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.
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 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.
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.
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 safe, 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 up-to-date 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.
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 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 Look

📌 Head of Information Technology (Winnipeg)
🏢 Talantir
📍 Winnipeg