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Industry

Recruitment / Staffing / B2B Services

Work Arrangement

Fully Remote

Job Type

Full-time

Work Schedule

40 hours per week, Monday to Friday

Core hours: 9 AM – 5 PM EST

United States

Pearl works with the top 1% of candidates from around the world and connects them with the best startups in the US and EU. Our clients have raised over $5B in aggregate and are backed by companies like OpenAI, a16z, and Founders Fund. They’re looking for the sharpest, hungriest candidates who they can consistently promote and work with over many years. Candidates we’ve hired have been flown out to the US and EU to work with their clients, and even promoted to roles that match folks onshore in the US.

Hear why we exist, what we believe in, and who we’re building for: here.

At Pearl, we’re not just another recruiting firm—we connect you with exceptional opportunities to work alongside visionary US and EU founders. Our focus is on placing you in roles where you can grow, make an impact, and build a long-term career. We believe in creating environments where your potential is recognized, your voice matters, and your success is tied to meaningful work—not short-term perks. Joining Pearl means stepping into opportunities that challenge you, support you, and set you up for lasting success.

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.

In this role, you will:

• Accelerate Pearl's monthly recurring revenue growth through world-class sales execution.
• Build an outbound sales engine that consistently produces qualified customers.
• 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.
• 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.

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.

• 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.

Within your first year, you'll:

• Consistently achieve approximately 70% close rates on highly qualified opportunities.
• Build an outbound engine that generates meaningful revenue.
• Hire and ramp a high-performing SDR team.
• Establish repeatable outbound processes that scale with the business.
• Create seamless coordination between outbound campaigns and founder-led sales.
• Become a key contributor in helping Pearl grow from approximately $1M to $3M in new ARR per month.

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.