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.
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
Skills Required
- Bachelor's degree in marketing, business administration, or related field
- 7+ years experience spanning Sales Enablement, Marketing, and/or direct Sales roles
- Demonstrated experience owning sales enablement content, training, and programs
- Background in B2B marketing, product marketing, or demand generation with strong messaging and positioning skills
- Experience working directly in or alongside Sales or Customer Success teams
- Exceptional written and verbal communication skills
- Strong presentation and visual storytelling skills
- Highly collaborative with experience building trust across Marketing, Sales, and Product
- Data-driven mindset; experience tracking enablement metrics and tying programs to business outcomes
- Proficiency with enablement tools and platforms (Highspot, Seismic, Showpad, Salesforce, Gong)
- Excellent project management skills and ability to manage multiple initiatives in a fast-paced environment
- Strong executive presence and ability to present to and influence senior stakeholders
- Authorized to work in the United States without the need for current or future visa sponsorship
- Digital media strategy and planning
- Direct experience working with Grocery and C-Store chains
- Experience in a high-growth SaaS or technology company
- Familiarity with sales methodologies (MEDDIC, Challenger, SPIN Selling)
- Experience building an enablement function from the ground up
- Background in Customer Success enablement and Sales
What We Do
Swiftly is a leading provider of technology and solutions for retailers worldwide. Founded in 2018, Swiftly offers innovative solutions that drive engagement and enable retailers to own the digital relationship with their customer. Swiftly’s Retail Tools, Mobile Platform, Analytics and Insights, and Retail Media Network are integrated into a unified platform, which enables retailers to accelerate sales and build loyalty while empowering brands to reach more shoppers and amplify campaigns reaching more customers by using their own 1st party data. Trusted by hundreds of iconic brands, Swiftly is democratizing the retail industry and giving retailers the technology they need to compete in today’s crowded marketplace.
Why Work With Us
We’re building a culture where personal and professional growth drive business growth. Make an impact on customers and community, work with cool technology and build things that impact millions of customers every day.
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