Management & Leadership Jobs in Annapolis, MD (Now Hiring) — 266 open — Page 4

Insurance Agent - Annapolis, MD

Annapolis, Maryland, United States · Remote OK

Mid level$600M raised

Join Horace Mann and Unlock Your Financial Potential Ready to take control of your financial future? At Horace Mann, we are here to support you in achieving your goals and making a meaningful difference in the lives of t…

Skills: Insurance sales, Financial services, Business management, Networking, Relationship building

Senior Director, Business Systems

Annapolis, Maryland, United States · Hybrid

$175k–$215k/yr

Senior+

About Crisis24 Crisis24 is a global, AI-enhanced provider of travel risk management, mass communications, critical event management, crisis-security consulting, personal protection solutions and global medical concierge …

Skills: Business Systems, Salesforce, Project Management, Program Management, Business Operations

Free People Key Holder

Annapolis, Maryland, United States · On-site

Entry level

Location This position is located at 1915 Towne Centre Blvd, Annapolis, Maryland, 21401 United States Role Summary A Key Holder collaborates with the management team in supervision of store operations functions and leadi…

Skills: Store Operations, Leadership, Sales Driving, Customer Service, Visual Merchandising

ASSISTANT MANAGER

Annapolis, Maryland, United States · On-site

$17/hr–$24/hr

Mid level$400M raised

Job DetailsJob Location: MD - Annapolis - Annapolis, MD 21401Position Type: Full TimeEducation Level: High SchoolSalary Range: $17.00 - $24.00 Base+Commission/monthTravel Percentage: NominalJob Shift: Any - Monday throug…

Skills: Sales, Customer Service, Leadership, Communication, Multitasking

Pickleball Lead

Annapolis, Maryland, United States · On-site

Mid level$2.0B raised

Position Summary The Lead-Pickleball is responsible for providing overall management and leadership for club pickleball programming, including but not limited to, open play, clinics, mixers, leagues, tournaments and even…

Skills: Pickleball instruction, Event planning, Customer service, Staff supervision, Program management

Assistant Store Manager - Annapolis Mall

Annapolis, Maryland, United States · On-site

Mid level$2.5B raised

Overview As an Assistant Store Manager, you will support the Store Manager to build a team that delivers results through providing an amazing customer experience. You also share the responsibility to execute all store op…

Skills: Team leadership, Customer experience, Store operations, Merchandising, Sales management

Sales Lead

Annapolis, Maryland, United States · On-site

$16/hr–$20/hr

Mid level

About us Built on the foundation of fashion’s most iconic color contrast – White + Black – WHBM inspires independent women to embrace their power and femininity through modern yet timeless styles. We’re proud to be a pla…

Skills: Retail management, Sales leadership, Customer service, Cash handling, Inventory management

Membership Manager

Annapolis, Maryland, United States · On-site

Mid level

Join our energetic club team and lead the member experience! As a Membership Manager you’ll keep members happy, drive consistent membership enrollment, and help manage day-to-day club operations. You’ll provide tours, co…

Skills: Sales, Customer service, Relationship building, Lead generation, CRM

Human Resources Generalist

Annapolis, Maryland, United States · Remote Solely

$45k–$60k/yr

Mid level

This position is open to receive applications until 9/15/26. We do not hire in these states: New York, California, Washington Although we are a remote company, we cannot sponsor candidates from outside of the U.S. for U.…

Skills: Human resources, Employee relations, Performance management, Onboarding, Offboarding

Supervisor - Annapolis Mall

Annapolis, Maryland, United States · On-site

Mid level$2.5B raised

Overview As a Part-Time Supervisor, you will support the management team to create the best experience for our customer and deliver desired results. You also share the responsibility to execute assigned store operations …

Skills: Supervisory experience, Sales management, Product knowledge, Customer service, Merchandising

Parts Manager

Annapolis, Maryland, United States · On-site

$15/hr–$30/hr

Mid level

Champions Do More As one of the fastest-growing and most exciting brands in the industry, Crash Champions is the largest founder-led multi-shop operator (MSO) of high-quality collision repair service in the U.S. The comp…

Skills: Parts ordering, Inventory management, Vendor communication, Estimating software, CCC One

Sales Leader

Annapolis, Maryland, United States · On-site

$15/hr

Mid level

NORMAN’S, the premiere, and fastest growing employee-owned Hallmark Gold Crown retailer in the East, is seeking a qualified Part Time Sales Leader for our store in the Annapolis Harbor Center, in Annapolis, MD. We …

