Director, GTM Enablement

Zillow

1d•$166,400 - $279,800•Remote

About The Position

About the team The Agent Sales organization at Zillow helps real estate professionals grow their business through advertising and productivity solutions across our product portfolio, including Showcase, Premier Agent buyer leads, Zillow Pro, Dotloop, and media offerings. About the role The Director, GTM Enablement reports to the Head of Revenue Strategy & Operations and owns the end-to-end enablement strategy for Agent Sales. You will lead a team of managers and enablement professionals to design and run programs spanning onboarding, everboarding, sales methodology, product and process readiness, and manager coaching. The strategy is AI-first and Challenger-led, delivered in the flow of work through Highspot (CMS/LMS), Gong (full platform), Salesforce, and data tools. You will partner closely with Sales, L&D, Marketing, and Product leaders to translate GTM strategy into practical programs that elevate our GTM operators into value-oriented sellers, confident across a diverse and growing product portfolio.

Requirements

10 to 14+ years in Sales Enablement, Strategy, or a related field, with 5+ years leading high-performing teams in technology, SaaS, or marketplace environments.
Proven track record designing and scaling enablement programs that measurably improve sales productivity, adoption, and revenue.
Direct experience implementing and operationalizing Challenger or a comparable insight-led methodology across sales teams.
A strong leader of leaders, skilled at influencing senior stakeholders and aligning cross-functional teams around shared priorities.
Comfortable operating in ambiguity, with a track record of moving complex, matrixed initiatives forward with clarity and conviction.
A strategic thinker who can translate business goals into clear enablement roadmaps, prioritizing by impact and effort.
Highly collaborative, field-centric, and customer-obsessed, passionate about helping both customers and internal teams succeed.
Curious, solutions-oriented, and committed to continuous improvement for the business, your team, and yourself.

Responsibilities

Define a multi-year, AI-first, Challenger-informed enablement roadmap aligned to Agent Sales strategy and revenue goals.
Embed Challenger behaviors (teach, tailor, take control) into day-to-day sales and success motions across new business, expansion, and retention.
Own onboarding, everboarding, certification, and methodology programs for sales and success roles, with clear proficiency standards and measurable business outcomes.
Co-own GTM launch readiness for multi-product motions and team integrations, ensuring every launch is supported by sharp narratives, practical tools, and field-tested plays.
Own and optimize the enablement tech stack, with Highspot as the central system for content, training, and plays, and Gong as the conversation intelligence and coaching engine.
Scale Gong programs (scorecards, trackers, libraries, and AI coaching) to reinforce Challenger behaviors and raise execution quality across the field.
Partner with Systems, Data, and AI teams to identify, pilot, and scale high-impact AI use cases, including intelligent content surfacing, role-based guidance, and AI-powered coaching and summarization.
Define and own a measurement framework that connects enablement directly to ramp time, conversion, attach and mix rates, adoption, win rates, and productivity, with success measured through business outcomes, not CSAT scores or completion rates alone.
Lead and develop a high-performing enablement team with clear goals, consistent operating rhythms, and meaningful development plans.
Foster a team culture that balances experimentation with operational rigor and a high bar for quality.
Serve as a trusted advisor to Sales, Marketing, Product, and Operations, representing the voice of the field and positioning enablement as a force multiplier for business outcomes.