WillHire

Principal, Strategic Customer Engagement – AI

WillHire

full-time

Posted on:

Location Type: Remote

Location: FloridaMassachusettsUnited States

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Salary

💰 $154,400 - $231,500 per year

Job Level

Tech Stack

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