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Director of Professional Services, WordPress VIP
Contract type
Ongoing
Work mode
Remote · Americas, Europe
Experience
Senior · 8+ years
Job description
Director of Professional Services at WordPress VIP, running the Professional Services delivery organization that handles migrations, implementations, and custom engagements for enterprise WordPress deployments. The role owns both delivery quality and the commercial result of the business, reporting to the VP of Customer Experience.
At a glance
- Employment
- Full-time · Employee (employment agreement)
- Work mode
- Remote · Americas, Europe
- Pay
- USD 130,000 – 190,000 / year
What you'll do
- 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.
- 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.
What we're looking for
- 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.
- Operator first: holds the strategy in their head and still shows up for the delivery details. More do than say.
- Commercially accountable: thinks about Professional Services as a business, not a function; knows the revenue number and the margin.
- Strong, persuasive communicator: can scope a hard engagement, write clearly under pressure, and hold executive attention without overstating their case.
- Coach, not just a manager: develops practitioners into delivery leads, gives direct feedback, steps in when something must be done a certain way, and knows when not to.
- Strategic and grounded: can recommend a services portfolio direction and also tell a project manager exactly where their engagement is going wrong.
Your team
Professional Services
A Professional Services delivery organization of engineers and delivery managers handling migrations, implementations, and custom engagements for enterprise WordPress deployments; part of the Customer Experience (CX) organization.
Benefits
- Salary range: $130,000 - $190,000 USD
- Straightforward, competitive base salary, providing financial clarity without complex variable components
- Fully-remote company with an open vacation policy
- Full list of benefits by country available on the Benefits Page
Apply
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.
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
Key facts
- more than 1500 Automatticians
- Now in our 20th year
- Distributed company with more than 1500 Automatticians in nearly every corner of the globe, speaking over a hundred different languages
- 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
- Products include WordPress.com, WooCommerce, Beeper, Tumblr, Simplenote, Jetpack, Longreads, Day One, PocketCasts
Partners & customers
MetaSalesforceDisney
What they value
- Making the web a better place
- Open Source
- Diversity