Outside Sales Representative (CBA15)

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

Benefits offered by this job

Medical, dental, and vision insurance

401(k) with employer contribution

Hybrid flexibility and significant 1:1

Professional development and careerAdv

Job summary

Delve Search & Recruiting seeks a Chicago-based Outside Sales Representative for a hybrid/field sales role. You will generate new business, build relationships with business owners and executives, and manage opportunities through the full sales cycle to develop a long-term book of business.

You’ll leverage a proven prospecting approach, meet annual targets, and work with leadership to translate needs into solutions.

Qualifications

• 3+ years of professional B2B sales or business development experience.
• Demonstrated record of meeting or exceeding sales objectives.
• Experience generating opportunities through personal prospecting.
• Experience engaging business owners, executives, or other decision-makers.
• Full-cycle sales experience is valuable but not required for greater responsibility.

Responsibilities

• Generate new business through cold calling, outreach, in-person prospecting, referrals, networking, and events.
• Identify and develop relationships with business owners, CFOs, HR executives, and other decision-makers in the Chicago market.
• Research prospective clients, identify opportunities, and tailor approaches to open new accounts.
• Build and execute prospecting strategies to generate qualified opportunities.
• Conduct introductory meetings and discovery conversations to understand client challenges and objectives.
• Collaborate with sales leadership and internal specialists to develop solutions and advance opportunities.
• Manage relationships and opportunities through the sales process with consistent communication.
• Develop referral relationships and establish a presence within the local business community.
• Maintain CRM records and track prospecting activity, meetings, pipeline development, and results.
• Build a long-term portfolio of client relationships for recurring business.

Job description

Outside Sales Representative | Chicago, IL

B2B Sales | New Business Development | Consultative Selling

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

Commission: Uncapped, with residual earning opportunities

Location: Chicago, IL | Hybrid / Field-Based

About the Opportunity

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

As the company continues expanding its Chicago presence, we are seeking a motivated B2B sales professional with a demonstrated track record of generating new business and developing relationships with decision-makers.

This opportunity is well suited for someone who has built a strong foundation in prospecting, business development, or outside sales and is ready to take greater ownership of the sales process.

The position offers the opportunity to transition into a more consultative, relationship-driven sales environment while developing a long-term book of business.

We are not necessarily looking for someone who has spent years in this particular industry. We are looking for someone who knows how to create opportunities, build relationships, and turn consistent effort into results.

What You'll Do

• Generate new business through cold calling, targeted outreach, in-person prospecting, referrals, networking, and industry events.
• Identify and develop relationships with business owners, CFOs, HR executives, and other decision-makers throughout the Chicago market.
• Research prospective clients, identify opportunities, and develop targeted approaches to opening new accounts.
• Build and execute prospecting strategies that consistently generate qualified opportunities.
• Conduct introductory meetings and discovery conversations to understand prospective clients' business challenges and objectives.
• Collaborate with experienced sales leadership and internal specialists to develop solutions and advance opportunities.
• Manage relationships and opportunities throughout the sales process, maintaining consistent communication and follow-up.
• Develop referral relationships and establish a presence within the local business community.
• Maintain accurate CRM records and track prospecting activity, meetings, pipeline development, and sales results.
• Build a long-term portfolio of client relationships that supports recurring business and income growth.

What We're Looking For

• Ideally 3+ years of professional B2B sales or business development experience.
• A demonstrated record of meeting or exceeding sales objectives.
• Meaningful experience generating opportunities through personal prospecting rather than relying primarily on inbound leads or inherited accounts.
• Experience engaging business owners, executives, or other organizational decision-makers.
• A solid understanding of prospecting, qualification, pipeline development, and sales follow-up.
• Experience with full-cycle sales is valuable, but not required for candidates who have demonstrated strong business development performance and are ready for greater responsibility.
• Comfortable operating independently and taking ownership of results.
• Able to research a market, identify prospective customers, develop an approach, and execute.
• Resourceful in finding ways to reach decision-makers and create opportunities.
• Disciplined with daily activity, territory planning, time management, and follow-up.
• Willing to take initiative rather than wait for detailed instructions or a steady flow of assigned leads.

Relationship Building & Communication

• Comfortable initiating conversations with new prospects, both over the phone and in person.
• Able to build credibility and establish trust with business owners and senior decision-makers.
• Naturally curious, with the ability to ask thoughtful questions and understand business challenges.
• Persistent and professional when navigating longer sales cycles.
• Interested in developing lasting business relationships rather than focusing exclusively on transactional sales.

Backgrounds That May Translate Well

We welcome candidates from a variety of B2B sales environments, including:

• Payroll and HR technology
• SaaS and technology sales
• Staffing and recruiting services
• Healthcare services and business development
• Financial and professional services
• Logistics and transportation sales
• Business services and other competitive B2B sales environments

Candidates with experience in structured sales organizations, high-volume outbound environments, or territory-based business development are encouraged to apply.

Who Will Succeed in This Role?

The ideal candidate has already demonstrated that they can generate business and is looking for an opportunity to take the next step professionally.

You may currently be:

• A successful BDR or SDR who wants to move beyond appointment setting and take greater ownership of the sales cycle.
• An outside sales representative who enjoys prospecting, territory development, and face-to-face relationship building.
• A B2B salesperson who has performed well in a structured environment and is ready for greater autonomy.
• A business development professional who enjoys researching prospective customers, developing creative outreach strategies, and building relationships from scratch.

Regardless of your background, you should enjoy the process of finding new business. This means being comfortable making calls, visiting prospective clients, attending networking events, developing referral relationships, and consistently following up with opportunities.

You should also be comfortable working toward broad objectives, identifying what needs to be done, and taking responsibility for executing your plan.

This is a Chicago-based, hybrid/field sales position requiring consistent engagement with the local business community.

Sales representatives typically spend three to four days per week in the field, meeting prospective clients, making in-person visits, attending networking events, and developing business relationships.

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

Candidates must reside in the Chicago area and be comfortable traveling regularly throughout the local market.

• Base salary of $70,000-$80,000
• Approximate Year 1 on-target earnings of $140,000-$160,000
• Uncapped commissions with residual earning opportunities
• Medical, dental, and vision insurance
• 401(k) with employer contribution
• Professional development and advancement opportunities
• Hybrid flexibility and significant field autonomy

Why Consider This Opportunity?

This is an opportunity for a proven B2B sales professional who wants more than simply generating meetings or managing an existing group of accounts.

You’ll have the ability to create your own opportunities, develop relationships with business leaders, and take greater ownership of the sales process.

The company offers the support of an established organization while providing the independence to build your own business within the Chicago market.

For someone who enjoys prospecting, values autonomy, and wants to develop a long-term career in consultative sales, this position offers meaningful professional and financial growth.