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Remote Software Sales Development Representative Jobs in Chicago, IL

RoofingSource

Business Development Representative

Niles, IL · Remote

$60K - $80K/yr

Develop and execute targeted sales plans for assigned markets * Maintain accurate records in the CR ... Remote work possible after successful evaluation period * Medical, Dental & Vision Insurance * Pet ...

BAI

Account Manager, Software Sales

Chicago, IL · On-site +1

$100K - $120K/yr

Group Director, Sales - Learning & Development BAI and RMA have come together as ProSight Financial ... Louis office, you will work as an inside sales representative, primarily calling bank, credit union ...

SS&C

Sr. Software Sales Executive

Chicago, IL · On-site +1

Remote or Hybrid US About the Role SS&C Technologies, Inc. is seeking a highly motivated and ... development reimbursement opportunity. Applications will be accepted on an ongoing basis until the ...

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Remote Software Sales Development Representative information

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$24.7K

$65.4K

$128.8K

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

As of Jul 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 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
Sales Development Representative - Chicago (Hybrid)

Sales Development Representative - Chicago (Hybrid)

Firstup

Chicago, IL • Remote

$27.50 - $31.25/hr

Full-time

Re-posted yesterday

Job description

Who We Are

At Firstup, our mission is to improve the employee experience at every moment that matters, large and small. As the communication pipeline for the world's workforce, we now serve 40 of the Fortune 100 companies, reaching and connecting more than 17 million employees daily.

Our employees are experts in the employee experience, workforce communications and technology. 
Joining Firstup means joining a movement to make work better for every worker. As the world’s first intelligent communication platform, Firstup meaningfully engages employees at every moment from hire to retire, and delivers engagement insights to help companies support, promote and retain their talent. Our movement has taken root and is evident in our world-class customer base. Now we need your help. Ready to make a difference in the world?


The SDR role at Firstup sits at the intersection of Sales and Marketing. You'll own top-of-funnel pipeline creation for a set of named enterprise accounts, working in close partnership with an Account Executive and aligned Marketing support. Your primary buyers are CHROs, VPs of Internal Communications, and Directors of Employee Experience — senior leaders who control meaningful budget and are actively looking for solutions to workforce engagement challenges.

Success here requires business acumen, intellectual curiosity, and the ability to build credibility with executives through relevance and insight — not persistence alone.


 
Responsibilities

  • Build and execute a multi-touch, multi-channel prospecting strategy (phone, email, LinkedIn, video, direct mail) targeting Director through C-suite buyers at named enterprise accounts.

  • Research target accounts and individual stakeholders to develop insight-led outreach — understanding their business priorities, recent initiatives, and internal communications challenges before making first contact.

  • Partner closely with your AE to align on account strategy, prioritize opportunities, and convert booked meetings into qualified pipeline.

  • Collaborate with Marketing to leverage campaigns, events, and content as outreach triggers and conversation starters.

  • Achieve and exceed monthly and quarterly KPIs including meetings booked, pipeline generated, and connect rates.

  • Maintain accurate activity logging and pipeline data in Salesforce and Groove, and use data to continuously refine your approach.

  • Participate actively in team enablement sessions, bringing feedback from the field to sharpen the team's collective messaging and sequencing.
Required Qualifications

  • 1+ year of SDR, BDR, or outbound sales experience

  • Demonstrated ability to self-source meetings with senior stakeholders

  • Strong written and verbal communication skills — executive-ready

  • Comfort with outreach platforms (Groove, SalesLoft, or equivalent)

  • High attention to detail in CRM hygiene and activity tracking

  • Bachelor's degree or equivalent practical experience

Strongly Preferred

  • Experience selling into HR, Internal Communications, or HCM buyers

  • Familiarity with enterprise SaaS sales cycles and multi-threaded account strategies

  • Working knowledge of MEDDPICC, Challenger, or similar sales frameworks

  • Experience with Sales Navigator and intent data tools like HockeyStack

  • Demonstrated coachability — examples of feedback you received and applied

Who Thrives Here

The SDRs who excel at Firstup share a specific profile. They are:

  • Insight-driven, not script-dependent. They do real research before reaching out and lead with business relevance — not feature lists.

  • Resilient and process-oriented. They understand that pipeline is built through consistent, disciplined execution, and they don't abandon what's working.

  • Growth-obsessed. They actively seek coaching, ask thoughtful questions in team sessions, and view feedback as currency.

  • Collaborative by default. They think of their AE as a partner, not just a handoff point, and take accountability for the quality of meetings they book — not just the quantity.

  • Ambitious with a long-term orientation. They want to build a career in enterprise sales and understand that the SDR seat is the foundation, not the ceiling.

Firstup expects the base salary for this role to be an hourly rate between $27.50-$31.25. The starting rate of pay may vary based on factors including, but not limited to, position offered, location, education, training, and/or experience.
 

Why Firstup?
 
Because you care - about people, the work you do, and the connections you make. Work is such a large part of life; it only makes sense to make it awesome.
 
If you want to engage brilliant minds in a high-growth and inclusive environment where ideas are rewarded regardless of who they come from, join us. This is a rapidly changing space so if you thrive on ambiguity, are hungry for a challenge, and have the guts to speak your mind, you could be a perfect fit.
 
We offer an excellent PTO program, great health benefits, a casual and friendly environment, remote work, and a leadership team who truly believes in your growth – both personally and professionally.
 
Firstup is committed to providing equal employment opportunities to all applicants for employment and to all employees, without regard to race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, protected disability, veteran status, or any other protected status in accordance with applicable federal, state or local laws.


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We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.