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Sales Development Representative, Outbound; Remote U.S

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60601, USA
Listing for: Seamless
Full Time, Remote/Work from Home position Listed on 2026-11-15
Job specializations:
Salary/Wage Range or Industry Benchmark: 50000 - 75000 USD Yearly USD 50000.00 75000.00 YEAR

Job Description & How to Apply Below

Position: Sales Development Representative, Outbound (Remote U.S.)
Why Seamless

Seamless is building the future of AI-powered sales and revenue technology.

Our platform brings together real-time B2B data, artificial intelligence, sales engagement, enrichment, automation, buyer signals, AI agents, APIs, integrations, and workflow capabilities to help revenue teams find the right buyers, improve contact and company data, personalize outreach, create pipeline, and convert more opportunities into revenue.

As a Sales Development Representative (Outbound) at Seamless, you will have the opportunity to:

  • Build a career in technology sales while developing the prospecting, communication, and consultative selling skills that create a foundation for long-term success in SaaS.
  • Take ownership of your earning potential with a competitive base salary, uncapped commission opportunities, and performance-based recognition.
  • Directly influence company growth by creating new sales opportunities, generating qualified pipeline, and connecting prospective customers with solutions that can improve their businesses.
  • Gain hands-on experience with AI-powered sales technology , including sales intelligence, buyer data, prospecting, sales engagement, and automation tools.
  • Develop valuable sales skills in cold calling, prospect research, discovery, objection handling, relationship building, and opportunity qualification.
  • Learn from experienced sales leaders through coaching, call reviews, feedback, product training, and ongoing sales development.
  • Partner closely with Account Executives and other commercial teams to understand how prospecting activity translates into qualified pipeline and closed revenue.
  • Build a foundation for career growth into Account Executive, account management, sales leadership, and other revenue-generating opportunities as your skills and performance develop.

At Seamless,
ownership, accountability, continuous learning, collaboration, and results matter. You’ll have the opportunity to develop your sales capabilities, take pride in your performance, and build a career in an industry being transformed by AI.

The Opportunity

Seamless is hiring motivated, competitive, and coachable Sales Development Representatives (SDRs) to help drive new-business growth through outbound prospecting and pipeline generation.

This is a high-activity, phone-first outbound sales role for someone who enjoys connecting with people, starting conversations, overcoming objections, and turning initial prospect interest into qualified sales opportunities.

As an Outbound SDR, you will be responsible for engaging prospective customers through cold calling, email, and other approved outreach channels. You’ll research target accounts, connect with decision-makers, uncover business challenges, and introduce how Seamless can help organizations improve prospecting, sales productivity, and revenue generation.

You’ll work closely with Account Executives to qualify prospects, schedule meaningful sales conversations, and create opportunities that contribute directly to the company’s pipeline and revenue goals.

You will succeed in this role if you are comfortable making outbound calls, motivated by measurable goals, receptive to coaching, and willing to consistently put in the effort required to develop your skills and improve your results.

Whether you’re beginning your career in technology sales or bringing previous business development experience, this is an opportunity to develop practical sales expertise while representing an AI-powered revenue technology platform.

What You’ll Own
  • Generate New Sales Opportunities: Proactively engage prospective customers through high-volume outbound cold calling, email, and other approved prospecting channels to create qualified sales opportunities.
  • Build Qualified Pipeline: Identif…
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