Director, CARET Private Cloud

CARET brings the latest in technology and automation to over 10,000 legal and accounting firms, empowering highly skilled professionals to refocus their expertise on what truly matters. CARET harnesses powerful and secure practice management, document automation, and payment processing to take firms, professionals, and their clients further.

Our team-defined values guide how we show up for each other, for our partners, and for our customers:

• We succeed together.
• We embrace progress.
• We care big.
• We create space.

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. Today these responsibilities are divided across several teams with no single owner. 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. You will be responsible for turning a stable, deeply embedded customer base into a scaled, growing managed services platform, while ensuring that customers moving to CARET Legal keep the experience they depend on.

The ideal candidate has run an MSP, ideally with P&L ownership, and has hands-on depth in the Microsoft and Azure ecosystem, including Azure Virtual Desktop, Microsoft 365, and the Cloud Solution Provider (CSP) program. This is not a sales-only or a delivery-only role. They must be equally strong at building a sales and marketing engine and running a 24/7 service operation, and accountable for the unit economics across both.

The Team You'll Lead

You will lead the CARET Private Cloud team, a multi-disciplinary group spanning cloud and infrastructure engineering, network operations and support, customer implementation, and customer success, supported by outsourced service partners. You will be accountable for the performance, development, and growth of the whole team, and you will build out the sales, marketing, and customer success capabilities the business needs to scale.

P&L Ownership & Strategy

• Own the full P&L for CARET Private Cloud, including revenue, gross margin, cost to serve, and EBITDA, and manage to a clear annual operating plan.
• Build and execute the multi-year strategy for the business, including the roadmap from today's private cloud offering to a broader managed services platform.
• Establish fully loaded per-user economics and pricing discipline across hosting, storage, Microsoft 365, and managed services.
• Lead modernization decisions on hosting architecture, including the evaluation and phasing of any move toward Azure when it is financially appropriate.
• Report to executive leadership and the board on performance, risks, and investment priorities.

Go-to-Market & Growth

• Build and lead the go-to-market function for CARET Private Cloud, including sales, marketing, and customer success, where today there is no dedicated team.
• Define positioning, packaging, and pricing for a managed workspace offering that includes virtual desktop, Microsoft 365, identity, security, backup, storage, and managed IT.
• Drive cross-sell and expansion across the installed base, raising revenue per user through security, managed IT, and consumption-based storage.
• Develop new-logo acquisition motions with partners and channels, and build qualified pipeline in the mid-market and enterprise legal and accounting segments.
• Partner with the CARET Legal sales and migration teams so customers get the right hosting and managed services offer at the moment they migrate, protecting revenue without slowing software adoption.

Customer Retention & Experience

• Own retention and churn for the hosted customer base, including gross and net revenue retention targets.
• Stand up proactive account management and structured renewal processes across the customer base.
• Establish clear, single-point ownership of customer offboarding and retention workflows that today span multiple teams.
• Reduce friction for enterprise customers by preserving their desktop, applications, security model, and workflows during transitions to CARET Legal.

Operations & Service Delivery

• Lead a 24/7 managed services operation covering infrastructure engineering, network operations, implementation, and support, working with in-house teams and outsourced partners.
• Drive service quality, uptime, and security and compliance posture, including SOC 2 and HIPAA-aligned practices.
• Lead automation and self-service initiatives that reduce support volume and cost to serve, such as password resets, user administration, and patching and update scheduling.
• Manage vendor and partner relationships, including Microsoft, datacenter providers, and technology partners, and oversee licensing, partner status, and certifications.
• Close process and financial gaps in Microsoft licensing, such as commitment terms that do not match customer contract terms.
• Oversee the hardware lifecycle, capacity planning, and datacenter lease strategy.

Leadership & Collaboration

• Lead, coach, and develop the full CARET Private Cloud team, including managers and individual contributors across engineering, operations, support, implementation, and customer success.
• Set clear goals, accountabilities, and performance metrics for each function, and build a culture of ownership and operational discipline.
• Hire ahead of demand, including the first dedicated go-to-market and customer success roles, and retain key technical talent.
• Manage and hold accountable the outsourced support and engineering partners that extend the team.
• Work closely with Product, Finance, Sales, Customer Success, and Engineering to align CARET Private Cloud with the broader CARET Legal strategy.
• Represent CARET Private Cloud with customers, partners, and industry events.

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.
• Has been the single accountable owner of both revenue growth and service delivery, and can unify sales, delivery, and customer success under one operating model.
• 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.

Preferred Experience

• Experience serving legal, accounting, or other regulated professional services firms.
• Experience leading an MSP through acquisition, integration, carve-out, or turnaround.
• Background in migrating customers from private cloud or hosted environments to Azure or SaaS platforms.
• Microsoft partner certifications or experience managing Microsoft partner status, such as Solutions Partner designations.
• Familiarity with PSA, RMM, and automation tooling used to run managed services at scale.

Role at a Glance

• Full-time, senior leadership role.
• Remote within the United States, with periodic travel to customers, partners, and CARET offices.
• Reports to Scott Rakestraw.
• Single accountable owner for go-to-market and operations, with authority across the teams that share these responsibilities today.
• People leader with direct and indirect reports across engineering, network operations, support, implementation, and customer success, plus responsibility for building the go-to-market team.

Success in This Role

• A clear, board-approved strategy and operating plan for CARET Private Cloud, with accountable owners for each initiative.
• Stabilized and improving gross and net revenue retention across the hosted customer base.
• A functioning go-to-market engine with measurable pipeline, cross-sell attach, and revenue per user growth.
• Improved gross margin and cost to serve, supported by automation and a fully loaded view of per-user economics.
• Faster, lower-friction customer transitions to CARET Legal, with revenue and customer experience preserved.
• Strong service levels, security posture, and customer satisfaction.

Benefits:

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

Equal Employment Opportunity: CARET is an Equal Opportunity, Affirmative Action Employer.

The compensation information below is provided in compliance with job posting disclosure requirements.

Pay range: $180,000 - $190,000 Actual base pay will depend on varying circumstances, including the position, location, individual qualifications, market finances, and other operations business needs.

Depending on the position, compensation may also include commission, bonuses, etc. Potential for bonuses is based on company performance and potential for merit increases is based on performance.