Full-Time

Account Executive

WordPress VIP

Automattic

Automattic

1,001-5,000 employees

Operates WordPress.com and online content tools

Compensation Overview

$95k - $160k/yr

+ Variable compensation

La Ronge, SK, Canada

Remote

Moderate travel required; remote role with East Coast US/Canada focus.

Category
Sales & Account Management (1)
Required Skills
Wordpress
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 experience in solutions-based selling and closing enterprise-level deals.
  • Ability to establish and maintain long-term customer relationships.
  • Experience in managing and growing business within named accounts and verticals.
  • Comfortable working with executive-level prospects, negotiating terms, and reviewing contracts.
  • Self-motivated with a drive to achieve revenue and growth targets, both individually and as part of the company.
  • Moderate travel is required.
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, and drive strategic improvement of forecasting processes.
  • Develop and execute innovative, vertical-specific sales strategies that accelerate market penetration.
  • Actively engage in pipeline generation activities, including regular outbound prospecting.
  • Enhance the product offering by providing valuable customer insights to inform the VIP roadmap.
  • Elevate WordPress VIP's brand and reputation in the enterprise CMS space through high-impact engagements.
  • Contribute to a high-performing sales culture by sharing best practices and mentoring team members.
Desired Qualifications
  • None

Automattic builds and runs online tools for creating and managing web content, most notably WordPress.com. Users can start for free and upgrade to premium plans that unlock advanced design options, more storage, and business features, while the free tier may display ads. The company also develops mobile apps and contributes to open source and nonprofit projects, leveraging a hosted WordPress experience with templates, plugins, and a content editor. Its goal is to make the web a better place by enabling easier creation, management, and distribution of online content while supporting open-source software and nonprofit efforts.

Company Size

1,001-5,000

Company Stage

Late Stage VC

Total Funding

$905.3M

Headquarters

San Francisco, California

Founded

2005

Simplify Jobs

Simplify's Take

What believers are saying

  • Kryterion partnership launched enterprise WordPress certification in February 2026.
  • Stephen Wolfram joined as Special Advisor in December 2025 to advance open-source.
  • Automattic for Agencies boosted Linchpin's client orders 10-20% via Pressable.

What critics are saying

  • Shopify's integrated ecommerce erodes WooCommerce's plugin model by 2027.
  • EU Digital Markets Act targets WordPress's 43% dominance with breakup in 2028.
  • VIP certification commoditizes skills, slashing high-margin revenue by 2028.

What makes Automattic unique

  • WordPress.com powers 43% of global websites, dwarfing Shopify's 5.1% share.
  • Acquired Tumblr, Texts, Beeper to cover publishing, commerce, and messaging.
  • Launched Passport with Ben Thompson, enabling Ankler's Substack migration in 2026.

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Benefits

Remote Work Options

Unlimited Paid Time Off

Flexible Work Hours

Professional Development Budget

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

0%
PR Newswire
Mar 20th, 2026
AI agents can now draft posts and manage content on WordPress.com through natural conversation

WordPress.com has launched new write capabilities for its Model Context Protocol server, enabling AI agents including Claude, ChatGPT and Cursor to create, edit and manage content on WordPress.com sites through natural conversation. The update allows AI agents to draft posts, build pages and manage comments directly, with explicit user confirmation required at every step. The feature builds on WordPress.com's AI initiatives from the past year, including an AI-powered website builder launched in April 2025 and the WordPress AI Assistant. The company first introduced its MCP server in October 2025, initially providing read-only access to site content and analytics. The write capabilities are available now on all paid WordPress.com plans at no additional cost. WordPress.com publishes 70 million new posts monthly across its platform.

StartUp Beat
Mar 19th, 2026
Kryterion and Automattic launch WordPress developer certification.

