VP of Training & Enablement at Go Cadre

United States

ABOUT CADRE AI Cadre AI is an AI strategy and integration consultancy that helps enterprises move from AI interest to AI execution. We partner with organizations to design, build, and deploy custom AI solutions that solve real business problems. Our team of AI strategists, engineers, and implementation specialists work directly with clients to identify high-impact use cases, architect AI-powered workflows, and deliver production-ready systems built on leading LLM and agentic AI platforms. We operate in delivery pods, each responsible for full-cycle AI engagements from discovery through deployment. Our clients range from mid-market companies taking their first steps with AI to Fortune 500 enterprises scaling AI across business units. We are known for translating technical complexity into business value and for building solutions that teams actually use. THE ROLE You will own Cadre AI's training and enablement. This means you are responsible for the strategy, content design, and delivery of all client-facing training programs, from live C-suite sessions to on-demand video libraries for clients. Your job is to ensure that every client who receives training from Cadre walks away understanding how to use the AI solutions we build for them and how to lead their teams through the adoption process. Additionally, your team would pioneer trainings on new hot AI topics so that we are always positioned as a thought leader in the space. You will emcee trainings, bring in technical experts as needed, and drive the experience end to end. You will build and launch a premium standalone training offering designed to generate incremental revenue beyond our core consulting engagements. This includes defining the product, building the go-to-market approach, and packaging our training expertise into a scalable service that clients will pay for separately. You will also lead change management efforts externally to help drive adoption with clients as well as internally to help Cadre teams adopt AI-first workflows and tooling as the company scales.  This role thrives on someone who is equal parts strategic thinker and exceptional performer - it’s a true player / coach role where you need to be in the details and execute on your own. You need to be charismatic and polished in front of senior executives, highly organized behind the scenes, and relentless about follow-through. You are comfortable designing the training strategy on Monday and delivering a live session to a client's C-suite on Wednesday. You think like an entrepreneur, not a traditional Learning and Development leader, meaning you tailor every engagement to the client's actual business context rather than delivering a generic curriculum. WHAT YOU'LL DO CLIENT TRAINING STRATEGY & DELIVERY * Own the full lifecycle of client training engagements, from intake and scoping through content design, delivery, and follow-up. Work with the sales team to understand what was sold, then conduct a deeper dive into the client's org structure, use cases, and adoption readiness to design training that actually moves the needle. * Deliver live training sessions to client C-suite, functional leaders, and end users. Act as the primary facilitator and subject matter expert, bringing in Cadre engineers or specialists as needed for deep technical topics. Ensure sessions are interactive, business-focused, and tailored to the audience's familiarity with AI. * Manage the content library offered to clients, working with your direct report to produce high-quality on-demand training videos, guides, and resources. Continuously refresh and improve the library based on client feedback and emerging AI capabilities. * Coordinate across delivery pods to standardize training best practices, share reusable content, and ensure consistency in how Cadre presents AI enablement to clients. Build systems that allow training to scale without requiring you to personally deliver every session. PREMIUM TRAINING PRODUCT DEVELOPMENT * Design and launch a standalone premium training and change management offering that generates new revenue streams for Cadre. Define what this product is, who it's for, what it costs, and how it's differentiated from the training embedded in our core consulting engagements. * Build the go-to-market plan for the premium offering, including positioning, pricing, packaging, and sales enablement materials. Work with the sales team to identify prospects who would be a fit for this service and support deal structuring. * Track financial performance of the premium offering and report on revenue contribution, client uptake, and product-market fit. Iterate on the offering based on what clients are willing to pay for and what drives the highest ROI. CHANGE MANAGEMENT & ENABLEMENT * Lead external (client) and internal (Cadre) change management initiatives to help teams adopt AI-first tools, workflows, and mindsets as the company scales. This includes onboarding new hires to our AI stack, training delivery teams on new client-facing AI products, and supporting operations teams as internal processes evolve. * Partner with leadership to identify areas where training or enablement can accelerate adoption of new systems, reduce friction in delivery workflows, or improve team productivity. Build lightweight, high-impact interventions rather than heavy-lift formal programs. WHAT YOU NEED TO SUCCEED * 7+ years of experience in consulting, enablement, training, or client-facing roles where you were responsible for designing and delivering high-stakes presentations or workshops to senior executives. You have stood in front of C-suite audiences and earned their trust through preparation, polish, and business acumen. * Proven ability to own a client engagement from end to end, not just execute a predefined curriculum. You know how to ask the right questions during discovery, tailor content to the client's industry and business model, and adjust your delivery style based on who is in the room. You think like a consultant, not a traditional trainer. * Strong understanding of the current AI landscape, including how LLMs, agentic AI, and enterprise AI platforms are being adopted in business contexts. You can speak credibly about AI trends, use cases, and implementation challenges in a way that resonates with business leaders, not just technical teams. You don't need to be an engineer, but you need to be able to hold your own in a conversation about what AI can and can't do. * Exceptional executive presence and communication skills. You are charismatic, polished, and engaging in front of an audience. You can MC a training session, manage group dynamics, handle tough questions on the fly, and keep a room energized for a full-day workshop. Clients leave your sessions feeling smarter and more confident about their AI strategy. * Highly organized and detail-oriented behind the scenes. You build run-of-show documents, prepare backup materials, rehearse transitions, and anticipate what could go wrong. You are relentless about follow-through, ensuring that every commitment you make to a client gets delivered on time and on spec. * Experience building or launching a new service offering, product line, or revenue stream. You have taken something from concept to market, including defining the positioning, pricing, and go-to-market strategy. You are comfortable with ambiguity and don't need a fully baked playbook to get started. * Bias toward systems and scalability. You don't want to be the only person who can deliver a great training session; you want to build the content, templates, and processes that allow others to do it well. You think about how to codify what works and make it repeatable across the organization. * Quick learner with strong technical fluency. You can pick up new platforms, tools, and content management systems without extensive hand-holding. You are comfortable in a fast-moving tech environment and can adapt to new AI capabilities, client portal systems, or internal tooling as the company evolves. * Collaborative leadership style with experience managing at least one direct report. You know how to delegate execution work while staying close enough to ensure quality and consistency. You give clear direction, provide constructive feedback, and develop your team's skills over time. * Ownership mentality and comfort with accountability. You are responsible for the quality and profitability of the training pillar, and you take that seriously. You track what's working, flag what isn't, and proactively bring solutions to leadership rather than waiting to be told what to fix. WHY CADRE AI * Work at the frontier of AI adoption. You will see how companies across industries are implementing AI in production environments, giving you a unique vantage point on what works, what doesn't, and where the technology is heading. You will train clients on solutions that are being built in real time, not last year's playbook. * Own a strategic pillar of the business. This isn't a support function. Training and enablement is one of Cadre's eight core pillars of AI enablement, and you will have full ownership of its strategy, execution, and financial performance. You will build the premium training product from scratch and have a direct line of sight to the revenue it generates. * Shape how enterprises adopt AI. The training and change management work you do will directly influence whether clients successfully adopt the AI solutions Cadre builds for them. You will help business leaders make sense of a rapidly evolving technology landscape and give their teams the tools to use AI confidently in their day-to-day work. * High-trust, high-autonomy environment. Cadre operates in delivery pods with minimal bureaucracy and maximum ownership. You will have the latitude to experiment, iterate, and build the training function in the way you think makes the most sense. Leadership trusts people to do their jobs without micromanagement. * Competitive compensation and equity. We offer market-rate salaries, meaningful equity, and performance-based bonuses tied to the success of the training pillar. As the premium offering scales, your compensation will scale with it.