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Sales Development Representative | Benefits & Insurance | February 2027

CBIZ Operations, Inc.

Cleveland, OH · HybridJobSeen todaySeen in employer's feed today

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At a glance

Compensation
No compensation found
Location
Cleveland, OHHybrid
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Job overview

The Sales Development Representative develops B2B outbound prospecting skills and builds a foundation for becoming a sales consultant. The role contacts prospective businesses, qualifies interest, and secures initial meetings for sales consultants. It uses data-driven systems and works with Marketing and Sales Management. The program includes sales training, business development, service-line training, and a transition toward a sales producer position.

Skills & qualifications

RequiredNice to have

Skills

Outbound ProspectingOutbound CallingEmail MessagingSocial SellingCustomer ResearchPhone CommunicationObjection HandlingCustomer Relationship ManagementSalesforceCompetitive DriveCoachabilityCommunicationMarketing Data AnalysisCuriosityVerbal CommunicationWritten CommunicationOrganizationTime Management

Qualifications

Bachelor's in Risk Management Insurance, Sales, Business, or Related FieldHigh School Diploma or GED1+ Year Sales and Customer Service Experience

Full job description

#LI-TL1 #LI-Hybrid Position Description The Sales Development Representative's primary objective is to develop the necessary new business development skills for B2B outbound prospecting and build the foundation to become a successful sales consultant. The initial goal in this role is to gain acceptance and agreement from prospective businesses to set up initial meetings with our revenue-producing sales consultants who then drive the process forward. Reporting to the B&I Sales Development Manager, the role will pursue a high volume of outbound suspects who are sourced through marketing efforts and partnerships with our service line sales leaders. The role will have access to data-driven systems such as Salesforce, SalesLoft, DemandBase, LinkedIn Sales Navigator, and other productivity tools to help you succeed. Essential Functions and Primary Duties - Utilize effective outbound calling strategies, effective email messaging, and social selling techniques developed in collaboration with Marketing and Sales Management to secure first appointments with prospective businesses. - Research potential customers and determine appropriate contacts to reach. - Evaluate and qualify interest by engaging and navigating phone conversations. - Overcome objections, engage with prospects in conversations, and gain their acceptance to connect with our sales consultants. - Initiate sales discussions between sales consultants and decision-makers. - Document findings in customer relationship management (CRM) software. - Maintain accurate and up-to-date records of prospect's interactions and sales activities in the CRM system. - Log appropriate follow up activities to stay connected with prospective companies and maintain business relevance. - Meet and exceed targets for scheduled meetings and conversion rates. - Stay informed about industry trends, market conditions, value differentiators, and competition to enhance inbound and outbound prospecting efforts. Preferred Qualifications - A bachelor's degree in Risk Management Insurance, Sales, Business, or a related field. - Strong drive to compete and succeed in a fast-paced sales environment. - A desire to be coached, accept advice, seek advice, implement strategies provided, and work to improve your skills. - Comfortable making a high volume of phone calls while maintaining quality output. - Excellent communication skills with an ability to connect with people in a short amount of time. - Successful experience using marketing-driven data to convert prospects from brand awareness to meeting-ready. - Demonstrated skill in overcoming objections and driving desired outcomes. - Proficiency in using Customer Relationship Management (CRM) systems- Salesforce experience preferred. - Relentlessly curious mindset and a willingness to learn about Advisory Services. Program Timeline - Training: Instructional, hands-on, sales tech process, sales coaching, role-playing. - Month 1: Sales development training, sales tech process, learning CBIZ and B&I service lines. - Months 2-9: Business development work, ongoing sales development training, B&I service line training, sales cycle fundamentals, sales presentation fundamentals. - Months 10-18: Transition to a B&I service line, obtain licensing, service line specific training and coaching, and service line sales process training. - Months 19+: Continuing to work toward sales producer position. Minimum Qualifications High School Diploma or GED required At least 1 year of sales and customer service experience Advanced verbal and written communication skills Advanced organizational and time management skills

How this job compares

Set against the 770 open Sales Development Representative jobs on Olive Jobs, counted October 31, 2026.

Pay
  • This postingNot listed
  • US median$60–75K/yr544 salary ranges
  • US median$28–32/hr36 hourly ranges
Openings
Olive Jobs lists 19 open Sales Development Representative jobs in Ohio and 770 across the US. 9% of them nationwide are listed as remote or flexible.
Hiring the most across the US
Experience
This posting asks for at least 1 year of experience; Sales Development Representative postings that state a minimum ask for 1 year at the median (414 postings).
Education
This posting asks for a high school diploma; 147 of the 770 open Sales Development Representative jobs (19%) ask for a high school diploma or higher.

Counted across the open, public US postings on Olive Jobs on October 31, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

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