Senior Manager, Sales Enablement

Summary

Join Prompt as a Senior Manager, Sales Enablement and strategically lead enablement initiatives across the company and its subsidiaries. Develop and execute a comprehensive sales enablement strategy, aligning with business goals and revenue targets. Design and deliver world-class sales training programs and coaching sessions. Partner with sales leaders to identify needs and develop targeted solutions. Oversee the creation and dissemination of sales content, tools, and playbooks. Optimize onboarding programs for new sales hires. Leverage technology and data to measure program effectiveness. Collaborate with marketing, product, and customer success teams. Mentor and develop a high-performing sales enablement team. This role requires a proven track record in sales enablement, strong analytical skills, and exceptional communication skills. The ideal candidate will have a strategic mindset and a passion for driving sales performance.

Requirements

• 7+ years of progressive experience in sales enablement, sales operations, or a direct sales role, with at least 2+ years in a leadership role overseeing enablement strategy. Experience working with multiple sales teams or across different business units is highly desirable
• Proven track record as an exceptional sales trainer and facilitator , with the ability to inspire, motivate, and educate diverse sales audiences
• Deep understanding of the end-to-end sales cycle and customer journey in complex B2B environments
• Expertise in designing, implementing, and measuring the impact of sales enablement programs
• Strong analytical skills with the ability to translate data into actionable insights and strategic recommendations
• Proficiency with sales enablement platforms (e.g. Gong) , CRM systems (e.g., HubSpot, Salesforce), and analytics tools
• Exceptional communication, presentation, and interpersonal skills, with the ability to influence and collaborate effectively at all levels of an organization
• A strategic mindset with a hands-on approach and a passion for driving sales performance
• Bachelor's degree in business, marketing, or a related field (continued post-grad education preferred)

Responsibilities

• Lead Sales Enablement Strategy: Develop and execute a comprehensive, organization-wide sales enablement strategy for all Prompt sales teams, including our subsidiary companies, aligning initiatives with overarching business goals and revenue targets
• Drive Sales Excellence: Design and deliver world-class sales training programs, workshops, and coaching sessions that cover the entire sales cycle, from prospecting and discovery to negotiation and closing. You'll be a master at making complex topics clear and actionable
• Empower Sales Leadership & Teams: Partner closely with sales leaders across all organizations to identify critical enablement needs, develop targeted solutions, and ensure consistent application of best practices
• Curate Content & Resources: Oversee the creation, curation, and dissemination of high-impact sales content, tools, and playbooks that support each stage of the customer journey and various sales motions across the Prompt ecosystem
• Optimize Onboarding Programs: Design and continuously refine scalable and effective onboarding programs for new sales hires across all entities, accelerating their ramp-up time and productivity
• Leverage Technology & Data: Champion the adoption and optimization of sales enablement technologies and CRMs, leveraging data and analytics to measure program effectiveness, identify areas for improvement, and demonstrate ROI
• Foster Cross-Functional Alignment: Collaborate strategically with marketing, product, and customer success leadership to ensure consistent messaging, seamless processes, and integrated strategies across all revenue-generating functions
• Mentor & Manage: Lead, mentor, and develop a high-performing sales enablement team, including the Sales Enablement Manager, fostering a culture of continuous learning and growth
• Define and Lead Enablement Strategy: Develop, implement, and continuously refine a comprehensive sales enablement strategy across Prompt and its subsidiaries, ensuring alignment with overarching business goals, sales objectives, and revenue targets. This includes maintaining a deep understanding of diverse sales processes, varied product offerings, and the end-to-end customer journey across all entities
• Drive Cross-Organizational Alignment: Partner strategically with sales, marketing, product, and customer success leadership across all Prompt companies to ensure cohesive support, consistent messaging, and integrated resources. This includes overseeing the creation of universal sales playbooks, scalable training programs, and impactful buyer-facing content tailored for diverse audiences
• Oversee World-Class Training & Development: Design, deliver, and continuously optimize advanced training sessions and workshops for all sales teams. This includes focusing on deep product knowledge, relevant industry insights, advanced sales methodologies, and best practices to significantly improve performance, effectiveness, and quota attainment across the organization. You will also oversee the delivery of enablement programs by your team
• Establish Centralized Knowledge Management: Build, maintain, and champion a centralized, accessible knowledge base for all sales teams. This encompasses developing onboarding materials, advanced sales scripts, competitive intelligence, and other critical resources to empower sales professionals with up-to-date and easily accessible information
• Champion Sales Team Excellence & Satisfaction: Proactively identify and address the unique challenges and skill gaps within various sales teams across Prompt and its subsidiaries. Design and deliver tailored, impactful enablement solutions that foster high performance, maximize productivity, and significantly contribute to overall sales team success and satisfaction. Partnering with sales leads to create personalized sales training and development plans for sales team members
• Optimize Global Sales Processes & Workflows: Establish, refine, and enforce consistent processes and workflows that enhance sales team efficiency and ensure disciplined execution of sales strategies across all Prompt organizations. Drive continuous improvement to reduce friction and accelerate the sales cycle
• Lead Data-Driven Enablement & Reporting: Define key performance indicators (KPIs) and rigorously analyze sales performance metrics, including quota attainment, win rates, sales cycle length, and tool adoption. Use these insights to assess the direct impact of enablement programs, identify strategic trends, and provide data-driven recommendations to sales leadership for continuous improvement and revenue growth
• Serve as a Strategic Cross-Functional Liaison: Act as the primary strategic liaison between sales teams and other critical departments (marketing, product, engineering), ensuring sales feedback and market insights are consistently incorporated into strategic planning, product development, go-to-market strategies, and marketing campaigns
• Innovate & Advocate for Sales Tools & Technology: Proactively identify, evaluate, and advocate for the adoption of new tools, technologies, and process enhancements that will significantly improve the overall sales experience, streamline workflows, and optimize customer engagement across all Prompt entities. This includes leveraging call recording software like Gong to develop AI led call feedback best practices and scorecards by analyzing historical data and trends and collaborating with sales leadership
• Influence Product & Market Strategy: Collaborate closely with product leadership across all Prompt companies to gather, prioritize, and articulate comprehensive customer and sales feedback, directly influencing the product roadmap to ensure the development of features that meet evolving market demands and drive substantial revenue

Benefits

• Competitive salaries
• Remote/hybrid environment
• Potential equity compensation for outstanding performance
• Flexible PTO
• Company-wide sponsored lunches
• Company-paid disability and life insurance benefits
• Company-paid family and medical leave
• Medical, dental, and vision insurance benefits
• Discounted pet insurance
• FSA/DCA and commuter benefits
• 401k
• Credits for online and in-person fitness classes/gym memberships
• Recovery suite at HQ – includes a cold plunge, sauna, and shower