Head of GTM Enablement

Three Pillars Recruiting; New York (NY); On-site; USD 180,000 - 260,000; Full time

Job summary

Three Pillars Recruiting is looking for a Head of GTM Enablement to lead onboarding, training, and continuing education for the company’s go-to-market teams. You will build scalable programs for sellers, Client Services, and marketing, working with Product Marketing and Revenue Operations to roll out new products and features.

You will measure program outcomes and drive adoption, designing content that accelerates ramp time and improves performance across the GTM organization.

Qualifications

• Experience building scalable GTM learning programs for B2B tech.
• Proven ability to design instructional content and collateral.
• Knowledge of sales methodologies (e.g., MEDDIC) and content/tools.
• Strong collaboration with Product Marketing, Sales and Revenue Ops.

Responsibilities

• Define and execute an L&D strategy aligned to commercial goals.
• Create engaging, outcome-driven learning experiences using modern instructional design.
• Identify capability gaps and translate into structured learning programs.
• Establish scalable onboarding across revenue roles.
• Own onboarding for the GTM team including Sales, Client Services, and Marketing.
• Measure program impact: completion rates, performance, business outcomes.
• Codify founder-led sales knowledge into repeatable playbooks and training.
• Develop tailored learning journeys for mid- to senior-career professionals.

Skills

GTM Enablement

Sales Training

Instructional Design

L&D Strategy

Adult Learning

Collaborative Leadership

Education

CPTD Certification

Tools

CRM (HubSpot/Salesforce)

Conversation intelligence (Gong/Chorus)

Confluence

PowerPoint/Google Slides

Drive/SharePoint

Job description

Head of GTM Enablement

As a leader on the go-to-market team, the Head of GTM Enablement will be responsible for building and scaling the onboarding, training, and continuing education programs for the company’s GTM organization. To continue in our fast-paced growth, you will play a crucial role leading the development and implementation of a robust onboarding, training and continuing education program for a rapidly growing team of sellers, Client Services professionals, and marketing teams. You also will work closely with Product Marketing in connection with the development of and updates to internal training and customer-facing collateral as we expand to new buyer personas and roll out new products and features. You will be responsible for identifying gaps in existing training and collateral and developing content and programming to fill them. You will leverage performance data and conversation intelligence to identify areas of opportunity for training and development.

In this position, you will report to the Co-CEO and Co-Founder, Matt Kalmans, and will work closely with executive leadership (including our Co-CEO and Co-Founder) and members of the Business Development, Product, Client Services, Marketing, and Revenue Operations teams. This is a hands‑on leadership role that blends strategy, program design, and execution.

What You’ll Do

• Define and execute a L&D strategy aligned to commercial goals (Sales, Client Services, and Marketing)
• Apply modern instructional design methodologies to create engaging, outcome-driven learning experiences
• Partner with GTM leadership to identify capability gaps and translate them into structured learning programs
• Establish a scalable onboarding framework across all revenue roles
• Own the new hire onboarding program for the go-to-market team, including Sales, Client Services, and Marketing:
• Oversee the establishment of the foundational onboarding, training, and certification programs for the GTM organization
• Iterate and improve upon the existing training curriculum for go-to-market roles to improve ramp time and effectiveness
• Manage the new hire onboarding process and work with GTM leadership to verify new team members’ readiness to represent products and services to customers
• Manage training and certification of the GTM team for new product/feature rollouts and new process rollouts
• Collaborate with stakeholders from Product, Product Marketing, Sales, and Client Services to develop the appropriate training and certification programs for new products or features
• Collaborate with GTM leadership and Revenue Operations to develop training and certification programs for customer-facing processes and skills
• Own the outcomes of the training programs you manage: continually measure program completion, participant performance, and business impact of each program
• Codify founder-led sales knowledge into repeatable playbooks, frameworks, and training
• Create tailored learning journeys for mid- to senior-career professionals who are SMEs but have non-traditional sales backgrounds
• Use adult learning theory and instructional design best practices to drive adoption and retention
• Focus on practical skill-building: storytelling, consultative selling, stakeholder management, and deal strategy
• Observe customer meetings and embed with the GTM team as needed to develop an independent perspective on necessary collateral and training
• Using performance data and conversation intelligence tools, collaborate with revenue leadership to identify knowledge and skills gaps across the GTM team, and build continuing education strategies to close those gaps
• Collaborate with the Product Marketing team to develop a communication strategy and calendar for effectively enabling the GTM team throughout the year and managing new product and feature rollouts
• Partner with Revenue Operations to source, implement, manage, and train on technologies that drive productivity for the GTM team

Experiences And Capabilities You Bring

• Significant experience coaching and training go-to-market teams within a fast-growing B2B technology-enabled services or software company that sells complex, high-ACV solutions to C-level buyers
• Experience building and scaling GTM learning programs from the ground up – you ideally have helped lead the transition from founder-led sales to a scalable GTM model
• Strong understanding of the sales ecosystem, including sales processes, methodologies (ie. MEDDIC or other similar sales methodologies), content, tools, and trainings
• Demonstrated excellence in development and design of sales collateral (presentations, templates, one-pagers, standard email copy, etc.)
• Experience managing GTM employee training and onboarding programs
• Proven experience in instructional design and adult learning principles
• Expertise in key software in the sales tech stack, including:
• CRM software like HubSpot or Salesforce
• Conversation intelligence tools like Gong or Chorus
• Knowledge management platforms like Confluence
• Presentation software like PowerPoint or Google Slides
• Shared drive software like Google Drive or Sharepoint
• CPTD (Certified Professional in Talent Development) strongly preferred (or equivalent L&D certification)