Location: Remote (Canada)
Reports To: Director of Strategy and Business Development
The Team: Strategy and Business Development
About ZestyAIZestyAI 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 risk—from wildfire and severe storms to roof condition and regulatory change. Trusted by the nation's 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 RoleWe 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 close—owning 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.
You’ll operate with a high degree of independence, but you won’t 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.
- Full Cycle Ownership: Own the full cycle for SMB/mid-market (and targeted enterprise "fast-track") opportunities in specific new product lines—from 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 Marketing—surfacing 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.
- Prior Seller, Future Founder: 2–5 years in SaaS/analytics inside or full-cycle sales. You’ve done the SDR grind, you’ve been promoted to AE, and you’ve 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.
- 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 "No's" are frequent but the "Yes's" 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.
Salesforce, Outreach, LinkedIn Sales Navigator, ZoomInfo, Google Workspace/Office, Calendly, Zoom/Meet.
