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

We’re looking for a Director of Product with a track record of success in fast-paced organizations and a bias for action that drives measurable business results. As an experienced product leader, you will coach and support product managers on your team to deliver meaningful customer and business outcomes.

You know how to set a clear product vision, translate strategy into actionable plans, build cross-functional alignment, and drive execution. You will lead the planning, design, and delivery of innovative product solutions grounded in user insight and data, while advocating for exceptional user experiences across the platform.

As a key member of the Sittercity Leadership Team, you will contribute to company-wide strategic planning and help shape organizational priorities. In this role, you will partner closely with leaders across Product, Engineering, Marketing, Operations, and Finance to ensure our product strategy aligns with broader company goals, the Sittercity brand promise, and delivers measurable impact.

Key Responsibilities

Develop and drive product strategy for our consumer and corporate businesses, based on business objectives and customer needs. Work collaboratively with product managers and stakeholders to develop this strategy into an achievable roadmap.
Drive quarterly OKR planning process for squads.
Clearly communicate strategy and goals across the company throughout all phases of work, from ideation to measurement.
Demonstrated skill in product leadership, including coaching product managers, product planning, feature prioritization and trade-off evaluation.
Serve as a member of the Sittercity Leadership Team, partnering with senior leaders to shape company strategy, culture, define organizational priorities, and align product initiatives with overall business objectives.
Define and analyze metrics that inform product success.
Drive improvements to our existing products and identify opportunities for new product ideas.
Partner closely with Product Design and Engineering to ensure solutions deliver intuitive, high-quality user experiences, balancing usability, performance, and business outcomes.
Champion human-centered design practices, including user research, prototyping, usability testing, and iterative design improvements.
Ensure product decisions incorporate design thinking principles, translating customer insights into elegant, scalable product experiences.
Guide teams in evaluating trade-offs between design quality, technical feasibility, and speed to market.

About You

7+ years experience in product management, preferably in consumer-facing and B2B marketplace models, 3+ years in a leadership/ management capacity
Strong business acumen and revenue orientation, with a solid technical foundation and appreciation for delightful design
Comfortable operating in dual-sided or multi-stakeholder ecosystems (e.g., marketplace, platform, employer/client-driven models)
Innovative problem solver who can quickly absorb complexity and translate ambiguous challenges into clear, actionable solutions
Demonstrated expertise in product planning, including product vision, roadmap development, feature prioritization, and rigorous trade-off analysis
Data-driven decision maker who uses product metrics, experimentation, and customer insights to validate assumptions and guide strategy
Curious and pragmatic about the role of AI in product development and user experiences, with a mindset focused on experimentation, efficiency, and responsible implementation.
Comfortable leveraging AI tools to accelerate product discovery, customer insight generation, prototyping, and team productivity, while maintaining strong product judgment and ethical standards.
Strong appreciation for product design and user experience, with experience collaborating closely with design teams to deliver intuitive, user-centric solutions.
Ability to evaluate product solutions through both a business and design lens, ensuring products are functional, delightful, aligned with user needs, and deliver financial impact
Familiarity with design systems, usability testing, and iterative product design processes.
Organized, with a strong attention to detail and a passion for getting the product right
Experience working with agile software development processes
Excellent written and verbal communication skills, including the ability to crystallize and broadly socialize insights
BA/BS required

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 $150,000-$180,000 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. This position is also eligible for bonus awards.

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 [xx] 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 May, 2026.

Sittercity

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