Lead Sales Development Representative, Enterprise

Automattic is hiring a Lead Sales Development Representative, Enterprise to join our fully remote team in the United States. As a Lead Sales Development Representative, Enterprise, you'll drive revenue by connecting customers with the right solutions. This is a freelance, work-from-home role open to candidates across the US (Remote — US (CST)). About the role You'll drive revenue by connecting customers with the right solutions, partnering with a friendly, distributed team across US time zones. We care about outcomes over hours and give you the autonomy, tools, and support to do your best work from home. What you'll do: • Collaborate with marketing and customer success • Run discovery calls and product demos • Prospect, qualify, and close new business • Manage a pipeline and forecast accurately • Consistently meet and exceed quota What we offer: • Annual learning and professional development budget • Generous paid time off and company holidays • 100% remote, work-from-anywhere-in-the-US culture • 401(k) retirement plan with company match • Home office and wellness stipends How we work We're remote-first and async-friendly. Expect clear documentation, regular feedback, supportive teammates, and real opportunities to grow your career. Automattic is proud to be an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for everyone.

Minimum qualifications: • 7+ years of experience, including leading teams or projects • B2B sales experience • Strong communication and negotiation skills • Self-motivated and goal-driven • CRM proficiency (Salesforce or HubSpot) Nice to have: • Familiarity with modern collaboration tools (Slack, Notion, Linear) • A growth mindset and eagerness to keep learning