About Sittercity

Sittercity, a Bright Horizons company, is a technology platform working to reimagine the child care industry. Finding, hiring and managing high-quality, trustworthy and enriching child care has never been simple, for parents or caregivers. We want to change that. At Sittercity, you can imagine and create solutions that will revolutionize a multi-billion industry and bring relief to parents and care providers alike, all while having a lot of fun! Boost your career as we launch into our next phase of growth and help build a platform that changes the way child care works.

The Opportunity

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.

Key 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.

Required Qualifications

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.
Utilize automation, machine learning, and AI-driven signals to detect risk, prioritize investigations, and improve decision accuracy.
Willingness to work occasionally on weekends.

Preferred Qualifications

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

Why you should join us

Recognized as one of the best places to work by Built In Chicago, we offer an inclusive, innovative, and fun environment that rewards passionate and curious individuals. You will have an opportunity to influence our [product and technology] in an entrepreneurial environment with enterprise backing that has a huge impact on the childcare industry.

Salary And Other Compensation Disclosures

The annual starting salary for this position is between $52,000-$62,000 annually. The pay range listed here is what Sittercity in good faith anticipates offering for this job opening. Actual compensation offered within this range will depend on a variety of factors including experience, education and training, certifications, geography, and other relevant business or organizational factors.

Benefits:

The Company offers the following benefits for this position, subject to applicable eligibility requirements: medical insurance, dental insurance, vision insurance, 401(k) retirement plan, life insurance, long-term disability insurance, and short-term disability insurance. Also, depending on hire date and subject to applicable eligibility requirements and accrual schedules, new employees in this role receive up to: 9 paid holidays annually; 40 hours of sick time per year based on full-time schedule, and 80 hours of vacation time per year based on full-time schedule (vacation time may be used for sick leave purposes under any applicable state or local sick or safe time law).

Perks:

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

Sittercity is committed to hiring a diverse workforce. We consider all applicants for employment without regard to race, color, sex, sexual orientation, gender identity, religion, age, national origin, disability, veteran status, or any other basis as prohibited by federal, state or local law. Sittercity participates in E-Verify and background checks all employees.

This role must be performed remotely in IL, MA, NJ, NY, OH, OR, TX, CO, NH, VT, WA, WI, FL,GA

This posting is anticipated to remain open until April 15, 2026.

Sittercity

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