Middle Insurance Account Executive

About First Gen Financial

We’re a fast-growing, purpose-driven B2B financial services company built on integrity, accountability, and continuous growth. We have developed our own proprietary insurance product for employers which is scaling rapidly. Our leadership team brings proven expertise from multiple sectors of finance, and every team member plays a direct role in expanding both our clients’ success and our company’s vision. We unlock capital to empower teams!

About Us

We’re a fast-growing, purpose-driven B2B financial services company built on integrity, accountability, and continuous growth. We have developed our own proprietary insurance product for employers which is scaling rapidly. Our leadership team brings proven expertise from multiple sectors of finance, and every team member plays a direct role in expanding both our clients’ success and our company’s vision.

The Role

We’re looking for a high-performing Insurance Account Executive who thrives in a fast-paced, performance-driven environment. You’ll lead full-cycle B2B sales from prospecting warm leads and consultative selling to closing and onboarding new accounts, while helping shape the standards and culture of our rapidly expanding sales team.  

You’ll build meaningful relationships with business owners and build your book of business which carries enterprise value.

Key Responsibilities

- Generate and close new B2B accounts through consultative, solution-based selling  

- Manage the full sales cycle: prospecting, discovery, pitching, negotiating, and onboarding  

- Consistently meet or exceed weekly, monthly, and quarterly sales goals  

- Build and maintain a robust sales pipeline using CRM tools and disciplined processes  

- Collaborate cross-functionally with Business Development Reps, Customer Success, and 

Leadership  

- Lead with integrity, clarity, and professionalism in every client and team interaction  

- Serve as a performance model and cultural leader for the growing sales team  

What You’ll Do Day-to-Day

- Prospect and consult with warm leads and current clients via Zoom and phone  

- Identify client pain points, communicate tailored financial solutions, and drive enrollment  

- Enroll multiple new accounts weekly while maintaining high quality and compliance standards  

- Own your pipeline, track KPIs, and execute consistent, disciplined follow-up  

- Work closely with BDRs and leadership to ensure smooth client transitions  

- Participate in call reviews, feedback sessions, and ongoing skill development  

Note: Appointments will be booked to your calendar by the team, but you are expected to supplement with your own prospecting.

What Success Looks Like

Within 3 Months:  

- Booking 2+ qualified appointments daily (while taking 7+ qualified appointments daily)  

- Enrolling 2 new accounts per week  

- Building strong baseline knowledge of our services, compliance, and tax structures  

Within 6 Months:  

- Training to grow into a Partnerships Account Executive

- Consistently enrolling 3–5+ accounts per week (200+ total employees onboarded)  

- Fully owning every stage of the sales process from prospecting to close.

Within 12 Months: 

- Managing a large book of business (target: 1,000+ W2 employees)  

- Consistently exceeding KPIs and setting new revenue records  

- Recognized as a top performer and culture leader on the sales team  

Requirements

- 3+ years of full-cycle B2B sales experience

- Group Insurance Experience

- Proven track record of consistently exceeding sales quotas and revenue goals  

- Strong consultative selling skills, business acumen, and emotional intelligence  

- Proficiency with CRM systems, pipeline management, and structured follow-up routines  

- Excellent communication, presentation, and active listening skills  

- Self-motivated, disciplined, and highly adaptable in a fast-moving startup environment  

Who You Are

You’re an A-Player. coachable, driven, and deeply mission-aligned. You thrive on ownership, competition, and personal growth. You embody First Gen’s core values:

- Ironclad Integrity: You do the right thing, even when no one is watching.  

- 24-Carat Accountability: You own your outcomes and stay humble when corrected.  

- Catalyst: You’re a constant learner with curiosity, discipline, and resilience.  

- Wholehearted: You put relationships before deals and build authentic trust.  

You’re not just looking for another sales job you’re seeking a purposeful career where your work directly impacts business owners and their teams.

Compensation OTE $190,000 (Base + Commissions + Equity in book of business)