Managing Director

Managing Director

Full-Time | Remote | Total Comp up to $125,000 | Reports to: Founder 

You Are ...

… A high-performance operator with a sharp mind, high standards, and a bias for action. You excel at bringing structure to chaos, turning vision into execution, and leading teams with clarity, candor, and heart.

You thrive behind a visionary founder—someone who moves fast, thinks big, and expects results. You love building systems that scale, aligning people around measurable outcomes, and making sure the trains not only run on time but run on excellence.

You think in systems. You use AI instinctively. You track performance like a hawk. You thrive in lean, high-ownership environments and don’t need a 10-slide deck to make a decisive, smart move.

You’re fired up about the chance to lead a rapidly growing team that’s changing lives inside 800+ jails and prisons—and to help build a future where purpose, technology, and performance coexist.

If you’ve ever been the second-in-command to a founder, you know exactly what this job is. If you’ve wanted to be, and you’re ready, this is your shot.

About Hustle 2.0

Hustle 2.0 is a Public Benefit Corporation transforming lives behind bars. We deliver personal development and reentry programming to people in jails and prisons—helping them turn their hustle into hope and their story into power.

We’re not a nonprofit, and we don’t move like one. We run lean. We move fast. We leverage AI and automation. We think like operators and execute like entrepreneurs. Our programs reduce violence, disrupt incarceration cycles, and help people become the first in their families to graduate college—and the last to go to prison.

We’ve served 20,000+ incarcerated people across 47 states. We’re scaling fast, and now we’re looking for a Managing Director who’s ready to build the operational backbone for our next phase of growth.

Mission-Critical Mandate

Within 90 days, bring structure, visibility, and rhythm to the organization.

Within 6 months, create full operational alignment across sales, programs, and finance.

Within 12 months, Hustle 2.0 runs on systems—not heroics.

What You'll Do

You’ll be the right hand to the Founder and take ownership of day-to-day operations. You’ll lead department heads, manage internal systems and external vendors, and ensure the entire organization executes with precision, discipline, and heart.

You’ll build the structure that allows our mission to scale.

Team & Culture

• Lead with high standards, clear accountability, and strong values. Build and maintain a performance-driven culture rooted in ownership, clarity, and consistent execution.
• Manage and coach department heads across Sales, Programs, Operations, and Administration, ensuring cross-functional alignment and results-focused collaboration.
• Drive talent excellence through performance reviews, goal setting, and leadership development. Oversee hiring, onboarding, and training processes that attract and retain “A players.”
• Reinforce a culture of clarity, feedback, and constant improvement. Promote candid, constructive communication and data-driven decision-making to elevate both individual and team performance.
• Model candor without drama and curiosity without slowing momentum. Demonstrate emotional intelligence and mental agility—balancing empathy and accountability to create a high-trust, high-velocity environment.
• Oversee Human Resources systems and processes to ensure compliance, efficiency, and alignment with company values. Lead HR strategy including workforce planning, performance management, compensation structure, and professional development programs.

Finance & Operations

• Leading the Director of Operations, working with our fractional CFO, and their teams, you’ll oversee budgeting, forecasting, financial reporting, and admin.
• Install “optics” systems—dashboards, KPIs, and scoreboards that make performance visible and actionable.
• Build scalable SOPs, systems, and processes for growth from $1M to $10M+.
• Identify risks, find efficiencies, and ensure operational excellence.

Sales & Growth

• Lead the Sales Manager and Director of Programs & AI, ensuring both the sales and customer success teams operate with clarity, consistency, and excellence.
• Drive predictable growth by tracking performance metrics, optimizing sales systems, and refining conversion processes to increase velocity, close rates, and lifetime value.
• Partner with the executive team to expand market reach, deepen relationships with facilities, and scale impact to serve more people nationwide.
• Align marketing, sales, and delivery around unified, measurable growth objectives—ensuring every department contributes directly to pipeline health, client retention, and revenue expansion.
• Foster a culture of ownership and continuous improvement, where data, feedback, and innovation drive smarter strategies and sustained performance.

Systems, Data & AI Integration

• Champion AI and automation across the organization.
• Supervise our automation lead and integrate tools like ChatGPT, Zapier, CRMs, and dashboards.
• Streamline workflows, remove friction, and make data-driven decisions.
• Stay ahead of emerging tech that increases speed, quality, and scale.

You're a Strong Match if You Have:

• A deep sense of purpose—you care about people and impact, even if you’ve never worked in the justice system.
• 10+ years of experience, including 5+ in senior leadership roles.
• Experience being the #2 to a founder/CEO or leading day-to-day ops at a lean, fast-paced org.
• Proven success managing teams of 5–50 people and hitting measurable outcomes.
• Strong financial literacy and comfort managing budgets, dashboards, and forecasts.
• Tech-savvy mindset—you’re fluent with CRMs, spreadsheets, and AI tools and love making tech work for you.
• Exceptional attention to detail + execution skills
• Experience managing Sales, CX, or Ops teams.
• Startup or scale-up experience where you built systems, wore multiple hats, and thrived.
• Remote leadership experience—you know how to drive culture and accountability in distributed teams.
• Excellent written and verbal communication—clear, concise, and direct.
• Calm under pressure. Confident without ego. Direct without drama.

This Role is for You, if ...

• You think in dashboards and systems, not feelings.
• You can turn a founder’s vision into execution without losing the soul of the mission.
• You believe accountability is an act of respect.
• You’re relentless about clarity, alignment, and results.
• You can hold both empathy and edge at the same time.

Logistics & Compensation

• Base Salary: $80,000–$100,000 depending on experience
• Performance-Based Bonus: Up to $25,000
• Location: Remote (open to international candidates who can work U.S. hours)
• Start Date: ASAP

How to Apply

Send your résumé to [email protected]

Include a written summary (up to 2 pages) answering:

1. Why are you interested in this role?
2. Why Hustle 2.0?
3. Have you worked directly with a visionary founder or CEO before? What worked—and what didn’t?