Director, GTM Enablement

About the role

At Second Nature, our people are our greatest differentiator. To build an industry-changing business, we don't just need talent; we need an environment where high standards, continuous improvement, and customer obsession are the default. Excellence is not a destination - it is how we show up every day. In twenty years time, we want every single employee to look back to their time at Second Nature and say: This is where I did my very best work. Where I grew the most. Where I pushed myself beyond what was comfortable. ✨ 💟 About Us Today, we live in a world where everything has become convenient. Now you can get a ride anywhere, buy anything, answer any question with just a couple clicks on your phone. Convenience isn't a luxury, it's an expectation. So why not renting? It's still a chore to get utilities set up, buy renters insurance, get air filters changed, handle pest control, and more. That's why we've built the world's first Resident Experience Platform that makes resident onboarding, resident services, and ancillary revenue effortless for property managers. We're passionate about turning friction into triple win experiences for residents, property managers, and investors. That way renting can be easy and rewarding for everyone. And now you can join us. Apply today to join 300+ passionate, creative people who strive to make a difference each day so residents, property managers, and investors all win; creating the ultimate Triple Win! 🔥🔥🔥 📝 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 fun

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