Founding Sales Development Representative (Outbound)

Hubstaff helps organizations around the world optimize productivity and workforce operations. Trusted by 95,000+ businesses, our platform powers time tracking, team management, project insights, and payroll automation.

We’ve been a remote-first company for over a decade — long before it became a trend — and we continue to believe that distributed work represents one of the most significant shifts in the modern workplace. Our product-led approach and strong momentum position us 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 (SDR) to join us at the ground level.

This is a rare opportunity to work directly with our VP of Sales to build Hubstaff’s outbound SDR playbook from scratch. Your outreach strategies, messaging ideas, and insights from the field will directly shape how we scale our sales engine.

You’ll be on the front lines identifying and engaging our highest-fit prospects, generating pipeline for Account Executives, and setting the standard for outbound excellence at Hubstaff.

• 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.

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

• Contribute ideas and feedback to shape the outbound playbook.

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

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

• 2+ years of experience as an outbound SDR in a SaaS company (required).

• Proven success generating pipeline through cold calls, email, and multi-channel outreach.

• 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 using HubSpot, Apollo, and modern sales tech.

• Experience building or contributing to outbound playbooks.

• Background in workforce management, productivity tools, or remote work solutions.

• Familiarity with enterprise or mid-market outbound motions.

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

• Base Salary: USD $65,000

• Variable Compensation: USD $25,000 OTE, with uncapped commission (Total OTE: $90,000)

• Location: Fully remote, U.S. only. Strong preference for Eastern region candidates (Georgia and Florida).

• Contract Type: Full-time employee

Perks & Benefits:

• Comprehensive private health insurance.

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

• Annual stipend for home office setup and professional development.

• Transparent career paths and regular performance reviews.

• A remote-first culture with 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.