Senior Managing Director

Title: Senior Managing Director, Vine Digital Studio

Location: United States

Job Description:

Senior Managing Director / General Manager, Vine Digital Studio

Reports To: Head of Marketing

Location: Remote, Atlanta/Malvern/River Falls

About Cantaloupe

Cantaloupe, Inc. is a global technology leader powering self-service commerce. Cantaloupe offers a comprehensive suite of solutions including micro-payment processing, self-checkout kiosks, mobile ordering, connected point of sale systems, enterprise cloud software, and marketing professional services. Handling more than a billion transactions annually, Cantaloupe's solutions enhance operational efficiency and consumer engagement across sectors like food & beverage markets, smart automated retail, hospitality, entertainment venues and more.

About Vine Digital Studio

Vine Digital Studio is Cantaloupe's in-house digital marketing services business, built to help operators grow through stronger online presence and demand generation. Vine provides practical, execution-focused marketing support for operators who want professional results without building or managing an internal marketing team.

Vine delivers a scalable set of digital marketing services-including websites, SEO, content, social media, email, and lead generation-tailored for operators in vending, micro markets, amusement, laundry, and other self-service commerce segments.

Overview

Vine Digital Studio is seeking a Managing Director / General Manager to lead the strategy, operations, and growth of its full-service digital marketing agency: Vine Digital Studio. This role has overall responsibility for agency performance, including team leadership, client delivery, revenue growth, and operational efficiency.

The ideal candidate is a proven agency leader who understands how to scale services, manage cross-functional teams, and own the full client lifecycle-from business development through delivery and renewal. This role requires a balance of strategic leadership and hands-on operational management.

Key Responsibilities

Agency Strategy & Leadership

• Set and lead the strategic direction of the agency in alignment with business goals
• Establish clear priorities and focus areas across all teams, particularly during periods of growth or organizational change
• Translate high-level strategy into executable plans and measurable outcomes
• Drive accountability for performance, quality, and results across the organization

Operational Oversight & Capacity Planning

• Maintain visibility into all work being delivered across the agency
• Oversee resource planning and capacity management across all functions
• Ensure teams are appropriately staffed and workloads are balanced
• Identify and resolve operational risks, bottlenecks, and delivery challenges, including those introduced by growth, new offerings, or changing client needs

Team Management & Development

• Lead and manage team leads across account management, project management, social media, content, design, development, SEO, analytics, and paid media
• Clarify roles, responsibilities, and expectations across teams
• Support hiring, onboarding, performance management, and professional development
• Foster strong cross-functional collaboration and a culture of ownership

Business Development & Revenue Ownership

• Lead business development efforts in partnership with internal sales teams
• Own the lead pipeline for new and existing clients
• Support pricing, scoping, and proposal development
• Ensure smooth handoff of new clients into onboarding and delivery

Client Relationship Management

• Oversee the full client lifecycle, including onboarding, ongoing delivery, renewals, and expansions
• Serve as an escalation point for client issues related to scope, deliverables, or billing
• Ensure high levels of client satisfaction, retention, and long-term value

Financial & Performance Management

• Own overall financial performance, including revenue growth, retention, and utilization
• Forecast capacity and revenue needs in collaboration with leadership
• Monitor key performance indicators to guide decision-making
• Ensure the agency operates efficiently and sustainably

Qualifications

• 7+ years of experience in a digital agency or professional services leadership role
• Demonstrated experience owning or leading a business unit, including responsibility for revenue, margins, and overall performance
• Proven ability to lead and scale cross-functional teams across creative, technical, and client-facing disciplines
• Strong understanding of digital marketing services, including websites, SEO, content, social, and paid media
• Experience owning revenue, pipeline management, and client relationships
• Demonstrated ability to scale operations and improve delivery processes
• Strong communication, leadership, and stakeholder management skills

Why choose Cantaloupe:

We offer competitive benefits not just limited to compensation but also offer:

• Medical, Dental, & Vision Benefits coverage, plus additional benefits (Life Assistance Program, Financial Wellness, and Nutritional Counseling)
• 401(K) with employer match effective upon the first day of employment
• 18 days PTO + (9) Observed Company Holidays
• Tuition Reimbursement

As part of our commitment to maintaining the highest standards of financial integrity, this position may also involve responsibilities related to SOX compliance.