Jeremy Whitcomb
Falling Waters
Summary
Strategic Sales Executive with expertise in health benefits, commercial insurance, and consultative selling. Skilled in simplifying complex solutions, building strong client relationships, and managing high-performing pipelines. Consistently drives revenue growth and delivers measurable business impact.
Overview
1
1
Certification
13
13
years of professional experience
Work History
SENIOR BENEFITS ACCOUNT EXECUTIVE
Rippling
Remote, West Virginia
03.2023 - Current
- Drove full-cycle sales for insurance and HR/PEO solutions carveouts, showcasing integrated platforms in benefits, payroll, HRIS, compliance, and onboarding to enhance client engagement
- Managed high-velocity pipeline through complex, multi-stakeholder sales cycles, ensuring alignment with client needs and facilitating timely decision-making
- Consistently meet and exceed quota through strategic prospecting and strong closing execution
- Execute consultative sales strategies to identify client pain points and deliver tailored solutions
- Partnered cross-functionally with product, onboarding, and support teams to deliver tailored solutions, driving successful client outcomes and satisfaction
MID/LARGE MARKET HEALTH AND BENEFITS BROKER
Paychex Insurance Agency
Remote, West Virginia
01.2014 - 03.2023
- Led open enrollment, benefits strategy, and client consulting for SMB, mid-market, and large market clients
- Managed full client lifecycle, including prospecting, quoting, closing, and ongoing account service, ensuring client satisfaction and retention
- Negotiated favorable terms with carriers, enhancing client value and increasing retention rates
- Consistently exceeded sales targets and retention goals
- Translated complex insurance concepts into clear, actionable recommendations
- Generated new business through targeted prospecting, referrals, and strategic networking, contributing to overall revenue growth
COMMERCIAL INSURANCE BROKER
Pie Insurance
Remote, West Virginia
01.2022 - 01.2023
- Educated small and medium-sized businesses on risk and insurance products, brokered business, presented and closed opportunities, and serviced accounts to enhance client understanding and satisfaction.
- Meets and exceeds personal and team sales targets as established, focusing on small to midsize accounts
- Collaborated with colleagues to address complex client requirements and deliver tailored insurance packages, ensuring comprehensive coverage and client retention.
- Collaborate with underwriting, marketing and development teams to develop, manage, and drive premium generation
- Leveraged analytical skills to assess client risk profiles accurately, enabling informed decision-making regarding coverage options.
COMMERCIAL INSURANCE BROKER
CoverWallet an AON Company
Remote, West Virginia
01.2019 - 01.2022
- Provided expert guidance on various commercial insurance products such as general liability, workers' compensation, property, marine cargo, cyber liability policies among others.
- Evaluated potential risks and crafted customized policies, effectively mitigating client exposure.
- Provided tailored insurance solutions to small and medium-sized businesses to address immediate and future needs.
- Streamlined internal processes in risk assessment and policy management, improving overall workflow efficiency.
Education
Bachelor of Arts - Liberal Arts, focus on American and European history
Christendom College
Front Royal, Virginia05.2009
Skills
- Consultative Sales Strategy
- SaaS & Benefits Solutions Selling
- Pipeline Development & Forecasting
- Negotiation & Closing
- Client Relationship Management
- Cross-Functional Collaboration
- CRM Systems (Salesforce, etc)
- Presentation & Communication
Certification
Life, Accident, and Health, Personal Lines, Property and Casualty
Accomplishments
- 8-time Presidents Club recipient
- 3-time Circle of Excellence recipient
- 6-time Representative of the Year
- 1-time Rookie of the Year
- Sales number achievements available upon request.
Timeline
SENIOR BENEFITS ACCOUNT EXECUTIVE
Rippling
03.2023 - Current
COMMERCIAL INSURANCE BROKER
Pie Insurance
01.2022 - 01.2023
COMMERCIAL INSURANCE BROKER
CoverWallet an AON Company
01.2019 - 01.2022
MID/LARGE MARKET HEALTH AND BENEFITS BROKER
Paychex Insurance Agency
01.2014 - 03.2023
Bachelor of Arts - Liberal Arts, focus on American and European history
Christendom College