Rapid7 VP Sales Strategy & Effectiveness 

United States, Massachusetts, Boston 

835669319

Strategic Leadership

• Define and execute the vision, strategy, and roadmap for sales and customer success enablement and training initiatives to support business goals.
• Collaborate with sales leadership to identify gaps in skills, tools, and processes and recommend tailored solutions.
• Establish metrics and KPIs to measure the effectiveness of sales and customer success enablement and training programs, ensuring continuous improvement.

Sales Enablement

• Develop and manage a framework for equipping sales and customer success teams with the knowledge, skills, and tools to improve productivity and performance.
• Partner with Product and Marketing teams to ensure sales has access to up-to-date product information, messaging, and competitive insights.
• Oversee the implementation of sales and customer success enablement technologies, including Salesforce, Gainsight, sales intelligence, and content management tools.

Training and Development

• Design, deliver, and manage onboarding programs for new sales hires to ensure rapid ramp-up to productivity.
• Create advanced training programs for ongoing skill development in areas such as consultative selling, negotiation, and account management.
• Ensure the development of training content tailored to different sales roles (e.g., SDRs, Account Executives, and Customer Success Managers).

Team Leadership

• Build and lead a high-performing sales enablement and training team, fostering a culture of collaboration and excellence.
• Manage budgets, resources, and vendor relationships to optimize training and enablement investments.

Cross-Functional Collaboration

• Act as a trusted advisor to the sales leadership team, providing insights and recommendations based on sales performance data.

• Work closely with marketing to align messaging, campaigns, and demand generation efforts with GTM objectives.

• Partner with product management to incorporate product positioning and competitive differentiation into sales and enablement strategies.

• Collaborate with sales and customer success teams to drive upsell, cross-sell, and renewal opportunities.

Education & Experience

• Bachelor’s degree in Business Administration, Marketing, or a related field; MBA or equivalent experience preferred.
• 10+ years of progressive experience in sales enablement, sales training, or related roles, with at least 5 years in a senior leadership capacity.
• Proven track record of designing and implementing successful sales enablement and training programs in high-growth organizations.

Skills & Competencies

• Strong understanding of sales processes, methodologies (e.g., MEDDIC, Challenger, SPIN), and tools.
• Expertise in training development and delivery, including e-learning and blended learning approaches.
• Exceptional leadership and team-building skills, with the ability to inspire and motivate cross-functional teams.
• Data-driven decision-making skills, with experience using analytics to measure training impact.
• Excellent communication, presentation, and stakeholder management skills.

Preferred:

• Experience in SaaS, Cybersecurity a plus.

• Familiarity with GTM tools and platforms (e.g., Salesforce, Clari, Gainsight, Gong, Tableau, etc).

• Demonstrated ability to thrive in a fast-paced, dynamic environment.