Head of Sales Readiness

Lone Wolf Technologies

• $141K — $156K *
Real Estate & Construction
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years in sales readiness, enablement, or training with a focus on building programs from scratch
  • Strong track record of leading high-performing teams
  • Deep knowledge of residential real estate or adjacent sectors
  • Experience managing a B2B SaaS technical demo environment
  • Expertise with conversation intelligence tools like Gong
  • Ability to connect readiness initiatives directly to revenue outcomes
  • Proficient in using AI tools for content creation and training efficiency
  • Exceptional writing skills for concise field communication.

Responsibilities

  • Build and lead the sales readiness team, maintaining a high quality standard for all sales assets
  • Collaborate with sales leadership to pinpoint and address stalled sales pitches
  • Provide clear readiness recommendations over a menu of options
  • Create a foundational onboarding program to accelerate new reps' time to first closed deal
  • Certify sales representatives rigorously to ensure readiness is measurable
  • Manage the sales knowledge library, ensuring easy access to resources for reps
  • Convert product marketing positioning into effective field training and clear call scripts
  • Maintain call scripts and competitive trackers within Gong, updating as necessary
  • Perform live call audits to identify and address execution gaps
  • Conduct structured win and loss analysis, providing actionable insights to leadership regarding deals.
  • Oversee the technical demo environment to ensure real-world relevance and alignment with product releases
  • Empower sellers to deliver flawless demos and recognize the need for solution consulting
  • Collaborate with product marketing and solution consulting for cohesive messaging.

Benefits

  • Opportunity to build and lead a critical sales readiness function
  • Strategic role partnering with sales leadership
  • Focus on innovative sales training methods and tools
  • Access to top-notch resources and technology for team efficiency
  • Potential for career growth within a rapidly evolving company.
Full 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.
  • 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.


Requirments:

  • 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.


$141,800 - $156,000 a year

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