Senior Director, Commercial Enablement

Siteimprove • Minneapolis, MN

3d

About The Position

Siteimprove is seeking a Senior Director, Commercial Enablement to lead the strategy, execution, and evolution of enablement across our global revenue organization. This highly visible leadership role will be responsible for designing and scaling enablement programs that empower our sales, partnerships, marketing and customer-facing teams to perform at their highest level and drive predictable revenue growth.
As a strategic and hands-on leader, you will develop and execute a modern enablement framework that accelerates ramp time, increases win rates, improves cross-sell and expansion opportunities, and enhances the effectiveness of our global GTM teams. You will partner closely with Sales, Marketing, Product, Customer Success, Revenue Operations, and executive leadership to ensure our customer-facing teams have the tools, content, methodologies, and training required to deliver exceptional customer outcomes.
This role will play a key part in shaping the future of our revenue organization by embedding scalable processes, leveraging data and insights, and integrating modern technologies and AI-enabled capabilities to drive sales productivity and performance.
With a focus on innovation, collaboration, customer-centricity, and data-driven decision making, the Senior Director of Commercial Enablement will build and lead a high-impact enablement function that supports Siteimprove’s continued growth.

Requirements

• 10+ years of professional experience in sales enablement, sales operations, or revenue leadership roles
• 5+ years leading enablement teams in high-growth B2B SaaS environments
• Proven success scaling enablement programs in global or multi-product organizations
• Experience implementing and evolving structured sales methodologies (e.g., MEDDIC, MEDDPICC, Value Selling)
• Deep understanding of the B2B SaaS sales lifecycle and go-to-market motions
• Experience with modern GTM technology platforms including Salesforce, Highspot (or similar), Gong (or similar), and Outreach (or similar)
• Strong analytical and strategic thinking with the ability to measure ROI and business impact
• Excellent cross-functional collaboration and stakeholder management skills
• Ability to influence senior leaders and drive alignment across complex organizations
• Strong written and verbal communication skills with the ability to translate complex concepts for diverse audiences

Nice To Haves

• Prior quota-carrying or customer-facing experience
• Experience leveraging AI-enabled tools to enhance sales coaching and productivity
• Experience supporting enterprise or multi-product SaaS platforms

Responsibilities

• Enablement Strategy and GTM Alignment
• Develop and execute a comprehensive commercial enablement strategy aligned with Siteimprove’s revenue objectives and GTM priorities.
• Partner with revenue leadership, marketing, product, and operations teams to ensure enablement programs support strategic initiatives including pipeline growth, product adoption, and cross-sell opportunities.
• Serve as a trusted advisor to commercial leadership, providing insights and recommendations to improve sales productivity and optimize revenue processes.
• Sales Methodology, Onboarding, and Continuous Development
• Lead the design and delivery of world-class onboarding programs that accelerate ramp time and enable new hires to quickly achieve productivity.
• Implement and reinforce scalable sales methodologies and frameworks that improve deal qualification, pipeline health, and win rates.
• Develop ongoing training and development programs that support skill building, product knowledge, and execution excellence across the revenue organization.
• Content, Playbooks, and Field Enablement
• Oversee the development and delivery of high-impact sales materials, playbooks, messaging frameworks, and enablement content.
• Partner with Product Marketing and Marketing to ensure field teams are equipped with the right assets to support product launches, positioning, and customer conversations.
• Ensure enablement resources are accessible, organized, and scalable across the organization.
• Systems, Tools, and AI-Driven Productivity
• Optimize the enablement ecosystem including platforms such as Salesforce, Highspot, Gong, Outreach, and other sales technologies.
• Drive adoption of tools and systems that improve seller productivity, visibility, and performance insights.
• Identify and implement AI-enabled capabilities such as conversation intelligence, automated coaching insights, content recommendations, and workflow automation to enhance execution.
• Performance Measurement and Insights
• Establish clear KPIs to measure the effectiveness of enablement initiatives including ramp time, win rates, pipeline growth, deal size, sales cycle velocity, and quota attainment.
• Leverage data-driven insights to continuously refine programs and ensure measurable business impact.
• Provide regular reporting and strategic insights to executive leadership on enablement performance and opportunities for improvement.
• Leadership and Organizational Development
• Build and lead a high-performing enablement team, fostering a culture of collaboration, accountability, and continuous learning.
• Drive alignment across sales, partnerships, customer success, marketing, and operations to ensure consistent messaging and execution across the GTM organization.
• Champion best practices and continuous improvement across the revenue organization.
• Travel may be required; a valid passport is required
• Perform other duties as assigned

Benefits

• Rest and relaxation: Open Paid Time Off (OPTO) program for vacation, personal illness, mental health, or to care for a family member, 11 paid holidays, and volunteer leave.
• Comprehensive benefits: National medical plan, dental, vision, paid maternity leave, paid paternity leave, HSA, Flex, employer-sponsored short-term, long-term disability, discounts to volunteer plans to meet your family needs, and more!
• Prepare for the future: 401(k) with a company match to provide a better future in your retirement years.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed