Automattic Careers - Director of Professional Services, WordPress VIP
Requirements
• 8+ years of leadership experience in Professional Services, implementation, or technical consulting. Direct experience leading a Professional Services or delivery organization is required. • 5+ years delivering services for enterprise SaaS or PaaS customers, ideally involving large-scale migrations or custom development. • Experience building a services portfolio—defining offerings, pricing them, and making them repeatable without killing the flexibility that enterprise customers need. • Experience working the full commercial loop—not just delivery, but scoping with Sales, pricing engagements, identifying expansion, and tying Professional Services outcomes to retention and revenue. • Comfortable operating in or alongside an AI-augmented delivery model. What we need is genuine fluency with how AI changes the work—not just awareness that it exists. • Demonstrated ability to engage with executive stakeholders, both internal and external. • Proven track record of performance management within a team, working closely with individual contributors, leads, and HR partners. • How you work • How you work • Operator first. You hold the strategy in your head and still show up for the delivery details. More do than say. • Operator first. • Commercially accountable. You think about Professional Services as a business, not a function. You know your revenue number, you know your margin, and you can talk about both with the same fluency you bring to delivery. • Commercially accountable. • Strong, persuasive communicator. You can scope a hard engagement, write clearly under pressure, and hold executive attention without overstating your case. • Strong, persuasive communicator. • Coach, not just a manager. You develop practitioners into delivery leads. You give direct feedback. You’ll step in when something must be done a certain way, and you know when not to. • Coach, not just a manager. • Strategic and grounded. You can recommend a services portfolio direction, and also tell a project manager exactly where their engagement is going wrong. • Strategic and grounded.
Responsibilities
• Build an agentic Professional Services organization—one where AI augments delivery, accelerates time-to-value, and creates capacity for higher-complexity work. • Build Professional Services into a growth lever: identify expansion opportunities within active engagements, and partner with Account Management and Sales to turn delivery relationships into commercial ones. • Lead a Professional Services team of engineers and delivery managers, delivering migrations, implementations, and custom engagements for enterprise customers. • Own delivery quality end-to-end: project health, escalation management, customer outcomes, and on-time, on-scope execution. • Build and maintain a clear menu of established service offerings, so Sales can sell them, customers can buy them, and the team can deliver them consistently. • Meet customers where they are. Not every engagement fits a playbook, and this role requires the judgment to scope and run custom work without losing the thread back to repeatable delivery. • Help set the strategic direction for Professional Services as part of the Customer Experience Senior Leadership Team, and translate it into an operating plan that the team can execute. • Help differentiate WordPress VIP’s services offering in the market: define what makes Professional Services at WordPress VIP distinct from what a customer could get elsewhere, and build the proof points behind it. • Partner with Sales & Accounts to scope and price engagements accurately, and own the hand-off from close to delivery. • Partner with Product, Support, and Account Management on feedback loops that continually improve WordPress VIP’s platform and services. • Represent Professional Services credibly with senior internal and external stakeholders, including customer executives, on complex or at-risk engagements.
Benefits
• Salary range: $130,000 - $190,000 USD. Please note that salary ranges are global, regardless of location, and we pay in local currency. • We are searching for high-caliber candidates with the skills and qualities to have a net positive for Automattic. Pay will reflect the potential contribution and the impact you can bring, which may, in some cases, go beyond the range stated. • We’re pleased to offer a straightforward, competitive base salary, providing financial clarity without complex variable components. 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. #LI-Remote • Now in our 20th year, we’re the people behind WordPress.com, WooCommerce, Beeper, Tumblr, Simplenote, Jetpack, Longreads, Day One, PocketCasts, and more. We believe in making the web a better place. • We’re a distributed company with more than 1500 Automatticians in nearly every corner of the globe, speaking over a hundred different languages. Enriched by this diversity, we’re united by a singular mission: to democratize publishing, commerce, and messaging so anyone with a story can tell it, anyone with a product can sell it, and everyone can manage their communications from a single source. In short, we help maintain a balance in society, creating and continually refining powerful tools people can use to compete fairly—regardless of income, gender, politics, language, or where they live in the world.
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