Sales & Business Development Expert (Retail SaaS) - Mid-Level (Remote,

Company Overview

Iterate.ai is an innovative enterprise AI application platform provider that builds secure, low-code, and agentic AI solutions to help large organizations innovate faster. Our cutting-edge technology powers automation and data-driven insights across industries – including retail – to accelerate digital transformation. As we continue to expand, we are seeking a results-driven sales and business development professional to drive our growth in the retail sector.

Role Overview

We are looking for a dynamic individual contributor with deep retail industry expertise and a passion for technology-driven innovation. In this role, you will leverage your extensive network and SaaS sales experience to identify and close new business with leading retail brands. You will work closely with our leadership and product teams to tailor solutions for retail clients, evangelize our AI platform’s value proposition, and help Iterate.ai establish a stronger footprint in the retail vertical. This is a high-impact, high-visibility position suited for a self-starter who thrives in a fast-paced startup environment and is eager to take ownership of ambitious revenue targets.

Key Responsibilities

Drive Retail SaaS Sales: Identify, target, and secure new enterprise SaaS deals within the retail industry, focusing on segments such as beauty, apparel, automotive, heavy equipment, and more. Develop a robust sales pipeline of retail prospects and consistently convert leads into wins.

Leverage Industry Connections: Utilize your extensive Rolodex of retail industry contacts to open doors with key decision-makers (C-level and VP-level executives) across various retail sectors. Actively network at industry events (e.g., NRF’s Big Show, Shoptalk) and through organizations like the National Retail Federation, Rethink Retail, and Shop.org to generate opportunities and elevate Iterate.ai’s presence.

Consultative Selling & Presentations: Engage prospects with a consultative sales approach – understand each retail client’s business challenges (e.g. omnichannel commerce, AI-driven personalization, Generative AI/Agents, Marketing/Social Applications) and demonstrate how Iterate.ai’s platform can deliver solutions. Conduct compelling product demos and presentations tailored to retail audiences, and effectively communicate ROI and business value.

Collaborate & Strategize: Work cross-functionally with Iterate.ai’s product, marketing, and solutions engineering teams to craft custom proposals and proof-of-concepts that address retailer needs. Provide market feedback and insights to help shape product roadmap and go-to-market strategies for the retail vertical.

Achieve Revenue Targets: Meet and strive to exceed your annual sales quota (expected to be in the multi-million dollar range). Diligently manage the full sales cycle from prospecting and initial contact through negotiation and closing, ensuring timely deal execution and accurate forecasting/reporting in our CRM.

Relationship Management: Build and maintain strong, long-term relationships with client stakeholders. Act as a trusted advisor to retail clients, ensuring customer satisfaction and identifying upsell or cross-sell opportunities for continued account growth.

Qualifications & Experience

Experience: 3–5 years of successful B2B software/SaaS sales experience, with at least 2+ of those years specifically selling into the retail industry (retail tech or enterprise solutions for retail). Prior experience at a startup or high-growth tech company is essential for understanding our fast-paced, agile culture.

Track Record: Proven history of meeting or exceeding sales targets . For example, you have owned annual quotas on the order of several million dollars in ARR (e.g. ~$5M+ annually) and have a track record of hitting or surpassing those numbers. Demonstrated ability to close complex SaaS deals with enterprise or mid-market retail clients, from leads, initial pitch through contract negotiation and signing.

Retail Network: Verifiable network of retail industry leaders and contacts. You are well-connected across sectors like beauty, fashion/apparel, consumer goods, automotive, equipment retail, etc., and can leverage those relationships to drive business. Active participation in retail industry groups or events (NRF, Shoptalk, Rethink Retail, Shop.org, etc.) is a strong plus.

Domain Knowledge: Deep understanding of retail sector trends and pain points – such as omnichannel customer experience, e-commerce and in-store integration, AI/automation in retail operations, supply chain and inventory challenges, and customer loyalty/personalization strategies. You can speak the language of retail business stakeholders and align technology solutions to their objectives.

Skills: Exceptional communication and interpersonal skills with an engaging, consultative approach. Comfortable pitching to and negotiating with senior executives (CTOs, CIOs, CMOs, Heads of Innovation, etc.). Strong presentation and storytelling abilities to convey value propositions clearly. Effective at strategic account planning, pipeline management, and proficient with CRM and sales tools.

Personal Attributes: Highly self-motivated and results-driven. Entrepreneurial mindset with the ability to work independently as an individual contributor while also collaborating effectively with a team. Personable and professional, able to build trust and rapport quickly. Adaptable and resourceful in navigating a startup environment and a dynamic market.

What We Offer

Impact & Growth: An opportunity to drive the growth of a cutting-edge AI platform in the retail space and make a tangible impact on the digital transformation of top retail brands. You’ll be joining a small, agile team where your contributions directly influence our success and strategy in the retail vertical.

Competitive Compensation: Competitive base salary plus a generous, uncapped commission plan. On-target earnings (OTE) for this role are designed to reward high performance, with top performers having potential to earn in the high six-figures (and even seven-figures) annually.

Benefits & Perks: [Option to include standard benefits] – e.g. comprehensive health insurance, 401(k) plan, stock options/equity, paid time off, and other startup perks. We value work-life balance and offer the flexibility and support you need to excel.

Flexibility: Remote work environment (work from anywhere in the U.S.) with approximately 30% travel for client meetings and team events. Our main team hubs are in San Jose, CA and Denver, CO, so occasional visits for on-site meetings or company gatherings will be part of the role (travel expenses covered).

Startup Culture: A collaborative, innovative culture that values initiative, creativity, and customer success. You’ll have the freedom to propose new ideas, experiment with go-to-market strategies, and truly “own” the retail sector strategy. We celebrate wins as a team and provide mentorship and resources to help you grow.