Director of Professional Services, WordPress VIP

• 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.

Experience

• 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

• Operator first. You hold the strategy in your head and still show up for the delivery details. More do than say.

• 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.

• Strong, persuasive communicator. You can scope a hard engagement, write clearly under pressure, and hold executive attention without overstating your case.

• 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.

• Strategic and grounded. You can recommend a services portfolio direction, and also tell a project manager exactly where their engagement is going wrong.

Compensation and 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

About Automattic

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.

We believe in Open Source , and the vast majority of our work is available under the GPL . Automattic is a Most Loved Company , an Equal Opportunity employer, and Disability Confident Committed . ( Here’s what that might mean for you .) If you need accommodations during the application or interview process, please fill out this form . We are committed to ensuring an accessible hiring process for all candidates. Learn more about our Employee Resource Groups .

You can track your application status and more at MyGreenhouse .

To learn about how we handle your data, please review our Job Applicant & Candidate Privacy Notice and our Privacy Policy .

All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. View the “Know Your Rights: Workplace Discrimination is Illegal” poster here . Automattic participates in the E-Verify program in certain locations, as required by law .

• Technical Account Manager

Source: Automattic careers page