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Remote Software Sales Development Representative Jobs in Chicago, IL

DocuSign

Account Executive, SMB Install

Chicago, IL · On-site +1

$26.30 - $38.50/hr

... post sales resources including Sales Development Representatives, Market Development ... Employee divides their time between in-office and remote work. Access to an office location is ...

Turing

Remote Software Engineer

Chicago, IL · Remote

$200 - $300/hr

Deep understanding of software architecture, design, development, debugging, and code quality/review assessment. * Excellent oral and written communication skills for clear, structured evaluation ...

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Remote Software Sales Development Representative information

See Chicago, IL salary details

$24.7K

$65.4K

$128.8K

How much do remote software sales development representative jobs pay per year?

As of Sep 14, 2026, the average yearly pay for remote software sales development representative in Chicago, IL is $65,414.00, according to ZipRecruiter salary data. Most workers in this role earn between $48,900.00 and $77,300.00 per year, depending on experience, location, and employer.

What is a remote software sales development representative?

A Remote Software Sales Development Representative (SDR) is a professional who works from a remote location to identify and qualify potential customers for a software company. Their main responsibilities include reaching out to prospects via email, phone, or social media, understanding customer needs, and setting up meetings or demos for the sales team. SDRs play a crucial role in generating new business opportunities and building the sales pipeline. They typically work closely with account executives and marketing teams to ensure a steady flow of qualified leads. This role requires strong communication skills, resilience, and a good understanding of the software products being sold.

What are the key skills and qualifications needed to thrive as a remote software sales development representative?

To thrive as a Remote Software Sales Development Representative, you need strong communication skills, a basic understanding of software products, and experience in sales or lead generation, often supported by a bachelor’s degree. Familiarity with CRM platforms like Salesforce, sales automation tools, and virtual meeting software is typically required. Exceptional self-motivation, resilience, and active listening are crucial soft skills for building relationships and handling rejection in a remote environment. These skills and qualities are important to effectively engage prospects, drive pipeline growth, and achieve sales targets from a remote setting.

What are some common challenges faced by remote software sales development representatives, and how can they be overcome?

Remote Software Sales Development Representatives often face challenges such as building rapport with prospects virtually, staying self-motivated without in-person team dynamics, and managing time effectively across different time zones. Overcoming these challenges typically involves leveraging strong communication tools, setting clear daily goals, and regularly collaborating with sales teams through virtual meetings. Many companies also offer mentorship programs and ongoing sales training to support remote SDRs in their professional growth.

What is the difference between Remote Software Sales Development Representative vs Remote Software Account Executive?

AspectRemote Software Sales Development RepresentativeRemote Software Account Executive
Primary RoleQualifies leads and sets appointments for sales teamsCloses deals and manages client relationships
Required SkillsLead generation, cold outreach, product knowledgeNegotiation, closing skills, account management
Work EnvironmentRemote, inside salesRemote or hybrid, client-facing
Typical MetricsNumber of qualified leads, outreach volumeSales closed, revenue generated

The main difference is that a Remote Software Sales Development Representative focuses on prospecting and qualifying leads, while a Remote Software Account Executive handles closing sales and managing client accounts. Both roles require strong communication skills and industry knowledge but serve different stages of the sales process.

What are the most commonly searched types of Software Sales Development Representative jobs in Chicago, IL?

The most popular types of Software Sales Development Representative jobs in Chicago, IL are:

What are popular job titles related to Remote Software Sales Development Representative jobs in Chicago, IL?

For Remote Software Sales Development Representative jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Software Sales Development Representative jobs in Chicago, IL look for?

The top searched job categories for Remote Software Sales Development Representative jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Remote Software Sales Development Representative jobs?

Cities near Chicago, IL with the most Remote Software Sales Development Representative job openings:

Remote Software Sales Development Representative jobs near you
Infographic showing various Remote Software Sales Development Representative job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 78% Full Time, 18% Part Time, and 3% Contract. Highlights an 90% Physical, 4% Hybrid, and 6% Remote job distribution, with an average salary of $65,414 per year, or $31.4 per hour.

