Senior Director, Agent Sales

Zillow

3d • $184,700 - $310,600 • Remote

About The Position

The Senior Director, Agent Sales will design and lead the go-to-market strategy for Zillow’s SMB and Mid-Market agent segments. This executive will step back from the day-to-day and architect the overall system: multi-year strategies, segment design, coverage models, compensation plans, and engagement motions that drive durable growth across multiple products and software solutions. This leader will own the end-to-end performance of a large, multi-layer organization focused on existing customers — reducing churn, increasing product adoption and value realization, and driving incremental revenue through upsell and cross-sell. They will be a key strategic partner across Sales Operations, Marketing, Product, HR, and Enablement, setting direction for how Zillow deepens relationships with agents and teams at scale.

Requirements

• Enterprise-scale strategic leadership. Proven experience building multi-year GTM or sales strategies across multiple segments or business units. Demonstrated ability to set direction, not just execute on an existing plan.
• Hands-on leadership in both high-velocity SMB and more complex Mid-Market motions (from one-call closes to multi-month, multi-stakeholder deals).
• Driving organizational transformation. Experience analyzing and redesigning org structures, sales motions, and coverage models. Track record leading teams through complex, multi-product or motion changes (e.g., advertising to software, transactional to consultative). Comfortable operating in ambiguity and complexity at scale, making and communicating clear trade-offs.
• Data-driven operational excellence. Uses data and insights to diagnose business performance, shape operating models, and prioritize investments. Strong command of forecasting, pipeline health, churn, and expansion metrics; able to connect them to strategic decisions. Communicates decisions and narratives anchored in metrics and trends, not anecdotes.
• Organizational talent architecture. Experience designing leadership structures, roles, and capacity plans that scale with the business. Proven ability to build, coach, and retain senior leaders and frontline managers, creating a strong internal pipeline.
• Executive-level influence with cross-functional partners. Demonstrated success influencing Product, Marketing, Sales Operations, Enablement, Finance, and HR at the executive level. Communicates in a way that guides decisions and aligns stakeholders, not just reports out on status.
• Proven success leading senior leaders — coaching Directors and Managers, raising the bar on leadership quality.
• Market and customer insight orientation. Deep understanding of how customer, market, and segment dynamics shape sales strategy, product mix, and engagement motions. Able to synthesize field feedback and customer insights into concrete recommendations for roadmap and GTM.
• Culture builder at scale. History of creating clarity, accountability, and cohesion across large, distributed organizations. Comfortable having tough conversations, making high-judgment calls, and holding the bar through change.

Nice To Haves

• Real estate or adjacent industry experience (e.g., marketplaces, SaaS, ad tech) working with SMB and Mid-Market customers.
• Familiarity with Zillow’s ecosystem and products; more important is the ability to quickly learn new domains and connect product capabilities to customer value.
• Experience using tools such as Salesforce, Tableau, Gong, and similar platforms; must be strongly data fluent, even if not tied to specific tools.
• Background in hypergrowth or turnaround environments, with examples of successfully leading teams through rapid change.
• Prior experience acting as an executive sponsor on strategic deals, building senior relationships with customers and representing the company externally.

Responsibilities

• Build culture and leadership at scale. Create clarity of direction, high standards, and accountability across a multi-layer sales organization. Role-model a culture that values learning, experimentation, and continuous improvement, especially as the team shifts to new products and sales motions. Coach senior leaders and managers to become multipliers who inspect effectively, diagnose performance, and develop their teams.
• Set multi-year strategy across segments. Design and evolve SMB and Mid-Market G&R strategies, including coverage models, account segmentation, and engagement plays across different customer needs and deal cycles. Build an integrated approach that spans high-velocity, in-week/in-month motions and more complex, multi-month, multi-stakeholder deals.
• Own revenue, retention, and growth outcomes. Own revenue performance, churn, and expansion outcomes across SMB and Mid-Market. Establish and refine operating cadences for forecasting, pipeline inspection, and performance management focused on both retention and Added MRR. Use data to diagnose portfolio health, identify risk/opportunity, and prioritize where leaders and reps spend time.
• Design the organizational architecture. Define organizational structure, leadership layers, roles, territories, and capacity plans that can scale efficiently. Align compensation plans and incentives with desired behaviors across segments (e.g., balance of retention, upsell, cross-sell, and product mix). Build, develop, and succession-plan senior leaders and frontline managers who can multiply impact across the org.
• Lead transformation from transactional to value-based, software-led selling. Guide the transition from primarily advertising-led selling to multi-product, software-led, value-based sales motions. Establish clear, repeatable sales frameworks and playbooks that work across SMB and Mid-Market but flex to segment needs. Simplify complex change into clear priorities and behaviors for leaders and reps.
• Drive data-driven operational excellence. Partner closely with Sales Operations on forecasting rigor, territory and coverage design, rules of engagement, and tooling. Define the core metrics and dashboards that senior leaders, managers, and reps rely on to run the business. Use insights from forecasting, churn, product usage, and sales performance to continually refine strategy and execution.
• Shape cross-functional strategy and partnerships. Sales Operations: Co-lead rules of engagement, quota design, forecasting frameworks, compensation plans, and tooling strategies to support a scaled G&R motion. Marketing: Align on inbound funnel strategies, events and conferences that build trust and pipeline, and outbound programs (email cadences, campaigns) that drive awareness, adoption, and expansion. HR: Partner on leadership expectations, performance management frameworks, career ladders, promotions, and succession planning for a large, distributed sales org. Enablement: Co-create training, coaching, and programmatic interventions that uplevel reps and leaders; rigorously measure what’s working and what’s not. Product & PM: Bring market and customer insights to influence roadmap, packaging, and pricing; provide feedback on what is selling, where customers are struggling, and where pricing and positioning need to evolve.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed