About the Role
We're looking for a highly organized, proactive Chief of Staff & Operations Manager to serve as the operational backbone of Dealer Merchandising and a trusted partner to the company's founders. This is a highly cross-functional role that touches nearly every part of the business—from customer onboarding and contracts to finance, payroll, vendor management, internal operations, and strategic projects.
You'll be responsible for keeping the company organized, ensuring nothing falls through the cracks, and building the operational systems that allow Dealer Merchandising to scale. One hour you may be coordinating a dealership launch, the next you may be processing invoices, improving an internal workflow, or helping leadership prepare for an important customer meeting.
If you thrive in fast-paced startup environments, enjoy solving complex operational challenges, and love bringing order to chaos, we'd love to meet you.
About Dealer Merchandising
Dealer Merchandising partners with automotive dealerships to transform underutilized showroom space into profitable retail environments. We design, merchandise, launch, and manage dealership retail stores that create meaningful customer experiences while generating incremental revenue.
We're building a company of self-starting individuals who take ownership, solve problems independently, and move quickly. Every person on our team has a meaningful impact on the business, and we're looking for someone who wants to help build the operational foundation of a fast-growing company.
What You'll Do
- Serve as a strategic partner to the founders, helping prioritize initiatives, coordinate projects, and keep the business moving forward
- Track company priorities, deadlines, and cross-functional action items to ensure projects stay on schedule
- Coordinate communication across Sales, Account Management, Retail Operations, eCommerce, and external partners
- Prepare, send, and manage customer agreements through DocuSign, ensuring contracts are executed quickly and accurately
- Coordinate the seamless transition of new dealership clients from Sales into Operations
- Schedule and organize dealership kickoff meetings with internal teams and implementation partners
- Process customer invoices, manage accounts receivable, monitor collections, and ensure timely payment processing
- Process vendor invoices, manage accounts payable, and coordinate vendor payments
- Support monthly financial reporting by maintaining accurate records and reconciling operational expenses
- Process payroll accurately and on schedule while supporting employee onboarding, offboarding, benefits administration, and HR documentation
- Maintain company records, operational documentation, templates, and standard operating procedures
- Coordinate recurring operational processes, internal meetings, and company-wide initiatives
- Support vendor relationships across fixtures, signage, logistics, merchandising, and other operational partners
- Identify operational bottlenecks and continuously improve workflows, systems, and internal processes
- Recommend and implement software, automation, and scalable operational solutions that improve efficiency across the business
- Assist leadership with special projects, strategic initiatives, and day-to-day operational support as the company grows
What You Bring
- 4+ years of experience in operations, business administration, executive support, project management, Chief of Staff, or a similar cross-functional role
- Exceptional organizational skills with the ability to manage multiple priorities simultaneously
- Strong written and verbal communication skills
- High attention to detail and outstanding follow-through
- Ability to handle confidential information with professionalism and discretion
- Experience with DocuSign, Google Workspace, Microsoft Office, and modern business software
- Familiarity with payroll processing, invoicing, accounts payable, and accounts receivable
- Ability to work independently, anticipate needs, and proactively solve problems in a fast-paced environment
Bonus Points For
- Startup or high-growth company experience
- Experience with QuickBooks, Gusto, Bill.com, Ramp, or similar financial platforms
- Experience using project management software such as Asana, Monday.com, ClickUp, or similar
- Experience supporting founders or executive leadership
- Automotive, retail, eCommerce, or multi-location business experience
What Success Looks Like
- Customer contracts are executed quickly, accurately, and without delays
- Every new dealership transitions seamlessly from Sales into Operations
- Payroll, invoicing, vendor payments, and financial processes run smoothly and consistently
- Leadership spends more time focused on growth because operational details are handled proactively
- Cross-functional projects stay organized, on schedule, and well-communicated
- Internal systems and processes become increasingly efficient as the company scales
- Team members know where to find information, understand next steps, and trust that operational details are under control
Compensation & Benefits
- Salary: $110,000–$150,000 per year (depending on experience)
- Fully remote position with occasional travel for team meetings and dealership visits
- 3 weeks paid vacation and 2 weeks paid sick time annually, granted January 1 and prorated for mid-year hires
- Annual performance reviews
- 401(k) account with company match
- Medical, dental, and vision coverage available from day one
Dealer Merchandising is an equal opportunity employer. We welcome applicants from all backgrounds and experiences.