Head of Sales – Player-Coach

🕒 April 20

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Unusual Ventures

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2018

💸 Finance

🏢 Enterprise

☁️ SaaS

Finance • Enterprise • SaaS

Unusual Ventures is a venture capital firm that specializes in early-stage investments, leading from pre-seed to Series A rounds in enterprise software and marketplace startups. The firm actively partners with founders, providing hands-on support in areas such as recruiting, sales, and marketing to enhance their chances of success. Unusual Ventures is known for its comprehensive support model, offering a live academy, tactical content, and expert operator assistance, making it a preferred choice for first-time founders looking for more than just financial backing.

📋 Description

• Carry and close your own enterprise pipeline end-to-end: prospecting, discovery, demos, deal structure, and close • Partner with the CRO on GTM strategy, sales process design, pricing, and competitive positioning • Hire, onboard, and develop a team of elite Account Executives who sell consultatively and close with conviction • Jump into your reps’ deals—diagnose what’s stuck, sharpen the narrative, and help close alongside them • Build and continuously refine sales playbooks, qualification frameworks, onboarding programs, and coaching rhythms • Approve quotes, structure creative deals, and navigate complex multi-stakeholder buying processes across the team’s pipeline • Own pipeline reporting, forecasting accuracy, and CRM discipline for the full sales organization, including all conference pipeline • Collaborate with Marketing, Product, and Client Success to tighten positioning, improve feedback loops, and accelerate revenue • Engage existing clients to deepen relationships and unlock expansion opportunities • Represent GovSignals at industry events, conferences, and in senior prospect conversations

🎯 Requirements

• Proven track record of building and scaling a sales team from early stage through meaningful revenue milestones—you’ve designed the system, not just run inside one • Strong personal selling record: history of closing six- and seven-figure enterprise SaaS deals as an individual contributor • Experience as a founder, early sales hire, or sales leader at a high-growth startup where ambiguity was the norm and you thrived anyway • Deep expertise in consultative, value-based selling—you diagnose before you prescribe • Ability to operate as a strategic partner to leadership on pricing, positioning, and GTM design • Strong hiring instincts: you know how to find, assess, and close elite sales talent • Exceptional executive presence and C-suite engagement skills • Proficiency in CRM systems and a belief in rigorous pipeline discipline • Government contracting familiarity preferred but not required.

🏖️ Benefits

• 100% employer-paid medical, vision, and dental (Bronze coverage)