Director of Enterprise Sales

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

About the role:

As one of the fastest-growing areas of Automattic, VIP presents a unique opportunity for an experienced Enterprise Sales Director to lead our sales efforts to the next level. With 40% year-on-year growth, we’re looking to capitalize on that momentum by bringing in a dynamic leader who is passionate about what WordPress can do for our existing and potential customers.

You will lead a team of 4-6 Enterprise Account Executives, driving significant revenue growth through new client acquisition and existing account expansion. Your leadership style emphasizes listening and learning from both your team and prospects, and positioning VIP as the premier Content Management System for the Global 2000.

You view enterprise customers and their messages as important parts of the web, and you can see how WordPress VIP and Automattic can help them along their journeys. You pride yourself in establishing long-term relationships and doing what’s best for the customer. You enjoy telling stories, doing demos, and giving “the pitch,” and are comfortable talking to CMOs and CTOs.

Responsibilities: 

• Lead and mentor a team of Enterprise Account Executives, fostering a high-performing sales culture.
• Develop and execute innovative, vertical-specific sales strategies that accelerate market penetration and drive team performance.
• Set and achieve ambitious revenue targets for your team, contributing significantly to VIP's overall growth objectives.
• Establish and nurture strategic C-level relationships that position VIP as a critical business partner.
• Oversee the management of both transactional deals and large multimillion-dollar opportunities within your team.
• Implement and refine sales processes, including accurate forecasting and pipeline management across the team.
• Collaborate with SDRs and Marketing teams to create compelling outreach strategies and content.
• Actively participate in high-stakes deals and pitch meetings, comfortably presenting to CMOs and CTOs.
• Provide valuable customer and market insights to inform the VIP product roadmap.
• Elevate WordPress VIP's brand and reputation in the enterprise CMS space through high-impact engagements and thought leadership.

Requirements: 

• 10+ years of enterprise software sales experience, with at least 3 years in a sales leadership role, preferably in SaaS or CMS-related technologies.
• Proven track record of leading sales teams to consistently meet or exceed quotas.
• Strong understanding of enterprise software, IT landscapes, and content management systems.
• Excellent leadership, coaching, and team development skills.
• Outstanding communication, presentation, and negotiation abilities.
• Demonstrated success in solutions-based selling and closing enterprise-level deals.
• Experience in strategic account planning and growing business within named accounts and verticals.
• Proficiency in sales operations, including CRM management, forecasting, and pipeline analysis.
• Ability to work effectively in a remote environment and foster team cohesion across distances.

This role requires you to have a deep understanding of the technology and platforms that we run, and be able to communicate effectively with different stakeholders such as engineers and content creators. Moderate travel is required as well.

Salary range: $360,000-$440,000 USD, plus variable compensation. Please note that salary ranges are global, regardless of location, and we pay in local currency.

This isn’t your typical work-from-home job—we are a fully-remote company with an open vacation policy. To see a full list of benefits by country, consult our Benefits Page. And check out these links to learn more about How We Hire and What We Expect from Ourselves.

About Automattic 

We are the people behind WordPress.com, WooCommerce, Tumblr, Simplenote, Jetpack, Longreads, Day One, Pocket Casts, and more. We believe in making the web a better place.

We’re a distributed company with more than 1700 Automatticians in 92 countries speaking 110+ different languages. And, even more than growth and profitability (although we’re plenty profitable), above all, we’re driven by a mission:  We democratize publishing and commerce so anyone with a story can tell it, and anyone with a product can sell it, regardless of income, gender, politics, language, or country.

We believe in Open Source, and the vast majority of our work is available under the GPL.

Diversity, Equity, & Inclusion at Automattic 

We’re improving diversity in the tech industry. At Automattic, we want people to love their work and show respect and empathy to all. We welcome differences and strive to increase participation from traditionally underrepresented groups. Our DEI committee involves Automatticians across the company and drives grassroots change. For example, this group has helped facilitate private online spaces for affiliated Automatticians to gather and helps run a monthly DEI People Lab series for further learning. DEI is a priority at Automattic, though our dedication influences far more than just Automatticians: We make our products freely available and translate our products into and offer customer support in numerous languages. We require unconscious bias training for our hiring teams and ensure our products are accessible across different bandwidths and devices. 

Automattic is a Most Loved Company and Disability Confident Committed. (Here’s what that might mean for you.) Learn more about our dedication to diversity, equity, and inclusion and our Employee Resource Groups.