Trust & Safety Specialist

Sittercity•Newton, MA

2d•$52,000 - $62,000•Remote

About The Position

As a Trust and Safety Specialist at Sittercity, you are responsible for protecting the integrity of the Sittercity marketplace by identifying, investigating, and mitigating risk across both caregivers and families. This role sits at the front line of platform safety - making high-stakes decisions that directly impact user trust and marketplace quality. You will review user activity, assess potential fraud or safety concerns, and take appropriate action based on internal policies and risk signals. This work often involves ambiguity, requiring strong judgement and the ability to make sound decisions with incomplete information. We’re looking for someone who is scrappy, learns quickly, and is comfortable operating in a fast-moving environment where processes continuously evolve and collaboration is required. This role also requires resilience - you will encounter sensitive and, at times, difficult content, and must be able to engage with it professionally without losing objectivity. You’ll play a key part in maintaining Sittercity’s reputation as one of the safest marketplaces in the caregiving space.

Requirements

2-3 years of experience in Trust & Safety, content moderation, fraud prevention, risk operations, or a related field.
Strong analytical and investigative skills.
Ability to make fair, consistent decisions in high-volume review environments.
Ability to exercise independent judgement in ambiguous or high-risk situations.
Excellent written communication and documentation skills.
Familiarity with online community guidelines, safety policies, and moderation tools.
Ability to handle sensitive or distressing content with professionalism and discretion.
Willingness to work occasionally on weekends.

Nice To Haves

Background in cybersecurity or risk management is preferred but not required.
Experience with Zendesk, IDV verification services, and background check tools is helpful.

Responsibilities

Monitor platform activity to identify, investigate, and resolve violations of community guidelines, safety policies, and terms of service.
Review user reports, flagged content, and suspicious behaviors and take the appropriate action.
Review and investigate user accounts, content, and activity for fraud, abuse, or policy violations.
Make timely, consistent enforcement decisions (warnings, removals, escalations) based on internal guidelines.
Collaborate with cross-functional and cross-company teams as a subject matter expert.
Provide training to other team members (Trust & Safety and Customer Success) as a subject matter expert.
Respond to escalated customer safety concerns with empathy and clarity.
Help develop and enforce Trust & Safety policies, procedures, and best practices. Maintain deep knowledge of those policies and apply them consistently.
Identify and analyze patterns seen in content reviewed.
Utilize automation, machine learning, and AI-driven signals to detect risk, prioritize investigations, and improve decision accuracy.

Benefits

medical insurance
dental insurance
vision insurance
401(k) retirement plan
life insurance
long-term disability insurance
short-term disability insurance
9 paid holidays annually
40 hours of sick time per year based on full-time schedule
80 hours of vacation time per year based on full-time schedule
Remote Role
Company events, social outings and volunteer opportunities
Tuition assistance, college coach, and enhanced family support
Sittercity membership, backup child/adult/elder care, and childcare center discounts