Sales Account Executive

About Checkmate 🛍 📲

Checkmate is an AI marketing platform modernizing eCommerce by enabling smarter, more connected buying experiences between brands and consumers.

Powered by AI, Checkmate enhances high-intent buying moments; delivering personalized, timely messaging that meets consumers where they are and drives them to act. By partnering with brands, Checkmate unlocks net-new revenue by reaching high-intent shoppers brands can’t otherwise access.

We’ve expanded our consumer reach beyond our fast-growing app (2M+ shoppers) to a broader network of 100M+ high-intent U.S. consumers. Our platform uses AI to de-anonymize site traffic, uncover missed conversion opportunities, and launch high-performance campaigns that engage shoppers who are ready to buy.Checkmate offers three core products for brands:

1. Enrichment: Reveal and resolve anonymous visitors to fuel smarter lifecycle flows.

2. Targeting: Deliver single-use offers through high-converting surfaces like our app, extension, email, and SMS.

3. Audiences: Capture pre-checkout emails via gated discounts and gain competitive insights.

Backed by Google Ventures (GV), Fuel Capital, Blackbird Ventures, Susa Ventures, F7 Ventures, Wischoff Ventures, and cultural icons like Paris Hilton and The Chainsmokers, Checkmate is poised to disrupt how brands connect with consumers.

Position Overview 💼

We’re seeking a dynamic and results-driven GTM founding Sales Account Executive to lead sales efforts within the fashion, beauty, and home verticals. In this role, you’ll be at the forefront of building high-impact partnerships with leading online fashion brands and Shopify+ merchants. You'll leverage your sales expertise to empower brands to maximize the value of Checkmate’s innovative shopping tools. This is an entrepreneurial position, ideal for someone who thrives in a fast-paced environment and is eager to drive growth in the eCommerce space.

At Checkmate, we already collaborate with top-tier brands like Stanley Cups, Quay, Billy Reid, Florence by Mills, ColourPop, Naadam, and Coola, and we’re excited to bring even more amazing partners on board!

Responsibilities 🌟

• Lead Generation & Prospecting:

  • Target Shopify merchants with $10M-$500M+ GMV/year.

  • Leverage cold calling, email outreach, social selling, and networking to find and engage prospects.

  • Establish relationships with growth agencies, tech platforms, and direct-to-consumer brands.

• Relationship Building and Consultative Selling - Building relationships:

  • You will not only be responsible for finding deal opportunities but closing them and onboarding a no-code drag Shopify App.

  • The relationship doesn’t end at the integration. You will be responsible for communicating metrics, success and enabling our brand partners to be successful for running more campaigns and adding additional surfaces.

• Data hygiene

  • Manage your own CRM (Hubspot) and maintain data hygiene.

  • Analyze sales performance, track commissions, and provide reports to retailers and internal teams.

• Team Player

  • Work closely with Sales, Partnerships, Product, and Marketing teams to provide innovative solutions for partners.

  • Contribute to product feedback and strategic initiatives to drive business growth.

• Upsell

  • Provide reporting to sales for upselling and renewals for Paid Programs / Commission Rate increase opportunities

Qualifications 🤓

• Background in banking, consulting or marketing that has moved into tech sales

• 5-10 years of experience in tech/eComm

• Experience selling into fashion, beauty, or home brands is a major plus.

• Skilled in presenting data-driven insights and creative pitches.

• Strong communication, organizational, and problem-solving skills.

• Proficiency with Excel/Google Sheets; Hubspot experience is a bonus.

• Bachelor’s Degree preferred.

What will make you stand out

• Background in fast-paced tech companies with exposure to scaling SaaS, AI, or eCommerce solutions

• Experience developing and executing GTM strategies to drive revenue growth

• Business strategy expertise - ability to translate complex market opportunities into actionable sales plays

• Investment banking or PE experience, demonstrating strong analytical and business strategy fundamentals

• Management consulting experience with exposure to growth strategy, digital transformation, or eCommerce verticals

Benefits 💸

• Competitive salary

• Healthcare

• Gym membership

• 4 weeks PTO and health days

• Company retreats 🏝

• Additional benefits

• US remote - Los Angeles or New York City preferred

If you are passionate about reshaping the future of e-commerce and have a track record of sales, we invite you to join us on our exciting journey at Checkmate.