Director, Sales Enablement

Swiftly is a retail digital technology company headquartered in the Bay Area that empowers regional and independent grocers to compete in a digital-first world. Swiftly provides best-in-class app, web, loyalty, and e-commerce solutions to retailer partners without SaaS fees, instead driving revenue through its retail media network and sharing profits with retailers.

With 70+ retailer banners and Series C funding, Swiftly is the first in the industry to seamlessly connect digital and in-store shopping. AI is at the core of how we build, operate, and scale, powering everything from shopper personalization to internal engineering velocity. Our solutions, including Audience Optimizer™, Alcohol Cashback, and Offsite Campaigns, drive shopper engagement and brand success.

Position Summary:

Swiftly is looking for a dynamic and experienced Director of Sales Enablement to join our team and serve as the critical bridge between Product Marketing, Sales, and Customer Success. This high impact role will translate complex product capabilities and go-to-market strategies into compelling, seller-ready training and certification materials that empower our revenue teams to effectively communicate our value proposition and close deals.

This position will own the end-to-end enablement lifecycle, from content creation (building upon existing and new materials generated from Product Marketing) and training program design to performance measurement, ensuring our sellers and success managers are confident, informed, and equipped to bring our capabilities to market with clarity and consistency.

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Responsibilities Include:

Design and produce high-quality sales enablement materials including pitch decks, one-pagers, talk tracks, battle cards, and objection-handling guides

Partner closely with Product Marketing to translate product updates and positioning into seller-ready narratives and assets

Maintain a centralized, up-to-date enablement content library accessible to all revenue-facing teams

Ensure all materials reflect consistent brand voice, messaging hierarchy, and competitive differentiation

Develop and deliver internal training programs, workshops, and onboarding curricula to educate sellers on product capabilities, positioning, and sales methodology

Build and manage role-specific learning paths for Sellers and Customer Success Managers

Lead ongoing enablement sessions including product launch readiness, competitive updates, and skills-based coaching

Partner with Sales leadership to identify skill gaps and design targeted programs to address them

Serve as the connective tissue between Product Marketing, Sales, and Customer Success, ensuring a cohesive and consistent go-to-market approach

Collaborate with Product Marketing on launch readiness, ensuring sellers understand new capabilities before they hit the market

Partner with Revenue Operations to align enablement efforts with pipeline metrics and sales performance data

Act as a feedback loop between the field and internal teams to continuously refine messaging and materials based on real-world seller experiences

Define and track key enablement KPIs including content adoption, training completion rates, ramp time, and impact on win rates

Continuously assess the effectiveness of enablement programs and iterate based on data and seller feedback

Manage enablement tools and platforms (e.g., LMS, sales content management systems)

Other duties as assigned

Required Qualifications:

Bachelor’s degree in marketing, business administration, or a related field

7+ years experience spanning Sales Enablement, Marketing, and/or direct Sales roles

Demonstrated experience in a Sales Enablement or Revenue Enablement function, with ownership over content, training, and programs

Background in B2B marketing, product marketing, or demand generation with a strong grasp of messaging, positioning, and content strategy

Experience working directly in or alongside a Sales or Customer Success team

Exceptional written and verbal communication skills with the ability to distill complex ideas into clear, compelling narratives

Strong presentation and visual storytelling skills, you know how to build a deck that sells

Highly collaborative with a track record of building trust across Marketing, Sales, and Product teams

Data-driven mindset with experience tracking enablement metrics and tying programs to business outcomes

Proficiency with enablement tools and platforms (e.g., Highspot, Seismic, Showpad, Salesforce, Gong)

Excellent project management skills with the ability to manage multiple initiatives simultaneously in a fast-paced environment

Strong executive presence and ability to present to and influence senior stakeholders

Must be authorized to work in the United States without the need for current or future visa sponsorship

Preferred Qualifications:

Digital Media strategy and planning

Direct experience working with Grocery and C-Store chain

Experience in a high-growth SaaS or technology company

Familiarity with sales methodologies (e.g., MEDDIC, Challenger, SPIN Selling)

Experience building an enablement function or practice from the ground up

Background in Customer Success enablement and Sales

\n$150,000 - $175,000 a year
The salary range is based on the candidates experience as it relates to the role.
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#LI-Remote

Note: This position is not eligible for visa sponsorship. Applicants must be authorized to work in the U.S. without the need for current or future sponsorship.

Working For Swiftly

We are working on a set of problems that require the best in the industry to get right. Our employees are the pillars of the future of the company and they are treated and compensated as such. We're a growing team of experienced industry professionals building an organization that can solve tough problems and values a collaborative environment.

Every Swiftly employee:

• Has demonstrated the ability to work collaboratively in an ambiguous, fast-paced environment

• Takes ownership of their domain from the ground up, from inception through deployment to customers

• Leaves their ego at the door and ensures the best idea leaves the room

• Is always experimenting with new technologies and learning new skillsets

If you've ever wanted to work on a project that blends a gorgeous consumer experience, sophisticated logistics, and scale that rivals the largest technology players, Swiftly is the place for you.

Equal Opportunity Employer

Swiftly is an Equal Employment Opportunity and Affirmative Action Employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, or disability status.

Swiftly will make reasonable accommodations in compliance with the Americans with Disabilities Act of 1990. Reasonable accommodations are available for qualified individuals with disabilities throughout the subsequent application process.