Small Company. BIG Opportunity.
Career Opportunities
City Wide of Boston is growing and we are always looking for individuals interested in growth, personal development and mentorship. We offer a highly competitive rewards package, dynamic culture and high growth potential for our team. Interested in joining our team? Visit our career center to learn more about our benefits and current openings. You can also simply join our talent community to stay up to date with opportunities!
Strategic Planning Manager
As a Strategic Planning Manager, you will work cross-functionally with leadership and operations teams to analyze market trends, evaluate performance metrics, and support strategic initiatives that drive growth, efficiency, and profitability. You’ll play a key role in shaping the future of City Wide by translating complex data into actionable business plans.
Sales/Corporate Trainer
As a Sales/Corporate Trainer, you will play a vital role in onboarding new employees, enhancing the skills of our current team, and driving performance through engaging, impactful training programs with a strong emphasis on our sales team. You’ll work closely with leadership to identify training needs, develop content, and deliver sessions that reflect City Wide’s standards of excellence and service.
Account Manager
This position is a hybrid role of sales, customer service, and relationship building with existing clients. The Account Manager is field based and will visit their clients regularly to build relationships and to establish trust and rapport.
Night Manager
Assist with management of contract compliance of designated building maintenance services (as noted in the client Scope of Services) as well as maintain the relationship between City Wide and the various Independent Contractors.
Sales Executive
We’re looking for a Sales Executive who thrives on hunting for new business, closing complex B2B deals, and building partnerships that deliver real value. This is a high-impact role focused on generating new revenue—not managing existing accounts.
Regional Sales Manager
We are looking for another “A Player” sales leader to add to our team. The ideal candidate is someone who is driven to succeed with a “roll-up-your-sleeves” attitude in supporting their team and driving revenue. A strong leadership IQ and a desire to drive success through coaching and mentoring is a must.
Associate Account Manager
As an Associate Account Manager, you’ll serve as a key point of contact for clients—ensuring satisfaction, identifying growth opportunities, and coordinating service delivery. This role is ideal for someone with a strong customer service or junior sales/account management background who’s ready to deepen their client-facing experience and contribute directly to revenue growth.
Employee Testimonials
Meet Our Amazing Team
We encourage and applaud our team for sharing ideas that help us steer the company to new successes. In fact, the most successful ideas we have executed have come from our team. Bring your ideas to City Wide of Boston, and you will be heard.
A Message from the Owner
“We were excited to start this business because we had confidence in our ability to work hard to build a business that would have an impact on our clients and employees. We are fortunate to be surrounded by an amazing team of people and have a wonderful list of clients who value our approach.”
Karen W Sommers, Owner
Benefits Overview
- 3 Weeks Paid Time Off
- 8 Paid Holidays
- 1 Volunteer Day Off
- Company Sponsored Health, Dental and Vision Insurances
- 401K Plan with a 4% company match
- Training program and ongoing access to company e-learning platform