Pearl Talent - Director of Sales

Pearl • Austin, TX

38d • $180,000 - $300,000 • Remote

About The Position

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. You'll personally close high-value opportunities while designing scalable outbound campaigns, hiring and developing SDRs, and ensuring coordination between founder-led relationship selling and outbound prospecting. Success in this role requires someone who has personally built outbound organizations—not simply managed one. You understand every stage of the sales funnel because you've done the work yourself, from prospecting to closing enterprise clients to coaching teams. You'll partner directly with leadership to help scale Pearl from approximately $1M in new ARR per month toward our next phase of growth.

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.

Nice To Haves

• 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.

Responsibilities

• 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.
• Lead by example through active participation in outbound efforts.
• 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.

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.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed