Forward Deployed AI Strategist

About Climb

Climb is a Data and AI consultancy that partners with enterprises to design, build, and operationalize modern data platforms and production AI systems. As a Databricks partner, we go deep on lakehouse architecture, machine learning, and applied AI, with a bias toward production over proof of concept. Our team brings deep technical expertise and a builder's mindset to every engagement, and we measure our work not just by what ships, but by the business impact it drives.

Role Summary

The Forward Deployed AI Strategist defines how organizations transform through AI before implementation begins. You partner with executive teams to identify where AI creates meaningful business value, assess the organization's readiness, and develop the transformation strategy, operating model, and investment roadmap that guide everything that follows.

Beyond individual engagements, you shape how Climb delivers AI transformation. You establish the methodologies, value frameworks, and executive playbooks that AI Leads apply across engagements, ensuring every customer benefits from a repeatable approach while every engagement improves the next.

This is an individual contributor leadership role operating at the executive level. You work directly with C-suite leaders, boards, and investors to align technology strategy with business outcomes, while guiding AI Leads and delivery teams through the successful execution of that strategy.

Key Responsibilities

• Lead blueprint engagements: current-state assessment, gap analysis, and a prioritized, sequenced initiative roadmap.

• Run executive discovery with C-Suite leadership and Boards to surface strategic goals, constraints, and success criteria.

• Quantify the value: size the business problem, model TCO and ROI, and define the pilot, MVP, success criteria, and timeline.

• Build board-ready transformation cases that connect AI investment to value-creation metrics: revenue per head, time-to-outcome, margin, and delivery predictability.

• Facilitate executive alignment workshops that move stakeholders from awareness to decision.

• Provide executive oversight across transformation programs, guiding AI Leads through strategic decisions, cross-workstream alignment, and evolving business priorities.

• Serve as the executive advisor and escalation point through delivery close; act as the escalation point that unblocks technical and political issues.

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

• Surface expansion signals across the client organization and route them to the account team.

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

• Mentor AI Leads on executive engagement, transformation strategy, value creation, and consultative leadership.

Required Qualifications

• 12+ years across software, technical consulting, or technology strategy, with demonstrable depth on both the engineering and product sides of a software organization.

• 5+ years leading transformation, strategy, or technical advisory engagements with engineering and product organizations.

• Proven track record building and presenting technology transformation roadmaps to C-level and board audiences.

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

• Experience sizing and sequencing multi-team, multi-quarter transformation programs.

• Hands-on familiarity with AI-assisted development and agentic tooling: you don't configure it daily, but you speak the language credibly and know what is and isn't real.

• Professional services delivery experience with scope ownership and deliverable accountability.

Preferred Qualifications

• Background in PE or growth-equity-backed companies: you understand value-creation timelines and board expectations.

• Experience designing AI governance and adoption guardrails for enterprise organizations.

• Familiarity with the Databricks platform and data-readiness considerations is a plus.

• Familiarity with delivery and developer-experience metrics frameworks (e.g., DORA, DevEx, SPACE).

Note on certification: Databricks experience is valued but not required at hire. Both Databricks and Anthropic certification are expected to be obtained post-hire.

Who Thrives Here

• You think in business transformations, not projects, and can connect AI investments to measurable enterprise value.

• You earn credibility with executives because you understand both technology and how businesses create value.

• You create repeatable methods that improve every engagement, not just the one in front of you.

• You influence organizations through strategy, alignment, and clear decision-making rather than authority.

Why Climb

• Ground floor, real backing. You are joining early, with founders who have built and exited firms like this before. You help write the playbook rather than inherit one.

• Outcomes, not hours. We sell and deliver against business results. Advancement is tied to delivery performance and account impact, not utilization targets.

• Senior team, no body-shop drag. Small pods of A-players, heavy internal AI leverage, and no bloated middle layers between you and the work.

• IP that compounds. Every engagement feeds reusable accelerators, patterns, and points of view back into the practice.

• Proximity to where decisions get made. Your clients are PE portcos and enterprise leadership teams making AI transformation calls right now.

What We Offer

• Competitive base salary with performance-based bonuses

• MacBook Pro and swag kit so you can do your best work

• Comprehensive health, dental, and vision insurance

• 401(k) with company match

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

• Professional development budget including Databricks and cloud certifications

• Spot bonuses for relevant certifications

• Conference attendance and thought leadership opportunities

• Collaborative, low-ego culture with direct access to leadership

• Opportunity to shape a growing practice from the ground floor

Climb is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.