Head of Sales

Valsoft Corporation

11h

About The Position

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 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.

Requirements

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

Nice To Haves

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

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