About Benmore Technologies
Benmore Technologies is a software development and AI transformation firm based in downtown Chicago. We build custom software, AI systems, and internal automation platforms for growing mid-market companies across the United States.
Our clients partner with us to modernize operations, eliminate manual work, and build software that creates a competitive advantage. We are profitable, growing quickly, and expanding our outbound sales team for the first time.
If you are excited about AI, enjoy talking to people, and want a clear path into a high-performing B2B sales career, we'd love to meet you.
Job Summary
The Sales Development Representative (SDR) is the front line of Benmore's growth. You will be introducing business leaders to AI and software solutions that can fundamentally change how their companies operate.
This role is designed for people who are competitive, coachable, and genuinely enjoy being on the phone. You will receive structured training, daily coaching, and a clear path into an Account Executive role as you consistently hit quota and develop your sales skills.
Your job is straightforward. Start conversations, qualify opportunities, and generate pipeline for our closing team.
Responsibilities
Build qualified pipeline by making high-volume outbound calls to executives and operators at mid-market companiesBecome an expert on Benmore's software development and AI transformation services so you can confidently speak to the business problems we solveExecute daily outbound prospecting through phone calls, LinkedIn outreach, and follow-up emails using our established playbooksWork from pre-built prospect lists and proven call scripts. Your time should be spent selling, not building lists or writing email campaignsQualify opportunities, schedule meetings for Account Executives, and ensure prospects are prepared for their discovery callsMaintain accurate CRM records and log all prospect activity, call outcomes, and follow-up tasksPartner closely with Account Executives to improve messaging, increase meeting quality, and generate more pipelineMaintain consistent activity levels while staying coachable, resilient, and focused on continuous improvementWhat's Involved?
We promote from within. SDRs who consistently perform, master the sales process, and take ownership of their development will have the opportunity to move into a full-cycle Account Executive role.
Sales Is Your Only Job
Your responsibility is generating pipeline through conversations. We provide prospect lists, outbound systems, call scripts, CRM workflows, and automated email sequences so you can focus on booking meetings instead of building infrastructure.
Learn AI From the Inside
Artificial intelligence is transforming every industry. You will work directly with a team building AI systems for real businesses, giving you firsthand exposure to one of the fastest-growing markets in technology.
High Standards. High Growth.
We are building a team of ambitious people who want to improve every week. You will receive live coaching, recorded call reviews, daily feedback, and mentorship designed to accelerate your development.
Requirements and Preferred Experience
0 to 2 years of experience in sales, business development, customer-facing roles, or other communication-focused workComfortable spending most of the day on the phone and motivated by outbound prospectingCompetitive mindset with resilience. Rejection does not throw off your dayHighly coachable and able to quickly apply feedback from recorded call reviewsNaturally curious about technology, software, and AIStrong verbal and written communication skillsA professional LinkedIn profile and online presenceCold calling or quota-carrying sales experience is a strong plusFormer athletes, military veterans, and people with competitive backgrounds are encouraged to applyAbility to work from our downtown Chicago office five days per weekCompensation
Chicago, IL
Base salary: $55,000 to $65,000On-target earnings: $75,000 to $90,000Compensation includes a competitive base salary plus uncapped commission based on qualified meetings held.
Final compensation will depend on experience, qualifications, and prior performance.
Why Benmore?
Build Your Sales Career
Whether this is your first SDR role or you already have outbound experience, you will receive structured onboarding, daily coaching, and a proven sales playbook that prepares you for a long-term career in B2B technology sales.
Work With Cutting-Edge Technology
You will represent a company building custom software and AI systems that help businesses operate more efficiently, automate manual work, and make better decisions.
Join a Company That Is Scaling
This is an opportunity to join an early outbound sales team where your work has a direct impact on company growth. You will work closely with leadership, help shape the sales organization, and develop skills that accelerate your career.
Performance Is Rewarded
We care about results, accountability, and continuous improvement. Strong performance is recognized, rewarded, and creates opportunities for increased responsibility and advancement.
Location
Downtown Chicago, Illinois
This is a full-time, in-office position, Monday through Friday.
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