Founding Sales Development Representative (Outbound)

\u003ch2\u003eCompany Overview\u003c/h2\u003e\u003cp style=\"min-height:1.5em\"\u003eAt Hubstaff, our mission is to empower people to have their most productive workday. We do this by providing the industry-leading workforce analytics and time tracking platform for remote and distributed teams.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003eWe’ve been fully remote for over a decade—long before it became a trend—and we continue to believe that remote work represents the most significant shift in the modern workplace since the advent of the PC. Our platform helps more than 95,000 businesses track time, manage schedules, and automate payments with transparency and accountability at its core.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003eWe’re a product-led company with a winning culture, strong momentum, and a long-term vision: to become an essential part of every remote company’s tech stack. And we’re just getting started.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003c/p\u003e\u003ch2\u003eThe Position\u003c/h2\u003e\u003cp style=\"min-height:1.5em\"\u003eWe’re expanding our outbound sales motion — and we’re looking for a \u003cstrong\u003eFounding Sales Development Representative\u003c/strong\u003e to join us at the ground level.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003eThis is a rare opportunity to work directly with our VP of Sales to build Hubstaff’s SDR playbook from scratch. Your outreach strategies, messaging ideas, and insights from the field will directly shape how we scale our outbound sales engine.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003eYou’ll be on the front lines identifying and engaging our highest-fit prospects. Your work will generate pipeline for our Account Executives and help define what “great” looks like in Hubstaff’s sales organization.\u003c/p\u003e\u003cp style=\"min-height:1.5em\"\u003c/p\u003e\u003ch2\u003eWhat You’ll Do\u003c/h2\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eIdentify and target ICP accounts in our core industries (digital agencies, IT services, BPOs, field services).\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eRun multi-channel outreach campaigns with personalized sequences (calls, emails, LinkedIn).\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eQualify prospects by uncovering goals, challenges, and buying triggers.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eBook high-quality meetings with decision-makers for AEs.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eContribute ideas and feedback to shape the outbound playbook.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eUse HubSpot CRM and Apollo to manage outreach and track performance.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eConsistently hit — and exceed — targets for meetings, show rates, and pipeline creation.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eCollaborate directly with the VP of Sales for coaching, strategy, and continuous improvement.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003ch2\u003eRequirements\u003c/h2\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eYou embody our core values.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e1+ year of outbound sales or SDR experience with proven cold calling success in B2B.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eSaaS experience is a plus.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eStrong written and verbal communication skills with executives.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eResilience and persistence — ability to bounce back from rejection and keep energy high.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eCuriosity to research prospects and personalize outreach.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eComfort learning and using tools like HubSpot, Apollo, and modern sales tech.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003c/p\u003e\u003ch3\u003eBonus Points if You Have\u003c/h3\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eExperience building or contributing to outbound playbooks.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eBackground in SaaS, workforce management, or remote work solutions.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eFamiliarity with enterprise or mid-market outbound sales motions.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eA track record of exceeding quota in fast-growth environments.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003c/p\u003e\u003ch2\u003eWhy You Should Apply\u003c/h2\u003e\u003ul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eJoin as a \u003cstrong\u003eFounding SDR\u003c/strong\u003e and directly shape Hubstaff’s outbound sales strategy.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eCollaborate closely with the VP of Sales and leadership team.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003ePreference for Orlando-based candidates (2 days/week in office), but open to remote for the right person.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eOpportunity for career growth with a direct path to closing roles.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eBe part of a fast-growing SaaS company serving thousands of customers worldwide.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003ch3\u003eCompensation \u0026 Benefits\u003c/h3\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eLocation:\u003c/strong\u003e Hybrid in Orlando, FL (preferred), or remote within the U.S.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eContract Type:\u003c/strong\u003e Full-time employee.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eBase Salary:\u003c/strong\u003e USD $60,000.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003eVariable Compensation:\u003c/strong\u003e USD $20,000 OTE, with uncapped commission.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003cstrong\u003ePerks \u0026amp; Benefits:\u003c/strong\u003e\u003c/p\u003e\u003cul style=\"min-height:1.5em\"\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eComprehensive private health insurance.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eGenerous paid time off policy that supports rest and well-being.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eAnnual stipend for home office setup, wellness, or professional development.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eTransparent career paths and regular performance reviews.\u003c/p\u003e\u003c/li\u003e\u003cli\u003e\u003cp style=\"min-height:1.5em\"\u003eA truly remote-first culture with the flexibility to design your workday.\u003c/p\u003e\u003c/li\u003e\u003c/ul\u003e\u003c/li\u003e\u003c/ul\u003e\u003cp style=\"min-height:1.5em\"\u003e\u003c/p\u003e\u003ch3\u003e\u003cem\u003eInclusion at Hubstaff\u003c/em\u003e\u003c/h3\u003e\u003cp style=\"min-height:1.5em\"\u003eHubstaff is proud to be an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all team members, regardless of background, identity, or lived experience.\u003c/p