Note: The job is a remote job and is open to candidates in USA. NextPlayU is hiring on behalf of an unnamed partner company building an AI platform for the insurance brokerage industry. The Mid-Market Account Executive will own the full sales cycle for mid-sized brokerages, source pipeline, close deals, and help shape the company’s sales playbook.

Responsibilities

• Own the full cycle: prospecting, qualification, demo, negotiation, and close
• Build self-sourced pipeline through cold outreach, sequencing, referrals, and industry events
• Run discovery and tailored demos with Operations, IT, and C-suite stakeholders
• Manage 30-50 active opportunities with strong CRM hygiene and deal discipline
• Feed customer insight and objections back to GTM and product teams
• Help build the playbook and scale it across the team
• Travel to industry events to represent the company

Skills

• Have 3-5+ years of B2B closing experience with $50K+ ACV deals
• Source most of your own pipeline and treat outbound as a craft, not just volume
• Write and speak with precision: your outreach gets replies and your demos move deals
• Are energized by ambiguity and building in a fast-moving environment
• Are competitive and coachable, applying feedback immediately
• Former elite athletes (collegiate, pro, and Olympic)
• Experience selling into insurance, insurtech, financial services, or adjacent verticals
• B2B SaaS or technical sales background
• Early-stage startup experience or building a sales motion from scratch
• Familiarity with Salesforce, Gong, Apollo, or similar GTM tools

Benefits

• Meaningful founding-team equity
• Full health, dental, and vision
• Regular team off-sites and dinners
• An office stocked for builders

Company Overview