Sales Enablement Lead

About Flipp

Flipp partners with the largest North American retailers and brands to deliver local promotions and savings to millions of engaged shoppers daily, driving superior returns on investments. 

We help people make smarter shopping decisions with autonomy and accountability. With rising living costs, Flipp's mission is crucial. Our Shopper Consideration Platform allows retailers and manufacturers to create digital experiences from their savings & deals content, aiding shoppers in deciding what to buy and where to buy it. Together, we make a difference.

Our five principles, Progress Over Perfection, Clarity Through Transparency, Learn Loudly, Challenge with Empathy, and Always Build Better, bring a relentless progress mindset to life. They’re not just slogans, but they’re the behaviours we expect, reward, and hold ourselves accountable to. You'll be equipped to make an impact, realize your potential, and stay inspired every step of the way.

The Sales Enablement Lead is a strategic and tactical role at Flipp, responsible for co-building and executing the Sales Enablement vision for Flipp’s key sales teams.

Reporting to the Sales Enablement Manager, you will be the dedicated enablement partner for multiple sales teams, focused on establishing the foundational infrastructure needed to achieve our winning aspiration: "Make selling easier." 

This role requires a data-driven approach to strategically focus on activities that enhance the overall seller experience. The Sales Enablement Lead is responsible for delivering measurable and impactful training, optimizing the content and usage of tools (like Highspot and Gong), and driving measurable improvements in sales efficiency and revenue growth. The Sales Enablement Lead will work closely with Sales Leaders and cross-functional teams (such as Product Marketing, Sales Engineering, and Revenue Operations) to maximize the potential and impact of the entire sales organization.

What you'll get the opportunity to do:

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  Build the Foundation of Sales Enablement 

  Adopt best-in-class practices to evolve foundational sales elements

  Sales Content Library: Ensure the sales teams has access to best-in-class resources that support the sell in of Flipp’s products and services. Content includes, but is not limited to, customer profiles (e.g., Ideal Customer Profiles), product assets (e.g., case studies, presentations), product training, industry analysis, and research

  Sales Methodology Support: Support the execution and adherance of selected sales methodologies (e.g., MEDDIC) and Flipp’s sales process through content assets, training, and analysis that links the impact to business outcomes and sales cycle efficiencies

  Support Sales Kick Off: Support the planning and execution of the Sales Kick Off, including determining the theme, goals/objectives, agenda, session outlines, swag and activities.


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  Operational Efficiency, Content and Tools

  Continuous improvement of the sales experience through tools, assets, systems and processes

  Technology Adoption and Usage: Drive measurable improvements in the adoption and use of core sales technologies, including Salesforce (as a traditional CRM), Highspot (to drive sales efficiency), and Gong (for learning and coaching integration). Evaluate the importance and impact of each tool for the sales team and explore new products, technology, and sales tools that will further support the sales team in “making selling easier.”

  Support Go-To-Market (GTM) Initiatives: Work with Product Marketing and Sales Engineering to ensure a cohesive and transparent launch of new products and processes and ongoing maintenance of resources

  Cross-functional Teamwork: Work with cross-functional teams such as Product Marketing, Sales Engineering, and Strategic Transformation to develop processes and collateral that drive efficiency and increase revenue for the sales team.


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  Training, Learning and Development 

  Create impactful learning experiences that drive sales success

  Curriculum & Content: Design, develop and deliver relevant learning content for the sales teams you support, focusing on foundational sales skills, product knowledge, industry trends, and emerging topics (e.g., AI). Leverage engagement and data post-training to evaluate the impact of TL&D initiatives on the sales team’s development and revenue impact 

  Manager Coaching: Develop and implement sales-coaching training for managers with a focus on continuous performance improvement coaching 

  People Team Alignment: Liaise closely with the People Team’s Learning and Growth Team to ensure training content is aligned with Flipp’s principles and represents best-in-class functional and leadership development


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  Onboarding 

  Deliver onboarding that reduces New Hires' ramp-up time and efficiency

  Onboarding Ownership: You will own, evolve, and deliver a best-in-class onboarding experience for New Hires, which includes a wide variety of learning mediums (e.g., Live sessions, recordings, activities), ensuring a clear path to productivity

  Continuous Learning during Onboarding: You will own the execution of ongoing learning experiences that deepen a New Hire’s knowledge of the industry, customer pain points, Flipp’s products and services, and what it means to be a Best-In-Class team member.

What you'll bring to the team:

• 3+ years of experience in Sales Enablement, Sales Operations, or a field-facing L&D role supporting a complex B2B sales organization.


• Strong analytical skills and a demonstrated ability to link enablement activities to business outcomes, using data to measure content usage, program impact, and sales cycle efficiencies


• Exceptional communication, influencing, and relationship-building skills with the ability to lead discussions with Sales Directors and cross-functional managers, directors and VPs with the ability to translate information in a clear and accessible manner


• Demonstrated ability of developing and implementing training, learning and development programs using data to measure engagement and impact to business outcomes


• Strong project management skills with the ability to manage multiple deliverables with minimal supervision within a dynamic, fast-paced and sometimes ambiguous environment


• Highly organized self-started dedicated to continuously improving and driving excellence in projects, processes and deliverables 


• Proven, in-depth working knowledge of major sales technologies such as Salesforce, Highspot and Gong is an asset


• Direct experience integrating and utilizing Gong (a conversation intelligence tool) for sales coaching, training validation, and measuring seller behaviour


• Direct experience integrating and utilizing Highspot (a content management system) for content organization and measuring seller behaviour


• Direct experience utilizing Salesforce (a Customer Relationship Management system) for measuring and analyzing sales cycle efficiencies


• Familiarity with foundational sales concepts, including sales methodology, sales play development, and defining Ideal Customer Profiles (ICPs) and Buyer Personas


• Expertise in preparing effective and visually appealing PowerPoint/Google Slide presentations is an asset


• Prior experience supporting a variety of sales teams from Account Management sales to New Business Development sales

How We Support You

Our Total Rewards philosophy is to ensure that you are rewarded for impact, take part in accelerated career growth, thrive with highly flexible benefits, and are empowered to do your best work in a remote-first environment. In alignment with our overall Total Rewards Philosophy, we believe compensation should be fair, clear, consistent, and aligned to growth. 

Hiring Range

$83 - $104 CAD

Our promise to each other:

Here's how to apply:

This position is currently vacant and open for applications. If you’re interested in working with us on the future of shopping, fill out the fields below and submit your application. While experience and skill sets are valuable, growth potential and attitudes are equally important. If you’re prepared to grow dramatically with your team at a world-class learning organization, consider applying. We understand that the most creative solutions require diversity in thought and life experiences.

Flipp is an equal opportunity employer. We do not discriminate on the basis of race, color, ancestry, religion, creed, sex, national or ethnic origin, sexual orientation, age, citizenship, marital status, family status, disability, or gender identity or expression or any other protected grounds. We are proud to be a welcoming space for employees, of every background, to bring their whole selves to work with confidence. Flipp is committed to providing appropriate accommodations to ensure our selection process is equitable, and such accommodations can be made available on request. If you require an accommodation, please contact your dedicated recruiter directly.

Hiring is a deeply human process; therefore, we use AI in limited, administrative ways to help streamline our hiring process. An AI-powered scheduling tool assists with coordinating interviews, and our applicant tracking system may use AI to identify relevant keywords within applications. We do not use AI to assess your application, make hiring decisions, or conduct interviews. All evaluations are completed by real people.

A member of our recruitment team will respond to you in the coming weeks.