Director, Revenue Enablement

The Director, Revenue Enablement, will be a strategic partner to senior leadership, driving measurable impact across our go-to-market teams. This leader will architect and scale a best-in-class enablement function that unifies data, process, and change management to accelerate revenue growth. The ideal candidate is an operator at heart—analytical, data-driven, and skilled at leading cross-functional transformation that empowers sales and customer success teams to perform at their peak.

This role reports to the VP of Product Marketing & Enablement

Role location: Chicago or NYC

Responsibilities

● Enablement Strategy: Partner with leadership to define and execute a roadmap aligned with company growth objectives.

● Data-Driven Change: Use analytics to identify gaps, influence behaviors, and measure ROI of enablement initiatives.

● Operational Excellence: Build scalable processes, playbooks, and learning programs that ensure teams have the right tools, content, and messaging.

● Change Management: Lead adoption of new technologies, processes, and go-to-market strategies, embedding reinforcement mechanisms for long-term success.

● Cross-Functional Collaboration: Align with Sales, CS, Product Marketing, and Operations to support product launches, market shifts, and evolving customer needs.

● Learning & Development: Design and deliver onboarding, certification, ongoing training, and annual revenue events across all levels.

● Performance Measurement: Establish KPIs and dashboards to connect enablement programs to business outcomes and communicate results to executives.

● Content & Playbooks: Oversee creation of sales playbooks, messaging, and supporting materials for consistency and pipeline impact.

● Team Leadership: Mentor and grow a high-performing Revenue Enablement team, fostering accountability and continuous improvement.

Qualifications

● 5+ years of experience in revenue enablement, sales operations, sales, or related fields, with at least 3 years in a leadership capacity.

● Proven track record of driving measurable impact on revenue through enablement strategy, process design, and change management.

● Deep expertise in data analysis, performance measurement, and using insights to drive organizational change.

● Experience in adtech, martech, SaaS, or retail media preferred.

● Skilled in change management, with an understanding of how to shift behaviors.

● Strong executive presence; comfortable presenting to senior leadership and influencing across all levels of the organization.

● Demonstrated success building scalable onboarding, training, and certification programs in a high-growth environment.

● Exceptional organizational skills, with the ability to prioritize, simplify complexity, and lead multiple initiatives simultaneously.

● Collaborative leader with a knack for empowering customer-facing teams to succeed.

The salary range for this position is $120,000-130,000. The actual salary amount will vary depending on the applicants experience, skills and abilities as well as internal equity and market data. This position is eligible for additional bonus compensation, full details will be provided during the recruitment process.

More about Us:

The company offers best-of-breed advertising technology on the most impactful, highest-ROI media channels as well as a suite of data-driven insights, planning and measurement solutions to complement and maximize return from our solutions.

Established in 2006, we are a thriving organization, with a unique, vibrant startup culture with an incredible track record of success and an amazing future in sight!

We are hybrid for the long term - with a great home/ office work mix​ (three days in office per week), passionate and diverse team members, and a vibrant company culture.

At Skai we have comprehensive medical coverage, employer match retirement savings and generous paid time off. More importantly, we offer the things that make Skai a great place to develop your potential, both professionally and personally. In addition, you will also receive:

• Dental and vision coverage
• Employee share options program
• Generous paid family leave policy
• Flexible hybrid working model
• Life insurance and short/long term disability
• Professional growth stipend
• Diversity and inclusion programs
• Office commuting benefits
• ClassPass Membership
• Volunteering and community opportunities
• Employee Assistance Program
• Company sponsored employee social events
• Office lunches and fully stocked kitchen

Equal Opportunity Employer

Skai is an Equal Opportunity Employer. At Skai, we believe ensuring a diverse, equitable, and inclusive workplace is not just an ideal to strive for; it is right, necessary, and our responsibility as humans. Our full DE&I commitment and global framework can be viewed on our company website and are aligned to our core values. We strongly encourage and seek applications from women, people of color, and bilingual and bicultural individuals, as well as members of the lesbian, gay, bisexual, and transgender communities. Applicants shall not be discriminated against because of race, religion, sex, national origin, ethnicity, age, disability, political affiliation, sexual orientation, gender identity, color, marital status, medical condition including acquired immune deficiency syndrome (AIDS) and AIDS-related conditions, or any other protected status. Also pursuant to the San Francisco Fair Chance Ordinance, we encourage and will consider for employment qualified applicants with arrest and conviction records.

Applicants with Disabilities

Reasonable accommodation will be made so that qualified disabled applicants may participate in the application process. Please advise in writing of special needs at the time of application.

Skai is an E-Verify employer.