Chief Strategic Architect (Boston)

About WorkatoWorkato delivers enterprise infrastructure for the agentic era, redefining iPaaS and helping enterprises unify data, applications, processes, and AI into a single, governed platform. A leader in Enterprise MCP and trusted by 50% of the Fortune 500, Workato’s cloud-native architecture connects every application, data source, and process to power real-time orchestration at scale. With enterprise-grade security and continuous innovation at its core, Workato provides the trusted foundation for organizations to automate with confidence and operationalize AI across the business. To learn more, visit Why join us?Ultimately, Workato believes in fostering a flexible, trust-oriented culture that empowers everyone to take full ownership of their roles. We are driven by innovation and looking for team players who want to actively build our company. But, we also believe in balancing productivity with self-care. That’s why we offer all of our employees a vibrant and dynamic work environment along with a multitude of benefits they can enjoy inside and outside of their work lives. If this sounds right up your alley, please submit an application. We look forward to getting to know you!Also, feel free to check out why:Business Insider named us an “enterprise startup to bet your career on”Forbes’ Cloud 100 recognized us as one of the top 100 private cloud companies in the worldDeloitte Tech Fast 500 ranked us as the 17th fastest growing tech company in the Bay Area, and 96th in North AmericaQuartz ranked us the #1 best company for remote workersResponsibilitiesWe are seeking a visionary Chief Strategic Architect to serve as Workato's technical authority and strategic advisor to our most critical prospects, customers, and the broader market within their assigned region. The Chief Strategic Architect operates at the nexus of technical credibility, executive influence, and market thought leadership, acting as the external-facing voice of Workato's innovation and technical vision.This is not a sales role. It is a strategic, hybrid operator-advisor-influencer position. You will act as an extension of the executive team in the field, elevating conversations with senior leaders and positioning Workato as the essential platform for enterprise integration, AI orchestration, and intelligent automation.This role is accountable for building technical trust across the customer lifecycle - from initial engagement through strategic expansion - while simultaneously shaping how the market understands enterprise integration, AI orchestration, and intelligent automation. The Chief Strategic Architect influences deal outcomes, product direction, and industry perception, ensuring Workato is recognized as the definitive leader in Enterprise Orchestration.First 90 DaysLearn & Align (Days 0-30)Deep immersion into Workato's AI vision, product roadmap, and GTM strategyShadow at least 10 executive customer conversationsDevelop initial point of view for engagement with CIO/CTO/CDO personasEngage & Formulate (Days 30-60)Lead first strategic engagements with enterprise accountsCo-develop executive playbooks with Sales and Product teamsEstablish feedback loops with Product and Engineering teamsInfluence & Scale (Days 60-90)Cultivate trusted relationships with C-level executives in 5+ strategic accountsCo-create first AI-driven integration use cases with customersEstablish thought leadership presence through content and speaking opportunitiesTechnical Trust & Executive RelationshipsEngage directly with C-level executives (CIOs, CTOs, Chief Data Officers, Chief AI Officers) at enterprise accounts to shape integration strategies that solve complex business challengesServe as trusted technical advisor throughout the customer lifecycle - from initial engagement through expansion - providing strategic guidance rooted in real-world operator experienceBuild lasting peer-to-peer relationships that position you as the go-to expert on enterprise integration, AI orchestration, and automation at scaleAct as technical closer in competitive deals, articulating why Workato's architecture differentiates us from competitors like MuleSoft and BoomiInfluence enterprise architecture decisions and multi-year technology strategies at the executive levelAI, Agentic Automation & Enterprise MCP StrategyShape and guide customers' AI and agentic automation journeys, leveraging Workato's AI capabilities and ecosystemAdvise on the design and adoption of agent-based workflows, human-in-the-loop models, and decision automation frameworksPartner with customer executives to define enterprise MCP (Model Context Protocol) strategies including context management, secure AI orchestration, and governanceTranslate emerging AI capabilities into practical, scalable enterprise use cases that drive measurable business outcomesPosition Workato as the integration and orchestration backbone for enterprise AI transformationDomain Expertise & Thought LeadershipEstablish yourself as the recognized authority across iPaaS, API Management (APIM), data orchestration, EDI, and AI/Agentic automationLead Art of the Possible workshops that fundamentally shift how customers think about enterprise integration and intelligent automationRepresent Workato at industry conferences, customer advisory boards, analyst briefings, and partner eventsCreate high-impact thought leadership content: blogs, white papers, webinars, reference architectures, and technical videosShape industry narratives and best practices that establish Workato as the category leaderDeal Acceleration & Commercial ImpactAccelerate deal velocity through technical validation, competitive differentiation, and executive trust-buildingIdentify and shape strategic expansion opportunities by uncovering automation, integration, and AI-driven transformation initiativesPartner with Account Executives and Sales Leadership on account strategy, competitive positioning, and C-level engagement tacticsArticulate compelling ROI narratives and business case frameworks that accelerate buying decisionsDemonstrate measurable impact on win rates, deal size, and sales cycle length in strategic opportunitiesStrategic Advisory & Technical LeadershipLead high-impact customer engagements requiring executive-level judgment, architectural vision, and industry expertiseGuide prospects and customers through Enterprise Orchestration vision and roadmap developmentDevelop prioritization frameworks for integration, automation, and AI use casesLead technology evaluation and vendor selection processes with enterprise customersDesign governance, scalability, and enterprise operating models for automation initiativesProduct Influence & Market IntelligenceAct as the voice of the customer to Product and Engineering teams, channeling field insights into actionable roadmap inputIdentify capability gaps, competitive threats, and market opportunities based on executive-level customer conversationsDevelop and refine competitive positioning, objection handling, and differentiation strategiesDefine reusable patterns, reference architectures, and technical frameworks that accelerate customer successInfluence industry analysts and thought leaders to strengthen Workato's market positionInternal Enablement & Team DevelopmentEducate and enable Sales Engineers, Account Executives, and Customer Success teams on complex technical capabilities and emerging trendsDevelop strategic frameworks, competitive positioning, and executive engagement playbooks for enterprise accountsMentor technical team members, helping them develop deeper domain expertise and executive engagement skillsCreate scalable technical enablement content and programs that amplify your expertise across the field organizationDrive customer reference creation and participation in case studies, speaking opportunities, and advisory boardsRequirementsQualifications / Experience / Technical SkillsBachelor's degree in Computer Science, Software Engineering, or a related field (or equivalent experience)20+ years of technology transformation experience, including integration, middleware, or API management platforms15+ years in an Enterprise Architect, CTO, VP Engineering, or similar senior architecture/leadership roleDemonstrated experience advising C-level executives on technology strategy and enterprise transformationStrong understanding of enterprise security, governance, and operating modelsProven track record of driving platform expansion and value realization in enterprise accountsExcellent executive communication skills, including board-level presentations and strategic documentationAbility to operate independently in complex, ambiguous environments and take ownership of outcomesTravel to client sites up to 50%, with flexibility based on regional needsSoft Skills / Personal CharacteristicsMaster's degree in Computer Science, Software Engineering, Business, or related fieldDeep knowledge of key enterprise applications: Salesforce, NetSuite, Workday, ServiceNow, SAP, OracleExperience with cloud platforms: AWS, Azure, and GCPHands-on experience with AI/ML platforms and agentic automation frameworksExperience in a high-growth startup or scale-up environmentEstablished personal brand and thought leadership presence in the integration/automation spaceMeasures of SuccessLong-term success for this leader will be measured by their ability to:Embed Workato at the heart of technology strategy conversations across the region's most influential enterprisesCultivate sustained engagement with senior technology and engineering leaders ensuring Workato becomes synonymous with Enterprise Orchestration and AI orchestrationCreate a robust pipeline of seven-figure opportunities tied to transformation initiativesReframe Workato in the minds of decision-makers and analysts as the essential platform for AI-enabled enterprise integrationLeave behind scalable playbo