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Remote Software Sales Development Representative Jobs in Chicago, IL

PHMG

Senior Sales Development Representative

Chicago, IL · On-site +1

$85K - $100K/yr

Senior Sales Development Representative - High Earnings & Career Growth with Global Audio Branding Leader Location: 401 N Michigan Ave, Chicago, IL 60611 Starting Salary: $60,000 (based on experience ...

Analyst1

Sales Development Representative (SDR)

Chicago, IL · Remote

$55K - $75K/yr

About the role As a Sales Development Rep , you will play a pivotal role in driving the growth of ... Remote-First Culture * Flexible Time Off Policy * 401(k), Life Insurance, Pet Insurance, Pre-paid ...

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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 Jul 13, 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 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 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, and why are they important?

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 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

Founding Sales Development Representative (SDR) U.S. remote

Venturous

Chicago, IL • Remote

$50K/yr

Full-time

Medical, Dental, Vision, PTO

Re-posted 12 days ago

Job description

Founding Sales Development Representative (SDR) U.S. Remote

Company: Venturous

Start Date: March 20, 2026

Location: Remote: U.S.

Salary: $50,000 plus commission

About the Company: Venturous is building a curated network of elite enterprise healthcare operators who help emerging healthcare companies solve critical go-to-market and operational challenges.

Many healthcare startups struggle to navigate complex enterprise buyers such as health systems, payers and large provider organizations. Venturous connects these companies with experienced operators who have spent decades inside those systems.

Examples include:


• Former hospital system procurement leaders


• Payer network executives


• Revenue cycle operators


• Digital health commercialization leaders

Our experts engage with companies through short-term problem-solving engagements, advisory work, fractional leadership roles and executive placements.

Venturous is backed by a leading healthcare venture studio and one of the most active healthcare technology investors in the United States.

Job Description:
Venturous is hiring a Founding Sales Development Representative (SDR) to identify emerging healthcare companies that can benefit from the Venturous expert network.

Your primary responsibility is to research, identify, and engage venture backed healthcare startups and book qualified meetings for the Venturous team.

This is an outbound role focused on prospecting and meeting generation, not closing.

You will play a key role in building the company's initial sales pipeline.

Key Responsibilities

Prospecting and Lead Generation

• Identify venture backed healthcare startups that fit the Venturous ideal customer profile


• Research companies, founders and leadership teams to understand their challenges


• Build targeted lead lists using tools such as Apollo, LinkedIn Sales Navigator and other sources

Outbound Engagement


• Conduct outbound outreach via email, Instantly, LinkedIn and other channels


• Craft personalized messaging tailored to each company and leadership team


• Book qualified meetings with founders and executives

Pipeline Development


• Maintain accurate records of outreach activity and pipeline in the CRM


• Track outreach performance and continuously improve messaging and targeting


• Work closely with Venturous leadership to refine the ideal customer profile and messaging

Market Intelligence


• Monitor venture activity and identify new healthcare startups entering the market


• Identify trends and opportunities in digital health and healthcare services companies

Ideal Candidate

You may be a strong fit if you:


• Have experience in outbound sales, business development, recruiting or lead generation


• Are curious about healthcare innovation and startup ecosystems


• Are comfortable researching companies and leadership teams independently


• Write clear and compelling outreach messages


• Are resilient and comfortable with high volumes of outbound activity


• Are organized and able to track activity and results in a CRM

Experience working with healthcare companies, venture backed startups, or enterprise healthcare buyers is a strong plus but not required.

Why This Role Is Unique

This is a founding sales role at a company building a new model for connecting healthcare startups with experienced enterprise operators.

You will gain exposure to:


• Leading healthcare startups


• Experienced healthcare executives


• Venture investors and venture studios


• The inner workings of early-stage company building

Compensation

Base salary: $50,000

Additional compensation includes commission based on qualified meetings and revenue generated from sourced opportunities.

Benefits


• Health insurance


• Generous PTO


• Fully remote work environment


• Opportunity to grow into senior sales or business development roles as the company scales