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About the role

  • Head of Sales Readiness building sales enablement, certification, scripting, and demo programs. Improving seller readiness and win rates for Lone Wolf’s real estate software platform.

Responsibilities

  • Build and lead the Sales Readiness function at Lone Wolf
  • Build, lead, and scale the sales readiness team
  • Partner with sales leadership and identify where pitches stall
  • Deliver prescriptive readiness recommendations
  • Build the foundational sales onboarding program
  • Certify and recertify sales representatives
  • Own and maintain the sales knowledge library
  • Translate product marketing positioning into field training and StoryBrand-aligned call scripts
  • Build and maintain call scripting and competitive trackers in Gong
  • Listen to live calls weekly and update scripts based on market feedback
  • Audit live pitches and build targeted tools to increase win rates
  • Own structured win and loss analysis and deliver deal intelligence to sales and product leadership
  • Own the technical demo environment with realistic data aligned to product releases
  • Equip sellers to deliver foundational demos and identify when to involve solution consulting
  • Partner with product marketing and solution consulting to align the pitch, script, and demo

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
  • Previous experience carrying a sales quota
  • Prior employment at a real estate brokerage or franchise

Job title

Job type

Full Time

Experience level

Lead

Salary

CA$141,800 - CA$156,000 per year

Degree requirement

No Education Requirement

Location requirements

RemoteCanada

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