Pearl Talent - Director of Sales

About the role

The Director of Sales will own Pearl’s outbound revenue engine from strategy through execution. This is a player-coach role combining enterprise sales, outbound strategy, sales leadership, and operational excellence.

Responsibilities

• Accelerate Pearl's monthly recurring revenue growth through world-class sales execution.
• Create repeatable sales systems that scale beyond individual contributors.
• Hire, coach, and develop a high-performing SDR organization.
• Ensure seamless coordination between outbound campaigns and relationship-driven sales efforts.
• Become a trusted advisor to founders and executives purchasing Pearl's services.
• Own the full sales cycle for highly qualified inbound and outbound opportunities.
• Consistently convert executive-level prospects into long-term clients.
• Build trusted relationships with founders, executives, and operators.
• Maintain exceptional closing performance across the sales pipeline.
• Leverage your existing professional network to generate strategic opportunities.
• Design, launch, and optimize outbound sales campaigns alongside Marketing.
• Develop messaging, targeting strategies, sequencing, and nurture campaigns.
• Continuously improve conversion metrics throughout the sales funnel.
• Maintain CRM hygiene, reporting, and forecasting.
• Collaborate closely with Marketing, Recruiting, and Leadership on revenue initiatives.
• Build scalable sales processes that improve organizational efficiency.

Requirements

• Must-Haves (Required): 5+ years of experience in B2B sales, staffing, recruiting, SaaS, or professional services.
• Proven experience closing six-figure or strategic B2B accounts.
• Experience building outbound sales systems from strategy through execution.
• Experience hiring, coaching, or leading SDRs or Account Executives.
• Demonstrated history of exceeding quota and revenue targets.
• Strong executive presence with exceptional communication skills.
• Experience selling directly to founders, executives, or operational leaders.
• Strong understanding of CRM systems and sales analytics.
• Highly organized with a systems-thinking mindset.
• Ability to thrive in high-growth startup environments.
• Existing network within venture-backed startups or technology companies.
• Experience selling recruiting, staffing, HR Tech, AI, or B2B services.
• Experience working in founder-led organizations.
• Familiarity with AI-powered sales workflows and automation tools.
• Experience scaling sales organizations from early-stage through growth.

Benefits

• Competitive base salary with uncapped performance-based earnings ($180K–$300K OTE).
• Unlimited PTO.
• Annual company retreat.
• Direct partnership with Pearl's founders.
• Significant ownership over company growth strategy.
• Opportunity to build and lead a world-class sales organization.
• Clear path toward VP of Sales or executive leadership as Pearl scales.