Founding Account Executive

Jaide Health; Toronto; On-site; CAD 100,000 - 150,000; Full time

Benefits offered by this job

Competitive compensation and equity

Flexible remote work

Collaborative team

Job summary

Jaide Health is looking for a Founding Account Executive in Toronto, Canada, to lead sales efforts targeting AmLaw 200 firms. You will own the entire sales cycle, leveraging your legal expertise to build credibility and drive deals. The role requires a JD and at least 5 years in litigation or restructuring at a prominent law firm. Join a pioneering team and make a meaningful impact in the legal tech sector while enjoying flexible remote work options.

Qualifications

• Juris Doctor (JD) degree and at least 5 years of experience at a BigLaw firm.
• Strong ability to communicate and drive outcomes with senior stakeholders.
• Proficient in writing and presenting effectively.

Responsibilities

• Own the entire sales cycle from prospecting to closing.
• Build trust with legal stakeholders using your expertise.
• Deliver engaging demos and proposals that resonate.

Skills

Persuasive communication

Trust-building

Strategic outreach

Presentation skills

Legal background

Education

JD

5 years of litigation experience

Tools

CRMs

Outbound tools

Job description

Founding Account Executive

About Us

Bench IQ leverages AI to gather intelligence on judges, enabling attorneys to tailor their arguments and strategies to how specific judges think—and gain a competitive edge in court.

Our customers are elite global law firms, with over a dozen AmLaw 200 firms—including four of the top five—among our clients. We’re making these insights available to law firms of all sizes, expanding access to the advantages Bench IQ provides.

Bench IQ is backed by top‑tier investors and law firms. We’ve raised $7.35 million from funds that were early investors in leading tech companies such as Instacart ($CART), Figma ($FIG), Coinbase ($COIN), and Afford ($AFRM), alongside investments from AmLaw 100 firms including Cooley, Fenwick, and Wilson Sonsini.

Our founding team (Ovbiagele, Gettleman, and Isakov) brings deep legal and technical expertise. Two of our founders built the world’s first AI legal research platform, ROSS Intelligence, and one was as a partner at Kirkland & Ellis, American Lawyer’s number one ranked law firm.

Since then, our co‑founders have assembled a world‑class team of former engineers and attorneys from Google, Tesla, Meta, Amazon, Airbnb, Instacart, and Kirkland & Ellis.

About the Role

This isn’t your typical enterprise sales role. We’re looking for pioneers—trailblazers who can thrive without the support of a marketing engine or a household brand. You’re resourceful, relentless, and persuasive. You know how to create momentum, open doors where none seem to exist, and earn trust through sharp storytelling, thoughtful questions, and strategic positioning.

As our first Account Executive, you’ll be responsible for sourcing and closing new business with AmLaw 200 firms. You’ll be selling a novel product in a category that doesn’t exist yet, to some of the most discerning buyers in the world. You’ll work directly with the founders, help shape the sales process, and define our go‑to‑market approach.

What You’ll Do

• Own the entire sales cycle with AmLaw 200 firms, from outbound prospecting to closing deals.
• Leverage your legal background to build trust and credibility with partners, senior litigators, operations leaders, and research leaders.
• Develop creative, persistent outreach strategies to open doors.
• Deliver high‑impact demos and discovery conversations that engage even the most time‑constrained legal buyers.
• Write sharp, strategic outreach and proposals that reflect how lawyers think and communicate.
• Negotiate complex deals in a new category, often without predefined budgets or established ROI models.
• Collaborate closely with the founders on positioning, pricing, and structuring pilots.
• Help lay the foundation for repeatable sales by shaping messaging, sales materials, ideal customer profiles, and deal structures.

What We're Looking For

• JD and at least 5 years of experience practicing litigation or restructuring at a BigLaw firm in the United States.
• Demonstrated ability to build trust, communicate persuasively, and drive outcomes with senior stakeholders.
• Strong writing and presentation skills—credible and concise in front of legal audiences.
• Resourceful, proactive, and comfortable working in a fast‑moving, ambiguous environment.
• Active "AI super user"—constantly leveraging AI to learn new skills and subjects, solve problems, and get work done faster and better.
• US‑based or Canada‑based.

Nice to Have

• Experience selling to or working with AmLaw 200 firms.
• Legal tech, AI, or early‑stage startup experience.
• Familiarity with CRMs, outbound tools, or sales automation platforms.

Why Join Us

• Receive competitive compensation plus own meaningful equity, sharing directly in the upside as we build a multi‑billion‑dollar category for ourselves.
• Build the sales function from the ground up—own the creation of our sales playbook, processes, and go‑to‑market strategy.
• Collaborate with high‑caliber colleagues—including former engineers, attorneys, and designers from Google, Tesla, Meta, Amazon, Airbnb, Instacart, and Kirkland & Ellis.
• Enjoy true flexibility—work remotely, set your own hours, and focus on results rather than face time or office politics.
• Most importantly, do work that matters—help bring transparency to a judicial system where judges provide written reasoning for only 3% of rulings. Your contributions will have a real, lasting impact on the legal field and society.