Enterprise Account Executive - Insurance

Feathery

$100K — $120K *
Finance & Insurance
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years of experience selling enterprise SaaS in the insurance industry or relevant commercial experience.
  • Proven success with enterprise deals, typically $100K to $1M+ in annual recurring revenue (ARR).
  • Demonstrated track record of meeting or exceeding sales quotas.
  • Strong consultative selling skills with the ability to engage high-level stakeholders.
  • Excellent communication skills, with a focus on storytelling and empathy for customer needs.
  • Experience in outbound pipeline generation and active prospecting strategies.
  • Ability to influence sales strategy and processes in a growth-oriented environment.

Responsibilities

  • Prospect and develop new enterprise accounts within the insurance sector.
  • Reach out to potential clients through various channels including email and LinkedIn.
  • Experiment with outreach strategies to maximize lead generation.
  • Attend industry events to expand professional network and gather leads.
  • Manage and execute the entire sales cycle from prospecting to closing.
  • Convert inbound leads into qualified opportunities through effective engagement.
  • Conduct needs discovery and create tailored presentations for diverse stakeholders.

Benefits

  • Comprehensive health, dental, and vision benefits.
  • Unlimited paid time off (PTO) policy.
  • Centrally located office in downtown Toronto.
  • Food perks, including office snacks and monthly catered lunches.
  • Opportunities for team bonding through company offsites.
  • Supportive and collaborative work environment that values ownership and personal growth.
Full Job Description
About the Role

This is a high-ownership role that blends:
  • Full-cycle enterprise sales across the insurance industry
  • Pipeline generation and deal execution
  • Strategic, consultative selling
  • Cross-functional collaboration with product, marketing, and leadership

You'll own the entire sales process - from sourcing opportunities to closing deals - while helping define how Feathery scales its enterprise revenue engine.

What You'll Do
Pipeline Generation & Prospecting
  • Prospect and develop new enterprise accounts across the insurance industry
  • Reach out to prospects via email, phone, and LinkedIn
  • Experiment with messaging, targeting, and channels to generate new opportunities
  • Attend insurance industry conferences and events to build relationships and source pipeline
  • Own pipeline generation strategy and continuously refine outbound approaches
Deal Execution & Sales Process
  • Manage the full sales cycle from initial outreach through close
  • Handle inbound and referred leads and convert them into qualified opportunities
  • Conduct discovery to understand customer needs and business challenges
  • Deliver tailored demos and presentations for different stakeholders
  • Navigate complex buying processes and multi-stakeholder deals
Sales Strategy & Cross-Functional Collaboration
  • Help define and refine sales playbooks, positioning, and processes
  • Partner with product and engineering to communicate customer needs and influence roadmap
  • Collaborate with marketing on campaigns and demand generation initiatives
  • Contribute to product launches and go-to-market strategy
About You
  • Experience selling enterprise SaaS into the insurance industry, or deep insurance industry experience in a commercial role
  • Experience with enterprise deals ($100K-$1M+ ARR)
  • Track record of high achievement in quota-carrying roles
  • Strong consultative selling skills and ability to engage senior stakeholders
  • Excellent communication and storytelling abilities with high customer empathy
  • Experience building pipeline through outbound prospecting
  • Builder mindset with a desire to shape processes and strategy
  • Highly motivated, resilient, and comfortable operating in a fast-paced environment
  • Passion for understanding customer problems and helping solve them


Bonus
  • Existing network within the insurance industry
  • Experience selling complex or technical products
  • Experience attending or sourcing pipeline through industry conferences
  • Background at a high-growth B2B SaaS or InsurTech company


What We Offer
  • Competitive compensation and equity
  • Health, dental, and vision coverage
  • Unlimited PTO
  • Downtown Toronto office location
  • Office snacks and monthly catered lunch
  • A supportive, low-ego team that values ownership and growth
  • Company offsite to connect and recharge

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