Redwood Services

Redwood Services is a national platform of leading residential HVAC, plumbing, and electrical businesses. Founded in 2020, Redwood partners with exceptional local operators while preserving the brands, cultures, and local accountability that made them successful. Today, our 23 Partner companies represent approximately $800 million to $1 billion in annual sales.

Redwood has built a strong acquisition engine and meaningful capabilities across our Partner Support Center (PSC). Our next opportunity is to work with Partner companies to build a system of practical operational playbooks for running a top-tier home services business. These playbooks will support organic growth and operational improvement across trades and markets while preserving Redwood’s people-first, Partner-led culture.

We are looking for a Director of Enterprise Initiatives to help lead that work. Reporting to the Chief Financial Officer, you will lead high-priority, cross-functional initiatives from planning through field implementation and value realization. Working with PSC and Partner-company teams, you will turn enterprise priorities into practical solutions and measurable operating and financial results. This role combines program and project management with hands-on implementation, bringing structure, financial rigor, and follow-through to work that spans PSC functions and Partner companies.

What You’ll Do

Enterprise Portfolio and Governance

• Develop or refine business cases and help leaders prioritize enterprise and functional initiatives based on expected value, resource needs, timing, and risk.
• Translate approved priorities into clear scope, owners, decision rights, milestones, and measures of success.
• Manage the operating cadence and integrated portfolio view, surfacing dependencies, capacity conflicts, risks, and decisions requiring escalation.

Enterprise Initiative and Field Delivery

• Lead program and project management for complex initiatives that span PSC functions and Partner companies.
• Build practical workplans, coordinate workstreams and decisions, resolve issues, and keep accountable owners on track.
• Work with PSC and Partner teams to design solutions around operating needs, frontline workflows, and differences across trades and markets.
• Lead pilots and field implementation, including readiness, communications, training, feedback, issue resolution, and post-launch support.
• Capture field learning, codify effective practices into operational playbooks, and transition them to long-term owners who can help Partner teams adapt and scale them.
• Drive initiatives such as improving job costing, cost of goods sold (COGS), and inventory processes by coordinating multiple PSC functions and working directly with Partner teams to implement changes in the field.

Value Realization and Performance Reporting

• Partner with FP&A to establish financial baselines, validate business cases, define how value will be measured, and confirm realized financial results.
• Report on progress, risks, adoption, and planned versus realized value, surfacing slippage early and coordinating corrective action with accountable owners.
• Confirm that new processes, tools, and operating routines are embedded and owned before program oversight ends.

What You Bring

Experience and Qualifications

• Ten or more years of experience in cross-functional initiative execution, transformation, program and project management, operations, consulting, or a related discipline.
• A record of moving complex, cross-functional initiatives from scoping through field implementation, adoption, and measurable results.
• Experience in multi-site, multi-brand, decentralized, Partner-led, or field-led environments. Experience in labor-intensive service businesses is especially relevant.
• Strong program and project management discipline, including charters, workplans, governance, dependencies, risk management, and executive escalation.
• Strong analytical and financial fluency, including business cases, performance measures, and interpretation of operating and financial data.
• Clear written and verbal communication, sound judgment, and the ability to influence without formal authority.

Leadership Characteristics

• Execution focused. You turn decisions into owners, workplans, and results.
• Structured and adaptable. You create clarity and adjust as facts or operating conditions change.
• Low ego and collaborative. You build trust, respect operating expertise, and solve problems with others.
• Partner first. You listen before prescribing and design support that works in the field.
• Clear communicator. You synthesize complexity and keep teams aligned.
• Trusted and discreet. You handle sensitive information with sound judgment and raise issues early.

Ready to Help Shape What Comes Next?

If you love bringing structure to complex work, earning trust in the field, and seeing initiatives through to real, measurable results, we want to hear from you. Apply today and help us build the playbooks that will define how top-tier home services businesses operate across the Redwood family.