About The Position

We are looking for a driven and entrepreneurial Account Representative Lead to join our growing team. As an early sales hire in a fast-scaling startup, you will play a pivotal role in shaping our go-to-market approach and driving new revenue growth. We are looking for someone with direct experience generating leads and converting those leads to partners within the Property & Casualty (P&C) insurance market.

Requirements

  • 5–8+ years of enterprise / strategic sales experience, ideally in SaaS, technology, or data/analytics.
  • Proven track record of exceeding quota in high-growth or startup environments.
  • Strong hunter mentality with expertise in prospecting and building new logos.
  • Comfortable navigating complex buying cycles with multiple stakeholders.
  • Exceptional communication, presentation, and negotiation skills.
  • Entrepreneurial mindset: scrappy, adaptable, and motivated by building from the ground up.

Responsibilities

  • Own the end-to-end sales cycle: prospecting, discovery, solution positioning, negotiations, and closing.
  • Drive new business acquisition with enterprise and mid-market accounts.
  • Expand existing customer relationships through up-sell and cross-sell opportunities.
  • Direct sales prospecting and lead generation experience within the Property & Casualty (P&C) insurance industry.
  • Full-cycle technology sales experience, including outbound lead generation and deal ownership from initial outreach through close, selling to P&C carriers.
  • Develop account plans for target accounts and build multi-stakeholder engagement strategies.
  • Build trusted advisor relationships with executives, decision-makers, and champions.
  • Ensure customer success teams are set up to deliver long-term value post-sale.
  • Collaborate with marketing to optimize lead generation, messaging, and campaigns.
  • Provide market feedback to product teams to shape roadmap and solution enhancements.
  • Help refine sales playbooks, pricing, and positioning to scale GTM execution.
  • Consistently meet or exceed revenue, pipeline, and activity targets.
  • Maintain accurate forecasting, pipeline hygiene, and CRM discipline.
  • Leverage data-driven insights to continuously improve sales effectiveness.

Benefits

  • healthcare benefits (medical, dental and vision, EAP)
  • competitive PTO
  • 401k match
  • parental leave
  • HSA contribution match
  • paid subscription to the Calm app
  • generous external learning and tuition reimbursement benefits
  • ability to work remotely up to two days a week

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What This Job Offers

Job Type

Full-time

Career Level

Mid Level

Education Level

No Education Listed

Number of Employees

1,001-5,000 employees

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