Director, GTM Enablement

Second Nature

Director of GTM Enablement leading the enablement function and a four-person team at Second Nature. Focus on strategy, coaching, and improving business outcomes tied to revenue metrics.

Posted 6/17/2026full-timeRemote • 🇺🇸 United StatesLead💰 $150,000 - $185,000 per yearWebsite

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Applicant Tracking System Keywords

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Hard Skills

GTM enablementrevenue enablementsales learning and developmentstructured learning programsonboarding pathsasynchronous eLearning modulesprogram governance frameworksdata analysiscoaching guidescall review frameworks

Soft Skills

leadershipcommunicationinfluencinganalytical thinkingcollaborationstrategic thinkingcoachingorganizational skillsproblem-solvingadaptability

Tools & Technologies

HighspotArticulateeLearning toolsSOPsCRM systemslearning management systemsdata analytics toolsproject management softwarevideo conferencing toolscollaboration platforms

Industry Keywords

B2B SaaSclient retentionrevenue metricsclient activationARR expansionenablement roadmapregulatory complianceperformance metricscohort-based trainingexecutive interface

About the role

Key responsibilities & impact

Lead and develop the enablement team
Manage four enablement ICs whose work spans Sales/AE, Implementation and Onboarding, CSM, and Client-Facing training
Serve as the primary coach and career development partner for each IC, equipping them to do the most impactful work of their careers
Translate the CRO's and Executive Team’s strategic direction into a quarterly enablement roadmap, maintained approximately two months in advance
Run regular 1:1s, team cadences, and roadmap reviews that keep priorities sharp and scope creep managed
Drive manager and leader readiness
Reinforce enablement delivery to equip first and second-line managers with coaching guides, call review frameworks, and policy reinforcement tools in parallel with individual contributor enablement.
Design and deliver monthly leadership readiness sessions per function covering playbooks, policies, and behavioral coaching
Build reinforcement loops that ensure what gets trained actually sticks at the front line
Govern strategy, programs, and asset quality
Implement and enforce a launch-tier framework that gates ad hoc requests and ensures every new enablement program has a defined business objective, reinforcement plan, and success metric
Partner with Exec Sponsors to prioritize the enablement roadmap for their functions and hold the line on scope
Manage Highspot as the single source of truth, driving cleanup, organization, and usage-based prioritization across all assets
Review and adjust structured onboarding paths to ensure clear ramp-complete milestones and mastery levels for new hires across the GTM org
Connect enablement to revenue outcomes
Own the function's performance against named revenue and operational metrics tied to net new CARR production, client activation, ARR expansion, and client retention
Build and expand asynchronous learning programs (via Articulate) to reduce dependence on synchronous delivery and increase per-person coaching capacity
Drive cohort-based client training under Customer Enablement Manager’s ownership, reducing 1:1 delivery volume and increasing scalable program reach
Collaborate with VP Marketing and PMM Team to ensure tight alignment between positioning, messaging, and how the field is trained to use it
Own cross-functional enablement programs
Lead team-level ownership of regulatory compliance updates, new hire onboarding, and product-level enablement across the GTM org
Serve as the executive interface for all cross-functional program launches that require enablement support
Ensure functional teams own their own SOPs; your team formats, trains, and reinforces, not authors from scratch

Requirements

What you’ll need

7+ years of experience in GTM enablement, revenue enablement, or sales learning and development, with at least 3 years in a leadership role
Proven track record leading enablement teams whose outcomes are tied to revenue metrics, not training volume or content output
Deep experience enabling sales, implementation, and post-sales teams at a B2B SaaS company
Strong instincts for manager and leader readiness: you know that what gets coached gets done, and you build programs accordingly
Experience designing and governing structured learning programs, including onboarding paths, ramp milestones, and asynchronous eLearning modules
Skilled at building and enforcing program governance frameworks that protect team capacity from reactive, ad hoc demand
Comfort operating with executive stakeholders: you can influence prioritization decisions, push back on scope, and hold the line when needed
Familiarity with Highspot (or comparable sales enablement platforms) as an organizational system, not just a file repository
Experience with eLearning tools like Articulate or equivalent is a plus
Clear communicator who can translate complex strategy into crisp direction for your team, your stakeholders, and the field
Analytically driven: you use data to identify where the gaps are, what programs are working, and where to focus next.

Benefits

Comp & perks

Health First: Medical, Dental, Vision, Life Insurance, & 401K Plan
Flexibility: Open PTO and sick days
Training: A supportive team to help you grow your career and unlock your full potential
Growth: The opportunity to get in on the ground floor of a fast-growing startup that’s designing and developing an exciting category
Diverse, Inclusive Culture: We embrace employees from all backgrounds with openness and respect