Kryterion and Automattic launch WordPress developer certification. The web developer industry has long lacked a rigorous, standardized benchmark for enterprise-level WordPress expertise. However, a new partnership has bridged that gap. Kryterion and Automattic announced today a strategic partnership in their Advanced Professional WordPress Developer certification - a rigorous, enterprise-grade credential that tests the skills required to build and maintain complex, high-traffic WordPress applications. The exam went live mid-February 2026. Why now? WordPress now powers 42.6% of all websites globally as of March 2026, with its nearest competitor sitting at just 5.1%. It is the indisputable backbone of the internet, and yet, the ecosystem had no meaningful way of distinguishing between an advanced enterprise developer from one operating at a basic level - until now. For startups and agencies building on WordPress, this credential addresses a real and long-standing operational pain point. WordPress VIP clients include Salesforce, Al Jazeera, Meta, Capgemini, and HelloFresh - organizations running WordPress at scale where every security gap, performance issue and poorly managed deployment carries real financial consequences. The new certification is built around the exact skill domains those environments demand: WordPress Core architecture, Custom Development, Security, Performance, Change Management, Debugging, Scalability and Architecture, and Disaster Recovery - built by practitioners, for enterprise environments. The credential was developed with direct input from the field. WordPress VIP - Automattic's enterprise division, which has run the world's most demanding WordPress environments for 18 years - led curriculum development. Some of the top WordPress agencies globally contributed to testing the credential before launch, grounding the exam in real-world enterprise challenges rather than theoretical frameworks. Kryterion provides the delivery infrastructure: its Webassessor platform with dual-camera online proctoring, psychometric validation, and global reach. Item development began in September 2025, a beta test was completed in January 2026, and the credential launched in February - a roughly five-month development cycle that is fast by any credentialing standard. "We're excited to join Automattic to empower developers with respected credentials that reflect their real-world skills... unlocking new opportunities for developers to grow their careers and help businesses thrive online," said Angela Street, Chief Customer Success at Kryterion. The ROI case. Most (97%) of decision makers say certified staff adds value to their organizations, as per Skillsoft's 2024 IT Skills & Salary Report. Beyond this, over a third estimated that value at $25,000 USD or more per year, plus measurable gains in productivity, faster problem solving, and reduced skill gaps. For firms building or scaling on WordPress, a certified developer translated directly into fewer security vulnerabilities, reduced downtime, and faster delivery cycles. And, from a macro perspective, the broader hiring landscape is also shifting in favor of credentials; 53% of employers removed degree requirements last year - up 30% the year prior - with tech roles leading the charge. Preparation materials for the Advanced Professional WordPress Developer exam are freely available through VIP Learn, making the pathway safe and accessible for developers of all career stages. In a market increasingly oriented around demonstrated competency, then, a rigorous third-party credential will carry more weight than ever. "This partnership marks a milestone in formalizing skills and expertise in advanced professional WordPress software development," concluded Klaus Harris, Credentialing Program Lead at WordPress VIP. Disclosure: This article mentions clients of an Espacio portfolio company.

The Sociable
Mar 18th, 2026
Kryterion and Automattic partner to create a gold standard in WordPress developer credentials.

Kryterion and Automattic partner to create a gold standard in WordPress developer credentials. March 18, 2026 Discover more Blogging Resources & Services Content Management Social Networks The web has a WordPress problem - not the platform itself, but the people who build on it. As of March 2026, in fact, WordPress powers 42.6% of all websites around the world - the undisputed backbone of the internet. WordPress is nine times as popular as its nearest competitor, Shopify, which holds a 5.1% share. Yet, for all the dominance, the industry has never had a rigorous and standardized way of verifying that a developer truly has the skills to operate at enterprise scale. The gap is finally closing. Phoenix-based firm Kryterion - which has over 25 years' experience in secure test development and delivery - and Automattic, the distributed technology company behind WordPress, WooCommerce, Tumblr, and Jetpack, among others, announced a strategic partnership to launch the Advanced Professional WordPress Developer certification program on March 18, 2026. While the exam went live in mid-February, following a beta test completed in January, it has already drawn attention from developers, agencies, and enterprise hiring teams worldwide. Why now? WordPress's reach extends far beyond the personal blogs it once powered: Salesforce pivoted 2,000 marketers to digital with WordPress VIP; Al Jazeera built its digital presence across more than 70 worldwide bureaus; Capgemini published over 20,000 pages in over 10 languages across 38 sites; Meta launched a secure e-commerce experience in under 30 days. These are not hobbyist deployments - they are mission-critical digital operations. And yet, until now, there was no single credential that could tell an enterprise CTO whether a developer was truly equipped to work at that level. The certification tests advanced competency across eight domains that map directly to real enterprise challenges: WordPress Core architecture, Custom Development, Security, Performance, Change Management, Debugging, Scalability and Architecture, and Disaster Recovery. Automattic's enterprise division, WordPress VIP - which has supported the largest WordPress deployments for more than 18 years - led the curriculum development. Some of the top WordPress agencies globally participated in testing the credential before launch. "We're excited to join Automattic to empower developers with respected credentials that reflect their real-world skills," said Angela Street, Chief Customer Success at Kryterion. "By combining Kryterion's full-service certification offerings with Automattic's deep connection to the web development community, we're unlocking new opportunities for developers to grow their careers and help businesses thrive online." The credentials economy is booming. The Kryterion and Automattic launch lands in the middle of a significant macro-shift in tech hiring. According to a 2025 report, 53% of employers removed degree requirements -representing a 30% increase from 2024. Cloud computing, cybersecurity, data analytics, and DevOps are fields where certifications and hands-on practice now carry more weight than a university transcript, and the same shift is beginning to reshape web development hiring. For developers in the WordPress ecosystem, a portable, third-party validated credential has never been more valuable. IT leaders report that certified staff add a value of $30,000 per year to the organization, with a noticeable increase in productivity from employees who earn certifications, according to Skillsoft. And, as per last year's C-Suite Perspectives report, organizations that invest in IT certifications report a 36% boost in productivity and a 35% reduction in time to troubleshoot issues. Kryterion brings its Webassessor platform to the delivery infrastructure: secure dual-camera online proctoring, psychometric support, and flexible multi-modal exam options. The company began supporting Automattic's item development process in September 2025 - a notably fast development track for a credential of this psychometric scope. For the WordPress ecosystem, this represents the kind of structural credentialing that cloud computing and cybersecurity sectors have had for years. It has been a long time coming. Disclosure: This article mentions clients of an Espacio portfolio company.