Account Manager, Software Sales

Chicago, IL • On-site, Remote

ProSight Financial Association
See more jobs at ProSight Financial Associationexternal

Full-time

Retirement, PTO

Re-posted yesterday

Key responsibilities

  • Call prospects daily to generate and close sales opportunities.

  • Research and develop account strategies to identify and penetrate top prospects within the financial industry.

  • Follow leads through all stages of the sales cycle, including needs assessment, proposal, negotiation, closing, and post-sale follow-up.

Job description

Account Manager – ERC Software Sales
Reports to:  Group Director, Sales – Learning & Development
 
BAI and RMA have come together as ProSight Financial Association, a leading industry organization whose purpose is to empower financial services leaders to strengthen and advance our industry. The strategic combination brings together RMA’s expertise in serving the commercial banking and risk management functions and BAI’s knowledge in serving the retail banking and regulatory compliance functions. It’s a complementary union of two non-profit organizations that have always had their members’ and customers’ best interests in mind. Our industry-leading offerings include: peer sharing events, thought leadership, learning and development, and decision support solutions. Our work creates positive ripple effects throughout financial services organizations and ultimately helps consumers, businesses and communities thrive.
As an Account Manager selling our enterprise risk and compliance related software products in our St. Louis office, you will work as an inside sales representative, primarily calling bank, credit union, and mortgage firms nationwide.  You will be a hunter and will identify business needs and propose appropriate solutions for regulatory compliance training and other related services.  Based on customer needs assessment and potential account value, you may travel occasionally to give executive-level presentations to key decision-makers.  As a member of the Learning & Development sales team, you will work in a fast-paced, team-oriented environment.  The successful candidate will contribute to the business goals by meeting monthly, quarterly and annual new sales objectives.   ProSight has a strong brand and a leading market position in an industry where compliance requirements are increasing dramatically, all creating much opportunity for sales growth. 
 
Responsibilities
  • Plan and organize work schedule to call prospects to close sales daily.
  • Research/profile financial vertical nationwide to identify and penetrate top prospects.
  • Develop account strategies and a network of contacts at various levels/functional responsibility within each organization in the assigned territory.
  • Follow leads through all stages of the sales cycle -- lead generation, proposal, negotiation, closing and post-sale follow-up.
  • Conduct a needs assessment and develop recommendations/proposals.
  • Demonstrate technology products and solutions over the phone and Internet.
  • Stay attuned to market trends, competition, customer needs, pricing and other factors that may impact sales and growth.
  • Provide prospects with information and advice on BAI products and services.
  • Manage and maintain a sales funnel to achieve steady growth within assigned territory.
  • Provide realistic sales forecasts to facilitate growth.
  • Manage contract negotiations, service requirements and details to close the sale.
  • Manage territory, sales cycle and customers in CRM system.
Requirements
  • Bachelor's degree required
  • A minimum of 2 years’ experience in an inside sales role and direct experience in business-to-business solutions selling
  • Experience in either selling or servicing clients in the financial space
  • A desire to grow a territory by generating new business through prospecting
  • Experience organizing and managing an assigned territory
  • Strong organizational skills and the ability to work in an independent, self-directed environment
  • Experience in a high-volume, telephone-based selling environment
  • Experience selling products in a Software as a Service (SaaS) business model a plus
  • Experience in the financial services industry a plus
  • Demonstrated success creating leads and sales through prospecting
  • A history of meeting or exceeding assigned sales quotas for new business
  • Technologically savvy, with extensive use of the Microsoft Office suite and ability to learn and demonstrate proprietary systems
  • Demonstrated high-energy, tenacity and dedication to excellence as a sales professional
  • Motivated by an internal desire to win and a desire to increase your own personal wealth 
 
The compensation range for this position is $100,000 - $120,000 which includes base salary and participation in a commission plan based on individual sales results. ProSight offers an outstanding benefits package with comprehensive insurance coverage, a 401(k) plan with company match, flexible paid time off, hybrid and remote working models, tuition assistance and the ability to work in a collaborative, team-oriented environment.
 
To learn more about our company please visit www.prosightfa.org, www.bai.org, and www.rmahq.org