Mid-Market Account Executive

Mid-Market Account Executive | New York City or San Francisco, CA (In-Office)

$200K-$250K OTE + meaningful founding-team equity

Hiring through NextPlayU on behalf of a partner company. Former elite athletes (collegiate, pro, and Olympic) are strongly preferred but not required. The office is in San Francisco, with flexibility for top-tier New York-based candidates. The team is also committed not to lose great candidates over compensation.

Our partner is building an AI platform that automates the drudgery of the $1.5 trillion insurance brokerage industry. Customers love it: it already saves them thousands of hours and millions of dollars a year, and it’s deployed across 30% of the top 50 brokers in the U.S. They’ve reached multiple seven figures in ARR in just over a year, and they just raised their Series A.

The role

You’ll own a mid-market territory end-to-end, selling to mid-sized brokerages across the U.S. This is not a hand-off role. You’ll source most of your own pipeline, run sharp discovery, and close with urgency, working directly with the founders and GTM leadership to shape how the sales motion scales.

What you’ll do

• 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

What success looks like in 90 days

• You can clearly articulate the ICP, value prop, and competitive differentiation across buyer personas
• You’re consistently generating your own pipeline, with active deals in motion
• You’ve run full discovery-to-demo cycles and know how to handle the objections
• You operate with rigor: clean Salesforce notes, strong follow-up, sharp prioritization
• You’ve closed, or are approaching close on, your first deal

You might be a fit if you

• 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

Bonus points

• 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

What’s offered

• Competitive base plus OTE of $200K-$250K and meaningful founding-team equity
• Compensation flexibility for the right candidate: the team won’t lose a top candidate over comp
• Full health, dental, and vision
• A high-ownership, high-trust culture with a lean, staff-level team from companies like Affirm, Uber, DoorDash, and McKinsey
• Regular team off-sites, dinners, and an office stocked for builders

Why athletes

If you’ve competed at the collegiate, pro, or Olympic level, you know what this job demands: relentless preparation, fast response to coaching, and the drive to win. This is a seat where that edge turns directly into results.

If this sounds like you, apply. Great closers come from every background, and we welcome them all.