Head of Sales Enablement

As Head of Sales Enablement, your mission is to equip our sales team with the tools, training, and insights needed to drive consistent, high-impact conversations that convert leads into revenue. You’ll collaborate closely with Marketing, Product, and Revenue teams to build scalable enablement programs that shorten ramp time, increase win rates, and accelerate ARR growth. Your focus is on empowering reps to sell value with confidence and drive urgency to close deals.

Key Responsibilities

1. Onboarding & Ramp

• Design and implement a scalable, structured onboarding program with certification pathways.
• Reduce ramp time by 30–50% through a combination of self-serve content, live training, and shadowing.
• Align onboarding with real-world selling scenarios and create 30/60/90-day enablement tracks.
• Enable new reps to achieve quota within their first full quarter.
  

2. Sales Process Optimization

• Map each stage of the sales process and centralize in Confluence as the source of truth.
• Build stage-specific resources including talk tracks, qualification frameworks (e.g., BANT), and objection-handling tools.
• Shorten average sales cycle time by 20% through improved buyer journey clarity.
  

3. Deal Size & Value Selling

• Train reps in value-based selling with a focus on outcomes over features.
• Introduce ROI tools, enterprise case studies, and multi-year deal strategies.
• Target a 20–30% increase in average deal size (ADS) over 12 months.
  

4. Segment-Specific Enablement

• Develop role- and vertical-specific enablement tracks (AE, SDR, CSM, etc.).
• Tailor sales narratives to construction industry buyer pain points.
• Provide competitive battlecards and segment performance analysis.
  

5. Pipeline & Forecasting Support

• Create stage-based playbooks and content to move deals forward.
• Build opportunity checklists and inspection frameworks to support forecasting and deal reviews.
• Help reps get unstuck and advance pipeline health.
  

6. Ongoing Learning & Training Culture

• Launch monthly micro-trainings, quarterly bootcamps, and certification cycles.
• Build a centralized learning hub using the LMS.
• Incorporate peer-led sessions and top-performer best practices.
• Use assessments to measure and reinforce learning outcomes.
  

7. Sales & Marketing Alignment

• Establish feedback loops between the sales floor and GTM leadership.
• Ensure marketing assets (case studies, sequences, collateral) are adopted and utilized.
• Co-own launch readiness, campaigns, and content alignment.
  

8. Sales Readiness & Analytics

• Track enablement metrics including conversion rates, time to first deal, and training impact.
• Use dashboards to tie initiatives to business results.
• Continuously refine enablement based on performance data and rep feedback.
  
  

9. Product Launch Support

• Lead GTM readiness for product and feature launches.
• Develop internal launch kits: FAQs, messaging, pitch decks, and email templates.
• Partner with product marketing to deliver training and certifications.
  
  

10. Tech Stack Ownership

• Drive adoption of tools including CRM, call recording, LMS, and content systems.
• Streamline and integrate systems to reduce friction and boost rep productivity.
• Regularly evaluate and optimize tech stack to support scale.

Requirements

Experience

• 5+ years in sales enablement, ideally in a fast-paced startup environment.
• Proven success leading onboarding, coaching programs, and enablement strategy.
  
  

Skills & Expertise

• Strategic thinker with a track record of aligning enablement to business goals.
• Strong business acumen and data literacy; comfortable using KPIs to iterate
• Cross-functional collaborator with experience partnering across Sales, Marketing, Product, and Ops.
• Experienced in adult learning, coaching, and performance-driven training delivery.
• Project manager capable of juggling multiple initiatives and hitting tight deadlines.
  
  

Tools & Platforms

• Familiarity with tools such as Confluence, Hubspot, Gong, Figma, G-Suite, Monday.com, and LMS platforms.
• Ability to design and manage content ecosystems including playbooks, talk tracks, and templates.
  

About You

We want you to be a part of the Clearstory success story so as you engage with us and our team members, it would be helpful for you to understand some of the core characteri