Head of Sales

About PenguinData PenguinData is the market leader in workforce management software purpose-built for broadband and telecommunications contractors. We serve a highly specialized vertical with strong competitive moats, long customer tenures, and meaningful switching costs. Our platform supports mission-critical operational workflows and offers clear opportunities for ARR expansion through pricing normalization and payroll/HRMS upsells. Following our recent acquisition, PenguinData is entering its next phase of growth—focused on professionalizing our go-to-market motion and building a scalable, repeatable revenue engine. The Opportunity The Head of Sales will play a critical role in transforming PenguinData’s sales function from founder-led execution to a scalable, process-driven organization. This leader will own the full revenue lifecycle, drive new logo acquisition, execute pricing and expansion strategies, and build the foundation for long-term growth within our core vertical and adjacent infrastructure markets. This role will also modernize PenguinData’s go-to-market stack, leveraging AI-native sales and marketing tools to enable more data-driven decision-making, improve pipeline efficiency, and support scalable growth. This is a hands-on leadership role suited for someone who thrives in post-acquisition environments and enjoys building systems, playbooks, and teams from the ground up. Key Responsibilities Own and lead all sales activities, including new customer acquisition, renewals, and expansion (upsell and cross-sell) initiatives Design and implement standardized sales processes, including CRM discipline, pipeline management, forecasting, and qualification frameworks Execute pricing normalization strategies across new and renewing customers Drive adoption and revenue growth of payroll processing and HRMS modules within the existing customer base Develop and execute account-based sales strategies tailored to broadband and telecommunications contractors Leverage AI-native sales and marketing tools to improve lead qualification, pipeline velocity, forecasting accuracy, and customer targeting Partner with marketing to apply AI-driven insights to account prioritization, messaging, and campaign performance Continuously evaluate and implement modern sales technologies to increase efficiency, consistency, and scalability across the go-to-market function Build repeatable sales playbooks and reduce dependency on founder-led demos and deal closings Establish and grow strategic channel partnerships (e.g., GIS providers, industry consultants, and utility ecosystem partners) Collaborate closely with product, operations, and leadership to align sales execution with broader business objectives What Success Looks Like Year 1 Professionalize sales operations with strong CRM adoption, forecasting accuracy, and process consistency Successfully execute pricing normalization across renewals Launch and scale payroll and HRMS cross-sell initiatives Establish foundational AI-enabled sales workflows and reporting Year 2 Scale new logo acquisition through repeatable, well-documented sales playbooks Significantly reduce founder dependency in sales execution Expand and activate channel partnerships as a meaningful revenue driver Long-Term Build a scalable sales organization capable of supporting expansion into adjacent infrastructure and services markets Qualifications & Experience Required 5+ years of sales leadership experience in vertical SaaS, workforce management, field service, or similar B2B software environments Proven track record of scaling ARR from approximately $5M to $20M+ Experience selling complex B2B software to operational and business buyers Strong understanding of pricing strategy, renewals, and expansion revenue models Experience using modern, AI-enabled sales and marketing tools to drive pipeline management, forecasting, and performance insights Comfort operating in founder-led and post-acquisition environments Hands-on mindse t with the ability to lead demos, close deals, and build processes concurrently Preferred Experience in telecommunications, broadband, utilities, or field service industries Familiarity with contractor-based labor models and operational workflows Prior experience building or scaling sales teams and GTM infrastructure in high-growth SaaS organizations About the Team PenguinData operates as part of Valsoft, specifically Fluent Software group of vertical market software businesses focused on long-term value creation. Our teams are lean, execution-oriented, and deeply embedded in the industries we serve. We value ownership, operational rigor, and leaders who are comfortable rolling up their sleeves to build durable, scalable businesses. #PenguinData #J-18808-Ljbffr