Account Executive

Overview

You close deals with mid-market employers (typically 100-500 employees) who need to cut health benefits costs. You're selling a combination of ICHRA and direct primary care access, which means you're explaining a fairly new benefits model and managing change management concerns. Deals involve HR, Finance, and often the CEO, and you're competing against their current broker or status quo.

Role Snapshot

Company Context

Stage: Series A-B (estimated based on 87 employees and active hiring)

Size: 87 employees

Growth: Actively hiring across multiple sales roles; expanding market presence

Market Position: Challenger in health benefits space, competing against traditional PEOs and insurance brokers

GTM Reality

Pipeline Sources:

• 40% SDR-generated - qualified meetings from outbound and broker referrals
• 35% Self-sourced - direct outreach to employers in target industries
• 25% Broker partnerships - benefit brokers bringing you into existing client conversations

SDR/AE Structure: SDRs book initial meetings; AEs own the full sales cycle after that

SE Support: No dedicated SE - AEs handle all demos and technical questions themselves

Competitive Landscape

Main Competitors: Traditional PEOs, incumbent benefit brokers, other ICHRA platforms, status quo (keeping current insurance)

How They Differentiate: Direct primary care access bundled with ICHRA makes it easier for employees to actually use healthcare

Common Objections: "This sounds risky for our employees," "Our broker says ICHRA won't work for us," "We can't make changes before next open enrollment," "What if employees hate it?"

Win Themes: Documented cost savings (20-40% reduction), better primary care access, simplified admin, ACA compliance

What You'll Actually Do

Time Breakdown

Active deals (40%) | Demos/discovery (25%) | Prospecting (20%) | Internal coordination (15%)

Key Activities

• Discovery and demos: You walk through how ICHRA works, map out their current benefits costs, and show projected savings. These are 45-60 min calls with multiple stakeholders.
• Proposal creation: Building custom proposals that show cost comparisons between their current setup and Vitable's model. Lots of spreadsheet work.
• Stakeholder management: You're juggling HR (wants simplicity), Finance (wants cost savings), and executives (worried about employee satisfaction). Getting all three aligned takes multiple meetings.
• Implementation coordination: Once deals close, you work with the implementation team to onboard the employer. You stay involved through the first renewal.

The Honest Reality

What's Hard

• You're selling change management as much as a product. HR leaders are risk-averse and scared of employee backlash.
• Deals slip constantly. Open enrollment windows are fixed, so if you miss the deadline, the deal pushes 12 months.
• Benefit brokers can kill deals - if the employer's broker doesn't support ICHRA, you're fighting an uphill battle.
• You need to deeply understand health insurance regulations (ACA, ERISA, COBRA) to answer questions credibly.

What Success Looks Like

• Closing 8-12 deals per year in the $50-200K range
• 30-40% win rate on qualified opportunities
• Renewals at 90%+ (if employees like the product, employers stick around)

Who You're Selling To

Primary Buyers:

• HR Directors/VPs at 100-500 employee companies
• CFOs (heavily involved due to cost savings)
• CEOs at smaller companies (150-300 employees)

What They Care About:

• Reducing benefits spend without cutting coverage quality
• Avoiding employee complaints and retention issues
• Compliance with ACA and state regulations
• Simplifying benefits administration (reducing HR workload)

Requirements

• 2-4 years closing experience, ideally in benefits, HR tech, or B2B SaaS
• Comfortable with consultative, multi-stakeholder deals
• Ability to learn complex subject matter (health insurance isn't simple)
• Self-sufficient - you own the full cycle and don't have a lot of support resources
• Genuinely care about making healthcare more accessible (helps when deals get tough)