Director of Field Enablement, Global at Contentsquare – Miami, Florida

About the role:

This is a high-impact, globally-scoped enablement leadership role at the heart of Contentsquare's GTM organization. You will own the enablement strategy and execution for our global field teams, lead a team of Enablement Business Partners, and serve as the primary driver of Command of the Message (CoM) adoption and proficiency across Sales, Pre-Sales, and Customer Success. This role requires a builder's mindset, deep partnership with GTM and Revenue Operations leadership, and the confidence to operate in a fast-paced, evolving environment.

Major Responsibilities:

Leadership and Strategy

• Lead the global Field Readiness strategy, ensuring enablement programs are directly tied to GTM priorities and measurable business outcomes

• Lead, develop and inspire a global team of Enablement Business Partners, setting clear direction, modeling enablement excellence, and building a culture of high performance and shared accountability

• Act as a strategic thought partner and trusted advisor to GTM, Revenue Operations, Marketing, and Product leadership

• Serve as the voice of the field within the enablement team, translating market realities and seller needs into actionable programs and priorities

• Conduct qualitative and quantitative analysis to identify enablement gaps and opportunities that drive productivity and revenue growth across knowledge, skills, process, and coaching

Command of the Message (CoM)

• Serve as the organization's primary enablement owner for CoM, driving proficiency, adoption and accountability across the GTM field

• Facilitate CoM certifications and ongoing skill development for sellers, managers and leaders

• Partner with RevOps to embed CoM into Salesforce workflows, deal review processes and reporting, ensuring methodology is operationalized and measurable

• Coach managers on CoM-based deal reviews and pipeline inspection, building a culture of methodology accountability

Program Design and Delivery

• Design and deliver a range of enablement programs, activities and interventions tied to improving field performance, including:

  • Trainings (instructor-led, e-learning, on-demand, workshops)

  • Content (playbooks, job aids, templates, vertical guides)

  • Tools (adoption, optimization, AI-assisted workflows)

  • Coaching (improving manager ability to drive field performance)

  • Peer learning (scaling best practices, highlighting best-in-class)

  • Reinforcement plans (embedding change and sustaining behavior)

  • Communications (dissemination of assets and critical information across the field)

• Think AI first and accelerated scale in a high paced product innovative environment

• Manage and contribute to scaled GTM programs including new product launches, methodology rollouts, process changes, and tool adoption initiatives

• Manage the onboarding curriculum for new GTM hires across segments and regions, with particular depth in the Enterprise business

• Identify and scale best practices from the field through peer learning programs and structured knowledge-sharing forums

Measurement and Accountability

• Define success metrics for all enablement programs and report results regularly to GTM leadership and key business stakeholders

• Use data to continuously evaluate program effectiveness and iterate based on what is and is not working

Requirements:

• 5+ years in sales enablement, with a demonstrable track record of building and executing global enablement strategies, programs and content

• Deep knowledge of and hands-on experience with Command of the Message (CoM) or equivalent value-based selling methodology, with the ability to coach and certify others

• Proven ability to lead, develop and retain a high-performing team of enablement professionals

• Demonstrated ability to influence and align senior GTM leaders around enablement priorities and outcomes

• Strong RevOps fluency: comfort with Salesforce reporting, pipeline data, and cross-functional partnership with Revenue Operations

• Proficiency with modern enablement technology: LMS (MindTickle or equivalent), conversation intelligence tools, CRM, and AI-powered productivity tools

• Ability to operate and make sound decisions in an environment of ambiguity and rapid change. This is a genuine requirement for success in this role, not a formality

• Proven ability to translate complex business priorities and skills gaps into clear, impactful learning programs and content

• Strong project management skills with the ability to manage multiple programs simultaneously across global stakeholders

• Experience working in fast-paced, high-growth SaaS companies; Martech or digital analytics experience a plus

• Ability to travel to global locations as required

• Demonstrable AI programme deployment and experience

Nice to have:

• Sales, Sales Management, or Product Marketing background

• 3+ years of people management experience

• Experience with MEDDIC / MEDDPICC qualification methodology

• Familiarity with Clari, Salesforce, and AI-assisted GTM tools (e.g., Dust, co-pilot tools)

• Progressive approach to learning materials and thought leadership in AI for scale