About XWP

XWP has collaborated on some of the most ambitious and successful WordPress projects to bring richer technologies and delightful user experiences to the open web.Our team of 50+ experts (from 20+ countries and 5 continents) enjoys challenging work, service-focused and collaborative teammates, and many opportunities to grow and lead. We're a fully remote team that prizes flexibility, autonomy, and trust in the workplace, making a rewarding career accessible wherever you are and whatever stage of life you're in.We care deeply about mastery, teamwork, and giving. We build for the open web.

And we are committed to evolving - especially as AI transforms how digital platforms are built and operated.We are currently looking for a Chief Technology Officer (CTO) to join our Senior Leadership Team and shape the future of technology at XWP. This is a fully remote role open to candidates worldwide.The Opportunity

This is an executive leadership role responsible for defining and stewarding:XWP's long-term technical visionOur enterprise WordPress solutioning standardsOur AI engineering strategy and transformationThe technical authority that strengthens our revenue engine and market credibilityYou will guide how technology differentiates XWP in the enterprise publishing and media landscape while ensuring engineering investments align with margin, growth, and long-term value creation.You will lead our Engineering leadership team, mentor Directors of Engineering, and serve as the executive technical authority in high-stakes client and industry environments.Who You Are

You are a recognized authority in the enterprise WordPress ecosystemYou think strategically about platforms, business models, and market positioning - not just architectureYou balance long-term vision with pragmatic executionYou believe in servant leadership and create psychologically protected, inclusive environmentsYou are deeply curious about AI and its impact on engineering productivity and digital agenciesYou are credible with engineers, persuasive with executives, and trusted by enterprise clientsYou are comfortable being an escalation point in high-stakes situationsYou thrive in a fully remote, distributed environment and operate confidently across cultures and time zonesWhat You've Done

15-20 years of experience in digital technology environments, with progressive responsibility shaping technical direction, delivery models,



or platform strategy within agency, publishing, or enterprise web organizations10+ years of hands-on experience working with WordPress, including deep involvement in enterprise-scale implementations, solution decisions, and the broader WordPress ecosystem5+ years in senior technical leadership roles, setting technical direction and guiding engineering organizations or leadership teams of 25+ people through growth, transformation, or organizational changeDeep expertise in enterprise WordPress architecture, including enterprise-level agency or publishing environmentsProven experience leading AI adoption and organizational transformationDefined technical standards for large-scale platforms with security, reliability, scalability, and performance at their corePartnered closely with Sales and Delivery to shape solutioning, estimation, and client strategyManaged budgets and made investment decisions with margin awarenessBuilt credibility in the WordPress or open web ecosystem through contribution, thought leadership, or industry engagementExperience in publishing, media, or content-driven enterprisesSignificant experience working on enterprise-level WordPress properties and platforms like WordPress VIPBonus

Experience creating and implementing productized services or SaaS-style offeringsActive participation in open-source communities, including WordPress core contributionsExperience operating in organizations under 100 peopleFamiliarity with modern JavaScript frameworks and CMS architectures at scaleWhat You'll Do at XWP

Define XWP's Technology Vision

Set and uphold enterprise WordPress standards for security, reliability, performance, and scalability.Define our evolving service offerings and capability model to meet market demand.Guide long-term architectural direction and reduce systemic reworkOwn Our AI Engineering Strategy

Lead company-wide AI transformation initiatives grounded in measurable business impactImprove productivity, delivery speed,



and code quality through AI-augmented workflowsIdentify and implement AI-enabled client offeringsEvaluate emerging tools and shifts in digital platform ecosystemsStrengthen Our Revenue Engine

Serve as executive technical authority in key sales engagementsContribute to technical discovery, solutioning, and strategic estimationsSupport the development of reusable, scalable service offeringsStrengthen our positioning within enterprise publishing and media marketsEngineering Leadership

Mentor and develop Directors of Engineering as strategic leadersEnsure engineering capability evolves with market demandsBuild a culture of mastery that engineers respect and aspire towardRepresent XWP Externally

Engage in open-source contribution and thought leadershipServe as a visible leader in the WordPress and open web ecosystemDeepen relationships with strategic technology partners and represent XWP credibly in high-stakes client and industry settingsContribute at the Senior Leadership LevelManage the engineering budget in alignment with company financial objectivesParticipate actively in agency-wide strategyEvaluate long-term technology investments against margin, growth, and differentiation goalsWhat Success Looks Like

Enterprise solutions excellence with fewer escalations and reduced reworkMeasurable AI-based impact on delivery speed, quality, or cost efficiencyIncreased win rates and deal sizes in enterprise WordPress opportunitiesStrengthened strategic partnerships and market credibilityEngineering leaders aligned around clear technical standardsHigh engagement and trust from the engineering teamExecutive peers are confident that our technology strategy supports business objectivesPayscale &

Benefits

Executive-level compensation aligned with experience and impact (range shared during initial conversations)Paid leave and a flexible scheduleUnleash+ allowance of USD $225 per month to enrich your lifeThe opportunity to shape the technical future of a globally respected WordPress agencyA collaborative, distributed culture built on trust, mastery, and mutual respectXWP is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all team members. Our distributed team consistently reports high levels of inclusion, and we actively support every individual in doing their best work together.

📌 Chief Technology Officer (Winnipeg)
🏢 Talantir
📍 Winnipeg