Head of Sales

Job Description

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 mindset 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.