Sales Development Representative
Roundstone Sales Development Representative
Position: Regional Growth Specialist
Role Description
Be the first point of connection between Roundstone and executives ready to solve one of their biggest cost problems: healthcare spend. Our self-funded captive model is growing fast, and this role sits at the center of that growth. As a Regional Growth Specialist, you're part of Roundstone's Sales Development team. From day one, you're learning directly from our Chief Revenue Officer, EVP of Sales, and our Regional Practice Leaders (RPLs), not sitting on the sidelines.
What's the day-to-day?
You'll conduct outreach across email, phone, and social media to inbound and outbound leads, using a modern sales engagement stack that automates the busywork so you can focus on conversations. You'll also travel with RPLs to learn the self-funding industry firsthand: how relationships with distributors and prospects are built, and how our captive product solves real client problems.
This role is the tip of the spear, converting prospects into appointments. You'll get qualified marketing leads, data tools to build strong outreach lists, and close support from both marketing and sales as you refine your approach.
A defined path to Account Executive
This role is Roundstone's developmental pipeline for future Regional Practice Leaders. You're not just generating pipeline, you're building the skills, industry knowledge, and relationships that prepare you to step into an RPL seat. High performers have a clear, proven track to advance into that role (timeline subject to individual performance and demonstrated readiness).
You'll thrive here if you:
- Want a long-term career in personal selling, not just a job
- Are energized by building long-lasting relationships
- Enjoy learning and take action without waiting to be told
- Have an instinct for solving problems and presenting solutions
Key Duties & Responsibilities
- Prospect and qualify leads through outbound calling, emailing, and social selling
- Build and manage email sequence workflows in our sales enablement tool to drive consistent, high-volume outreach
- Set qualified appointments for the sales executive team and manage pipeline in our CRM
- Partner with marketing to shape targeted campaigns and refine messaging, targeting, and conversion strategy
- Nurture warm leads through consistent, value-driven follow-up
- Support event marketing efforts alongside our Marketing Event Coordinator
- Travel at least once a month for in-market prospecting, events, or team training
- Maintain accurate records of outreach and next steps in our sales platforms
Skills and Qualifications:
- 1-4 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, HubSpot, etc.), sales automation (SalesLoft, Gong, Outreach, etc.), and LinkedIn and go-to-market data platforms such as ZoomInfo or ApolloIO highly preferred.
- 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.
- Bachelor’s degree required
- Ability to study and pass the Life & Health Insurance license exam for the state of Ohio, to be completed within 6-8 weeks of hiring. Roundstone will help you obtain your license if you are not already licensed.
Better Benefits:
- 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
- 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
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 eight consecutive years, reflecting our continued growth and success.
Our Core Values
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 eight 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.
Culture and fit are integral to success and in an effort to achieve a better match both from a candidate's perspective and our organization, please take a minute, click on the link and take the really brief survey:
https://go.cultureindex.com/p/apWUAEe3ykHGx39
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.