Head of Sales Readiness
This is the employer's own posting, not a copy on a job board.
What we know
Is it still open?
Confirmed removed at the source
Last checked 9h ago — checked against the employer's own applicant tracking system, which is the company answering directly.
How old is it?
Posted 2d ago
The date the source published, not the day we noticed it (2026-09-29). Last seen at its source 13h ago.
Is it remote?
Toronto, ON (Remote)
That is the location the employer filed this posting under. Quoted as written — we do not re-word the source's own location.
Who may apply?
Toronto
The description states no restriction of its own. This is the source's own tag.
Pay not stated
Similar roles pay $165k–237.5k/yr
Middle 50% of 25 listings that do state pay — Sales & Marketing · Head · Canada · USD/year. This employer has published no salary; this is what comparable listings we hold disclose, never converted between currencies or periods. How this is calculated.
Skills named in the ad
Recognised terms only, from a fixed vocabulary — this is what CV matching compares against.
Carried by 1 source
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lever employer's own board first seen 2d ago · last seen 13h ago
The listing
Responsibilities:
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Build, lead, and scale the sales readiness team, holding an exceptionally high quality bar for all field facing assets.
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Partner directly with sales leadership, sitting in on pipeline reviews to identify exactly where pitches stall.
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Deliver prescriptive readiness recommendations rather than a menu of options.
Onboarding, Certification & Knowledge
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Build the foundational sales onboarding program to drastically accelerate time to first closed deal.
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Certify and recertify reps to ensure readiness is rigorously measured, never assumed.
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Own the sales knowledge library, retiring stale assets and ensuring reps easily find exactly what they need.
Positioning, Scripting & Intelligence
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Translate product marketing positioning into immediate, actionable field training and StoryBrand aligned call scripts.
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Build and maintain call scripting and competitive trackers directly within Gong.
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Listen to live calls weekly and update the script when the market proves it wrong.
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Audit live pitches to identify execution gaps and build targeted tools that increase win rates.
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Own structured win and loss analysis, delivering unvarnished deal intelligence to sales and product leadership.
Demo Environment & Technical Readiness
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Own the technical demo environment, ensuring realistic data and perfect alignment with current product releases.
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Equip every seller to deliver a flawless foundational demo and know exactly when to bring in solution consulting.
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Partner tightly with product marketing and solution consulting to ensure the pitch, script, and demo tell one seamless story.
Team Leadership & Sales Partnership
Requirments:
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8 or more years in sales readiness, enablement, or training, including proven success building programs from scratch.
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Track record of leading and developing high performing teams.
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Deep knowledge of residential real estate, proptech, or closely adjacent verticals.
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Hands on experience building or managing a technical demo environment for a B2B SaaS platform.
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Proven expertise building scripts and trackers within conversation intelligence tools like Gong
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Experience running structured win and loss analysis that directly influenced business decisions.
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Documented ability to tie readiness initiatives directly to revenue metrics.
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Daily proficiency using AI tools to accelerate content creation and scale training.
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Exceptional and highly direct writing skills designed for quick field consumption.
- Previous experience carrying a sales quota
- Prior employment at a real estate brokerage or franchise.