Principal AI GTM Strategist – Outbound & Demand Generation

Workday; Chicago (IL); Hybrid; USD 158,000 - 238,000; Full time

Benefits offered by this job

Flexible work arrangement

Stock grants

Job summary

Workday is seeking a strategic operator to bridge business strategy and technical execution for AI-driven demand generation. You will map the end-to-end process and translate business needs into clear system requirements, collaborating with Sales, SDR, Product, and Marketing leadership.

You will define governance and guardrails for AI workflows, ensuring alignment with ICP targets, pipeline goals, and revenue metrics, while coordinating with GTM tech and data teams to implement scalable

Qualifications

• 8 years of GTM/revenue operations or outbound prospecting experience, specifically in AI‑driven demand generation and prospecting strategy.
• 6 years of designing and mapping end‑to‑end GTM process architecture (signal identification, intent scoring, enrichment logic, outbound workflows) across an enterprise‑scale revenue organization.
• 5 years of experience influencing VP and SVP‑level stakeholders across Sales, SDR, and Marketing to drive organizational pivots toward modern, AI‑driven GTM models.

Responsibilities

• Map the operational framework: Define and map the end-to-end strategy for our AI-driven demand-generation and prospecting process — from signal identification and intent scoring to enrichment logic and outbound workflows — without performing the hands‑on technical build.
• Translate business requirements for technical teams: Serve as the primary translator between frontline GTM leaders (Sales, SDR, Marketing, Partner, Product, CS) and technical/systems teams. Gather real‑world use cases, analyze buyer behavior, and convert commercial objectives into clear functional requirements and system logic for engineers to execute.
• Align cross‑functional strategy: Partner with Sales, SDR, Partner, Product and Marketing executives to ensure every AI demand gen initiative supports ICP targeting, pipeline goals, deliverability standards, and revenue metrics.
• Define system logic and guardrails: Establish the governance, brand‑safety rules, and decision logic for AI workflows, leaving day‑to‑day tool configuration to systems teams and campaign execution to functional GTM teams.
• Track industry best practices: Monitor fast‑moving trends in GTM AI, demand generation, and prospecting strategy to advise leadership on where to innovate and how to prioritize system investments.
• Partner with Industry analysts and key vendors to deliver ahead of the curve innovation.
• Measure prospecting effectiveness: Partner with analytics to measure the performance of prospecting frameworks and continuously optimize conversion pathways.
• Proactively assess frameworks on a regular basis and make recommendations for areas of opportunity in QBRs to consistently improve our demand generation engine.

Skills

GTM strategy

Revenue operations

AI-driven demand gen

Tools

Clay

6sense

Salesforce

SalesLoft

Outreach

Job description

About the Team

The Global Customer Operations (GCO) Demand and Voice of the Customer team is responsible for driving global strategic pipeline growth through innovative demand generation programs, scalable processes, and customer-informed initiatives. The team brings together global market insights, industry best practices, and modern AI-driven approaches to help Workday build pipeline, generate demand, and better understand customer needs across regions. By partnering closely with stakeholders around the world, the team helps shape programs that improve execution, strengthen customer engagement, and support Workday’s continued global growth.

About the Role

We're looking for a strategic operator who pairs deep demand gen and prospecting experience with the ability to bridge business strategy and technical execution. This role does not configure software or build workflows in code. Instead, you'll act as the strategic translator and GTM architect — working shoulder to shoulder with Sales, SDR, Product, and Marketing leadership to map our AI-driven demand-generation process and turn business needs into clear, high-level system requirements. You'll be the key liaison to our GTM Tech & Systems, BT, and Data Engineering teams, giving them the logic, functional specs, and business guardrails they need to build and maintain a modern demand-generation engine.

Key Responsibilities

• Map the operational framework: Define and map the end-to-end strategy for our AI-driven demand-generation and prospecting process — from signal identification and intent scoring to enrichment logic and outbound workflows — without performing the hands‑on technical build.
• Translate business requirements for technical teams: Serve as the primary translator between frontline GTM leaders (Sales, SDR, Marketing, Partner, Product, CS) and technical/systems teams. Gather real‑world use cases, analyze buyer behavior, and convert commercial objectives into clear functional requirements and system logic for engineers to execute.
• Align cross‑functional strategy: Partner with Sales, SDR, Partner, Product and Marketing executives to ensure every AI demand gen initiative supports ICP targeting, pipeline goals, deliverability standards, and revenue metrics.
• Define system logic and guardrails: Establish the governance, brand‑safety rules, and decision logic for AI workflows, leaving day‑to‑day tool configuration to systems teams and campaign execution to functional GTM teams.
• Track industry best practices: Monitor fast‑moving trends in GTM AI, demand generation, and prospecting strategy to advise leadership on where to innovate and how to prioritize system investments.
• Partner with Industry analysts and key vendors to deliver ahead of the curve innovation.
• Measure prospecting effectiveness: Partner with analytics to measure the performance of prospecting frameworks and continuously optimize conversion pathways.
• Proactively assess frameworks on a regular basis and make recommendations for areas of opportunity in QBRs to consistently improve our demand generation engine.

