Head of Outbound Sales Development

Who We AreAt Justworks, you’ll enjoy a welcoming and casual environment, great benefits, wellness program offerings, company retreats, and the ability to interact with and learn from leaders in the startup community. We work hard and care about our most prized asset - our people.We’re helping businesses get off the ground by enabling them to focus on running their business. We’re data-driven and never stop iterating. If you’d like to work in a supportive, entrepreneurial environment, are interested in building something meaningful and having fun while doing it, we’d love to hear from you.Who You AreYou are a dependable, natural leader who doesn’t just manage a team—you build a winning culture. You are a master of outbound sales fundamentals, and a data-driven coach who uses insights, signals, and modern tools to develop your team into top performers who consistently exceed expectations and drive meaningful pipeline.As the Manager of Sales Development, you will be responsible for driving a significant portion of the company's revenue, building and motivating a high-performing team, and developing future Account Executives. We view Sales Development Representatives as the primary pipeline for our AE organization, and your leadership will directly shape the next generation of top-performing sellers at Justworks.You are comfortable questioning existing processes and leading change that improves productivity, pipeline quality, and the overall customer experience.Coaching & Performance: Lead high-impact weekly 1:1s focused on skill development, pipeline quality, and career progression. Use data and real interactions (e.g., Gong) to deliver targeted, actionable coaching.Train your team on Justworks’ evolving outbound approach, including signal-based prospecting, thoughtful outreach, and effective use of AI tools to increase productivity and relevance.Sales Motivation: Partner with leadership to drive accountability, performance, and healthy competition across the team.Pipeline Integrity & ExecutionYou are accountable for both the quality and accuracy of your team’s pipeline:Data-Driven Coaching: Use Salesforce, Gong, and other tools to identify performance gaps, coach in real time, and ensure activity translates into high-quality pipeline.CRM Excellence: Maintain strong CRM hygiene and data accuracy, while also leveraging automation to reduce manual work and improve consistency.Performance Management: Signal & Conversion Focus: Help your team prioritize the right accounts and opportunities, improving not just volume, but conversion and pipeline quality.Culture & Talent DevelopmentYou are responsible for building both performance and long-term talent:Talent Development: Effective Enablement: Partner with Revenue Operations and Enablement to roll out training, workflows, and tools that improve both performance and efficiency.AI Adoption & Upskilling: Help your team effectively use AI and automation in their day-to-day work, ensuring tools are used thoughtfully to enhance—not replace—human engagement.Maintain a high-performance, supportive team environment aligned with Justworks values.Actively support diverse hiring, development, and inclusion across your team.Good judgment - ability to interpret data, identify patterns, and make sound decisionsDetail-oriented - strong attention to data accuracy, pipeline quality, and executionResults-driven - consistently delivers against outbound targetsModern Sales Acumen - strong foundation in outbound sales, with an openness to evolving approaches through AI, automation, and signal-based sellingClear communication - ability to coach effectively and communicate across stakeholdersOur Core Values (COGIS): Camaraderie, Openness, Grit, Integrity, and SimplicityQualificationsExperience: 2+ years in a sales role (HCM/PEO preferred) and 2+ years of management experienceTechnical Fluency: Experience with Salesforce and Gong required; familiarity with modern sales engagement and AI-driven tools (e.g., ai) strongly preferredLeadership: Proven ability to manage and develop a team to achieve performance goalsDrive: The base wage range for this position is targeted at $147,000.00-$190,000.00 in our New York City office, and competitive On-Target Earnings, inclusive of incentive compensation, of *$226,200.00-$292,300.00. Diversity At JustworksJustworks is committed to maintaining a workplace where diversity of identity, culture, and life experience is the norm and is celebrated authentically and respected consistently. Diversity in our work, our people, and our product drives creativity and innovation, entrepreneurial leadership and integrity, competitiveness, and collaboration throughout our business and in the market. We depend on our differences to make our team stronger, our workplace more dynamic, and our product accessible to all of our customers.We’re proud to be an equal opportunity employer open to all qualified applicants regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital or familial status, disability, pregnancy, gender identity or expression, veteran status, genetic information, or any other legally protected status. Justworks is fully dedicated to providing necessary support to candidates with disabilities who may require reasonable accommodations. We also provide reasonable accommodations to employees based on their sincerely held religious beliefs, as well as for other covered reasons consistent with applicable federal, state, and local laws.