Founding Sales Development Representative (Outbound)

At 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.

We’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.

We’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.

We’re expanding our outbound sales motion — and we’re looking for a Founding Sales Development Representative to join us at the ground level.

This 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.

You’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.

• Identify and target ICP accounts in our core industries (digital agencies, IT services, BPOs, field services).

• Run multi-channel outreach campaigns with personalized sequences (calls, emails, LinkedIn).

• Qualify prospects by uncovering goals, challenges, and buying triggers.

• Book high-quality meetings with decision-makers for AEs.

• Contribute ideas and feedback to shape the outbound playbook.

• Use HubSpot CRM and Apollo to manage outreach and track performance.

• Consistently hit — and exceed — targets for meetings, show rates, and pipeline creation.

• Collaborate directly with the VP of Sales for coaching, strategy, and continuous improvement.

• You embody our core values.

• 1+ year of outbound sales or SDR experience with proven cold calling success in B2B.

• SaaS experience is a plus.

• Strong written and verbal communication skills with executives.

• Resilience and persistence — ability to bounce back from rejection and keep energy high.

• Curiosity to research prospects and personalize outreach.

• Comfort learning and using tools like HubSpot, Apollo, and modern sales tech.

• Experience building or contributing to outbound playbooks.

• Background in SaaS, workforce management, or remote work solutions.

• Familiarity with enterprise or mid-market outbound sales motions.

• A track record of exceeding quota in fast-growth environments.

• Join as a Founding SDR and directly shape Hubstaff’s outbound sales strategy.

• Collaborate closely with the VP of Sales and leadership team.

• Preference for Orlando-based candidates (2 days/week in office), but open to remote for the right person.

• Opportunity for career growth with a direct path to closing roles.

• Be part of a fast-growing SaaS company serving thousands of customers worldwide.

• Location: Hybrid in Orlando, FL (preferred), or remote within the U.S.

• Contract Type: Full-time employee.

• Base Salary: USD $60,000.

• Variable Compensation: USD $20,000 OTE, with uncapped commission.

• Perks & Benefits:

  • Comprehensive private health insurance.

  • Generous paid time off policy that supports rest and well-being.

  • Annual stipend for home office setup, wellness, or professional development.

  • Transparent career paths and regular performance reviews.

  • A truly remote-first culture with the flexibility to design your workday.

Hubstaff 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.