Basic Qualifications

• 8 years of GTM/revenue operations or outbound prospecting experience, specifically in AI‑driven demand generation and prospecting strategy.
• 6 years of designing and mapping end‑to‑end GTM process architecture (signal identification, intent scoring, enrichment logic, outbound workflows) across an enterprise‑scale revenue organization.
• 5 years of experience influencing VP and SVP‑level stakeholders across Sales, SDR, and Marketing to drive organizational pivots toward modern, AI‑driven GTM models.

Preferred Qualifications

• Hands‑on outbound experience in B2B prospecting, SDR leadership, or outbound strategy, with a working knowledge of what drives prospect engagement and how sales teams operate day to day.
• Ability to analyze pipeline metrics, sales cycles, and conversion rates to ensure technical capabilities are directed toward real revenue outcomes.
• Proven capability designing decision trees and system logic (if‑this‑then‑that triggers, data‑enrichment waterfalls, signal prioritization).
• Deep familiarity with modern GTM AI concepts, LLM capabilities, and revenue tech stacks (i.e. Clay, 6sense, Salesforce, Sales Engagement Platforms, Outreach, SalesLoft).
• Experience writing clear BRDs, functional specs, or user stories for systems, IT, and software development teams.

Workday Pay Transparency Statement

The annualized base salary ranges for the primary location and any additional locations are listed below. Workday pay ranges vary based on work location. As a part of the total compensation package, this role may be eligible for the Workday Bonus Plan or a role‑specific commission/bonus, as well as annual refresh stock grants.

Primary Location: USA.CA.Pleasanton

Primary Location Base Pay Range: $158,400 USD - $237,600 USD

Additional US Location(s) Base Pay Range: $133,800 USD - $237,600 USD

Our Approach to Flexible Work

With Flex Work, we’re combining the best of both worlds: in‑person time and remote. Our approach enables our teams to deepen connections, maintain a strong community, and do their best work. We know that flexibility can take shape in many ways, so rather than a number of required days in‑office each week, we simply spend at least half (50%) of our time each quarter in the office or in the field with our customers, prospects, and partners (depending on role). This means you'll have the freedom to create a flexible schedule that caters to your business, team, and personal needs, while being intentional to make the most of time spent together. Those in our remote “home office” roles also have the opportunity to come together in our offices for important moments that matter.

Pursuant to applicable Fair Chance law, Workday will consider for employment qualified applicants with arrest and conviction records.

Workday is an Equal Opportunity Employer including individuals with disabilities and protected veterans. Workday is committed to providing reasonable accommodations for qualified individuals during our application process, in order to perform one or more essential functions of their job, as well as regarding the use of AI tools for employment decision‑making to any degree. Please see below for more details including how to request an accommodation as a qualified veteran, due to a disability or for religious reasons, or as otherwise provided under applicable law.

Workday prohibits taking adverse action against any candidate or employee for reporting a possible violation of this policy, requesting one or more work accommodations, exercising a privacy right, or cooperating in an investigation in accordance with applicable law. Any employee who retaliates against a candidate or employee for doing so may be subject to disciplinary action, up to and including termination of employment, to the fullest extent allowable under applicable law.

If you require a reasonable accommodation, you may email [e-mail], as far in advance as possible.

Workday is proud to be an equal opportunity workplace. Individuals seeking employment at Workday are considered without regards to age, ancestry, color, gender (including pregnancy, childbirth, or related medical conditions), gender identity or expression, genetic information, marital status, medical condition, mental or physical disability, national origin, protected family care or medical leave status, race, religion (including beliefs and practices or the absence thereof), sexual orientation, military or veteran status, or any other characteristic protected by federal, state, or local laws. Further, pursuant to applicable local ordinances, Workday will consider for employment qualified applicants with arrest and conviction records. We do not accept resumes from headhunters, placement agencies, or other suppliers that have not signed a formal agreement with us.

Workday is committed to providing reasonable accommodations for qualified individuals during our application process, in order to perform one or more essential functions of their job, as well as regarding the use of AI tools for employment decision‑making to any degree. Please see below for more details including how to request an accommodation as a qualified veteran, due to a disability or for religious reasons, or as otherwise provided under applicable law.

Workday prohibits taking adverse action against any candidate or employee for reporting a possible violation of this policy, requesting one or more work accommodation, exercising a privacy right, or cooperating in an investigation in accordance with applicable law. Any employee who retaliates against a candidate or employee for doing so may be subject to disciplinary action, up to and including termination of employment, to the fullest extent allowable under applicable law.

If you require a reasonable accommodation, you may email [e-mail], as far in advance as possible.