Maintenance Specialist

Our Company

Doorstead is a full-service, digitally-driven tenant placements company that puts both the owner and tenant customers at the center of what they do. In 5 years of operations, we’ve booked 60M+grossrents,indexed rental prices for over 10MM properties,and raised from the investors who backed Redfin with participation from executives at Opendoor and Uber. We believe that without the smart, hard-working individuals who make up our winning team, we would not be where it is today. We have a once-in-a-lifetime opportunity to reimagine an entire industry and create the right way for today.

The Role

The Maintenance Specialist is a senior member of Doorstead's Maintenance Operations Team, responsible for resolving our most sensitive, complex, and costly maintenance situations while guiding and supporting Maintenance Coordinators. You will own high-stakes escalations, including habitability issues and time-sensitive or high-cost repairs, and ensure they are handled with urgency, sound judgment, and care for tenants and owners. You will manage vendor relationships, apply strong cost awareness to protect owner value, and turn what you learn into SOPs and best practices that raise the standard for the whole team.

How the Work Flows

1. Escalation Intake and Assessment: Take on escalated cases from Coordinators and Tenant and Owner Support Teams. Assess urgency, habitability risk, financial exposure, and the needs of each party before acting.
2. Scoping and Cost Review: Evaluate repair scope, compare estimates, and challenge inflated or out-of-scope quotes. Recommend cost-effective solutions and prepare clear, well-supported approval requests for owners.
3. Vendor Selection and Management: Assign and direct qualified vendors for complex or urgent work, set expectations on timeline and quality, and escalate or replace vendors who fall short.
4. Stakeholder Communication: Lead communication with tenants, owners, and internal teams on sensitive cases, providing clear updates at defined touchpoints and de-escalating where needed.
5. Resolution and Quality Assurance: Verify completion through inspection, photos, invoices, and feedback. Confirm the underlying issue is resolved, and close out only when documentation is complete.
6. Documentation and Improvement: Analyze escalation trends, vendor performance, and cost patterns. Turn lessons learned into new or updated SOPs, checklists, and best practices, and roll them out to the team.

Responsibilities

• Own and resolve sensitive escalations, including habitability issues, complex repairs, and time-sensitive or costly work, in line with SLAs and compliance requirements.
• Manage communication with escalated tenants and owners, de-escalating tense situations while protecting the relationship and Doorstead's standards.
• Draft, maintain, and continuously improve SOPs, playbooks, templates, and best practices for maintenance workflows, escalation handling, vendor management, and cost review.
• Identify process gaps and recurring issues, and translate them into clear, actionable documentation that Coordinators can follow consistently.
• Provide day-to-day guidance, coaching, and oversight to Maintenance Coordinators, including case consultation, workload support, and quality reviews of work orders and communications.
• Train and onboard new Coordinators, using SOPs and best practices as the foundation, and gather feedback to keep documentation current.
• Review and approve repair scopes and estimates within defined authority, and recommend cost-saving alternatives without compromising quality or safety.
• Build and maintain strong vendor relationships, including onboarding, performance tracking, rate negotiation, and accountability to quality and timeline standards.
• Track CSAT, SLA adherence, repair costs, and escalation volume, and report on trends and risks to leadership.
• Partner with the Support Teams on complex cases and cross-functional initiatives.
• Embody Doorstead's values and team culture (Athlete, Lifelong Learner, Troupe, Pioneer).

Requirements

• 2+ years of experience in property management, maintenance coordination, or a similar operations role, including time handling escalations.
• Proven experience managing sensitive or high-pressure situations, including habitability issues and upset parties.
• Strong cost awareness, with the ability to evaluate estimates, spot out-of-scope or inflated quotes, and make sound financial recommendations.
• Demonstrated vendor management skills, including relationship building, negotiation, and performance accountability.
• Experience mentoring, coaching, or informally leading team members.
• Experience writing or improving SOPs, process documentation, or training materials, with the ability to make complex workflows clear and easy to follow.
• Strong written and verbal English communication skills.
• Process-oriented, with excellent attention to detail and documentation.
• Decisive, proactive, and comfortable making judgment calls under time pressure.
• Prior experience as a virtual assistant or remote worker.
• Reliable internet connection.
• Flexible schedule.

Nice to Have

• Experience with work order or property management software.
• Familiarity with SLAs, CSAT, and ticketing systems.
• Working knowledge of habitability standards and landlord-tenant requirements.
• Basic knowledge of building systems and repair trades.
• Experience building process documentation in tools like Notion, Miro, or Google Workspace.

Our Values

• An owner mentality with high empathy and customer obsession
• An athlete mindset focused on deliberate practice and building momentum
• A lifelong learner who has an internal compass and believes in radical candor
• A member of a troupe that believes we’re better together and it is important to be on time, every time
• A pioneer who fearlessly breaks through challenges and believes in working hard, smart, and being disciplined.

Benefits

• Flexibility: We believe in a flexible work-life balance and offer the option to work remotely from anywhere with an internet connection.
• Wellness Leave: International Coordinators will earn eight (8) hours of bonus pay per calendar month to support their ability to take time off for well-being purposes, family-related reasons, sick leave, etc. This wellness bonus will be distributed as four (4) hours of pay included in each of their bi-monthly paychecks, totaling eight (8) hours of bonus pay each calendar month.
• New Parent Leave: As part of Doorstead's commitment to supporting family formation, we offer ten (10) days of New Parent Bonus for new parent leave. This leave is available to contractors who become parents through adoption or childbirth, providing them with the necessary time off.