Director of Field Enablement, Global

Contentsquare • Washington, DC

1d • $175,000 - $200,000 • Hybrid

About The Position

This is a high-impact, globally-scoped enablement leadership role at the heart of Contentsquare's GTM organization. The Director will own the enablement strategy and execution for 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.

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 Haves

• 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

Responsibilities

• 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
• 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
• 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
• 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

Benefits

• We invest in our people through career development, mentorship, social events, philanthropic activities, and competitive benefits.
• Virtual onboarding, Hackathon, and various opportunities to interact with your team and global colleagues both on and offsite each year
• Work flexibility: hybrid and remote work policies
• Generous paid time-off policy (every location is different)
• Lifestyle allowance
• A Culture Crew in every country we’re based in to coordinate regular activities for employees to get to know each other and bond outside of work
• Every full-time employee receives stock options, allowing them to share in the company’s success
• We have multiple Employee Resource Groups, that offer a safe space for individuals who share common identities, life experiences, or allyship to connect, support one another, and passionately advocate for the issues close to their hearts
• And more benefits tailored to each country

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed
• Number of Employees: 1-10 employees