Head of Sales Readiness

Lone-Wolf-Technologies; United States; Remote; USD 100,000 - 105,000; Full time

Job summary

Lone Wolf is seeking a senior leader to build and run the Sales Readiness function. You will own the core readiness engine, including call scripting, the demo environment, and rigorous certification programs, ensuring every seller articulates value, pricing, and differentiation.

You will partner with sales leadership to drive prescriptive readiness, maintain Gong-based scripts and trackers, and tie initiatives to revenue metrics, with a strong emphasis on real estate/proptech verticals and a B2B

Qualifications

• 8+ years in sales readiness, enablement, or training with proven programs built from scratch.
• Proven leadership of high-performing teams.
• Deep knowledge of residential real estate, proptech, or related verticals.
• Experience building/managing a technical demo environment for a B2B SaaS platform.
• Experience creating scripts and trackers for conversational intelligence.
• Ability to tie readiness initiatives to revenue metrics.
• Proficient with AI tools to accelerate content creation and scale training.
• Strong, direct writing skills for quick field consumption.

Responsibilities

• Build, lead, and scale the sales readiness team with high standards.
• Partner with sales leadership to target where pitches stall.
• Deliver prescriptive readiness recommendations.
• Develop onboarding, certification, and knowledge library.
• Own call scripting and competitive trackers in Gong.
• Audit live pitches and create targeted tools to boost win rates.
• Own win/loss analysis and share actionable insights.
• Manage the demo environment and align with product releases.
• Ensure flawless foundational demos and know when to bring solution consulting.

Skills

Sales readiness

Team leadership

Training program development

Call scripting

B2B SaaS

AI content creation

Technical demos

Writing skills

Tools

Gong

Job description

You will build and lead the Sales Readiness function at Lone Wolf. While sales leadership drives daily methodology and coaching, your team owns the product, market, and competitive fluency of the sales organization. You are responsible for the core readiness engine, which includes call scripting, the technical demo environment, and rigorous certification programs. Your objective is to ensure every seller can clearly and accurately articulate our value, pricing, and competitive differentiation to the market.

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.
• Vertify and certify 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 GongExperience 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.

$100,000 - $105,000 a year