Dataconomy
Feb 5th, 2026
Internet Archive and Automattic launch new tool to combat link rot

Internet Archive and Automattic launch new tool to combat link rot. Digital decay affects nearly 40 percent of links from the last decade. The Internet Archive and Automattic launched the Link Fixer WordPress plug-in to address link rot, where URLs become broken, by scanning links, archiving pages via the Wayback Machine, and redirecting users to preserved versions. The Internet Archive operates as a nonprofit organization focused on archiving the internet to preserve digital content for future generations. Its Wayback Machine indexes the web by capturing widespread snapshots of pages over time. This week, the organization announced a new tool aimed at assisting WordPress users in maintaining the digital health of their articles through automated link preservation. Automattic, the company responsible for developing WordPress, collaborated with the Wayback Machine on this initiative. The resulting Link Fixer plug-in targets the problem of link rot, defined as the process where online articles accumulate broken links - URLs that previously directed to active pages but now produce error messages or lead to dead ends. Stay ahead of the curve! A 2024 study by Pew Research revealed that nearly 40 percent of links existing in 2013 were no longer active. This digital decay affects a wide range of web content, including pages from news outlets, government websites, Wikipedia entries, and tweets. The plug-in functions by examining WordPress posts for outbound links. It then cross-references these links against the Wayback Machine's database of archived versions. In cases where no archived version exists, Link Fixer automatically captures new snapshots of the referenced articles to create backups. When an originally linked web page becomes inaccessible, the plug-in intervenes by redirecting readers to the corresponding archived version stored in the Wayback Machine. This mechanism ensures continuous access without interrupting the user's reading experience or causing a loss of service. Beyond external links, the tool also archives the user's own WordPress posts. This feature contributes to the long-term preservation of the site's original content, safeguarding it against potential future unavailability. Link Fixer operates continuously to monitor the status of a page's links. If a link that previously went offline becomes available again at its original location, the plug-in updates its behavior to redirect users back to that restored original page rather than the archived copy. This dynamic adjustment prioritizes the most current accessible version. A detailed write-up on GitHub describes the plug-in's controls as user-friendly and highly customizable. Users can adjust settings such as the frequency of link validity scans. The program sets this interval to every three days by default, allowing site administrators to tailor the process to their specific needs.

TechCrunch
Feb 4th, 2026
Internet Archive launches WordPress plugin to automatically fix broken links with archived versions

The Internet Archive's Wayback Machine has partnered with Automattic to launch Link Fixer, a WordPress plugin designed to combat "link rot"—the phenomenon of online links becoming inactive over time. A 2024 Pew Research study found nearly 40% of links from 2013 were no longer active. The plugin scans WordPress posts for outbound links and cross-references them with the Wayback Machine's archives. If no archived version exists, it automatically creates new snapshots. When a linked webpage goes offline, the tool redirects readers to archived versions. The plugin also archives users' own posts to ensure longevity. Link Fixer continuously monitors links and will redirect to original pages if they come back online. Users can customise scanning frequency, with a default setting of every three days.