Forward Deployed AI Strategist

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead blueprint initiatives: assess the current state, conduct gap analyses, and create a prioritized, sequenced initiative roadmap.

• Conduct executive discovery sessions with C-Suite leaders and Boards to identify strategic objectives, constraints, and criteria for success.

• Quantify value by sizing the business challenge, modeling TCO and ROI, and defining the pilot, MVP, success metrics, and timeline.

• Develop board-ready transformation cases that link AI investments to value-creation metrics such as revenue per head, time-to-outcome, margin, and delivery predictability.

• Facilitate executive alignment workshops that transition stakeholders from awareness to decision-making.

• Provide executive oversight for transformation programs, guiding AI Leads through strategic choices, cross-workstream alignment, and shifting business priorities.

• Act as the executive advisor and escalation point through the delivery phase; serve as the escalation point for unblocking technical and political challenges.

• Shape follow-on scope throughout the delivery process; by the handoff, you will have a working hypothesis for the execution program and present it at the readout.

• Identify expansion signals across the client organization and direct them to the account team.

• Own and continuously refine Climb's AI transformation methodology, encompassing blueprint frameworks, value models, executive workshops, and delivery playbooks.

• Mentor AI Leads in areas such as executive engagement, transformation strategy, value creation, and consultative leadership.

⛳️ Requirements

• 12+ years of experience in software, technical consulting, or technology strategy, with proven expertise in both engineering and product aspects of a software organization.

• 5+ years of experience leading transformation, strategy, or technical advisory projects within engineering and product teams.

• A strong track record of developing and presenting technology transformation roadmaps to C-level executives and board members.

• Demonstrated proficiency in value-based scoping (TCO/ROI), authoring requirements documents, and managing delivery to achieve measurable outcomes.

• Experience in sizing and sequencing transformation programs involving multiple teams over multiple quarters.

• Hands-on knowledge of AI-assisted development and agentic tooling: while you may not configure it daily, you can speak the language credibly and know what is feasible.

• Experience in professional services delivery with ownership of scope and accountability for deliverables.

🏝️ Benefits

• Competitive base salary with performance-based bonuses

• MacBook Pro and swag kit to support your best work

• Comprehensive health, dental, and vision insurance

• Generous holidays, flexible PTO, and a remote-first work environment

• Professional development budget including Databricks and cloud certifications

• Spot bonuses for obtaining relevant certifications

• Opportunities for conference attendance and thought leadership

• A collaborative, low-ego culture with direct access to leadership

• A chance to influence and shape a growing practice from the ground up