Director of Enterprise Sales, Automattic

• 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
• 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

• 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
• 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

• Professional Development · “I will never stop learning” is part of our company creed. From leadership development to improving your writing skills, we have a comprehensive list of programs and resources available to everyone, and we’re also happy to pay for any hardware, software, books, or conferences that promote continued learning.
• Career Coaching · Coaching sessions to help you set and achieve professional goals are available for all Automatticians – team members and team leads. This benefit resets each calendar year.
• Time off · Our open vacation policy (no set number of days per year) is designed to help you to be at your best! There is no minimum or maximum, but we encourage you to take at least 25 days of time off per year.
• Home Office · We offer home office setup and coworking allowances. Working from a coffee shop? You can use your coworking allowance for the requisite latte!
• Wellness · We offer mental wellness benefits including an Employee Assistance Program, a monthly subscription to a mindfulness app (including Calm, Headspace, Ten Percent Happier, Waking up, and Insight timer), and virtual ergonomic consultations and access to a wealth of virtual ergonomic tips, stretch videos and yoga exercises.
• Parental leave · Open parental leave (including maternity, paternity, LGBTQ+, and adoption for all parents). If you’ve been with Automattic for 12 months, your leave up to 6 months is fully paid.
• Anniversary Awards · Paid three-month sabbatical encouraged every five years and other cool anniversary surprises.
• Automattic Stock · Check out Buying and selling Automattic Stock!
• Life Insurance · Company-sponsored life insurance.
• Compensation · We attract talent around the world and pay global salary ranges. We prioritize internal equity and review your pay every 12-18 months.
• Sabbatical · Working at Automattic provides numerous opportunities to learn new skills, grow in your career, and have a significant and positive impact on the lives of millions. It also offers the rare (and juicy!) benefit of a paid, three-month sabbatical every five years.

Total funding: $778.6m

At a time when companies like Facebook, Apple, and Google were turning into monopolistic market leaders, Automattic was building its open-source infrastructure on a distributed, volunteer-run workforce. Since its launch in 2005, the company has continued to evolve and expand as it built its new web empire.