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Remote Outside Sales Jobs in Silver Spring, MD (NOW HIRING)

Have you led a remote outside sales team in a solutions based sales environment? Do you have leadership experience showing your ability to hold a team accountable for their results? Would you enjoy ...

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... options · Sales Training · Weekly Gas Allowance and Gas Bonuses · Health and Dental Benefits · Paid Vacation · 401(k) Qualifications · Valid driver's license and reliable means of ...

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... options · Sales Training · Weekly Gas Allowance and Gas Bonuses · Health and Dental Benefits · Paid Vacation · 401(k) Qualifications · Valid driver's license and reliable means of ...

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Remote Outside Sales information

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$31K

$80.7K

$171.1K

How much do remote outside sales jobs pay per year?

As of Aug 10, 2026, the average yearly pay for remote outside sales in Silver Spring, MD is $80,678.00, according to ZipRecruiter salary data. Most workers in this role earn between $54,300.00 and $93,000.00 per year, depending on experience, location, and employer.

What are the common challenges faced in a remote outside sales role, and how can I overcome them?

Working in Remote Outside Sales often involves challenges such as managing your own schedule, staying self-motivated, and building trust with clients without frequent face-to-face contact. It's important to use effective time-management strategies and maintain regular communication with both your team and clients through virtual meetings and prompt follow-ups. Utilizing CRM tools to track your progress and customer interactions can help keep you organized. Overcoming these challenges allows you to build a robust network, consistently meet sales goals, and thrive in a remote, client-oriented environment.

What is a remote outside sales?

A Remote Outside Sales job involves selling products or services to clients without being tied to a physical office. Sales representatives work from home or other remote locations, using phone calls, emails, and virtual meetings to connect with potential customers. While traditional outside sales require in-person visits, remote outside sales focus on digital communication and occasional travel. Success in this role depends on strong self-motivation, relationship-building skills, and the ability to close deals remotely.

What are the key skills and qualifications needed to thrive in remote outside sales?

To thrive as a Remote Outside Sales professional, you need strong sales acumen, self-motivation, and experience in prospecting and closing deals, often supported by a background in business or marketing. Familiarity with CRM software, virtual communication tools, and sales tracking systems is typically required. Excellent communication, relationship-building, and time management skills enable high performance in remote and client-facing settings. These abilities are crucial for meeting sales targets, maintaining customer satisfaction, and succeeding in a competitive, largely independent work environment.

What are the most commonly searched types of Outside Sales jobs in Silver Spring, MD? The most popular types of Outside Sales jobs in Silver Spring, MD are:
What are popular job titles related to Remote Outside Sales jobs in Silver Spring, MD? For Remote Outside Sales jobs in Silver Spring, MD, the most frequently searched job titles are:
What job categories do people searching Remote Outside Sales jobs in Silver Spring, MD look for? The top searched job categories for Remote Outside Sales jobs in Silver Spring, MD are:
What cities near Silver Spring, MD are hiring for Remote Outside Sales jobs? Cities near Silver Spring, MD with the most Remote Outside Sales job openings:
Infographic showing various Remote Outside Sales job openings in Silver Spring, MD as of August 2026, with employment types broken down into 75% Full Time, 23% Part Time, and 2% Contract. Highlights an 92% Physical, 1% Hybrid, and 7% Remote job distribution, with an average salary of $80,678 per year, or $38.8 per hour.

Regional Sales Manager

Rewards Network

Baltimore, MD • Remote

Full-time

Medical, Dental, Life, Retirement, PTO

Re-posted 22 days ago


Job description

Company Description

Rewards Network is the leading provider of capital & marketing services to the restaurant industry and the premier provider of dining rewards programs to the largest loyalty brands in the U.S. We offer unique products that use advanced technology to bring diners to restaurant clients. Our employee's work hard knowing Rewards Network is focused on results in every aspect - from people and processes to our final product. In return, our employees receive autonomy to make decisions that affect the business, provide career satisfaction and financial rewards.

Our culture is one of collaboration, accountability, and fun. Expectations are high, whether you're working in our corporate office nestled along the Chicago River, providing support to customers & clients from our Hollywood-based support center, or bringing value directly to clients in field sales.

Join us; you'll find a respectful environment that empowers employees, embraces trust and collaboration, provides challenges, and promotes transparency in your daily work-life.

