Director, GTM Enablement

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 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.

Second Nature is an Equal Opportunity Employer and prohibits discrimination and harassment of any kind. We take action to ensure equal employment opportunities for all candidates and employees and to provide employees with a workplace free of discrimination and harassment. Our hiring decisions are based on business needs, job requirements and individual qualifications, without regard to race, color, religion or belief, family or parental status, or any other status protected by federal and/or state law.