Head of SaaS Sales

Job Overview: Smart. Choice Communications is looking for a Head of SaaS Sales to lead Smart. Tile, our modular IT automation platform. Reporting to the CEO, this person will own the Smart. Tile business from start to finish: strategy, P&L, go-to-market, product direction, customer success and team leadership. The goal is to grow Smart.

Tile from its first production environments into a scalable recurring-revenue business alongside Smart. Choice's carrier and managed services. This role suits an experienced B2B SaaS leader who has scaled a product from early customers and understands how multi-location IT teams work. Supervisory Responsibilities:

• Hire, train, and lead the Smart. Tile team across product, solutions engineering, customer success, and sales.
• Set clear goals and OKRs; run regular performance and career conversations.
• Build a culture of customer focus, automation-first thinking, and data-driven decisions.

Key Responsibilities

Strategy and P&L

• Own the Smart. Tile business end to end: strategy, roadmap priorities, annual plan, and P&L.
• Grow Smart. Tile from its first production environments into a scalable recurring-revenue line alongside Smart. Choice's carrier and managed services.
• Define pricing and packaging for Smart. Tile's modular model (Carrier. Automate, Service. Automate, Ticket. Automate, Cloud. Automate and the other modules), including land-and-expand paths from a customer's first workflow to the full platform.
• Report ARR, pipeline, retention, and unit economics to the executive team. Go-to-market and revenue
• Build the go-to-market motion for multi-location IT teams, starting with core verticals in healthcare and multi-site luxury retail, then expanding into financial services, legal, real estate, construction, private equity portfolios, and nonprofits.
• Own the path from demo and discovery call to pilot (cloud or in-customer-environment) to signed contract.
• Partner with Smart. Choice sales to cross-sell Smart. Tile into existing carrier and managed-services accounts.
• Turn customer results (for example, ticket capacity, resolution time, and hours returned to IT teams) into case studies, ROI tools, and sales enablement. Product and platform
• Work with Product and Engineering to set the Smart. Tile roadmap across modules, platform tools, and the Joey AI voice agent.
• Prioritize integrations that unlock new customers across ITSM/PSA platforms (Service. Now, Connect. Wise, Freshservice, Manage. Engine and others), network devices (Cisco Meraki, Fortinet, Ubiquiti), cloud providers (AWS, Azure), and carriers (AT&T, Verizon, Lumen, Comcast, Spectrum, Zayo).
• Use production data from customer environments to decide which workflows to automate next. Customer success and retention
• Own onboarding, adoption, and expansion so customers turn on more modules and add sites over time.
• Build a customer success model for multi-site IT teams: implementation playbooks, health scores, and quarterly business reviews.
• Coordinate with Smart. Choice's 24/7/365 U.S. NOC so escalations and carrier cases are handled seamlessly.
• Serve as executive sponsor for strategic accounts, such as large healthcare networks and global retail groups. Operations
• Set up Smart. Tile's metrics and operating rhythm: ARR, module adoption, automated tickets, resolution time, and churn.
• Ensure security, data-handling, and compliance standards meet the needs of regulated customers, especially in healthcare and financial services.
• Improve implementation processes so new customer environments go live faster.

Who you are

Required Experience & Education:

• 10+ years 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 (e.g. Service. Now, Connect. Wise, Freshservice) and how IT teams run ticketing, monitoring, and incident workflows.
• Fluency in SaaS metrics: ARR/MRR, NRR, GRR, churn, CAC, LTV, payback period.
• Clear executive communication with customers, partners, and leadership.
• Bachelor's degree or equivalent experience. Preferred Education and Experience:
• Experience in telecommunications, managed services (MSP/MSSP), or carrier services, including how circuits and carrier trouble tickets work.
• Experience selling into multi-location healthcare organizations or retail chains.
• Familiarity with network platforms such as Cisco Meraki, Fortinet, or Ubiquiti, and with cloud environments (AWS, Azure).
• Experience launching AI or automation products, such as AI agents.
• Experience building integration and channel partnerships.
• Understanding of compliance needs in regulated industries (e.g. HIPAA, SOC 2).
• MBA or advanced degree. Physical Requirements:
• Prolonged periods of sitting at a desk and working on a computer.
• Must be able to lift up to 15 pounds at times. Perks:
• Competitive salary with performance-based incentives
• Comprehensive health benefits (medical, dental, vision, life insurance)
• Generous paid time off
• Employer-matched 401(k)
• Monthly cell phone stipend
• Employee Assistance Program What We Offer:
• Culture of Innovation: You’ll be part of a forward-thinking team that’s driving the future of business communications.
• Growth Opportunities: As Smart. Choice continues to expand, so do the opportunities for our team members to take on new challenges.
• Fun & Collaborative Environment: We’re serious about our work, but we also know how to have a good time. From team-building events to spontaneous brainstorming sessions, Smart. Choice is a place where your voice will be heard, and your efforts will be recognized. At Smart. Choice, we embrace a work culture that champions teamwork, creativity, and fun while striving for excellence in everything we do. We believe that when passionate individuals come together, great things happen. If you’re looking to contribute to a growing company that is shaping the future of business communication, we want you on our team. Apply now and start making your mark at Smart. Choice! Smart. Choice provides equal employment opportunity to all individuals regardless of their race, color, creed, religion, gender, age, sexual orientation, national origin, disability, veteran status, or any other characteristic protected by state, federal, or local law. Discrimination of any type is not tolerated. Recruiting agencies, please do not submit unsolicited referrals for this or any open role. We have a roster of agencies with whom we partner, and we will not pay any fee associated with unsolicited referrals. About Smart Choice Communications Who we are: Smart. Choice is a North American technology partner delivering telecommunications, internet connectivity, network infrastructure, integrated software platforms, and physical security for multi‑location and large organizations. We support organizations that demand reliability at scale, from regional operations to complex, multi‑site enterprises. Our integrated software connects directly with the telecom, network, and security solutions we deploy, giving customers a unified ecosystem rather than a fragmented technology stack. With teams positioned across the country and a 24/7/365 U.S.-based signature service model, we provide the reach of a national provider with the responsiveness of a dedicated partner—keeping every location connected, protected, and operating with confidence. Why join us? At Smart. Choice, we believe that greatness is achieved through collaboration, creativity, and a relentless commitment to white-glove service and customer success. We don’t just provide services—we build partnerships and create lasting impacts for businesses across the country. As a leading provider of advanced telecom, internet, security, and infrastructure solutions, we empower our clients with the tools they need to thrive in today’s fast-paced, tech-driven world. Our people are the heart of what we do, and we pride ourselves on fostering a dynamic and inclusive work environment where everyone’s voice is heard. Our culture thrives on creativity , collaboration , and celebrating successes —big and small. As part of our team, you'll be joining a company that values innovation , teamwork , community engagement , and professional growth . Whether it's through professional development, team-building events, or mentorship opportunities, we ensure that our employees feel supported and empowered to achieve their goals. If you're driven, passionate, and ready to make an impact, we want you to be part of our journey.