Chief of Staff

Company Overview

Renterra is a Series A–backed SaaS company modernizing the $100B+ heavy equipment rental industry. We’ve built an end-to-end platform that helps rental businesses run smarter — spanning operations, payments, marketing, and accounting integrations and so much more.

We’re growing quickly, scaling our team, and tackling complex problems across sales, product, customer success, and go-to-market. As we enter our next phase of growth, we’re looking to add a Chief of Staff to work directly alongside the Co-Founder & CEO.

Position Overview

We are hiring a Chief of Staff to act as the right-hand partner to the CEO, supporting and driving execution across the most important priorities in the business.

This is a highly cross-functional, fast-moving role designed for someone who thrives in ambiguity, loves getting things done, and wants a front-row seat to building and scaling a startup. You’ll be deeply involved in projects spanning sales, customer success, marketing, product, operations, finance, and internal execution, often owning initiatives end-to-end.

This role is ideal for someone with 2–3 years of experience at Bain, BCG, or McKinsey who is looking to transition from advisory work into an operating role with real ownership and impact.

This is a Chicago-based, hybrid role, with an expectation of working from the office three days per week.

Responsibilities

• Serve as the CEO’s right-hand partner, focusing on whatever is most important for the business at any given moment. If you want a front-row seat to what it's like to be the CEO of a startup, this role is for you
• Drive execution on high-priority, cross-functional initiatives spanning sales, customer success, marketing, product, operations, and finance
• Translate strategic ideas into concrete plans, timelines, and deliverables and ensure they actually get done
• Step in to own ambiguous problems with limited structure, from analysis through execution
• Support company planning and operating cadence, including budgeting support, goal tracking, and leadership coordination
• Prepare materials, analyses, and recommendations for internal meetings, leadership discussions, and key decisions
• Help plan and execute internal meetings, offsites, customer events, and other high-impact initiatives
• Act as a connective tissue across teams, following up on decisions, unblocking issues, and maintaining momentum

Qualifications

• 2–3+ years of experience at Bain, BCG, or McKinsey (required)
• Bachelor’s degree from a top-tier academic institution
• Exceptional organizational and project management skills
• Strong analytical and problem-solving abilities
• Proven ability to manage multiple workstreams simultaneously
• Comfortable operating in ambiguity and fast-changing environments
• Clear, concise communicator — both written and verbal

Skills & Attributes

• Highly execution-oriented — a true “doer” who gets things done
• Extremely organized with strong attention to detail
• Proactive, resourceful, and comfortable taking ownership
• Strong judgment and ability to prioritize what matters most
• Low ego, high accountability, and willing to roll up sleeves
• Excited by startups, learning by doing, and working closely with founders

What We Offer

• Competitive compensation and equity
• Health, dental, and vision insurance
• Flexible PTO policy
• Direct exposure to company leadership and decision-making
• Broad responsibility and rapid professional growth
• A unique opportunity to learn how to scale a high-growth SaaS company from the inside

This is a rare opportunity to step into a high-trust, high-impact role and gain deep exposure to how a venture-backed startup is built and operated. If you’re excited about moving from strategy to execution and working side-by-side with a founder, we’d love to hear from you.

Renterra is an Equal Opportunity Employer.