Role Description 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. Qualifications - 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. Requirements - 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). - 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.

• Conduct outbound and inbound sales calls to generate new business opportunities and nurture existing accounts • Deliver compelling consultations tailored to client needs • Conduct remote phone or virtual sales conversations with qualified prospects and present solutions, address objections, and close sales. • Utilize CRM software to track leads, manage customer interactions, and analyze sales data • Provide exceptional customer service throughout the sales process, ensuring client retention and long-term relationships

• 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.

Role Description We are seeking a highly professional and articulate Business Development Representative (BDR) / Sales Development Representative (SDR) to engage medical facilities and introduce modern staffing solutions. This role is responsible for initiating conversations with healthcare organizations to understand their staffing needs, current workflows, decision-making structures, and openness to new solutions. Responsibilities - Outbound Prospecting & Engagement - Conduct high-volume outbound calls, emails, and multi-channel outreach to hospitals, clinics, long-term care facilities, and other healthcare organizations. - Navigate front desks, operators, and clinical staff professionally and respectfully. - Identify and engage key decision-makers (e.g., staffing coordinators, HR leaders, DONs, administrators). - Value Communication - Clearly and concisely communicate pricing models and value propositions. - Position solutions in a way that respects time constraints and clinical priorities. - Stakeholder Mapping - Identify the appropriate stakeholder at the local (facility) and enterprise levels. - Identify and set meetings with appropriate decision makers. - CRM & Pipeline Management - Maintain accurate and detailed records of outreach, conversations, and insights in CRM. - Track key metrics such as connection rates, qualified leads, and meetings set. - Collaborate with Account Executives to ensure smooth handoff of qualified opportunities. Qualifications - Communication Excellence (Critical) - Exceptional verbal communication skills with a polished, professional phone presence. - Strong written communication skills (clear, concise, and tailored messaging). - Ability to engage busy healthcare professionals without being disruptive or intrusive. - High emotional intelligence and situational awareness. - Sales & Discovery Skills - Strong ability to ask thoughtful, relevant questions and actively listen. - Skilled in navigating gatekeepers and complex organizations. - Ability to quickly build rapport and credibility. - Professionalism & Judgment - Demonstrates respect for clinical environments and competing priorities. - Knows when to advance a conversation vs. when to disengage gracefully. - Maintains a consultative, non-pushy approach. - Organizational Skills - Detail-oriented with strong note-taking and CRM discipline. - Able to manage a high volume of outreach while maintaining quality. - Preferred Qualifications - Experience in healthcare, healthcare staffing, or SaaS sales. - Familiarity with hospital or facility operations (e.g., staffing coordinators, nurse scheduling). - Experience with tools such as Slack, Excel, Salesforce, or similar CRM platforms. - Bonus - experience with Sonar (or other SMS-based platform for drip campaigns) & email marketing campaigns (Groove, MailMerge, Other). - Background in marketplace or two-sided platform environments is a plus. Success Metrics - Qualified meetings booked with target facilities. - Conversion rate from outreach → conversation → qualified opportunity. - Quality and completeness of discovery insights captured. - Positive feedback from prospects on professionalism and communication. What Success Looks Like in This Role - You consistently create meaningful conversations—not interruptions. - You uncover actionable insights that improve targeting and conversion. - You build trust quickly, even in short interactions. - You represent the company with professionalism that reflects healthcare standards. Tone & Candidate Profile - This role is ideal for someone who: - Communicates with precision, confidence, and empathy. - Thrives in structured outreach but adapts fluidly to real conversations. - Understands that how you say something matters as much as what you say. - Takes pride in being respectful, relevant, and effective in every interaction. Required Skills - Sales Development Rep (Inbound) Years of Experience Needed - 3