The Role

We’re hiring a Project Manager to coordinate 30+ concurrent projects while ensuring exceptional customer experiences across our portfolio businesses. You’ll manage client projects for medical/dental practices, game development initiatives, and internal infrastructure projects—while also evaluating and improving how clients interact with our systems, processes, and services. This role starts immediately to prepare for an expanding technical team (7+ infrastructure specialists completing training in 90 days). You’ll have scheduling authority across all technical resources, including leadership.

Primary Responsibilities

Project Orchestration (Primary Focus)

• Track and coordinate 30+ concurrent projects across Mastiff client work (medical/dental IT implementations), Bitrograde game development, and internal initiatives
• Schedule technical resources (including leadership) to project needs based on priorities and capacity
• Manage project timelines, resources, and deliverables using Basecamp and Notion
• Extract regular status updates from technical team members and escalate blockers proactively
• Coordinate handoffs between specialists (DBAs, network admins, security officers, etc.)
• Make tactical day-to-day decisions (timeline adjustments, task reassignment, unblocking team members)
• Escalate strategic decisions (scope changes, priority shifts, resource allocation) to leadership with context and recommendations
• Monitor project health across entire portfolio and identify potential issues before they become problems

Customer Experience Evaluation

• Regularly audit customer touchpoints: test office phone experience, review invoice clarity, evaluate help desk intuitiveness
• Identify friction points in client interactions and document improvement opportunities
• Think from the client’s perspective: “Is this confusing? Is this intuitive? Does this reflect our quality?”
• Propose and implement process improvements that enhance customer experience
• Bridge the gap between technical execution and client perception

Training & Development Administration

• Ensure all team members complete assigned Udemy coursework on schedule
• Rip and upload purchased courses to internal Moodle LMS
• Track training completion rates and follow up with team members
• Monitor onboarding progress for new hires during 60-day ramp period
• Coordinate with leadership on training priorities and gaps

Quote Coordination

• Work with technical team to develop project quotes
• Ensure quotes align with current capacity and scheduling realities
• Track quote-to-close conversion and project kickoffs

What We’re Looking For:

Technical Requirements:

Required Skills & Experience:

• 3+ years project management experience coordinating 20+ concurrent projects
• Assertive but diplomatic - comfortable scheduling leadership and technical staff without being pushy, but able to hold people accountable
• Customer empathy - genuine ability to identify what’s confusing or broken from a client’s perspective
• Systems thinking - understand how scheduling, customer experience, project delivery, and training interconnect
• Experience with project management tools (Basecamp experience is a plus)
• Strong organizational skills and obsessive attention to detail
• Ability to context-switch rapidly between different project types (client services, product development, internal infrastructure)
• Basic technical literacy - you don’t need to code, but you should understand servers, networks, databases enough to track technical work
• Self-starter who can work independently and manage chaos across 30+ projects
• Comfortable working fully remote with distributed teams
• Growth mindset - eager to learn and improve continuously
• Strong written and verbal English communication

Nice To Have

• Experience in healthcare/medical technology environments
• Background coordinating both client services and product development
• MSP (Managed Service Provider) or IT services experience
• Familiarity with open-source tools and workflows
• Experience managing remote/distributed teams across time zones
• Learning Management System (LMS) or Moodle experience
• Previous work in customer experience or quality assurance roles

What We Offer

• Fully remote position - work from anywhere
• 60-day comprehensive training program with extensive Udemy access
• Ongoing training and professional development - we invest heavily in our team’s growth
• Work across diverse projects (never boring)
• Collaborative team culture that values versatility and growth
• We celebrate personal victories and calibrate goals to help you succeed
• Access to extensive internal knowledge base and documented processes
• Opportunity to shape project management and customer experience practices as we scale
• Authority to coordinate resources and drive improvements across the organization

Why This Role Matters

You’ll be the operational backbone that enables our technical team to focus on excellent technical work while ensuring nothing falls through the cracks. You’ll have visibility into everything happening across 30+ projects, the authority to schedule resources effectively, and the responsibility to ensure our customers have exceptional experiences at every touchpoint. As we scale from 9 to 16+ employees, your systematization of projects, training, and customer experience will be critical to maintaining our quality standards.