Enterprise Account Executive

Why This Role Matters

Our Enterprise Account Executives guide prospects through the sales cycle, collaborate closely with our Business Development team while also generating >50% of their own pipeline, and consistently meet or exceed sales targets while utilizing HubSpot CRM.

What You'll Do

• Manage the full sales cycle for Vertical Insure's embedded insurance solutions, from initial discovery calls to deal closure, sourcing 50% or more of your own pipeline
• Work closely with Client Development Representatives (CDRs) to support outreach efforts and ensure smooth handoffs
• Conduct thorough discovery calls to understand vertical SaaS platforms' needs and align our solutions with their business objectives
• Prospect and develop new business opportunities within the vertical SaaS market
• Build and maintain strong relationships with decision-makers in vertical SaaS companies
• Act as the “quarterback” in navigating complex sales cycles with multiple stakeholders across the C-suite, product, compliance, operations, and technical teams
• Collaborate with internal teams to ensure client satisfaction and identify upsell opportunities
• Meet or exceed assigned sales targets and revenue goals
• Maintain accurate records of all sales activities in HubSpot CRM
• Stay informed about insurtech trends, competitors, and vertical SaaS market conditions
• Partner with product and engineering teams to support technical evaluations, integrations, and API-driven use cases
• Estimated travel is 10-25%, typically consisting of 1–2 regional/national trips per quarter for tradeshows and client visits

Who You Are

• 3+ years of successful enterprise sales experience, preferably in B2B SaaS or insurtech
• Proven track record of meeting or exceeding sales quotas in an enterprise sales environment, with average deal sizes exceeding $100k ARR
• Strong understanding of embedded finance/insurance concepts and value propositions
• Excellent communication, negotiation, and presentation skills
• Proficiency with HubSpot CRM and other sales tools
• Experience working collaboratively with Client Development or Lead Generation teams
• Self-motivated with a results-driven approach
• Ability to work independently and as part of a team
• Experience sourcing and closing $1M+ deals
• Demonstrated success managing complex, multi-stakeholder enterprise deals involving legal, product, compliance, and technical review

Experience That Goes the Extra Mile

• Experience and/or knowledge of vertical SaaS markets and their specific needs in any of the following industries:
• Class/Studio Management (dance studios, yoga studios, gyms, etc)
• Fitness
• Residential real estate rental and leasing
• Experience in fintech, insurtech, and/or insurance sales
• Outside sales experience
• Familiarity with API-driven platforms and integrations
• Ability to leverage AI
• Insurance producer licensing is a plus

Metrics of Success

• First 30 Days: Successfully complete onboarding, gain a deep understanding of Vertical Insure’s products, business objectives, and target verticals, and actively participate in team and client meetings. Complete insurance licensing requirements
• First 90 Days: Build an initial qualified pipeline by consistently creating new opportunities and advancing active deals through the sales cycle.
• First 6 Months: Achieve full ramp after closing 2-3 deals and demonstrating mastery of Vertical Insure’s sales process, value proposition, and key verticals.
• 12 Months: Deliver $750k+ in combined ARR through closed deals, while establishing a foundation of repeatable, predictable enterprise sales execution.

What We Offer

The estimated base salary for this role is: $80,000 - $125,000 per year, based on experience, skills, and scope of responsibility. In addition to base salary, this role is eligible for performance-based variable compensation tied to performance results.

We offer a comprehensive benefits package, including health, dental, life insurance, flexible PTO, 401(k), gym membership, paid parental leave, and more.