Outside Sales Representative (CBA01)

Delve Search & Recruiting; Chicago (IL); Hybrid; USD 70,000 - 80,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401(k) with employer contribution

Hybrid work model

Field autonomy

Professional development

Job summary

Delve Search & Recruiting is seeking an energetic Outside Sales Representative for the Chicago area. This B2B role focuses on new business development, prospecting, and building a long‑term book of business across the Chicago market.

The ideal candidate has 2+ years in outside sales, a proven ability to open doors, generate opportunities, and meet or exceed sales goals. You will cold call, visit prospects, attend events, and manage relationships with executives.

Qualifications

• 2+ years of B2B outside sales or new-business development.
• Proven success generating opportunities through personal prospecting, not just inbound leads.
• Experience managing a sales pipeline and meeting/exceeding sales goals.
• Comfort with cold calls, in-person visits, and initiating conversations with executives.

Responsibilities

• Generate new business through cold outreach, in-person prospecting, referrals, networking, and industry events.
• Identify and develop relationships with business owners, CFOs, HR leaders, and other executive decision-makers.
• Research prospective clients and independently identify opportunities throughout the Chicago market.
• Develop and execute weekly prospecting plans to maintain consistent pipeline activity.
• Conduct introductory meetings and discovery conversations to understand prospective clients’ business challenges.
• Collaborate with senior team members and internal specialists throughout the sales process.
• Manage opportunities from initial outreach through the sales cycle, maintaining consistent communication and follow-up.
• Build referral relationships and maintain an active presence within the local business community.
• Maintain accurate CRM records and track prospecting activity, meetings, pipeline development, and sales results.

Skills

B2B sales

Prospecting

Cold calling

Relationship building

CRM

Tools

CRM software

Job description

Outside Sales Representative | Chicago, IL

B2B Outside Sales | New Business Development | Professional Services

Year 1 On-Target Earnings: $140,000–$160,000

Location: Chicago, IL | Hybrid / Field-Based

About the Opportunity

Our client is a growing professional services firm specializing in employee and workforce solutions for mid‑sized businesses. The organization partners with employers to help them manage costs, improve employee programs, and develop long‑term strategies that support their business and workforce.

Due to continued growth, the company is expanding its business development team in the Chicago market.

We are seeking a motivated B2B sales professional who has developed a strong foundation in prospecting and new‑business development and is ready for greater autonomy and responsibility.

This is a hands‑on outside sales opportunity focused on generating new business, developing relationships with local decision‑makers, and building a long‑term book of business throughout the Chicago area.

The ideal candidate enjoys the challenge of opening doors, creating opportunities from scratch, and turning consistent sales activity into measurable results.

Responsibilities

• Generate new business through cold outreach, in‑person prospecting, referrals, networking, and industry events.
• Identify and develop relationships with business owners, CFOs, HR leaders, and other executive decision‑makers.
• Research prospective clients and independently identify opportunities throughout the Chicago market.
• Develop and execute weekly prospecting plans to maintain consistent pipeline activity.
• Conduct introductory meetings and discovery conversations to understand prospective clients’ business challenges.
• Collaborate with senior team members and internal specialists throughout the sales process.
• Manage opportunities from initial outreach through the sales cycle, maintaining consistent communication and follow‑up.
• Build referral relationships and maintain an active presence within the local business community.
• Maintain accurate CRM records and track prospecting activity, meetings, pipeline development, and sales results.

Preferred Background

• 2+ years of professional B2B sales experience, preferably in an outside sales or new‑business development role.
• Demonstrated success generating opportunities through personal prospecting rather than relying primarily on inbound leads or inherited accounts.
• Experience managing a sales pipeline and taking ownership of individual sales objectives.
• A track record of meeting or exceeding sales goals.
• Comfortable making cold calls, conducting in‑person visits, and initiating conversations with prospective clients.
• Strong communication and relationship‑building skills, with the ability to engage business owners and executive decision‑makers.
• Organized, resourceful, and disciplined with prospecting activity and follow‑up.
• Able to manage a schedule, identify priorities, and execute independently.
• Interested in developing a long‑term career in consultative B2B sales.

Experience in payroll, HR technology, staffing, workforce solutions, business services, or other B2B sales environments is preferred but not required.

Additional Information

This opportunity is particularly well suited for a sales professional who has built strong prospecting habits, demonstrated success in a structured B2B sales environment, and is ready to take greater ownership of the full sales cycle.

The successful candidate will enjoy the hands‑on work of generating new business. They will be comfortable picking up the phone, visiting prospective clients, attending networking events, and finding creative ways to develop relationships.

Our client values initiative and follow‑through. You should be able to identify an opportunity, develop a plan, and execute without needing constant direction.

This is an individual contributor position focused on developing new business in the Chicago market. It is not a sales management role, an account management position, or an opportunity built around an inherited book of business.

Candidates who enjoy prospecting, value independence, and want to develop their skills in a more consultative sales environment will find an opportunity to grow here.

This position requires a consistent presence in the Chicago market.

Salespeople typically spend three to four days per week in the field, meeting prospective clients, making in‑person visits, attending networking events, and developing relationships throughout the area.

You will have access to experienced leadership and internal resources while maintaining responsibility for your own prospecting, scheduling, and pipeline development.

Candidates must be based in the Chicago area and comfortable with regular local travel.

• Base salary of $70,000–$80,000
• Year 1 on‑target earnings of approximately $140,000–$160,000
• Uncapped commission structure. Residual commissions.
• Medical, dental, and vision coverage
• 401(k) with employer contribution
• Professional development and advancement opportunities
• Hybrid flexibility with significant field autonomy

Why Consider This Opportunity?

If you have built a strong foundation in B2B sales and are looking for an opportunity to take greater ownership of your results, this position offers a compelling next step.

You will have the freedom to develop your own business, the support of an established organization, and the opportunity to build long‑term client relationships in the Chicago market.

This is an opportunity for someone who enjoys the hunt, takes pride in creating opportunities, and wants their initiative and consistent performance to translate into long‑term career growth.