Enterprise Account Executive

Applied Systems, Inc.•,

11d•$300,000 - $330,000•Remote

About The Position

Applied Systems, Inc., a worldwide leader in insurance technology, is currently searching for an Enterprise Account Executive that will be selling Cytora’s Risk Digitization platform to Canadian and US insurers, MGAs and brokers. You’ll run full‑cycle enterprise sales—prospecting, discovery, POC/evaluation, and close—and be responsible for new logos and expansion. This is primarily an outside sales role operating with minimal supervision. Cytora, now part of Applied Systems, applies vertical AI at global scale to transform commercial insurance. Founded in 2012, Cytora leverages GenAI to enable brokers, insurers and reinsurers to digitize and automate the risk intake across commercial insurance. Applied Systems are a global leader in insurance technology since 1983, powering more than 18,000 agencies and 160,000+ users across North America and Europe with its cloud-based software solutions. Together, Cytora and Applied Systems are accelerating digitization of risk flows across the insurance industry—driving greater efficiency, improved service and connectivity between insurers and brokers worldwide.

Requirements

10+ years enterprise sales experience, including 5+ years in insurance/insurtech and 5+ years selling enterprise SaaS to large carriers/brokers (multi-stakeholder, long-cycle deals).
Ownership mentality: lead end-to-end, run first-touch demos, and run POCs
Product/AI-curious and a crisp communicator: explain LLMs, data flows, and APIs clearly, translating technical concepts into underwriting/operations business value for executives and working teams.
Willing to travel frequently in Canada and the U.S. up to 50%
Bachelor’s degree or equivalent experience.

Nice To Haves

We encourage military members and their spouses as well as candidates without a degree or a background in tech to apply!

Responsibilities

Run full-cycle enterprise sales from prospecting through evaluation/POC to close
Translate discovery into a written, time-boxed POC plan with clear success criteria, datasets/documents, user roles, checkpoints, and exit criteria to keep evaluations decision-oriented.
Systematize early-stage motions - capture what works, codify repeatable steps, and help scale GTM alongside Applied/Ivans account teams.
Multithread senior relationships (CUO, CIO, Ops, IT) and speak to technical concepts (LLMs, data flows, APIs), translating them into insurance business value for executives and working teams.
Captain a team of cross-functional partners (Sales, Solutions Consulting, Product, Security, Legal) to remove blockers and maintain momentum.
Maintain disciplined pipeline hygiene and forecasting (using all required tools, including Salesforce CRM) while following Applied Solution Selling and Cytora's evaluation/POC playbook; travel as needed for client discovery sessions, workshops, POCs, and checkpoints.