climb-ai - Forward Deployed AI Strategist
Requirements
• 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. • 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. • 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.
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.
Benefits
• 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. • 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 • 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
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