About this Head of Sales Readiness role at Lwolf
Responsibilities:
Team Leadership & Sales Partnership
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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.
Requirements:
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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.
- Bonus Qualifications
- Previous experience carrying a sales quota
- Prior employment at a real estate brokerage or franchise.