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
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