Sales Development Representative

Roundstone Insurance is hiring a Regional Growth Specialist to expand pipeline by prospecting into marketing-generated leads and executing outbound outreach. This hybrid role in Cleveland, OH focuses on identifying qualified prospects, initiating conversations, and booking meetings for sales leadership while building expertise across channels.

Location and Compensation

• Location: Cleveland, OH (hybrid)
• Salary: USD 70,000 - 120,000 per year

Role Overview

The position prospects into marketing-generated leads and creates pipeline through outbound efforts. You will identify prospects, begin outreach conversations, and set qualified appointments for sales leaders. The role also emphasizes building capability across outreach channels and improving execution over time.

Key Responsibilities

• Prospect and qualify leads using outbound calling, emailing, and social selling.
• Create sequence-based workflows in a sales enablement tool to manage follow-up and support high-volume outreach.
• Perform high-volume outreach through calls, LinkedIn, and email to connect with potential clients and decision-makers.
• Partner with marketing to develop and execute targeted campaigns that drive engagement and interest.
• Set qualified appointments and meetings for the sales team and track pipeline movement in the CRM.
• Support warm leads with value-driven communication and consistent follow-up.
• Collaborate with marketing and senior sales reps to improve messaging, targeting, and conversion strategies.
• Assist event marketing efforts by coordinating with the company’s Marketing Event Coordinator.
• Travel at least once per month for in-market prospecting, events, training, or team collaboration.
• Maintain detailed records of outreach, conversations, and next steps across sales systems.

Requirements

• 3-5 years of sales experience preferred (internships, inside sales, retail, or customer-facing roles count).
• Comfort making cold calls daily and confidence using phone-based outreach.
• Strong verbal and written communication skills.
• Experience or familiarity with CRMs (e.g., Salesforce, Pardot), sales automation, and LinkedIn and go-to-market platform such as ZoomInfo.
• Experience using Sales Enablement tools such as Outreach or similar platforms.
• Entrepreneurial, innovative mindset with motivation to contribute new ideas.
• Curious, coachable approach and motivation by performance-based growth and earnings.
• Ability and willingness to travel monthly to support relationship-building and team events.
• Bonus: Experience in insurance, benefits, or healthcare B2B sales is a plus (not required).
• Bachelor’s degree preferred.
• Life & Health Insurance license required to start selling (Roundstone will help obtain if not already licensed).

Technology and Tools

• Salesforce
• Pardot
• LinkedIn
• ZoomInfo
• Outreach
• Sales enablement tools
• Customer Relationship Management (CRM)
• Sales automation
• Zoom

Benefits

• Medical, dental and vision benefits
• Annual bonus
• Dependent care 100% match up to max allowable
• Parental leave
• PTO beginning on Day 1
• Tuition reimbursement
• Healthy work/life balance
• Hybrid office schedule
• 401(k) plan with company match
• Employee Assistance Program
• On-site gym with personal trainer access
• Life insurance and short term disability insurance

Core Values

• Live well: Be healthier and bring positive energy to all you do.
• Work smarter: Get things done, better.
• Own it: Accountability is your middle name. Be on time, do what you say, and finish what you start.
• Be intellectually curious: Always be learning. See opportunity everywhere and have a drive to know.

Culture and Fit

Culture and fit are integral to success. Additional details are available here: https://go.cultureindex.com/p/apWUAEe3ykHGx39