Head of Sales Readiness

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.