Account Executive (Sales), DTC Brands

📋 Description

• • As an Account Executive at Checkmate, you will be at the forefront of revolutionizing how Direct-to-Consumer (DTC) brands maximize their revenue by acting as a strategic growth advisor and quota-carrying sales professional.
• • Your primary mission will be to identify and engage high-potential DTC brands within the fashion, beauty, and home verticals, diagnosing their unique conversion challenges, and prescribing tailored solutions using Checkmate's cutting-edge AI-powered platform.
• • This role demands a deep understanding of the e-commerce landscape, a knack for building trusted partnerships with growth teams, and the ability to navigate complex sales cycles to close new business.
• • You will be instrumental in helping brands overcome the common problem of leaving significant revenue on the table due to issues like cart abandonment, anonymous browsing, and missed retargeting opportunities.
• • Checkmate's AI platform is designed to capture intent signals from millions of shoppers, transforming them into high-converting campaigns that deliver measurable revenue uplift within a short timeframe.
• • Your responsibilities will include building strategic partnerships by targeting high-growth Shopify merchants (ranging from $10M to $500M in Gross Merchandise Volume).
• • You will conduct in-depth discovery sessions to thoroughly understand each prospect's growth challenges, operational constraints, and strategic priorities.
• • A key part of your role will involve presenting compelling, data-driven business cases that clearly articulate projected Return on Ad Spend (ROAS), incremental revenue gains, and payback periods for potential clients.
• • You will need to skillfully navigate complex buying committees, engaging with stakeholders across Growth, Marketing, Revenue Operations (RevOps), and Finance departments.
• • The expectation is for you to establish yourself as a trusted advisor and strategic partner, rather than merely a vendor, fostering long-term relationships.
• • You will be directly responsible for driving revenue by owning a quota and managing the full sales cycle, from initial prospecting through to closing deals.
• • Pipeline generation will be a critical function, achieved through proactive outbound prospecting efforts, cultivating agency partnerships, and leveraging existing ecosystem relationships.
• • Maintaining disciplined pipeline management and accurate forecasting within Hubspot will be essential for team success and personal accountability.
• • Beyond closing new business, you will also support the onboarding process for new clients and actively identify opportunities for account expansion based on performance data and evolving client needs.
• • This role offers a unique opportunity to shape the future of Checkmate's go-to-market strategy.
• • You will contribute valuable product feedback, informed by real customer needs and identified market gaps, directly influencing product development.
• • You will play a key role in refining our GTM strategy as the company scales into new verticals and explores emerging use cases for our AI platform.
• • Close collaboration with the Product, Marketing, and Customer Success teams will be vital to continuously improve the overall customer journey and ensure client satisfaction.
• • As a founding member of the sales organization, your contributions will lay the groundwork for future growth and scalability, making this a truly impactful role.
• • You will be empowered to build your own playbook, demonstrating an entrepreneurial and resourceful approach to sales and client engagement.
• • The ideal candidate possesses a strong understanding of DTC economics, including Customer Acquisition Cost (CAC), Lifetime Value (LTV), and ROAS, and is familiar with the common DTC tech stack (e.g., Klaviyo, Attentive, Shopify).
• • You should be comfortable discussing email/SMS flows, cart abandonment campaigns, and retargeting strategies with prospects, showcasing your practical marketing knowledge.
• • An understanding of promotional strategy, seasonality, and customer segmentation is also crucial for developing effective sales approaches.
• • This position is ideal for a commercially driven individual who is comfortable with sales accountability and possesses strong discovery skills to build data-driven business cases for senior marketing leaders.
• • Your passion for eCommerce and DTC brand strategy will be a driving force in your success.
• • You will be working with a dynamic AI marketing platform that helps leading DTC brands like Stanley, Quay, ColourPop, Laneige, and Dockers capture anonymous shoppers, launch targeted campaigns, and drive measurable revenue.
• • Checkmate's three core products—Enrichment, Targeting, and Audiences—provide a comprehensive suite of tools to de-anonymize site traffic, uncover missed conversion opportunities, and launch high-performance campaigns.
• • This role is not for those seeking a traditional, heavily structured AE position but rather for an individual eager to build, innovate, and make a significant impact in a fast-paced environment.