About the Company At BenefitHub, our commitment is to offer employee perks and voluntary benefits that give real value to employees, focusing on enhancing the quality of their daily lives. We continuously strive to add unique and exciting values to the offers available to our members, partnering with a diverse range of global brands to achieve this. This role provides a unique opportunity to become part of one of the fastest-growing benefits technology companies in the US, with expanding influence globally. Join our mission to improve the daily life of millions by providing access to the world’s largest selection of personally relevant benefits. By contributing to our goal of becoming the most widely used benefits platform, you will be enhancing the lives of millions of people around the globe. BenefitHub does not currently offer H-1B Sponsorship Position Summary This position reports into the CEO of BenefitHub and is responsible for driving both commerce revenue and advertising sales growth. This role blends eCommerce strategy, Ad sales growth, CRO experimentation, merchandising, and business impact into one. The EVP, Advertising & eCommerce oversees two distinct, but integrated functions – (a) BenefitHub’s merchandising team and operations and (b) BenefitHub’s advertising sales and ad ops teams. The EVP has direct responsibility for driving mid-eight figures in sales revenue and is expected to drive continued double-digit growth per annum. As the head of BenefitHub’s commerce and advertising teams, the EVP oversees end-to-end strategy and execution for revenue generation, marketplace growth, and operational excellence, ensuring that advertising, merchant and eCommerce strategies and initiatives integrate to maximize profitability and customer engagement. At the core of this role is advertising and merchandising strategy and innovation – designing and scaling solutions that create value for merchants/advertisers and customers alike. What You’ll Do • Lead & Inspire - Manage and mentor a team of 15 sales representatives and merchandisers. You will shape the sales organization by recruiting top talent and transforming skilled merchandisers into proactive growth builders. • Drive Aggressive Growth - Take full ownership of scaling a $40MM+ business with a consistent 20+% year over year growth target. • Own the Numbers - Command the entire sales pipeline with rigorous, data driven insights. You will deliver accurate forecasting and strategic refinements to optimize execution and deliver predictable revenue growth. Key Duties & Responsibilities: Advertising • Architect, articulate and execute a vision and high-impact digital and newsletter ad sales strategy that aligns with the company’s long-term goals. • Lead the design, development and execution of advertising products and solutions across digital affiliate, and omni-channel platforms including newsletters, web, and mobile. • Leverage data analytics to optimize targeting, measurement, and campaign performance with a core understanding of conversion funnels and user flows and the importance of delivering high ROI for our merchant partners/advertisers. • Continue to position advertising as a core growth engine for the company. • Manage the ad sales team and ad ops team including P&L responsibility and ensuring sales quota attainment. • Actively support the ad sales team in closing critical partnerships and in upselling. • Track sales metrics and performance; report regularly on pipeline and closed revenue to CEO and board. • Represent BenefitHub at industry events and in relevant advertising/commerce communities Merchant Operations & Partnerships • Drive revenue growth through best-in-class merchandising approaches/strategies • Oversee merchant partnerships, onboarding and relationship management to optimize revenue growth from affiliate commerce. • Champion BenefitHub’s own storefront and commerce initiatives including negotiating with key entertainment and travel partners. • Refine programs that help merchants maximize visibility and value. • Optimize operational processes to improve efficiency and scalability. • Negotiate and manage merchant and vendor contracts to maximize BenefitHub’s affiliate and direct commissions. • Leverage AI solutions to drive down expenses and improve the user experience. eCommerce & Marketplace Growth • Lead strategy and execution for the company’s e-commerce platform and discount marketplace. • Partnering with product and technology teams, lead the development and execution of a conversion-optimized, premium-feeling shopping and marketplace experience that builds trust and drives measurable impact (CVR, AOV, RPV, CAC, LTV). • Drive revenue and engagement through merchandising, conversion optimization, pricing strategy and user experience. • Ensure every customer journey is seamless, high-converting, and premium, blending storytelling, merchandising, and offer strategy. • Translate consumer psychology, data insights, and creative direction into recommended actionable UX improvements. • Align marketplace value creation with advertising initiatives to expand both customer and merchant impact. • Make recommendations on increasing BenefitHub’s and advertisers conversion rates and improving any internal processes. • Manage and mentor a team of merchandisers and work collaboratively cross-departmentally with UX/UI designers, copywriters, developers, and project managers. • Build scalable processes and workflows that enable rapid design, testing, and iteration without sacrificing quality. Qualifications: • Hands-on growth mindset - you don't just manage, you roll up your sleeves to dig into funnels, analytics, newsletter products, ad sales solutions, UX flows, and testing frameworks. • 15+ years of executive leadership experience in advertising, eCommerce and marketplace operations. • Track record of building and scaling successful e-commerce and/or ad sales teams of at least $30MM in sales with prior commensurate P&L responsibility. • Successfully and consistent record of driving double-digit CAGR growth for a commerce or advertising business; with preference for someone who has done both. • Strong innovation mindset, identifying new opportunities beyond current market solutions. • Extensive experience in contract negotiation and partnership management and “ability to close” deals/partnerships. • Proven ability to manage an ad sales team in a results driven and team-oriented environment. • Excellent communication, strategic thinking, and relationship building skills. BenefitHub is proud to offer highly competitive salaries along with a very generous perks & benefits package for full-time Team Members: • Medical, Vision, and Dental (Employer paid 75% of monthly contributions) • Domestic Partner Coverage for all insurance plans • 100% employer-paid Life Insurance • 401(K) retirement plan options (including employer contribution) • Generous Paid Time Off (PTO) • Generous Paid Paternity and Maternity Leave Policies • 11 Holidays (Including office closed day after Thanksgiving) • Professional development opportunities • Flexible work schedules • Collaborative and innovative work environment • Remote-friendly work arrangements • Employee discount program • Flexible Spending Account program • Voluntary Benefit Programs (STD, LTD, Life Insurance, Accident)