Outside Sales Representative

About the Role

Payeload is seeking an Outside Sales Representative to develop new business, grow customer relationships, and turn sales opportunities into lasting partnerships. This role requires a proactive salesperson who is comfortable prospecting, meeting customers in person, understanding their needs, and managing the sales process from initial contact through close and onboarding.

Key Responsibilities

• Identify and pursue new customers within an assigned territory.
• Generate opportunities through cold calling, outreach, referrals, and in-person visits.
• Schedule and conduct customer meetings to understand needs and present Payeload’s services.
• Develop proposals, coordinate pricing approvals, address objections, and close business.
• Build relationships with decision-makers and identify opportunities to expand existing accounts.
• Coordinate with internal teams to ensure a smooth customer onboarding experience and follow through on commitments.
• Maintain accurate CRM records, including contacts, meeting notes, opportunities, and next steps.
• Meet established goals for sales activity, new customers, revenue, and account growth.
• Share customer feedback, competitive insights, and territory opportunities with leadership.

Weekly Planning & Travel

• Travel within the assigned territory Tuesday through Thursday to meet customers and prospects.
• Submit a weekly travel and sales plan by Sunday night outlining each day’s customer meetings, planned activities, desired outcomes, and action items.
• Participate in Monday’s team meeting to review the weekly plan, discuss opportunities, and identify support needed.
• Manage preparation, proposals, follow-ups, and CRM updates throughout the week.

Qualifications

• Experience in outside sales, business development, or a related customer-facing role.
• Ability to prospect independently, build relationships, and close opportunities.
• Strong communication, presentation, negotiation, and organizational skills.
• Consistent follow-through and accountability for results.
• Comfort using a CRM and standard business productivity tools.
• Willingness and ability to travel regularly within the assigned territory.
• Valid driver’s license and reliable transportation for required travel.
• Experience in transportation, logistics, delivery, or a related industry preferred.

What Success Looks Like

Success means building a healthy pipeline, winning new customers, growing accounts, and delivering on customer commitments. The representative consistently arrives prepared, maintains clear next steps for active opportunities, and meets established sales goals.