Mission: For over 30 years, Rewards Network has worked to help restaurants grow. As the leading provider of capital and marketing products to the restaurant industry, we focus on bringing value to our clients every day.

Most recently since 2014, we enhanced our leadership, technology, and sales teams, fostering a rapid open working environment, team collaboration, and innovation. Above all, we let data and informed experimentation drive our decision-making.

And we've only just begun.



Job Description

Are you motivated by leading and mentoring a team of outside sales professionals? Do you pride yourself on your ability to motivate and support your team in achieving their sales goals? Do you a have the ability to keep a positive attitude when the going gets tough? Have you led a remote outside sales team in a solutions based sales environment? Do you have leadership experience showing your ability to hold a team accountable for their results? Would you enjoy developing a to achieve their professional and personal financial goals?

If those competencies are ones you possess then Rewards Network's Regional Sales Manager (of outside sales) role is right for you. This position is heavily focused on coaching and mentoring a team of Account Executives while growing regional revenue year over year. Rewards Network's Sales team's focus is generating new clients within the restaurant and bar industries. You need to be able to achieve business results through coaching and motivating, not by "making the sale" for your team. This role requires 80% travel and the ability to be a road warrior.

What We Offer:

  • Competitive base salary, monthly bonus, uncapped commission, and unlimited residual earnings on future renewed business. Plus, monthly transportation allowance.
  • Virtual work environment including the newest technology (iPhone, new HP laptop, cloud -based CRM - Salesforce, DocuSign, etc.) enabling you to succeed on the go in a remote capacity.
  • Robust group benefits, including, but not limited to dental, long & short-term disability, and life insurance and medical benefits through Blue Cross and Blue Shield of Illinois.
  • 401K plan with company match along with a robust annual paid time off package.
  • A Sales Training support team that provides an in-depth training to all sales new hires to learn as a group; providing real life lessons and a thorough understanding of our products and solutions giving your new team members vast confidence as you coach and mentor in the field with clients. After all, their success is your success.
  • Reimbursement when you dine with any of our nationwide restaurant and bar clients.
  • Dedication to diversity in the workplace.

Essential Duties and Responsibilities

  • Lead a team of Account Executives and Account Managers in an assigned territory who will be responsible for developing long lasting partnerships with restauranteurs.
  • Lead, coach and mentor an outside sales force; this will include positive motivation and performance evaluation, coaching, providing regular feedback, communication of goals, leading regular team calls, etc.
  • Recruit, retain and develop the necessary team within your region to ensure your team and region succeed in achieving results.
  • Maintain clear communication lines and a sense of camaraderie with sales team from a distance.
  • Develop, implement and attain regional sales objectives. Manage the team to meet/exceed new prospect sales and retention goals on a monthly, quarterly, and annual basis.
  • Assume P&L responsibility for assigned region and manage accountability for sales team's performance.
  • Spend 80% of the time in the field with Account Executives and Account Managers, joining them on sales calls and coaching them through the sales process.
  • Participate in higher level sales negotiations to ensure company policies and procedures are being followed as they relate to the sales process. Review and approve higher level deals as necessary.
  • Maintain an expert level of understanding of all products and services offered by Rewards Network.
  • Stay current with organizational changes, initiatives, and vision. Lead and motivate sales team around these.
  • Operate in a fast-paced, entrepreneurial setting where success is rewarded.



Qualifications

Position Requirements

  • Bachelor's Degree preferred.
  • At least 5-7 years of experience leading and managing an outside sales team selling consultative services in a business to business environment.
  • Must have experience leading a sales team that operates in a cold calling sales environment.
  • Experience in the restaurant industry or small-to-medium business strongly preferred; financial services or merchant cash advance industry experience is also highly advantageous.
  • MS Office skills and experience (Excel, Word, PowerPoint, Outlook).
  • Experience using Salesforce.com is a plus.
  • Demonstrated ability to motivate and achieve results through sales team.
  • Strategic, organized and technologically savvy in approach to managing a region and team.
  • Bring high-level problem solving, quantitative analysis and strong management skills to the team.
  • Willingness to travel up to 80% within assigned geographical territory.
  • Must be willing to work flexible hours and have a home-based office.



Additional Information

Rewards Network is an Equal Opportunity Employer (EOE). We encourage and strongly support workplace diversity.