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Chief of Staff

$120k - $160k
Full-time
Chicago, IL

About Mainland

Mainland is a fast-growing marketing, media, and technology company serving franchise brands, multi-unit operators, and private-equity-backed platforms. We sit at the intersection of content, data, AI, and growth, and we’re building a company designed to scale—with people, systems, and culture that can grow with it.

We’re hiring a Chief of Staff to act as a force multiplier for leadership and the organization as a whole.

The Role

This is a high-impact, highly visible leadership role. You will help run the company day-to-day—owning operations, driving internal alignment, leading people initiatives, and ensuring Mainland scales with clarity, accountability, and momentum.

You will work directly with the CEO and leadership team to turn strategy into execution.

This role is ideal for someone who:

  • Thinks like an operator
  • Cares deeply about people and culture
  • Loves building systems that make teams better
  • Wants real ownership and influence
  • Is outgoing and influential

What You’ll Own

Operations & Execution

  • Translate company strategy into clear priorities, goals, and operating rhythms
  • Own internal planning, OKRs, and cross-department execution
  • Improve processes across accounts, delivery, and internal workflows
  • Identify bottlenecks early and drive solutions to keep the business moving fast and clean

Culture, Leadership & Recruiting

  • Be the keeper of the culture—values, standards, and accountability
  • Lead recruiting efforts across the company (role definition, hiring process, interviews, onboarding)
  • Build strong onboarding and performance feedback systems
  • Support managers with structure, clarity, and expectations

Human Resources Ownership

  • Own HR operations: policies, compliance, performance reviews, compensation tracking
  • Partner with leadership on org design, role clarity, and career paths
  • Help resolve people issues with empathy, fairness, and firmness
  • Ensure we are scaling responsibly and professionally

Leadership Partner

  • Act as a thought partner to the CEO and leadership team
  • Prepare leadership meetings, track decisions, and ensure follow-through
  • Surface issues early and bring structured solutions
  • Keep the company aligned, informed, and moving in the same direction

What We’re Looking For

  • 5–10+ years of experience in operations, chief of staff, consulting, or senior leadership roles
  • Strong people leadership instincts—culture matters to you
  • Exceptionally organized with strong written and verbal communication
  • Comfortable operating in ambiguity and building structure from scratch
  • High emotional intelligence and sound judgment
  • Experience in fast-growth, agency, tech, or services environments is a plus

Why This Role Is Special

  • Real ownership—not a support role
  • Direct access to leadership and strategic decision-making
  • Opportunity to shape the company’s culture and future
  • A seat at the table as Mainland scales into its next chapter
Contact employer
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