Head of Sales Readiness

Lone Wolf Technologies

• $141K — $156K *
US-AnywhereRemote in Toronto, ON
Real Estate & Construction
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years in sales readiness, enablement, or training with a record of successfully building programs from scratch
  • Experience leading and developing high-performing teams
  • Deep knowledge of residential real estate, proptech, or adjacent verticals
  • Hands-on experience managing a technical demo environment for a B2B SaaS platform
  • Expertise in conversation intelligence tools like Gong for building scripts and trackers
  • Experience in conducting structured win and loss analysis
  • Strong writing skills for field-ready communications

Responsibilities

  • Build and lead the sales readiness team with high-quality standards for all assets
  • Collaborate with sales leadership to identify pitching issues during pipeline reviews
  • Deliver tailored readiness recommendations to sales teams
  • Develop a foundational onboarding program to accelerate deal closures
  • Certify and recertify sales reps to ensure measurable readiness
  • Maintain an up-to-date sales knowledge library for rep accessibility
  • Create actionable field training from product marketing positioning and maintain call scripts
  • Conduct regular audits of live pitches to identify gaps and enhance tools for win rates
  • Manage the technical demo environment with realistic data aligned to product releases
  • Ensure sales teams can deliver effective demos and know when to involve solution consulting
  • Collaborate with product marketing and consulting to present a cohesive story through pitches and demos

Benefits

  • Comprehensive onboarding resources
  • Access to cutting-edge conversation intelligence tools
  • Opportunities for professional development and team leadership
  • Direct influence on sales strategies and outcomes
  • Work collaboratively with cross-functional teams to elevate sales performance
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

Similar Jobs

More Jobs at Lone Wolf Technologies

More Real Estate & Construction Jobs

Find similar Head of Sales Readiness jobs: