Remote LATAM Outbound Sales Leader & Playbooks Coach

Skyline Payment Systems, LLC; United States; Remote; USD 24,000 - 32,000; Full time

Benefits offered by this job

Equipment provided

Individual Contractor

Remote in LATAM

Career growth opportunities

Job summary

Skyline Payments is seeking a Sales Manager to lead and grow a remote outbound SDR team across LATAM. You’ll coach, train, and develop playbooks, tracking metrics to drive conversion and pipeline growth.

This contractor role offers a structured schedule and equipment provisioning, with a focus on data-driven results and collaboration with SDR members. Ideal candidates have 3+ years managing outbound teams, strong coaching skills, and experience in fintech or payments.

Qualifications

• 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

Responsibilities

• Build and manage a high-performing outbound sales team, with a strong emphasis on training, coaching, and skill development.
• Develop and refine sales playbooks, talk tracks, and training modules focused on cold calling, lead generation, objection handling, negotiation, and sales scripting.
• Oversee daily sales operations, establish team goals, and monitor performance metrics.
• Conduct regular call reviews to improve sales techniques, identify coaching opportunities, and enhance team effectiveness.
• Act as a hands-on leader and collaborative team player, working closely with SDR team members to achieve and exceed sales goals.
• Drive data-driven outcomes, including improved cold call conversion rates, increased outbound-sourced revenue, and month-over-month growth in qualified meetings.

Skills

Outbound SDR management

Sales coaching

Playbook development

Lead qualification

Data-driven mindset

People management

Communication skills

Job description

Skyline Payments is seeking a Sales Manager to lead and grow a remote outbound SDR team across LATAM. You’ll coach, train, and develop playbooks, tracking metrics to drive conversion and pipeline growth.

This contractor role offers a structured schedule and equipment provisioning, with a focus on data-driven results and collaboration with SDR members. Ideal candidates have 3+ years managing outbound teams, strong coaching skills, and experience in fintech or payments.