Head of Sales Readiness

Lone Wolf TechnologiesUnited StatesRemoteFull-timeSenior, 5–8 yearsListed 6 hours ago

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About this role

Responsibilities:

Team Leadership & Sales Partnership

- Build, lead, and scale the sales readiness team, holding an exceptionally high quality bar for all field facing assets.

- Partner directly with sales leadership, sitting in on pipeline reviews to identify exactly where pitches stall.

- Deliver prescriptive readiness recommendations rather than a menu of options.

Onboarding, Certification & Knowledge

- Build the foundational sales onboarding program to drastically accelerate time to first closed deal.

- Certify and recertify reps to ensure readiness is rigorously measured, never assumed.

- Own the sales knowledge library, retiring stale assets and ensuring reps easily find exactly what they need.

Positioning, Scripting & Intelligence

- Translate product marketing positioning into immediate, actionable field training and StoryBrand aligned call scripts.

- Build and maintain call scripting and competitive trackers directly within Gong.

- Listen to live calls weekly and update the script when the market proves it wrong.

- Audit live pitches to identify execution gaps and build targeted tools that increase win rates.

- Own structured win and loss analysis, delivering unvarnished deal intelligence to sales and product leadership.

Demo Environment & Technical Readiness

- Own the technical demo environment, ensuring realistic data and perfect alignment with current product releases.

- Equip every seller to deliver a flawless foundational demo and know exactly when to bring in solution consulting.

- Partner tightly with product marketing and solution consulting to ensure the pitch, script, and demo tell one seamless story.

Requirements:

- 8 or more years in sales readiness, enablement, or training, including proven success building programs from scratch.

- Track record of leading and developing high performing teams.

- Deep knowledge of residential real estate, proptech, or closely adjacent verticals.

- Hands on experience building or managing a technical demo environment for a B2B SaaS platform.

- Proven expertise building scripts and trackers within conversation intelligence tools like Gong

- Experience running structured win and loss analysis that directly influenced business decisions.

- Documented ability to tie readiness initiatives directly to revenue metrics.

- Daily proficiency using AI tools to accelerate content creation and scale training.

- 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.