VP, Sales Strategy & Effectiveness

Job Title: Vice President, GTM Strategy and Enablement
Location: Hybrid (Boston, MA)
Reports To: SVP, GTC Operations
Department: Business Operations
Job Overview
The Vice President of GTM (Go-to-Market) Strategy and Enablement is a strategic leadership role responsible for developing and implementing comprehensive enablement strategies, training programs, and tools that empower the sales and customer success teams to achieve their goals. This leader will develop and execute comprehensive go-to-market strategies, oversee enablement initiatives, and ensure the company's revenue teams are equipped to perform at the highest level. This role partners closely with Sales, Marketing, Product, and People Strategy teams to align enablement efforts with the organization's strategic priorities and drive GTM excellence
Key Responsibilities
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.

Qualifications
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.

About Rapid7
Rapid7 is creating a more secure digital future for all by helping organizations strengthen their security programs in the face of accelerating digital transformation. Our portfolio of best-in-class solutions empowers security professionals to manage risk and eliminate threats across the entire threat landscape from apps to the cloud to traditional infrastructure to the dark web. We foster open source communities and cutting-edge research-using these insights to optimize our products and arm the global security community with the latest in attackers methods. Trusted by more than 10,000 customers worldwide, our industry-leading solutions and services help businesses stay ahead of attackers, ahead of the competition, and future-ready for what's next.
All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, protected veteran status or any other status protected by applicable national, federal, state or local law.
Security and Compliance
Rapid7 is committed to keeping customers secure. As a first line of defense, all employees are expected to uphold the highest standards of security and privacy, ensuring the protection of sensitive information and compliance with relevant regulations.
All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, protected veteran status or any other status protected by applicable national, federal, state or local law.