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Chief Strategic Architect

Boston, Massachusetts; Charlotte, North Carolina; New York, New York

About Workato

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. Learn how Workato helps businesses of all sizes achieve more at workato.com.

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 world

  • Deloitte Tech Fast 500 ranked us as the 17th fastest growing tech company in the Bay Area, and 96th in North America

  • Quartz ranked us the #1 best company for remote workers

Responsibilities

We 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 Days

Learn & Align (Days 0-30)

  • Deep immersion into Workato's AI vision, product roadmap, and GTM strategy

  • Shadow at least 10 executive customer conversations

  • Develop initial point of view for engagement with CIO/CTO/CDO personas

Engage & Formulate (Days 30-60)

  • Lead first strategic engagements with enterprise accounts

  • Co-develop executive playbooks with Sales and Product teams

  • Establish feedback loops with Product and Engineering teams

Influence & Scale (Days 60-90)

  • Cultivate trusted relationships with C-level executives in 5+ strategic accounts

  • Co-create first AI-driven integration use cases with customers

  • Establish thought leadership presence through content and speaking opportunities

Technical Trust & Executive Relationships

  • 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

AI, Agentic Automation & Enterprise MCP Strategy

  • 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

Domain Expertise & Thought Leadership

  • 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

Deal Acceleration & Commercial Impact

  • 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

Strategic Advisory & Technical Leadership

  • 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

Product Influence & Market Intelligence

  • 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

Internal Enablement & Team Development

  • 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

Requirements

Qualifications / Experience / Technical Skills

  • 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

Soft Skills / Personal Characteristics

  • 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

Measures of Success

Long-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 enterprises

  • Cultivate sustained engagement with senior technology and engineering leaders ensuring Workato becomes synonymous with Enterprise Orchestration and AI orchestration

  • Create a robust pipeline of seven-figure opportunities tied to transformation initiatives

  • Reframe Workato in the minds of decision-makers and analysts as the essential platform for AI-enabled enterprise integration

  • Leave behind scalable playbooks and repeatable narratives that enable go-to-market teams to engage enterprise audiences with authority and credibility.

 

The estimated pay range for this role is between  $240,000 - $280,000 + Bonus, but candidates outside of this band are encouraged to apply.

Job Req ID: 2645

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