Senior Director, Agent Sales

About the team The team is responsible for all revenue, customer retention, and revenue growth across SMB & Mid-Market segments. This is a farmer-focused organization — not new-logo hunting — centered on maximizing value within an existing BoB (book of business). The team is accountable for: 1. Retaining and growing revenue within their BoB. 2. Managing churn to reasonable levels while expanding existing relationships. 3. Driving product usage and value realization across all products purchased. 4. Upselling within existing product lines and cross-selling into new Zillow products and software. The organization operates on a recurring forecasting rhythm, currently monthly (with potential to move Mid-Market to quarterly), reporting on total expected revenue by forecasting both anticipated churn and new product sales. Quotas and performance expectations are tied to both churn and Added MRR, requiring a balanced focus on protection and growth. About the role 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. What they will do 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 tha ... (truncated, view full listing at source)