Director of Sales

Role Overview

• 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.
• Monitor campaign performance using data to drive optimization.
• Build repeatable outbound systems that generate predictable revenue.
• Recruit, onboard, and develop high-performing SDRs.
• Create training programs, playbooks, and coaching frameworks.
• Establish performance standards and accountability across the team.
• Mentor SDRs into successful Account Executives.
• Coordinate outbound activity with founder-led networking initiatives.
• Prevent duplicate outreach across strategic accounts.
• Improve CRM hygiene, reporting, and forecasting.
• Collaborate closely with Marketing, Recruiting, and Leadership on revenue initiatives.
• Build scalable sales processes that improve organizational efficiency.

Requirements

• 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.

Benefits

• Competitive base salary with uncapped performance-based earnings ($180K–$300K OTE).
• Fully remote work environment.
• 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.