Entry Level Mckesson Field Sales Development Jobs in Chicago, IL

ProcIndex is hiring a confident, resourceful B2B Field Sales Development Representative to build relationships with finance leaders at construction and manufacturing companies across the mid west.

You will spend most of your week in the field: researching high-value companies, planning efficient routes, making professional visits to corporate offices without prior appointments, navigating gatekeepers, and securing qualified meetings with CFOs, Controllers, and other finance leaders.

You will work closely with ProcIndex’s founder, learn a field-prospecting playbook that is already producing executive conversations, and help turn it into a repeatable sales motion.

About ProcIndex

ProcIndex is an early-stage AI accounting software company helping construction and manufacturing finance teams automate accounts payable, accounts receivable, vendor communication, and other repetitive accounting operations. We sell directly to CFOs, Controllers, and accounting leaders at mid-market and enterprise companies.

What you will do

• Research target construction and manufacturing companies before visiting them.
• Build efficient daily and weekly travel routes across assigned Illinois territories.
• Make professional, unscheduled visits to corporate offices and introduce ProcIndex with thoughtful leave-behinds.
• Start credible conversations with reception teams, executive assistants, accounting professionals, Controllers, CFOs, and other decision-makers.
• Identify the right finance leader, understand the company’s accounting environment, and secure qualified introductory meetings.
• Follow up promptly by phone, email, and LinkedIn after each visit.
• Maintain accurate activity, contact, and follow-up notes in the CRM.
• Share field intelligence about company locations, decision-makers, timing, objections, and competing priorities.
• Work directly with the founder to improve messaging, routes, materials, and the overall field-sales playbook.
• Represent ProcIndex with good judgment, persistence, warmth, and professionalism.

Performance will be measured primarily by qualified meetings that take place and the sales pipeline created—not simply by the number of materials distributed.

You may be a strong fit if you

• Have at least one year of B2B outside sales, field sales, territory development, appointment setting, or other face-to-face business-development experience.
• Can walk into an unfamiliar corporate office, start a conversation naturally, and remain composed when the answer is initially “no.”
• Are polished and credible enough to represent a software company in front of senior finance executives.
• Are persistent without being pushy and can build rapport with people at every level of an organization.
• Plan carefully, manage time well, and can operate independently without needing constant supervision.
• Write clear follow-up messages and keep disciplined CRM records.
• Are comfortable learning accounting and financial-operations concepts well enough to have an intelligent initial conversation.
• Have a valid driver’s license, current automobile insurance, and reliable access to a vehicle.
• Are available for frequent travel throughout Illinois, including occasional overnight trips.

A college degree is not required. Demonstrated initiative, judgment, resilience, and face-to-face prospecting ability matter more to us.

Preferred, but not required

• Experience selling B2B software or professional services.
• Experience reaching CFOs, Controllers, or other senior executives.
• Familiarity with construction, manufacturing, accounting, ERP systems, accounts payable, or accounts receivable.
• Experience working in About the role

ProcIndex is hiring an experienced sales representative to generate new business opportunities across Chicago and its suburbs through in-person prospecting.

We provide AI-powered accounting software to construction and manufacturing companies. You will visit prospective customers, connect with CFOs, Controllers, and accounting teams, qualify their needs, and schedule discovery meetings and product demonstrations.

Your initial focus will be prospecting and appointment setting, with our founder handling product demos and closing. Strong performance can lead to expanded responsibilities in demonstrations, deal management, and closing.

Responsibilities

• Develop a pipeline of prospective customers through business visits, cold outreach, referrals, and consistent follow-up.
• Conduct regular in-person prospecting, including unannounced visits to corporate offices.
• Identify finance decision-makers, introduce ProcIndex, and uncover relevant accounting challenges.
• Qualify opportunities and schedule meetings with appropriate decision-makers.
• Coordinate meeting confirmations and provide clear prospect notes for the founder.
• Organize efficient daily routes and prioritize accounts across your territory.
• Maintain accurate contact information, activities, and next steps in the CRM.
• Meet agreed activity and qualified-meeting targets, and review results with the founder.

Qualifications

• At least one year of experience in outside sales, field sales, business development, or another sales role involving proactive customer acquisition.
• Demonstrated success generating new leads, securing appointments, or meeting sales targets.
• Confidence conducting cold outreach and initiating face-to-face business conversations.
• Strong communication, objection-handling, organization, and follow-up skills.
• Ability to manage a local territory and work independently.
• Experience using a CRM or similar system to track sales activity.
• Valid driver’s license and a reliable, insured personal vehicle.
• Ability to travel regularly throughout Chicago and the surrounding suburbs during business hours.

B2B field sales experience is preferred. Experience selling business services, payroll, staffing, merchant services, telecom, or industrial products is relevant. Prior software or accounting experience is helpful but not required.

an early-stage startup or building a territory from the ground up.