B2B Sales Executive

Founded in 1989, The Holmes Organisation of Florida, Inc. is an independent, family-owned risk management and insurance agency headquartered in Jacksonville, FL. For more than 35 years, we've grown alongside the businesses and individuals we serve, building deep expertise in commercial insurance, private client protection, employee benefits, and bonding.

What sets us apart is our consultative approach. We don't sell policies—we build programs. By taking the time to understand each client's unique risks and exposures, our team delivers tailored solutions that larger, transactional firms simply can't match.

As private equity continues to consolidate local agencies into national call centers, staying independent and locally owned is our competitive advantage—and it's why growth matters. We're investing in our people, our newly renovated open-concept office, and the next generation of talent who will help carry the firm forward. Our culture is built on a clear set of values: do the right thing, deliver your best work, communicate with honesty and warmth, and never stop improving. We believe that when our team wins, our clients win.

If you're a driven, forward-thinking sales professional who wants to build a meaningful career with uncapped, compounding earnings potential, The Holmes Organisation is where you belong.

Job Description

The B2B Sales Executive is a new business sales role focused on commercial insurance and risk management solutions. In this role, you’ll prospect, win, and grow relationships with business owners and senior executives across the Jacksonville market, working four or five target industry verticals. It's relationship-driven, targeted sales with training and mentoring provided by experienced insurance professionals.

No insurance background is required—and that's by design. We hire proven salespeople from outside the industry and teach them the insurance side from day one. Your first step after starting is getting licensed; from there, we'll train you on the technical side while you do what you already do well: build pipeline and close. Then the business is yours to keep growing. Accounts renew year after year, so you're not starting from zero every January; you're building a residual book of business that compounds into real long-term income.

What you'll do:

• Prospect and develop new commercial clients through cold calling, in-person visits, networking, referrals, involvement in professional associations, social media, and other targeted outreach within assigned industry verticals
• Build your own pipeline from scratch and own it end to end, maintaining strong relationships with business owners, executives, and referral partners
• Meet with prospects and clients to understand business operations, risk exposures, and insurance needs
• Earn business from established competitors through consultative, value-based selling
• Collaborate with internal service and marketing teams to build tailored commercial insurance and risk management solutions
• Present proposals and recommendations to prospects and clients in a clear, professional manner
• Support long-term client retention through advocacy, communication, and ongoing relationship management
• Stay curious about the industries you serve in addition to the insurance industry itself, staying informed on industry trends, insurance products, and market conditions
• Participate in sales meetings, training programs, and mentoring opportunities
• Represent the agency professionally in the Jacksonville business community
  

Qualifications

• Bachelor's degree preferred
• 2+ years of B2B sales experience (services or solutions, not commodities)
• Comfort and credibility selling to business owners and senior executives, with demonstrated experience in professional relationship building
• Strong written and verbal communication and presentation skills
• High personal integrity and a genuine commitment to excellence
• Florida 2-20 Property & Casualty license, obtained after hire (we'll set you up to start the day you join); prior insurance experience is not required

What makes someone successful here

• You sell on value, not price, and can walk into a room and earn trust
• You've sold something that required displacing an incumbent, convincing a prospect to leave an existing provider for you
• You're coming out of a non-recurring-revenue role and want to build a book of business that pays residual income annually
• You're comfortable with a longer sales cycle and don't get frustrated when a deal takes months to land
• You're resilient—you can point to wins that didn't come easy
• You know Jacksonville and understand the nuances of doing business in a "large small town"
• You're looking for a 10-year career, not a stepping stone

Prior insurance experience is not required and is not what we're looking for—we train every producer from the ground up.

Additional Information

Compensation
This role pairs a competitive base salary with uncapped commission and residual income that grows as your book renews and expands.

Benefits 
Holmes invests in its people with a benefits package that includes:

• A choice of three UnitedHealthcare medical plans – including a high-deductible HSA option – with Holmes contributing toward your premium (and a company contribution to your HSA on the HSA plan)
• Dental and vision coverage, with an employer contribution to dental
• Company-paid term life, AD&D, and short-term disability insurance—100% covered by Holmes
• 401(k) with company match
• Paid time off starting at 15 days and increasing with tenure, plus paid company holidays
• Optional supplemental coverage

In-Office, Travel & Training

• This is a full-time, onsite, client-facing sales position based in Jacksonville, FL (5 days/week in office).
• Local travel to client, prospect, and business development meetings is expected, with occasional out-of-town travel.
• New hires begin licensing immediately via a self-paced online course and state exam; formal training and ongoing in-person mentoring are provided throughout your first year and beyond.

All communications will be treated confidentially to protect your current employment.

The Holmes Organisation provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, citizenship status, age, disability, or any other category protected under applicable law. This policy applies to all terms and conditions of employment, including, but not limited to, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation, and training.

This job posting is being managed by FractionalRecruiter on behalf of The Holmes Organisation.