Account Executive, WordPress VIP - Automattic

About the Role

WordPress VIP is the world’s leading enterprise content management platform, helping the world’s largest companies (including Meta, Salesforce, and Disney) create innovative digital experiences with WordPress.

As one of the fastest growing areas of Automattic, VIP presents a unique opportunity for experienced Account Executives to help take us to the next level. We're looking for AEs who are passionate about what WordPress can do for enterprise customers.

Your style is to listen and learn from prospects, positioning VIP as the best Content Management System for the Global 2000. You don’t sit and wait for leads to come to you—instead, you research the market, identify opportunities within specific verticals, and design high-touch, creative sales strategies.

You’ll work closely with SDRs and leverage Marketing teams for outreach and content, while actively generating your own leads. You pride yourself on building long-term relationships, pitching, leading demos, and engaging confidently with C-level executives.

Responsibilities

• Drive significant revenue growth by securing new enterprise clients and expanding existing accounts.
• Establish and nurture strategic C-level relationships that position VIP as a critical business partner.
• Successfully manage both transactional deals and large multimillion-dollar opportunities.
• Maintain accurate sales forecasts and pipeline information, driving strategic improvements in forecasting processes.
• Develop and execute innovative, vertical-specific sales strategies that accelerate market penetration.
• Actively engage in pipeline generation activities, including outbound prospecting.
• Enhance the product offering by sharing customer insights to inform the VIP roadmap.
• Elevate WordPress VIP's brand and reputation in the enterprise CMS space.
• Contribute to a high-performing sales culture by sharing best practices and mentoring team members.

Requirements

• 7+ years of enterprise software sales experience, preferably in SaaS or CMS-related technologies.
• Demonstrated ability to consistently meet or exceed sales quotas.
• Strong understanding of enterprise software, IT landscapes, and content management systems.
• Excellent communication, presentation, and negotiation skills.
• Proven track record in solutions-based selling and closing enterprise-level deals.
• Experience managing and growing business within named accounts and specific verticals.
• Comfort working with executive-level prospects, negotiating terms, and reviewing contracts.
• Self-motivated with a drive to achieve revenue and growth targets.
• Moderate travel required as needed.

Compensation & Location

• Location: Remote (East Coast of United States / Canada)
• Base Salary: $95,000–$160,000 USD (plus variable compensation / commission)
• Open vacation policy