[Hiring] Director, CARET Private Cloud @CARET

Role Description

CARET is seeking a Director, CARET Private Cloud to own and lead our managed cloud services business (formerly Abacus Private Cloud), including its strategy, go-to-market, operations, and P&L. This role is the single accountable leader for both growth and delivery.

This is a Director role with true general management scope. You will lead a vertically focused managed service provider (MSP) serving legal and accounting firms across North America, delivering private cloud hosting, virtual desktops, backup and disaster recovery, and security services to more than 1,000 customers.

Your responsibilities include:

• Turning a stable, deeply embedded customer base into a scaled, growing managed services platform.
• Ensuring that customers moving to CARET Legal keep the experience they depend on.

Qualifications

• 10+ years of experience in managed services, cloud services, or IT infrastructure, including senior leadership of an MSP or a managed services business unit.
• Demonstrated P&L ownership with a track record of growing recurring revenue, improving margins, and managing retention.
• Deep experience on the Microsoft and Azure technology stack, including Azure Virtual Desktop or Windows 365, Microsoft 365, Entra ID, and the Microsoft CSP program.
• Proven ability to build and scale a go-to-market engine, including selling managed services and cross-selling security and managed IT.
• Strong operational background in service delivery, including NOC and help desk operations, security, backup and disaster recovery, and compliance frameworks such as SOC 2 or HIPAA.
• Experience managing vendors, outsourced support partners, and licensing economics.
• Proven track record leading and developing multi-disciplinary teams, including managers of managers, and building new functions from the ground up.
• Excellent executive communication and the ability to present performance and strategy to a board or senior leadership team.
• Bachelor's degree or equivalent experience.

Requirements

• Own the full P&L for CARET Private Cloud, including revenue, gross margin, cost to serve, and EBITDA.
• Build and execute the multi-year strategy for the business.
• Establish fully loaded per-user economics and pricing discipline across hosting, storage, Microsoft 365, and managed services.
• Lead modernization decisions on hosting architecture.
• Report to executive leadership and the board on performance, risks, and investment priorities.
• Build and lead the go-to-market function for CARET Private Cloud.
• Define positioning, packaging, and pricing for a managed workspace offering.
• Drive cross-sell and expansion across the installed base.
• Develop new-logo acquisition motions with partners and channels.
• Own retention and churn for the hosted customer base.
• Lead a 24/7 managed services operation covering infrastructure engineering, network operations, implementation, and support.
• Manage vendor and partner relationships.
• Lead, coach, and develop the full CARET Private Cloud team.

Benefits

• Flexible PTO
• Medical, Dental, Paid Sick Days, Vision, and Supplemental Coverage
• Flexible Spending Account
• Health Savings Account
• 401(k) match