Head of Sales Enablement

Head of Sales Enablement

Job Summary

The Head of Sales Enablement is responsible for designing, building, and scaling RebelMouse’s global sales enablement engine and tools to maximize sales productivity, consistency, and revenue performance across all products and segments. This also includes strengthening our internal CRM workflows so we can track the full customer lifecycle — from lead generation through go-live status — supporting clean handoffs, process visibility, and automated contract management within the CRM.

This role sits at the intersection of Sales, Marketing, Product, RevOps, and Customer Success, ensuring that every seller is equipped with the right messaging, playbooks, training, tools, data, and processes to win at every stage of the customer journey.

The ideal candidate is both strategic and deeply hands on at every step. This is someone who can architect enablement systems from end to end, while also rolling up their sleeves to create content, run trainings, analyze performance gaps, and continuously improve sales execution. They think like an operator, act like a coach, and own measurable outcomes, such as conversion rates, ramp-up time, win rates, deal velocity, and revenue expansion.

About RebelMouse

RebelMouse is an always-modern, AI-enabled SaaS CMS where more than 100 enterprise brands and media companies grow their digital audience. Websites running on RebelMouse serve more than half a billion pageviews per month thanks to our powerful publishing tools, modern tech stack, and world-class performance across search and social.

Our People

Our fully distributed team spans 30+ countries. Led by Andrea Berry, our Mexican-American, gender-fluid founder and CEO, we value diversity, kindness, creativity, and strong challenges. We’re a supportive environment where collaboration and curiosity matter, and where work-life balance is something we strive to protect.

Key Responsibilities

• Define and own RebelMouse’s global sales enablement strategy, aligned with company growth goals, go-to-market motion, and product roadmap.

• Act as a strategic partner to Sales, RevOps, Marketing, Product, and Customer Success.

• Ensure tight alignment between positioning, messaging, pricing, packaging, and sales execution.

• Build and maintain sales playbooks and sales slide decks by segment (enterprise, mid-market, SMB), product, and use case.

• Translate product capabilities, technical features, and performance advantages into clear, compelling, buyer-centric narratives.

• Ensure consistent messaging across outbound, inbound, demos, proposals, and renewals.

• Design and run sales onboarding programs to reduce ramp time and accelerate time to first deal.

• Develop continuous training programs for:

• Discovery and qualification

• Product demos

• Objection handling

• Competitive positioning

• Negotiation and closing

• Partner with sales leaders and product general managers to reinforce enablement through coaching frameworks and feedback loops.

• Own the enablement tech stack (CRM enablement, LMS, content repositories, sales tools).

• Partner with RevOps and other departments to optimize workflows, handoffs, and pipeline hygiene.

• Ensure sales teams have easy access to:

• Pitch decks

• One-pagers

• Case studies

• Competitive battlecards

• ROI calculators and pricing tools

Why Join RebelMouse

• Sell a best-in-class, high-performance SaaS CMS platform with real differentiation from the competition.

• Work closely with the leadership, product, and engineering teams in a highly collaborative, low-ego environment.

• Be a part of a culture that values ownership, clarity, and execution over politics, hierarchy, or performative behavior.

• Join a team that is direct, transparent, and genuinely supportive — where high standards and respect coexist.

• Competitive compensation with strong upside for top performers.

• Real autonomy, real accountability, and real impact.

Benefits Package

• Remote work forever.

• Monthly wellness subsidy.

• Flexible work hours.

• Flexible paid time off (PTO), including 12 national holidays, 20 vacation days, sick days, and personal celebration days.

Diversity Statement

RebelMouse is committed to providing a diverse work environment. We honor the unique strengths every person brings to our company. We encourage applicants from all backgrounds and provide equal employment opportunities regardless of race, color, religion, age, sex, sexual orientation, gender identity/expression, veteran status, or disability status.

Qualifications and Skills

• 5+ years of experience in sales enablement and sales excellence at B2B SaaS companies.

• Strong English skills

• Proven experience supporting and elevating B2B SaaS sales teams, ideally across both enterprise and mid-market and throughout different sales channels (inbound, outbound).

• Strong understanding of B2B sales cycles and buying committees, SaaS commercial models and revenue drivers (ARR, MRR, expansion, retention, value creation, messaging, positioning, and value-based selling).

• Demonstrated success in building sales playbooks, onboarding programs, orchestrating demo backbones, and training curricula from scratch.

• Ability to translate technical and product-driven capabilities into clear, compelling business-value narratives.

• Comfortable working with a CRM (preferably Salesforce) and sales tools in partnership with SalesOps, but not as the primary system owner.

• Proactive, self-directed mindset, and able to drive enablement programs end to end with minimal oversight.

• Exceptional collaborator who naturally connects the dots across Product, Marketing, Sales, RevOps, and Customer Success, transforming insights into training, tools, and field enablement.

• Strong relationship builder, capable of influencing without authority and earning trust across technical and commercial teams.

• Highly communicative and engaging presenter that’s comfortable leading workshops, trainings, and internal rollouts.

• Creative problem-solver who designs practical enablement assets that improve productivity, accelerate deal quality, and support revenue outcomes.

• Flexible and adaptable, and continuously evolves content and programs based on feedback, market learnings, and results.

• Comfortable operating in ambiguity with a bias toward clarity, action, and continuous improvement.

• Curious, disciplined, and entrepreneurial, with strong ownership and accountability for outcomes.