Head of Sales Learning and Development

As the Head of Sales Learning & Development at ShopDeck, your role is crucial in setting up and scaling the Sales L&D function from scratch. You will play a foundational leadership role focused on building high-quality onboarding, continuous upskilling, and performance improvement systems across the sales team. Working directly with the Head of GTM and Sales Leadership, you will drive consistency, capability, and excellence across every sales representative. **Key Responsibilities:** - Build the L&D Function - Define the charter, roadmap, and structure for Sales L&D. - Design and implement structured onboarding, role-specific learning paths, and growth frameworks. - Hire and mentor a high-quality team as the function scales. - Develop Playbooks and Content - Codify key sales processes into clear, modular playbooks covering ICP, discovery, demo, objection handling, pricing, and more. - Create engaging learning content in various formats (documents, video, role-play guides, assessments, etc). - Collaborate with Sales Leaders to document and scale best practices. - Set Up Ongoing Learning Systems - Establish learning calendars and cadences for continuous development. - Drive regular sessions including peer-led learning, mock pitches, win/loss reviews, and product deep-dives. - Create rituals that embed learning into daily sales operations. - Performance Auditing and Feedback Loops - Build a call audit and coaching framework manual or via AI tools to evaluate sales conversations at scale. - Analyze performance data to identify skill gaps and recommend learning interventions. - Partner with Sales Ops to integrate learning outcomes into appraisals, promotions, and role readiness. **Ideal Candidate Profile:** - 6-12 years of experience in Sales Enablement, L&D, Business Coaching, or Inside Sales Leadership. - Has built L&D or enablement systems from the ground up not just executed predefined modules. - Deep understanding of sales capability-building across demo-led or consultative selling environments. - High ownership mindset and ability to work independently in fast-moving environments. - Excellent communication and instructional design skills. **Why This Role Matters:** - This role directly influences revenue by accelerating rep productivity and improving conversion. - You will shape the bar for every sales hire from how they're onboarded to how they scale into leadership. - You'll work closely with GTM, Product Marketing, Sales Ops, and Founders on building a high-performance, learning-first culture. **Preferred (but Not Required):** - Experience using or designing internal knowledge systems, AI-enabled coaching tools, or performance audit processes. - Exposure to high-velocity sales teams in D2C, SaaS, or marketplace businesses. - Familiarity with building scalable learning systems in ambiguous or fast-growth environments.,