Head of SaaS Sales

Smart Choice Communications • Saint Petersburg, FL

6h

About The Position

SmartChoice Communications is seeking a Head of SaaS Sales to lead SmartTile, its modular IT automation platform. Reporting to the CEO, this person owns the SmartTile business end to end, including strategy, P&L, go-to-market, product direction, customer success, and team leadership. The objective is to grow SmartTile from its first production environments into a scalable recurring-revenue business alongside SmartChoice's carrier and managed services. The role is suited to an experienced B2B SaaS leader who has scaled a product from early customers and understands how multi-location IT teams operate.

The role includes building and leading the SmartTile team across product, solutions engineering, customer success, and sales; setting goals and OKRs; and establishing a customer-focused, automation-first, data-driven culture. The Head of SaaS Sales will define strategy, roadmap priorities, annual plans, P&L, pricing, and packaging; build the go-to-market and revenue motion; and work with Product and Engineering on the platform roadmap and integrations. The position also owns customer onboarding, adoption, expansion, retention, operating metrics, implementation improvements, and coordination with SmartChoice's 24/7/365 U.S. NOC.

The role is based on managing a business that serves multi-location IT teams, initially in healthcare and multi-site luxury retail and later in other industries. It requires attention to security, data handling, and compliance requirements for regulated customers.

Requirements

• 10+ years of experience in B2B SaaS, including 5+ years leading teams.
• Direct P&L or ARR ownership of a SaaS product or business line, ideally one taken from early customers to scale.
• Background in IT operations, network management, ITSM, or automation software, selling to IT directors, CIOs, and network operations leaders.
• Track record of growing ARR while improving retention and expansion revenue.
• Experience pricing and packaging modular or usage-based software.
• Working knowledge of the ITSM/PSA ecosystem and how IT teams manage ticketing, monitoring, and incident workflows.
• Fluency in SaaS metrics, including ARR/MRR, NRR, GRR, churn, CAC, LTV, and payback period.
• Clear executive communication with customers, partners, and leadership.
• Bachelor's degree or equivalent experience.

Nice To Haves

• Experience in telecommunications, managed services (MSP/MSSP), or carrier services, including knowledge of circuits and carrier trouble tickets.
• Experience selling into multi-location healthcare organizations or retail chains.
• Familiarity with network platforms such as Cisco Meraki, Fortinet, or Ubiquiti, and cloud environments such as AWS or Azure.
• Experience launching AI or automation products, such as AI agents.
• Experience building integration and channel partnerships.
• Understanding of compliance needs in regulated industries, such as HIPAA and SOC 2.
• MBA or advanced degree.

Responsibilities

• Own SmartTile's strategy, roadmap priorities, annual plan, P&L, and business growth.
• Grow SmartTile from its first production environments into a scalable recurring-revenue business.
• Define pricing and packaging for SmartTile's modular offerings and develop land-and-expand paths.
• Report ARR, pipeline, retention, and unit economics to the executive team.
• Build the go-to-market motion for multi-location IT teams, beginning with healthcare and multi-site luxury retail and expanding to other listed industries.
• Own the customer journey from demo and discovery through pilot and signed contract.
• Partner with SmartChoice sales to cross-sell SmartTile to existing carrier and managed-services accounts.
• Turn customer outcomes into case studies, ROI tools, and sales enablement materials.
• Work with Product and Engineering to set the roadmap across SmartTile modules, platform tools, and the Joey AI voice agent.
• Prioritize integrations across ITSM/PSA platforms, network devices, cloud providers, and carriers.
• Use production data from customer environments to determine which workflows to automate next.
• Own onboarding, adoption, and expansion to help customers activate more modules and add sites.
• Build customer success processes for multi-site IT teams, including implementation playbooks, health scores, and quarterly business reviews.
• Coordinate with SmartChoice's 24/7/365 U.S. NOC to ensure escalations and carrier cases are handled seamlessly.
• Serve as executive sponsor for strategic accounts, including large healthcare networks and global retail groups.
• Establish SmartTile metrics and operating rhythms for ARR, module adoption, automated tickets, resolution time, and churn.
• Ensure security, data-handling, and compliance standards meet regulated-customer needs.
• Improve implementation processes so new customer environments go live faster.
• Hire, train, and lead the SmartTile team across product, solutions engineering, customer success, and sales.
• Set clear goals and OKRs and conduct regular performance and career conversations.
• Build a culture of customer focus, automation-first thinking, and data-driven decisions.

Benefits

• Competitive salary with performance-based incentives.
• Comprehensive health benefits, including medical, dental, vision, and life insurance.
• Generous paid time off.
• Employer-matched 401(k).
• Monthly cell phone stipend.
• Employee Assistance Program.
• Growth opportunities as SmartChoice expands.
• Collaborative environment with team-building events and brainstorming sessions.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior