Chief Strategic Architect

Workato•Boston, MA

5h•Hybrid

About The Position

Workato transforms technology complexity into business opportunity. As the leader in enterprise orchestration, Workato helps businesses globally streamline operations by connecting data, processes, applications, and experiences. Its AI-powered platform enables teams to navigate complex workflows in real-time, driving efficiency and agility. Trusted by a community of 400,000 global customers, Workato empowers organizations of every size to unlock new value and lead in today’s fast-changing world. Workato believes in fostering a flexible, trust-oriented culture that empowers everyone to take full ownership of their roles. They are driven by innovation and looking for team players who want to actively build the company. They also believe in balancing productivity with self-care, offering a vibrant and dynamic work environment along with a multitude of benefits.

Requirements

Bachelor'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 platforms
15+ years in an Enterprise Architect, CTO, VP Engineering, or similar senior architecture/leadership role
Demonstrated experience advising C-level executives on technology strategy and enterprise transformation
Strong understanding of enterprise security, governance, and operating models
Proven track record of driving platform expansion and value realization in enterprise accounts
Excellent executive communication skills, including board-level presentations and strategic documentation
Ability to operate independently in complex, ambiguous environments and take ownership of outcomes
Travel to client sites up to 50%, with flexibility based on regional needs

Nice To Haves

Master's degree in Computer Science, Software Engineering, Business, or related field
Deep knowledge of key enterprise applications: Salesforce, NetSuite, Workday, ServiceNow, SAP, Oracle
Experience with cloud platforms: AWS, Azure, and GCP
Hands-on experience with AI/ML platforms and agentic automation frameworks
Experience in a high-growth startup or scale-up environment
Established personal brand and thought leadership presence in the integration/automation space

Responsibilities

Serve as Workato's technical authority and strategic advisor to our most critical prospects, customers, and the broader market within their assigned region.
Operate 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.
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.
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.
Influence deal outcomes, product direction, and industry perception, ensuring Workato is recognized as the definitive leader in Enterprise Orchestration.
Deep immersion into Workato's AI vision, product roadmap, and GTM strategy (Days 0-30)
Shadow at least 10 executive customer conversations (Days 0-30)
Develop initial point of view for engagement with CIO/CTO/CDO personas (Days 0-30)
Lead first strategic engagements with enterprise accounts (Days 30-60)
Co-develop executive playbooks with Sales and Product teams (Days 30-60)
Establish feedback loops with Product and Engineering teams (Days 30-60)
Cultivate trusted relationships with C-level executives in 5+ strategic accounts (Days 60-90)
Co-create first AI-driven integration use cases with customers (Days 60-90)
Establish thought leadership presence through content and speaking opportunities (Days 60-90)
Engage directly with C-level executives (CIOs, CTOs, Chief Data Officers, Chief AI Officers) at enterprise accounts to shape integration strategies that solve complex business challenges
Serve as trusted technical advisor throughout the customer lifecycle - from initial engagement through expansion - providing strategic guidance rooted in real-world operator experience
Build lasting peer-to-peer relationships that position you as the go-to expert on enterprise integration, AI orchestration, and automation at scale
Act as technical closer in competitive deals, articulating why Workato's architecture differentiates us from competitors like MuleSoft and Boomi
Influence enterprise architecture decisions and multi-year technology strategies at the executive level
Shape and guide customers' AI and agentic automation journeys, leveraging Workato's AI capabilities and ecosystem
Advise on the design and adoption of agent-based workflows, human-in-the-loop models, and decision automation frameworks
Partner with customer executives to define enterprise MCP (Model Context Protocol) strategies including context management, secure AI orchestration, and governance
Translate emerging AI capabilities into practical, scalable enterprise use cases that drive measurable business outcomes
Position Workato as the integration and orchestration backbone for enterprise AI transformation
Establish yourself as the recognized authority across iPaaS, API Management (APIM), data orchestration, EDI, and AI/Agentic automation
Lead "Art of the Possible" workshops that fundamentally shift how customers think about enterprise integration and intelligent automation
Represent Workato at industry conferences, customer advisory boards, analyst briefings, and partner events
Create high-impact thought leadership content: blogs, white papers, webinars, reference architectures, and technical videos
Shape industry narratives and best practices that establish Workato as the category leader
Accelerate deal velocity through technical validation, competitive differentiation, and executive trust-building
Identify and shape strategic expansion opportunities by uncovering automation, integration, and AI-driven transformation initiatives
Partner with Account Executives and Sales Leadership on account strategy, competitive positioning, and C-level engagement tactics
Articulate compelling ROI narratives and business case frameworks that accelerate buying decisions
Demonstrate measurable impact on win rates, deal size, and sales cycle length in strategic opportunities
Lead high-impact customer engagements requiring executive-level judgment, architectural vision, and industry expertise
Guide prospects and customers through Enterprise Orchestration vision and roadmap development
Develop prioritization frameworks for integration, automation, and AI use cases
Lead technology evaluation and vendor selection processes with enterprise customers
Design governance, scalability, and enterprise operating models for automation initiatives
Act as the voice of the customer to Product and Engineering teams, channeling field insights into actionable roadmap input
Identify capability gaps, competitive threats, and market opportunities based on executive-level customer conversations
Develop and refine competitive positioning, objection handling, and differentiation strategies
Define reusable patterns, reference architectures, and technical frameworks that accelerate customer success
Influence industry analysts and thought leaders to strengthen Workato's market position
Educate and enable Sales Engineers, Account Executives, and Customer Success teams on complex technical capabilities and emerging trends
Develop strategic frameworks, competitive positioning, and executive engagement playbooks for enterprise accounts
Mentor technical team members, helping them develop deeper domain expertise and executive engagement skills
Create scalable technical enablement content and programs that amplify your expertise across the field organization
Drive customer reference creation and participation in case studies, speaking opportunities, and advisory boards