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Lead Dog Walker

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Windy City Paws
Part Time position
Listed on 2026-08-17
Job specializations:
  • Outdoor/Nature/Animal Care
    Animal / Pet Care, Outdoor / Nature
Salary/Wage Range or Industry Benchmark: 19 USD Hourly USD 19.00 HOUR
Job Description & How to Apply Below

Join Windy City Paws as a Lead Dog Walker in Chicago!

Are you passionate about pets?

So are we! Windy City Paws is Chicago's top-rated dog walker and cat sitter for busy professionals. Our clients experience the convenience of our advanced services, featuring GPS verification for added reassurance and seamless online scheduling for effortless coordination.

Dependability is one of the most important aspects to consider when selecting a pet care service provider. A cancellation can cause extreme stress for clients and pets, which is why Windy City Paws never cancels appointments. There is always someone on staff ready to step in. At Windy City Paws, we love what we do and we want to grow our team with like-minded pet lovers!

Role Overview

Windy City Paws is looking for a dependable person to join our professional team! As an experienced dog walker, you'll take a lead position to ensure our clients' dogs are happy, healthy, and well cared for during weekday visits and walks. This role includes 30 guaranteed hours per week and benefits such as Paid Time Off (PTO) and 401(k) payroll contributions.

What You'll Do

  • Commute to different service areas to cover dog walking routes or run keys.
  • Provide coverage for emergencies in the field to ensure all dogs are being walked.
  • Accompany new staff on their routes for training and observation purposes.
  • Handle new client routes and distribute marketing materials in the field.
  • Monitor and respond to chat messages from staff and clients in a timely manner.
  • Assist in recording staff performance and compliance with safety protocols.
  • Audit staff onboarding, keys and client account information.
Why Windy City Paws?
  • Founded in 2009: an experienced, trusted, and passionate Chicago team.
  • W2, part-time positions with PTO and 401(k) benefits.
  • Paid training and hands-on education in dog behavior.
  • Guaranteed Hours

Chicago Service Areas: Andersonville, Bucktown, Gold Coast, Irving Park, Lakeview, Lincoln Park, Lincoln Square, Logan Square, Loop, North Center, Old Town, Ravenswood, River North, Roscoe Village, South Loop, Streeterville, West Loop, Wicker Park

What We're Looking For:

  • Experienced dog walkers with availability each weekday (Monday through Friday) 9am to 5pm.
  • A vehicle is required.
  • Reliability, punctuality, and great communication skills.
  • Ability to withstand all weather conditions outside and several hours of walking each day.
  • Familiarity with Chicago streets.
  • Eligibility to work in the U.S. and a minimum age of 18.
  • Prior experience with clients and dogs.
  • A working smartphone with a data plan for communication and tracking walks.

Pay & Perks

  • $19/hour with 30 hours a week guaranteed ($570.00 per week)
  • PTO accrual and 401(k) eligibility after 6 months.
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