Sales Development Representative

Roundstone, Inc.; Cleveland (OH); Hybrid; USD 60,000 - 100,000; Full time

Benefits offered by this job

Medical, dental and vision benefits

Dependent care 100% match

Parental leave

PTO Day 1

Hybrid office schedule

401(k) with company match

Employee Assistance Program

On-site gym with trainer access

Life insurance

Job summary

Roundstone, Inc. is seeking a motivated Regional Growth Specialist to drive pipeline and revenue growth from the Greater Cleveland area.

You will prospect, qualify, and engage with target organizations via outbound calls, email, and social channels, while collaborating with marketing to convert warm leads and set meetings for the sales team. You will develop expertise across channels, execute high-volume outreach, and travel monthly to support in-market activities and events.

Qualifications

• 3-5 years of sales experience preferred (internships, inside sales, retail, or customer-facing roles count).
• Unshakable hunger and grit to grow into a closer-level role in a high-paced sales environment.
• Fearless with the phone and comfortable making cold calls daily.
• Excellent verbal and written communication skills.
• Familiarity with CRMs (e.g., Salesforce, Pardot), sales automation, and LinkedIn/go-to-market platforms such as ZoomInfo.
• Experience with Sales Enablement tools like Outreach or similar platforms.
• Entrepreneurial and innovative mindset with a drive for performance-based growth and earnings.
• Willingness to travel monthly to support relationship-building and events.
• Bonus: Insurance/healthcare B2B sales experience is a plus but not required.
• Life & Health Insurance license to start selling (Roundsstone will assist if not licensed)

Responsibilities

• Prospect & qualify leads through outbound calling, emailing, and social selling.
• Create sequence-based workflows in our sales enablement tool to manage follow-up and improve high-volume outreach.
• Conduct high-volume outreach (calls, LinkedIn, email) to connect with potential clients and decision-makers.
• Collaborate with marketing to develop and execute targeted campaigns that generate engagement.
• Set qualified appointments and meetings for the sales team; track pipeline progress in the CRM.
• Nurture warm leads with value-driven communication and persistent follow-ups.
• Work cross-functionally with marketing and senior sales reps to refine messaging and targeting.
• Assist event marketing by coordinating with the Marketing Event Coordinator.
• Travel at least monthly for in-market prospecting, events, training or team collaboration.
• Maintain detailed records of outreach and next steps in sales platforms.

Skills

Sales experience

Cold calling

Communication skills

CRM tools

LinkedIn prospecting

Sales automation

ZoomInfo

Outreach

Entrepreneurial mindset

Willingness to travel

Tools

Salesforce

Pardot

ZoomInfo

Outreach

Job description

Location: Greater Cleveland, OH

Job Id:392

# of Openings:2

Internal Position Title: Regional Growth Specialist

Role Description

Do you thrive on opening doors, creating opportunities, and building pipeline from the ground up? Roundstone Insurance is looking for a motivated, proactive, and ambitious individual to join our growing sales team as a Regional Growth Specialist.

This role plays a critical part in our continued growth. As a Regional Growth Specialist, you’ll ensure no opportunity goes untouched prospecting into leads generated by our marketing team while also creating your own through outbound efforts. In this role, you’ll serve as the tip of the spear identifying prospects, initiating conversations, and setting the stage for our sales leaders to close new business. You’ll develop expertise across multiple channels including LinkedIn, cold calling, email, and events, all while playing a key role in building pipeline and driving revenue growth.

You’ll work closely with both marketing and sales, helping refine outreach strategies, engage warm leads, and uncover organizations ready for a better approach to healthcare. With our proven model, this role not only supports our rapid growth but also provides a clear path for your own career advancement within the organization.

Key Duties & Responsibilities

• Prospect & qualify leads through outbound calling, emailing, and social selling.
• Create sequence-based workflows in our sales enablement tool to manage your follow-up and help promote high volume, efficient outreach.
• Conduct high-volume outreach (calls, LinkedIn, email) to connect with potential clients and decision-makers.
• Collaborate with marketing to develop and execute targeted campaigns that generate engagement and interest.
• Set qualified appointments and meetings for the sales team, tracking and managing pipeline progress in our Customer Relationship Management (CRM) system.
• Nurture warm leads and stay engaged through value-driven communication and consistent follow-ups.
• Work cross-functionally with marketing and senior sales reps to improve messaging, targeting, and conversion strategies.
• Assist event marketing efforts by coordinating with company’s Marketing Event Coordinator.
• Travel at least once a month for in-market prospecting, events, training or team collaboration.
• Maintain detailed records of outreach, conversations, and next steps within sales platforms.

Skills and Qualifications

• 3-5 years of sales experience preferred (internships, inside sales, retail, or customer-facing roles count).
• Unshakable hunger and grit you want to be in a high-paced sales and grow into a closer-level role.
• Fearless with the phone and comfortable making cold calls daily.
• Excellent verbal and written communication skills.
• Familiarity with CRMs (e.g., Salesforce, Pardot), sales automation, and LinkedIn and go-to-market platform such as ZoomInfo.
• Experience with Sales Enablement tools like Outreach or other similar platforms.
• Entrepreneurial and innovative mindset motivated to bring new ideas to the table.
• Curious, coachable, and motivated by performance-based growth and earnings.
• Able and willing to travel monthly to support relationship-building efforts and team events.
• Bonus: Experience in insurance, benefits, or healthcare B2B sales is a plus but not required.
• Life & Health Insurance license required to start selling (Roundstone will help you obtain if you are not already licensed.)

We’re leaders in our industry, so naturally, we look out for our employees’ best interests with a robust benefits package. Roundstone employees are eligible for:

• Medical, dental and vision benefits
• Dependent care 100% match up to max allowable
• Parental leave
• PTO beginning on Day 1
• 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

More About Roundstone

Headquartered in Rocky River, Ohio, Roundstone is proud to be a Northeast Ohio Top Workplace, as recognized by The Plain Dealer and cleveland.com, based on anonymous employee feedback. We foster a supportive, values-driven culture where employees feel engaged, valued, and celebrated. Roundstone has also been named an Inc. 5000 award recipient for nine consecutive years, reflecting our continued growth and success.

Our 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.

Don't meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every single qualification. At Roundstone Insurance we are dedicated to building a diverse, inclusive, and authentic workplace, so if you're excited about this role but your past experience doesn't align perfectly with every qualification in the job description, we encourage you to apply anyways. You may be just the right candidate for this or other roles.