.
• Experience in startup or VC-backed environments.

Responsibilities

• Serve as a thought partner to the executive leadership team on key priorities.
• Own sales reporting and deal desk operations to improve visibility.
• Develop and standardize business operations for scalability.

Skills

Analytical

Problem Solving

Communication

Job description

Overview:

Cloverpop is a pioneer in Decision Intelligence technologies, transforming enterprise decision-making through our industry-leading platform. At Cloverpop, we merge the “art” and “science” of decision-making by equipping enterprises with the ability to model, orchestrate, automate, and learn from their most mission-critical decision processes. Our technology bridges the gap between data and decisions, removing human biases, increasing stakeholder buy-in, and driving decision speed and quality.

Founded by experienced entrepreneurs and thought leaders in decision intelligence, behavioral science, AI, and the future of work, Cloverpop empowers companies to make smarter decisions faster. We are proud to serve Fortune 100 companies across consumer goods, pharmaceuticals, retail, and technology, all of whom rely on our platform to reshape how they approach critical decisions. Join us as we lead the way in Decision Intelligence and revolutionize how businesses operate in the digital era.

Role Description:

As a Manager of Strategic Initiatives & Business Operations (Chief of Staff) at Cloverpop, you will play a pivotal role in aligning strategic priorities, optimizing business operations / processes, and supporting commercial execution. This role blends strategic planning, revenue operations, and business process improvement, ensuring our leadership team has the insights and processes needed to scale effectively. You will work directly with the President and collaborate across Sales, Finance, and Operations teams to drive efficiency, improve decision-making, and accelerate growth.

This is an ideal role for a highly analytical, strategic thinker with 3-5 years of management consulting, Chief of Staff or business operations experience, looking to take on a high-impact role in a fast-growing AI-driven company.

Responsibilities:

Executive Enablement & Strategic Projects

• Serve as a thought partner to the executive leadership team (ELT) on key priorities, managing a portfolio of high-impact special projects across functions (e.g., Pricing strategy, partner ecosystem development, etc…).
• Translate strategic ideas into executable workstreams, ensuring alignment and momentum.
• Lead internal operating cadences (e.g., weekly leadership meetings, account / sales reports, quarterly planning, KPIs).
• Drive executive communications, including board decks, investor updates, and fundraising materials.

Commercial & Sales Operations

• Own sales reporting, deal desk operations, and pipeline analytics to improve visibility into business performance.
• Optimize pricing models, commission structures, and go-to-market processes to enhance revenue growth.
• Own internal OKRs and decision tracking mechanisms, ensuring a data-informed operating rhythm.
• Support sales strategy and enablement, ensuring teams have the data and tools to succeed.

Business & Operational Excellence

• Develop and standardize business operations, ensuring scalability and efficiency.
• Lead special projects focused on process automation, decision intelligence adoption, and organizational improvements.
• Support hiring, onboarding, and HR processes, contributing to a strong company culture and operational effectiveness.

Qualifications:

• 3-5 years of experience in management consulting, business operations, chief of staff or strategy roles.
• Demonstrated experience in startup, VC-backed, or founder-adjacent environments.
• Strong analytical and problem-solving skills, with experience in financial modeling and data analysis.
• Experience in revenue operations, or commercial strategy is a plus.
• Ability to navigate cross-functional teams and work closely with executive leadership.
• SaaS, AI, or enterprise software experience preferred, but not required.
• Exceptional written communication and executive presence.
• Highly proactive, resourceful, and mission-driven.