Head of Sales Readiness

This is a fully remote position, open to applicants in Canada.

📋 Description

• Develop and oversee the Sales Readiness function at Lone Wolf.

• Establish, lead, and expand the sales readiness team.

• Collaborate with sales leadership to identify points where pitches encounter obstacles.

• Provide targeted readiness recommendations.

• Create a foundational sales onboarding program.

• Certify and recertify sales representatives.

• Manage and update the sales knowledge library.

• Convert product marketing positioning into field training and StoryBrand-aligned call scripts.

• Create and maintain call scripting and competitive trackers in Gong.

• Monitor live calls weekly and adjust scripts based on market insights.

• Review live pitches and develop targeted tools to boost win rates.

• Conduct structured win and loss analysis and provide deal intelligence to sales and product leadership.

• Manage the technical demo environment with realistic data that aligns with product releases.

• Prepare sellers to deliver foundational demos and recognize when to engage solution consulting.

• Collaborate with product marketing and solution consulting to synchronize the pitch, script, and demo.

⛳️ Requirements

• 8 or more years of experience in sales readiness, enablement, or training, with a proven track record of building programs from the ground up.

• Demonstrated ability to lead and develop high-performing teams.

• Extensive knowledge of residential real estate, proptech, or closely related industries.

• Practical experience in building or managing a technical demo environment for a B2B SaaS platform.

• Proven proficiency in creating scripts and trackers using conversation intelligence tools such as Gong.

• Experience conducting structured win and loss analyses that have directly impacted business decisions.

• Documented ability to link readiness initiatives directly to revenue outcomes.

• Daily competence in using AI tools to enhance content creation and scale training efforts.

• Outstanding and concise writing skills tailored for rapid field use.

• Prior experience with a sales quota.

• Prior work experience at a real estate brokerage or franchise.

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Comprehensive health, dental, and vision insurance.

• Opportunities for professional development and growth.

• Flexible work arrangements and a supportive work environment.