
Principal, Strategic Customer Engagement – AI
WillHire
full-time
Posted on:
Location Type: Remote
Location: Florida • Massachusetts • United States
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Salary
💰 $154,400 - $231,500 per year
Job Level
About the role
- Lead strategic AI engagements and serve as the architect of the joint AI roadmap with senior customer stakeholders.
- Partner with sales and account teams to drive AI opportunities through evaluation and decision phases in the sales process.
- Shape and scale how Workday shows up in the AI market: what we say, where we play, and how we prove value.
- Maintain and deepen relationships with account teams, customers, and channel partners to connect their challenges with the Workday AI product suite.
- Lead executive‑level AI conversations to help customers define an AI vision, roadmap, and operating model grounded in Workday’s capabilities; facilitate executive workshops, advisory sessions, and briefings to align on AI strategy and secure buy‑in across the C‑suite and functional leaders.
- Act as a consultative advisor, diving deep into a customer’s business to diagnose problems and position Workday’s AI solutions to unlock value; translate customer priorities (e.g., revenue growth, cost optimization, productivity, employee experience) into concrete AI use cases and value hypotheses.
- Serve as a Workday AI solutions expert, clearly articulating how our AI products, agents, and platform capabilities solve real problems and deliver business outcomes.
- Maintain deep, current expertise on the AI market—including LLMs, generative AI, copilots, agents, deployment approaches, and competitive dynamics—and use this to sharpen how we position Workday AI.
- Execute AI GTM programs and plays that can be scaled across regions, segments, and industries.
- Collaborate closely with internal stakeholders across Product, Sales, Engineering, Marketing, and Strategy to ensure our offerings address the evolving challenges of leading global enterprises.
- Provide structured, customer‑backed feedback on needs, competitive dynamics, and emerging use cases, acting as a connector between field and product teams so learnings from pilots and lighthouse customers inform how we build and position Workday AI.
- Maintain accurate and timely customer/prospect, pipeline, and service forecast data in alignment with Workday standards.
- Contribute to developing and refining field‑ready assets (narratives, pitch materials, case studies, playbooks, talk tracks) to support Sales, Solution Consulting, and Customer Success.
- Contribute to thought leadership efforts (e.g., blogs, events, webinars, customer forums) to strengthen Workday’s voice in the AI market.
Requirements
- 7+ years in relevant roles (e.g., AI Sales, AI Product Strategy, AI Sales Strategy, Customer Strategy, Management Consulting, or similar customer‑facing strategic roles).
- Demonstrated experience leading executive‑level conversations, public speaking, and producing strategic content (presentations, narratives, or thought leadership).
- Experience in or with regulated industries; HR technology experience strongly preferred.
- Strong background in sales strategy, AI‑related sales or GTM strategy, or similar roles focused on technology or AI‑driven solutions.
- Proven ability to map AI capabilities to business value (e.g., revenue growth, cost savings, experience improvements, operational efficiencies) and to build compelling business cases.
- Solid technical understanding of AI concepts (LLMs, generative AI, data platforms, ML, copilots/agents) sufficient to partner credibly with product and engineering in a senior, business‑facing capacity.
- Deep understanding of the end‑to‑end customer lifecycle (Sales, Deployment, Post‑Go‑Live / Adoption / Expansion).
- Experience working in entrepreneurial or high‑growth environments and with global, cross‑functional teams.
- Strong executive presence with the ability to influence and align senior stakeholders, both externally with customers and internally.
- Experience working with Fortune 500 or large enterprise clients.
- Deep understanding of the AI market, including copilots, agents, ML, and LLMs, with demonstrated curiosity and a willingness to continuously learn new AI solutions.
- Proficiency with Workday (or similar HCM/ERP platforms), including experience with intelligent features such as agents, copilots, or AI‑powered workflows.
- Passion for revenue impact, commercialization, and scaling customer adoption.
- Strong program and project management skills; able to self‑manage, prioritize, and deliver complex cross‑functional initiatives end‑to‑end.
- Excellent written and verbal communication skills, including the ability to simplify complex AI concepts into clear, business‑oriented narratives.
- Interest in AI and the future of work, including emerging trends in talent, productivity, and organizational design.
- BA / BS / BE degree or higher.
Benefits
- Health insurance
- 401(k) matching
- Flexible work hours
- Paid time off
- Remote work options
- Professional development opportunities
- Stock options
- Equipment allowances
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
Hard Skills & Tools
AI SalesAI Product StrategySales StrategyGTM StrategyLLMsGenerative AIData PlatformsMachine LearningCopilotsAI-powered Workflows
Soft Skills
Executive PresencePublic SpeakingInfluencing StakeholdersCommunication SkillsProgram ManagementProject ManagementConsultative AdvisoryRelationship ManagementStrategic Content ProductionCross-functional Collaboration
Certifications
BA DegreeBS DegreeBE Degree