Skills: Retail Sales, Customer Service, Supervisory Skills, Team Leadership, Product Knowledge

Environmental Services - Manager in Training

Annapolis, Maryland, United States · On-site

$18/hr–$20/hr

Entry level

Overview Join Healthcare Services Group (HCSG) as an Environmental Services Manager in Training, where you will learn to manage your own account and oversee housekeeping, laundry, and floor care operations at a long-term…

Skills: Housekeeping management, Laundry operations, Floor care, Staff supervision, Compliance management

RN Unit Manager - FT Days

Annapolis, Maryland, United States · On-site

$94k–$112k/yr

Mid level

Overview At FutureCare our RN Unit Managers are highly regarded as health care providers that lead a dedicated nursing team. They have a positive impact on staff and residents and set the standard of excellence for our c…

Skills: Nursing Leadership, Clinical Operations, Resident Care Planning, Staff Supervision, Regulatory Compliance

Digital Technology Site Services Lead (Onsite)

Annapolis, Maryland, United States · On-site

$87k–$165k/yr

Senior$200K raised

Date Posted: 2026-08-31 Country: United States of America Location: US-MD-ANNAPOLIS-904 ~ 2551 Riva Rd ~ BLDG 904 Position Role Type: Onsite U.S. Citizen, U.S. Person, or Immigration Status Requirements: U.S. citizenship…

Skills: Site leadership, Infrastructure management, Vendor management, SLA management, Network technology

Pickleball Lead

Annapolis, Maryland, United States · On-site

Mid level$2.0B raised

Position Summary The Lead-Pickleball is responsible for providing overall management and leadership for club pickleball programming, including but not limited to, open play, clinics, mixers, leagues, tournaments and even…

Skills: Pickleball instruction, Event planning, Customer service, Program management, Scheduling

Executive Sous Chef

Annapolis, Maryland, United States · On-site

$75k–$85k/yr

Mid level

Job DetailsJob Location: Annapolis, MD 21401Position Type: Full TimeSalary Range: $75,000.00 - $85,000.00 Salary/yearJob Shift: AnyJob Category: Restaurant - Food ServiceAn Exciting Opportunity at Ginger Cove! Ginger Cov…

Skills: Food preparation, Culinary leadership, Sanitation standards, HACCP compliance, Inventory management

Enterprise Mobility logoEnterprise Mobility

Management Trainee

Annapolis, Maryland, United States · On-site

$55k–$58k/yr

Entry level

Overview Start your career with Enterprise Mobility! We’re hiring immediately for our respected Management Training Program. Whether you see yourself in sales, business development, customer service, retail management, o…

Skills: Customer Service, Sales, Business Development, Retail Management, Operations

Veterinary Nursing Manager - Annapolis, MD

Annapolis, Maryland, United States · On-site

Senior

ABOUT VEG In 2014, VEG was born with a mission to help people and their pets when they need it most. This meant challenging the status quo and fixing everything that was wrong with the ER experience. Since then, we’ve ex…

Skills: Veterinary Nursing Leadership, Team Management, Scheduling, Payroll Management, Hiring and Onboarding

Hospital Manager - Annapolis MD

Annapolis, Maryland, United States · On-site

Senior

ABOUT VEG In 2014, VEG was born with a mission to help people and their pets when they need it most. This meant challenging the status quo and fixing everything that was wrong with the ER experience. Since then, we’ve ex…

Skills: Leadership, Team management, Financial management, P&L oversight, Operations management

Frequently asked questions

How many Management & Leadership jobs are open in Annapolis, MD right now?

There are currently 266 open management & leadership positions in Annapolis, MD listed on Clera. New openings are added daily as companies post roles.

Which companies are hiring for Management & Leadership roles in Annapolis, MD?

Companies currently hiring include Luminis Health, HASI, CVS Health, New Energy Equity, Soccer Shots Company Owned Units (Baltimore-Washington, Miami, Nashville, and New York City), among others. Browse the listings above to see every active employer.

Are there remote or hybrid Management & Leadership jobs in Annapolis, MD?

Yes — 53 of the 266 open management & leadership positions offer remote or hybrid work (14 remote, 39 hybrid).

How do I apply for Management & Leadership jobs in Annapolis, MD?

Each listing links directly to the employer's application page. Apply early — fresh listings get the most recruiter attention in the first two weeks.