Senior Director, Omni Channel Sales

About Flywheel 

The Opportunity  

We are looking for a Senior Director, Omni Channel Sales (Walmart/Target) to join our North American New Business team and drive strategic revenue growth across some of the world’s largest brands. This role will focus specifically on accelerating Flywheel’s growth within the Walmart and Target segments, building senior-level relationships, identifying high-value opportunities, and expanding our presence across priority accounts.

As a Senior Director, you will develop and lead a consultative sales strategy within an assigned portfolio of target brands, with a focus on unlocking enterprise-level partnerships and long-term commercial success. You will work cross-functionally with pre-sales, marketing, product marketing, and client services teams to shape compelling solutions, engage executive stakeholders, and drive opportunities through the full sales lifecycle.  

This role is ideal for a highly strategic, commercially minded sales leader with deep experience selling into large brands, ideally across retail media, commerce, CPG, or adjacent digital services. You bring executive presence, strong business acumen, and a proven ability to influence complex buying groups while translating market trends into meaningful client solutions. 

What You Will Do:  

• Own and drive revenue growth against goal for a defined portfolio of targeted brands within the Walmart and Target segments  
• Develop and execute a strategic new business plan to grow Flywheel’s presence with large enterprise brands and priority prospects  
• Build, manage, and advance a qualified pipeline of new business opportunities, with a focus on high-value, multi-service engagements  
• Lead complex, consultative sales cycles from initial engagement through solution development, negotiation, and close  
• Build and maintain senior and executive-level client relationships, serving as a trusted advisor to key decision-makers across prospective accounts  
• Act as a subject matter expert on Flywheel’s capabilities, services, and value proposition, clearly articulating how our solutions solve client pain points and drive measurable outcomes  
• Partner with internal stakeholders to shape and deliver tailored proposals, business cases, and pitch presentations that align Flywheel’s offerings to client priorities  
• Translate industry news, macro trends, retailer dynamics, and competitive developments into actionable recommendations for prospects and clients  
• Collaborate closely with pre-sales, product marketing, and marketing teams to create joint demand generation strategies, use cases, and account-based engagement plans  
• Work with Client Services and broader commercial teams to ensure strong alignment on service capabilities, go-to-market messaging, and market demand  
• Maintain accurate and disciplined lead, pipeline, and forecast reporting, providing visibility into performance, opportunity health, and revenue outlook  
• Represent Flywheel at industry events, trade shows, and networking opportunities to build market presence and identify future clients  
• Contribute to the ongoing refinement of sales strategy, territory planning, and commercial best practices across the broader North American New Business team  
• Mentor and influence others across the organization through leadership, collaboration, and a strong point of view on market opportunities and growth strategy 

Who You Are:  

• You have 10+ years of sales or business development experience, with a strong track record of selling mid-market to enterprise solutions into large organizations 
• You have meaningful experience working within or selling into Walmart and/or Target ecosystems; experience in retail media, commerce, CPG, or digital marketing services is strongly preferred 
• You have a proven ability to build executive relationships, navigate complex organizations, and align multiple stakeholders around a strategic solution 
• You bring a strong understanding of the end-to-end enterprise sales process, including prospecting, solution development, negotiation, forecasting, and closing 
• You are a highly motivated hunter with the strategic mindset to identify, develop, and convert large-scale business opportunities 
• You are an exceptional communicator who can confidently engage audiences from day-to-day operators to senior executives 
• You are naturally curious, commercially sharp, and deeply focused on delivering positive client outcomes 
• You have a solutions-oriented mindset and are comfortable operating in ambiguity, solving complex problems, and building structure where needed 
• You can analyze performance dashboards and use spreadsheets, including Excel formulas and pivot tables, to extract insights and tell a clear story from imperfect or complex data 
• You are highly organized, detail-oriented, and able to manage multiple priorities and sales opportunities simultaneously 
• You have a strong sense of ownership and a bias for action, with a willingness to roll up your sleeves and do what it takes to move the business forward 
• You are a collaborative team player who contributes positively to cross-functional partnerships and the overall success of the team 
• You are comfortable traveling as needed 

This position is commission eligible. 

The Interview Process:

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