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Skyline Payments Systems seeks a Sales Manager to build and lead a remote SDR team focused on cold calling, lead generation, and discovery to drive outbound revenue. You will design tailored sales playbooks, review calls, and coach on best practices for objection handling, qualification, and pipeline development.
As a hands-on leader, you will set team goals, monitor metrics, and collaborate with SDRs to exceed targets.
Job Description
About the Role: At Skyline Payments, we empower small and medium-sized businesses (SMBs) by delivering payment solutions that enhance their growth and operational efficiency. We are seeking a Sales Manager who will focus on developing our remote SDR teams by enhancing their cold calling, lead generation, and discovery skills. The ideal candidate will create and implement tailored sales playbooks, review and analyze recorded calls, and provide ongoing coaching on best practices for objection handling, pipeline creation, and lead qualification.
This role will be instrumental in driving data-driven results, including increased conversion rates, qualified meetings, and outbound-sourced revenue.
What you'll do:
What we are looking for:
What We Offer
About Skyline Payments
Who We Are
Skyline Payments is a trusted FinTech partner with over 10 years in the payments industry, serving thousands of small and medium‑sized enterprises (SMEs) with innovative and reliable payment solutions. Our mission is to empower SMBs by simplifying transactions, enhancing cash flow management, and providing exceptional support with our user‑friendly software. Over the past decade, we have built a solid foundation and experienced stable growth, and we are now poised to take our expansion to the next level. With ambitious goals and a full‑force approach to growth, we're scaling our impact and continuing to drive value for our clients as we push the boundaries of what's possible in payment technology.
Find more about our history here.
Why Join Us?
At Skyline Payments, we foster a collaborative, high‑energy environment where every team member's contributions drive our shared success. As we embark on our next phase of growth, our goal is to expand our reach and elevate our impact across the payments industry. We are scaling up operations, exploring new markets, and enhancing our product offerings to meet the evolving needs of small and medium‑sized businesses globally.
Joining Skyline Payments now means being part of a transformative period of expansion, where your work will directly contribute to our ambitious growth and help shape the future of payment solutions. We offer significant opportunities for professional development and career advancement, including leadership paths and impactful projects that make a real difference for our clients.
At least 3 years of experience managing outbound SDR teams. Proven experience training and developing SDR teams, particularly in cold calling, lead generation, and multi-threading. Demonstrated success in building and leading outbound sales. Strong sales management and coaching skills, with experience developing soft skills for engaging decision-makers. Background in people management, including experience launching and training first‑time sales teams. Industry experience in Fintech or Payments is a plus, but not required. Experience working with small and mid‑sized businesses is preferred. Data‑driven mindset with the ability to analyze and improve conversion rates, lead generation efforts, and pipeline creation. Excellent verbal and written communication skills Strong attention to detail and organizational skills