Director of Customer Service Operations

Director of Customer Service Operations

Location: Remote (United States)

Compensation: $150,000 - $175,000 base, OTE $175,000 - $225,000 + Equity

👤 Reports to: Vice President, Customer Experience
About the Role

We are looking for a hands-on customer service and operations leader for Customer Success and Matching. Customer Success supports customers across phone, email, SMS, escalations, issue resolution, customer feedback, and cross-team handoffs. Matching connects customers with partner agents across multiple stages and channels.

The Director will lead managers and individual contributors, set priorities, stabilize the frontline team, and improve service, reporting, documentation, routing, onboarding, and ownership. They will stay close to the work, use customer, team, and performance data to form an independent view, and step into frontline work when needed.
Key Responsibilities

Operational Strategy and Performance

• Own service quality, capacity, and performance across Customer Success and Matching. Establish clear measures and turn customer and performance insights into priorities and action.
• Build and manage a focused improvement roadmap that balances process, technology, automation, and staffing. Partner across Product, Data, and Operations to test changes, measure results, and scale, adjust, or stop them based on what works.

Customer Service and Matching Operations

• Own and improve the end-to-end customer matching operation, with clear standards, ownership, and measures for speed, completion, and quality.
• Identify and implement process and technology improvements, partnering with Product when needed, to improve match quality, increase capacity, and reduce manual work.
• Own Customer Success operations across phone, email, SMS, and other channels. Set clear standards for service, quality, coverage, and capacity.
• Improve routing, handoffs, escalations, and documentation so work reaches the right owner and customers receive timely support.
• Use customer feedback and demand trends to guide process, technology, automation, and staffing decisions that improve quality and increase capacity.

Team Leadership and Development

• Lead, coach, and develop team leads and individual contributors. Set clear expectations, establish ownership and accountability, and address performance issues directly.
• Strengthen hiring and onboarding, and build team routines, documentation, and backup coverage that distribute ownership and keep work moving.
• Be willing to personally handle customer contacts and complete matching work during staffing gaps, urgent issues, or key learning periods. Use that firsthand experience to improve the operation, then return ownership to the team.

Ideal Candidate

You are a hands-on customer service and operations builder who can quickly understand a complex, evolving environment and turn the highest-impact opportunities into a focused roadmap. You combine sound judgment, customer insight, and data to improve service and capacity while building a team that can operate without depending on you.
What You Need

• 10+ years in customer-facing operations with direct responsibility for service, quality, capacity, and performance.
• 3+ years in a people leadership role, with direct experience managing frontline individual contributors and managers, developing leaders, handling performance problems, and stepping into frontline work.
• Experience building or improving service operations, including workflows, ticketing, routing, escalations, documentation, onboarding, and reporting.
• Strong business judgment and the ability to make sound decisions using customer insights and imperfect data.
• A track record of using process improvements, technology, and automation to produce measurable gains in service quality or capacity.
• Experience leading teams through high volume and changing priorities while influencing senior leaders and cross-functional partners.

Helpful Experience

• Experience in real estate, proptech, or another technology-enabled service business is helpful. Familiarity with HubSpot, Front, or Five9 is a plus.

What Success Looks Like

In 90 days...You have developed a clear understanding of our customers, team, operations, systems, and performance across Customer Success and Matching. You have established initial performance baselines and clarified near-term priorities, ownership, coverage, and escalation paths. You have aligned leaders on a focused improvement roadmap, identified staffing and onboarding needs, and launched at least one targeted improvement with an agreed measure of success and early results.

In 6 months...The highest-priority workflows and service standards are clear and consistently followed across Customer Success and Matching Team members have clear ownership and accountability, with the coaching and support needed to grow in their roles. Onboarding follows a consistent process, and critical work has documented backup coverage. Leaders use trustworthy reporting to guide decisions, and process and technology improvements have produced measurable gains while balancing customer experience, service quality, speed, cost, capacity, and business outcomes.
What We Offer

Salary: $150,000 - $175,000 base, OTE $175,000 - $225,000 + Equity

Comprehensive Benefits: Medical, dental, vision, and life insurance

Paid Time Off: 18 days of PTO (increases with tenure) plus 10 paid holidays

Professional Development: Annual budget for learning and career growth

Tenure Sabbaticals: Paid sabbaticals to celebrate major milestones

Clever Product Benefit: Exclusive access to Clever homeownership perks

🖥 Work-From-Home Stipend: Support for your remote workspace

401(k): Retirement plan administered through Betterment

Parental Leave: 6-12 weeks of paid parental leave

💙 Wellness Benefits: Free counseling sessions and optional weekly meditation