About the Role

Second Nature is looking for a Director of GTM Enablement to lead our enablement function. Reporting to the CRO, you will own the strategy, execution, and outcomes of a four-person enablement team aligned directly to our most important FY '26 revenue goals. Each IC on your team is dedicated to a specific GTM domain (Sales, Implementation, CSM, and Client-Facing Enablement), and each is accountable to named business outcomes. Across the team, you will also oversee aspects of new hire onboarding, and process and product enablement for the full GTM org. Your job is to make the entire team better at making the business move faster.

This role is for someone who is energized by coaching leaders, building structured programs, and connecting learning investments directly to pipeline, activation, and retention outcomes. You are comfortable operating at the executive level and comfortable getting your hands dirty when the work requires it.

☆ What You'll Do
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

About You

• 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

💟 Why Second Nature?

Health First: Medical, Dental, Vision, Life Insurance, & 401K Plan

Location: Work remotely from anywhere in the US

Flexibility: Open PTO and sick days

🤩 The Product: Beyond the awards and 5-star reviews, our clients and customers love what they can do with the world's first Resident Experience Platform

🤗 Diverse, Inclusive Culture: We embrace employees from all backgrounds with openness and respect

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

We get it. Requirements can sometimes hold people back from applying to a job, but don't let that be the case here. If you believe you have the skills it takes to elevate this role, team, and company, we encourage you to apply for this role.