About Milestone

Milestone Inc. is a leading Digital Experience Software and Services company dedicated to providing comprehensive solutions across all touchpoints that enhance customer engagement and drive business growth. Milestone's mission is to pioneer the distribution and visibility of content with an innovative platform that drives discovery, personalized experiences, and conversions powered by data and AI. We pride ourselves on our collaborative culture and commitment to excellence — and are a certified Great Place to Work.

We are creating a new strategic role at the intersection of digital experience architecture, technical search, and AI-powered automation. The Director - Martech & Digital Experience will own the end-to-end technical strategy for CMS/DXP platforms, Search & Technical SEO, and intelligent workflow automation — driving measurable outcomes for Milestone's diverse client portfolio.

This is not a conventional SEO or CMS role. This leader will operate as a hands-on systems architect and AI practitioner — designing scalable platforms, automating complex workflows using AI tools, and elevating the martech function from reactive delivery to proactive, AI-native technical excellence.

1. Digital Experience Architecture & CMS Strategy

• Define and own the end-to-end architecture for enterprise websites built on CMS/DXP technologies (e.g., Sitecore, headless CMS).
• Design scalable, modular, and reusable architectures for multi-site and multi-brand implementations.
• Architect headless and hybrid CMS solutions supporting omnichannel delivery.
• Establish best practices for component architecture, content modelling, and template structures.
• Design integrations with enterprise systems: CRM, DAM, PMS, analytics, personalization engines, and identity/auth systems.
• Architect API-first integrations and microservices for composable martech stacks.

2. Technical SEO Architecture & Search Strategy

• Design and own enterprise-scale Technical SEO frameworks across Milestone's client base.
• Build repeatable technical architecture models for crawlability, indexability, site speed, Core Web Vitals, and structured data.
• Define and enforce Technical SEO standards across CMS platforms, page templates, and site infrastructure.
• Build entity-based SEO frameworks integrating schema markup, knowledge graph optimization, and semantic SEO.
• Drive AI search readiness — ensuring client content surfaces in AI Overviews, SGE, ChatGPT, Perplexity, and other AI-native engines.
• Own the technical layer of Generative Engine Optimization (GEO) initiatives.
• Stay ahead of algorithm updates, AI search shifts (SGE/AIO), and Core Web Vitals changes.

3. AI Workflow Automation

• Identify and implement automation across site auditing, log file analysis, rank tracking, content workflows, and reporting using AI tools.
• Build AI-assisted workflows for Technical SEO diagnostics, fix validation, and QA using tools like OpenAI, Claude, Gemini, or custom LLM pipelines.
• Automate repetitive martech delivery tasks: briefing, schema deployment, audit reporting, content tagging, and performance alerting.
• Leverage AI coding tools (GitHub Copilot, Cursor, etc.) and scripting (Python/JS) to build internal automation tools.
• Evaluate, prototype, and implement emerging AI tools across the digital experience and search stack.
• Drive a culture of AI-first problem solving across delivery teams — training and enabling team members to leverage AI tools in daily workflows.

4. Performance, Measurement & Governance

• Define North Star KPIs: crawl efficiency, Core Web Vitals scores, indexation rates, AI Presence Rate, organic traffic lift, and platform performance metrics.
• Build dashboards integrating Google Search Console, Screaming Frog, Lighthouse, and internal data systems.
• Define standards for CDN strategy, caching frameworks, high availability, and disaster recovery.
• Ensure compliance with security standards, privacy regulations, and accessibility guidelines (WCAG/ADA).
• Maintain architecture documentation, design patterns, and solution blueprints.

5. Technical Leadership & Team Building

• Provide technical leadership and architecture governance across development and SEO delivery teams.
• Mentor senior engineers, technical leads, and SEO specialists.
• Upskill the team toward Technical SEO Engineering — fluent in Python, data analysis, structured data, and AI search.
• Define competency frameworks and career paths for technical team members.
• Run weekly operations meetings tied to team OKRs and client priorities.

6. Cross-Functional Collaboration & Client Engagement

• Partner with Content, Schema, GEO, Product, Engineering, UX, and Client Success teams.
• Translate complex client technical challenges into structured, actionable roadmaps with business-impact prioritization.
• Serve as senior technical SEO and martech authority in client engagements; present executive-ready ROI narratives.
• Support Sales and CS teams with technical SEO scoping, pitches, and RFP responses.
• Align technical roadmaps with CMS product releases and platform capabilities.

You are a senior technologist and hands-on practitioner who has thrived in Martech, Digital Agency, or SaaS environments. You have deep expertise in CMS/DXP platforms and Technical SEO, and you have personally automated workflows using AI tools — not just managed teams who did. You are energized by building from the ground up, comfortable in ambiguity, and driven by measurable business impact.

Experience

• 12-18 years of progressive experience in digital experience, martech, CMS architecture, and/or Technical SEO.
• 3+ years in a senior leadership or director-level role within a Martech, Digital Agency, or SaaS company.
• Proven hands-on experience building and deploying AI-powered workflow automations using tools such as OpenAI API, Claude, LangChain, n8n, Zapier AI, or equivalent.
• Deep expertise with enterprise CMS/DXP platforms: Sitecore, WordPress, or comparable headless CMS platforms.
• Demonstrated success in Technical SEO at enterprise scale: crawl optimization, Core Web Vitals, JavaScript SEO, schema markup, site architecture.
• Experience delivering multi-brand, multi-region websites with millions of users.
• Track record of building repeatable, scalable frameworks and automating manual delivery processes.

Technical Skills

Leadership & Soft Skills

• Strong executive presence and communication skills — able to engage C-level stakeholders and enterprise clients.
• Demonstrated ability to build, mentor, and scale high-performing technical teams.
• Systems-thinking mindset — able to write product requirements and collaborate directly with engineering teams.
• Analytical and data-driven — comfortable translating complex data into business narratives.
• Comfort working in fast-changing, ambiguous environments with autonomous decision-making.

Education

• Bachelor's or Master's degree in Computer Science, Information Technology, Digital Marketing, or related field.

First 30 Days: Assess & Stabilize

• Full audit of team capacity, active CMS and SEO projects, and client technical health status.
• Deep dive into current martech workflows, tooling stack, and AI/automation gaps.
• Align with CS, Product, and Engineering on client delivery timelines and expectations.
• Document top 5 immediate risks and present a written 90-day transformation plan.

60 Days: Standardize & Automate

• Launch 2-3 standardized technical SEO and CMS audit packages.
• Pilot 2+ AI automation workflows in auditing, reporting, or schema deployment.
• Implement QA checklists for technical delivery across all active clients.
• Define technical competency framework for the martech/SEO team.

90 Days: Scale & Prove Value

• 30%+ improvement in workflow efficiency through AI automation.
• Full automation adoption across team reporting and audit workflows.
• Reporting template tied to ROI, organic revenue, and AI visibility metrics.
• Present 6-month martech + SEO roadmap to leadership.

• Competitive salary and performance-based incentives.
• Comprehensive benefits package.
• Opportunity to work in a collaborative, AI-first, innovative environment.
• Career growth and professional development opportunities.
• A chance to shape the martech and digital experience strategy of a global platform.