The Opportunity We are hiring Account Executives to convert qualified demand into scalable growth. The next 10–20 deals will materially shape our customer base, brand, and long-term trajectory. Early AEs will help define the sales motion from the ground up.
Why Top AEs Join Jolly Mission-critical product. Incentives sit at the intersection of pay, productivity, and retention. Once deployed, Jolly becomes operational infrastructure not discretionary
Early leverage. Shape comp design and territory strategy, help define the playbook, influence hiring standards, and grow into leadership as the team scales.
Meaningful Equity. This is a founding sales hire, and we want you to own a piece of what you help build.
Uncapped commission with accelerators . Rate increases the further over quota you go, so top reps earn beyond OTE instead of flattening at 100%
The Role Own a full pipeline of qualified inbound opportunities
Run 3–6 month sales cycles
Lead discovery, demos, and proposals with c-suite executives
Navigate multi-stakeholder buying committees in legacy industries
Partner with our Incentive Engineering team — former private equity investors and data scientists — to deliver rigorous, ROI-backed solutions
Help refine ICP, pricing, and go-to-market strategy
This is a true closing role focused on conversion, not pipeline generation.
Who Thrives Here AEs consistently closing $50K–$300K+ ACV deals, experience in C-suite conversations
Top performers - President’s Club, Top 10%, #1 in segment
Reps who have sold mission-critical software: ERP, workforce systems, service management, financial systems, supply chain




Builders who want ownership and asymmetric upside rather than a capped role inside a large organization
Why This Is a Massive Chance Horizontal TAM. Any company with workers is a potential customer. Incentives are relevant across every industry.
Structural tailwinds. Labor shortages, wage pressure, retention challenges, and regulatory scrutiny are forcing executives to rethink how they motivate frontline teams.
Embedded infrastructure. Jolly integrates directly into systems of record and operational workflows. Once deployed, it becomes part of how work gets done — not a surface-level engagement tool.
Defensible category creation. There is no true like-for-like competitor offering incentive design rigor, operational integration, and behavioral iteration at scale. Replicating our position requires more than software — it requires distribution, embedded trust, and learning across deployments.
Growth Path This is not a seat-filling role, it is a foundational one. You are joining before the playbook is written, which means the way Jolly sells for the next decade gets shaped by the people in these first seats.
Shape the go-to-market motion itself. Which segments we press, which verticals we build for, how we package and price,



where the ICP tightens or widens — you will be in the room for those calls, with real weight on the outcome. What you learn in live deals becomes company strategy, not a note in a CRM.
Own the sales iteration loop. Discovery frameworks, qualification criteria, ROI models, objection handling, exec narrative, proposal structure, deal desk. You will run the experiment, read the result with our Incentive Engineering team, and codify what works into the playbook every future rep uses.
Build the team you will eventually lead. Founding AEs help set the hiring bar, interview and select future reps, and mentor and onboard the class behind them. The standard you hold becomes the standard of the org.
Influence how the team is paid and structured. Comp design, quota philosophy, territory and account strategy, ramp expectations, and how success gets measured. You will have a genuine voice in the system you sell inside of.
Feed the product roadmap. You sit closest to the buyer. Patterns you surface in the market — objections, integration gaps, campaign designs customers ask for — go directly to product and engineering, and ship.
Expand your surface area as we scale. Multi-product and multi-vertical ownership, strategic and enterprise accounts, expansion motions inside existing customers — the scope grows as fast as you can absorb it.
Grow into leadership. The people who build the motion are the natural candidates to run it. As revenue scales, we expect the first AEs to become the team leads, sales managers, and revenue leaders here. We promote from this class rather than hire over it.

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📌 Enterprise Account Executive Toronto • (Ontario)
🏢 Jolly Labs
📍 Ontario