Outbound Account Executive New Verticals

Location: Remote (Canada)

Reports To: Director of Strategy and Business Development

The Team: Strategy and Business Development

About ZestyAI

ZestyAI is the leading decision intelligence platform for the property and casualty (P&C) insurance industry. Our platform unifies property-level data predictive AI models and Agentic AI automation to transform how insurers see price and manage riskfrom wildfire and severe storms to roof condition and regulatory change. Trusted by the nations top property insurers we are growing rapidly as we help protect families businesses and communities from the increasing impacts of climate and property risk.

The Role

We are looking for a seller who thrives with a high degree of outbound ownership in developing new markets. You will be the first dedicated hire to run a high-velocity inside sales motion for one of our newest product lines. You will own the full sales cycle from first touch to closeowning discovery demos proof points and negotiations entirely over Zoom and email/LinkedIn. You will prospect demo and close high-velocity deals to prove the market and build the playbook for the rest of the company.

Youll operate with a high degree of independence but you wont operate alone. This role sits within the Strategy & Business Development team and works closely with GTM and Product to ensure market feedback directly shapes messaging roadmap and execution.

This is an outbound role focused on market development not a If you are energized by the idea of getting a list of accounts to go after and persisting with that list until they convert this is the role for you.

How Success Is Measured

• Contracted New ARR: Hitting and exceeding quota through predictable execution.
• Velocity: Maintaining a shorter sales cycle compared to our direct enterprise motion.
• Win Ratio: Converting qualified opportunities into closed-won revenue at a high clip.

The Day-to-Day

• Full Cycle Ownership: Own the full cycle for SMB/mid-market (and targeted enterprise fast-track) opportunities in specific new product linesfrom qualification through close.
• High-Tempo Outreach: Partner with other GTM stakeholders on targeted sequences but primarily drive your own pipeline through high-volume outbound activity. The successful candidate absolutely must be comfortable with cold calling.
• Value-Led Demos: Deliver value-led demos and lightweight POCs/sandboxes that show time-to-value within days not months.
• Crisp Discovery: Run discovery tailored to sophisticated insurance buyers (Underwriting Actuarial Product Cat Modeling) to identify compelling use cases.
• Feedback Loop: Be the voice of the customer to Product and Marketingsurfacing feature requests data needs and blockers from the field to help shape the roadmap.
• Forecast Discipline: Forecast accurately in Salesforce and maintain hygienic pipeline with clear next steps MEDDICC/BANT notes and close plans.
  
  

Ideal Experience

• Prior Seller Future Founder: 25 years in SaaS/analytics inside or full-cycle sales. Youve done the SDR grind youve been promoted to AE and youve crushed a quota. Now you want a bigger challenge. This is market development 101 for one of the most exciting growth areas in the company.
• Virtual Closing: Proven success in shorter sales cycles (30-60 days) with virtual-first closing. A track record of closing deals is the most important selection factor.
• Insurance Fluency: You must be able to speak credibly with Chief Actuaries Heads of Underwriting and Analytics Leads. Familiarity with P&C workflows (submissions risk modeling portfolio analytics) is a massive plus.
• Technical Comfort: Comfortable selling data software (APIs dashboards LLM-based products) and articulating ROI to both business and technical stakeholders.
  
  

Skills & Attributes

• Unafraid of No: You are comfortable iterating messaging quickly in early market development environments. You have the resilience to push through a new product launch where the Nos are frequent but the Yess are lucrative.

Hustle: This is absolutely table stakes. No task will be beneath the successful candidate. If it stands between you and a close you get it done.

• Commercial Acumen: You understand pricing packaging and how to close clean contracts without excessive discounting or bending on terms.
• Writing That Sells: Your follow-ups close plans and proposals are succinct and executive-level.
• Coachability: You embrace call reviews feedback and rapid iteration.
• Culture: We very actively foster the culture at ZestyAI and guard it ferociously. We are looking for top talent who will amplify our culture not disrupt it.
  
  

Tools Youll Use:

Salesforce Outreach LinkedIn Sales Navigator ZoomInfo Google Workspace/Office Calendly Zoom/Meet.