Head of Sales Readiness

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

📋 Description

• Lead, develop, and expand the sales readiness team.

• Collaborate directly with sales leadership and engage in pipeline assessments to pinpoint areas where pitches encounter delays.

• Provide targeted readiness recommendations.

• Create a comprehensive sales onboarding program to expedite the time to the first closed deal.

• Certify and re-certify sales representatives.

• Manage and update the sales knowledge repository, phasing out outdated resources.

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

• Develop and oversee call scripting and competitive monitoring tools in Gong.

• Listen to live calls on a weekly basis and revise scripts based on market insights.

• Review live pitches and create focused tools to enhance win rates.

• Conduct structured win and loss analyses and provide deal insights to sales and product leadership.

• Manage the technical demo environment and ensure alignment with current product launches.

• Equip sales representatives to deliver foundational demos and determine when to engage solution consulting.

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

⛳️ Requirements

• A minimum of 8 years in sales readiness, enablement, or training, demonstrating a successful track record in developing programs from the ground up.

• Proven experience in leading and nurturing high-performing teams.

• In-depth understanding of residential real estate, proptech, or related sectors.

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

• Established expertise in creating scripts and trackers within conversation intelligence tools such as Gong.

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

• Documented ability to connect readiness initiatives to revenue outcomes.

• Daily adeptness in utilizing AI tools to enhance content creation and scale training efforts.

• Outstanding and straightforward writing skills tailored for swift field application.

• Previous experience holding a sales quota (preferred qualification).

• Background in a real estate brokerage or franchise (preferred qualification).

🏝️ Benefits

• Competitive salary and performance-based bonuses.

• Comprehensive health, dental, and vision insurance.

• Flexible work arrangements and remote work opportunities.

• Professional development and training programs.

• A collaborative and inclusive company culture.