Director of Systems & Enablement

About the Role

We are seeking an experienced Director of Systems & Enablement to own and evolve the business systems ecosystem supporting a rapidly growing, multi-market organization. This is a highly visible leadership role responsible for the systems, integrations, data standards, and technology strategy that connect Sales, Operations, Finance, Growth, and other business functions.

The organization relies on a connected technology stack to manage leads, appointments, contracts, jobs, payroll, financial information, and reporting. This individual will own not just individual applications, but the overall systems architecture and the connections between platforms.

This is a build and transformation role rather than a maintenance position. As the organization expands into new markets and brands, the Director will determine how systems and processes need to evolve, establish scalable standards, and make key architecture and technology decisions.

The role reports to the Chief Growth Officer and serves as the organization’s senior systems leader.

Key Responsibilities

Business Systems & Architecture

• Own the overall business systems ecosystem, architecture, integrations, and technology roadmap.
• Serve as the senior systems leader responsible for determining how platforms should scale as the organization expands into additional markets and brands.
• Own and optimize i360 / improveit 360, the Salesforce-based CRM, including configuration, permissions, territories, lead sources, product setup, reporting, and data governance.
• Own the technical configuration of Leap / SalesPro, including pricing configuration, discount thresholds, approval rules, and integrations.
• Partner with Sales leadership to ensure system configuration accurately reflects approved pricing and business policies.
• Identify discrepancies between approved business policies and actual system configuration and proactively address them with leadership.
• Select, implement, and roll out an enterprise project management platform, such as Monday.com, Asana, or a comparable solution, for market launches, system implementations, and cross-functional initiatives.
• Oversee how the broader technology ecosystem—including Rippling, Sage, Ramp, Google Workspace, and growth technology platforms—connects and shares information.
• Partner with third-party IT providers while maintaining ownership of business systems architecture and integration strategy.

Integrations & Data

• Own integrations across the end-to-end business lifecycle, including lead ? appointment ? contract ? job ? invoice.
• Design, build, maintain, and improve integrations between enterprise applications.
• Provide technical leadership around APIs, middleware, synchronization, error handling, monitoring, and integration reliability.
• Establish shared data definitions and governance standards across Sales, Finance, Operations, and Growth.
• Ensure reporting consistency so teams are working from trusted and aligned business data.
• Design systems and integrations that can scale efficiently into new markets and brands.
• Own the technology configuration required for new-market launches, including routing, territories, pricing, compensation, integrations, and reporting.
• Create scalable configurations and repeatable processes that minimize custom implementation work when entering new markets.

AI Strategy & Governance

• Develop and maintain organizational standards governing the responsible and effective use of AI technologies.
• Partner with Legal, HR, Finance, and executive leadership to establish appropriate AI policies, data standards, and usage guidelines.
• Identify practical opportunities where AI can eliminate manual work, improve efficiency, or enhance business processes.
• Evaluate AI solutions based on measurable business value rather than technology adoption alone.
• Establish standards for what information can be used with AI platforms and appropriate quality controls for AI-generated output.
• Develop and facilitate AI training for employees and business leaders.
• Monitor adherence to established AI standards and identify areas where business practices have drifted from policy.
• Provide executive leadership with recommendations regarding emerging AI capabilities, risks, and opportunities.

Systems Governance & Enablement

• Establish and manage a centralized intake process for technology and systems requests across Sales, Operations, Finance, and Growth.
• Develop transparent prioritization and governance processes for system enhancements and initiatives.
• Partner with cross-functional leadership to determine priorities and allocate systems capacity.
• Establish shared definitions and data standards with Finance and other business functions.
• Determine which capabilities should be built internally, purchased, or delivered through external partners.
• Identify redundant technologies, unnecessary spending, and opportunities to simplify the technology ecosystem.
• Establish documentation and operating standards for systems and integrations.

Leadership

• Lead existing team members supporting Salesforce administration and growth/integration systems.
• Build and expand the systems function as the organization grows.
• Recruit, hire, mentor, and develop systems talent.
• Serve as the primary escalation point when technology or system limitations interfere with business operations.
• Partner closely with executive leadership while independently owning systems architecture decisions.
• Communicate complex technical decisions and trade-offs clearly to both technical and non-technical audiences.

What Success Looks Like

First 30 Days: Establish baseline metrics for market-launch timelines, reporting integrity, systems intake cycle time, technology adoption, tool count, and technology spend.

First 90 Days: Complete an end-to-end assessment of the technology stack, identifying fragile integrations, duplicated functionality, unnecessary costs, and scalability risks. Provide a recommendation for the enterprise project management platform.

Within 6 Months: Launch the selected project management platform in at least one market, document inherited integrations, establish AI governance standards, and provide employee training.

Within 12 Months: Establish a repeatable technology framework that allows new markets to launch primarily through configuration rather than extensive custom implementation. Sales, Finance, and Operations should operate from consistent data and reporting standards, while the systems organization continues to scale.

Required Qualifications

• 8+ years of experience in business systems, revenue operations, enterprise applications, IT, or a related discipline.
• Significant experience owning a CRM environment within a growing organization.
• Deep hands-on Salesforce expertise, including configuration, objects, permissions, flows, and reporting.
• Demonstrated experience designing and maintaining system integrations, with a strong understanding of APIs, middleware, synchronization, monitoring, and error handling.
• Experience implementing enterprise systems across multiple locations, markets, or business units.
• Previous people-management experience, including hiring and developing team members.
• Demonstrated ability to establish systems governance, including intake processes, prioritization frameworks, shared data definitions, and cross-functional standards.
• Experience working directly with Sales, Operations, Finance, Growth, and executive stakeholders.
• Ability to independently evaluate technical architecture and make informed build-versus-buy-versus-partner decisions.
• Strong executive communication skills with the ability to explain technical decisions and trade-offs clearly to non-technical leaders.
• Practical understanding of AI within business operations, including appropriate use cases, limitations, governance, data considerations, and risk.
• Proven ability to drive technology adoption and organizational change.

Preferred Qualifications

• Experience within home services, home improvement, field services, trades, or another multi-location field operation.
• Experience with i360 / improveit 360, Leap / SalesPro, or comparable field-sales platforms.
• Experience working within a private-equity-backed, acquisition-driven, or rapidly scaling organization.
• Previous experience serving as the first or most senior business systems leader within an organization.
• Salesforce certification is preferred but not required; demonstrated hands-on expertise is more important.