Director of Sales

Agentic Enterprise SaaS | Player-Coach | Commercial Buildout Location: New York, New York Type: On-site Reporting to: CEO About unPLUG unPLUG is building the Autonomous Growth Engine for restaurants: an AI-native platform that replaces fragmented tools, disconnected channels, and manual workflows with one integrated system for driving revenue growth. We start by powering the first-party guest experience, then expand across guest data, lifecycle marketing, and AI-powered execution. We are building towards becoming the AI Operating System for restaurant growth, unifying first-party channels, third-party marketplaces, and performance marketing through autonomous agents that plan, execute, and optimize against real-time business outcomes. Today, unPLUG supports a growing portfolio of multi-unit restaurant brands and is already driving meaningful improvements in first-party revenue, guest engagement, and retention. We are entering the next stage of the company: scaling the core platform while building the agentic layer that can become the system of action for restaurant growth. The Opportunity unPLUG has built meaningful traction through a founder-led enterprise sales motion. Our next challenge is turning that motion into a predictable, repeatable, scalable commercial engine. We are looking for a Director of Sales who has already done this before. Your mandate is straightforward: Win customers. Build the machine. Build the team. Own the number. This is not a traditional management role. This is a leadership role. During the next stage of unPLUG’s growth, you will personally own and close strategic enterprise opportunities while simultaneously building the processes, systems, operating cadence, and team required to scale the commercial organization. We are looking for an experienced enterprise sales leader whose judgment, operating discipline, and closing ability immediately increase the capabilities of the company. The right person should eventually make the CEO less necessary in day-to-day sales execution. What You’ll Own Own the Revenue Number Take direct accountability for new-logo revenue performance. Build a clear operating plan connecting pipeline creation, pipeline coverage, conversion rates, sales capacity, hiring, and closed-won revenue. Identify performance gaps early and implement corrective action before they become missed quarters. Operate from measurable outcomes rather than activity. Personally Close Strategic Enterprise Deals Remain deeply involved in selling. Personally own and close some of unPLUG’s largest and most strategically important enterprise opportunities. Lead sophisticated executive conversations with CEOs, CFOs, CMOs, CIOs, CTOs, digital leaders, and senior operators. Navigate complex buying processes involving business cases, integrations, security, procurement, legal, franchise stakeholders, executive committees, and competing organizational priorities. This is a true player-coach role. Build a Repeatable Enterprise Sales Machine Turn founder-led sales knowledge into an institutionalized system. Create a sales process that improves performance without creating unnecessary bureaucracy. Build a repeatable system for creating sufficient enterprise pipeline. Remain willing and able to personally create pipeline rather than relying entirely on others. Build and Lead the Sales Team Determine the right commercial organization for each stage of growth. Recruit, onboard, coach, develop, and retain exceptional sales talent. Establish clear expectations, accountability, performance standards, and operating rhythms. Develop future sales leaders rather than creating dependency on yourself. Partner with the CEO Operate as a trusted commercial counterpart to the CEO. Bring recommendations, not just problems. Challenge the CEO when your commercial judgment differs. Provide clear, concise visibility into performance, opportunities, risks, and decisions. Over time, progressively remove the CEO from sales activities that do not require founder involvement. What We’re Looking For Non-Negotiables 8–15+ years of B2B SaaS sales experience, including substantial enterprise closing experience. 3+ years of meaningful sales leadership responsibility. Repeated history personally closing complex six-figure enterprise software agreements. Experience building or materially improving a sales motion at an early-stage or high-growth company. Proven ability to personally generate pipeline rather than exclusively relying on SDRs or marketing. Exceptional enterprise discovery, value selling, multithreading, negotiation, and closing ability. Deep understanding of qualification, forecasting, sales stages, pipeline management, and deal inspection. Demonstrated ability to distinguish genuine opportunities from false-positive pipeline. Strong commercial judgment and the ability to diagnose why deals are winning, stalling, or losing. Highly autonomous operating style with a history of identifying problems early and acting without waiting for executive direction. Strong analytical ability and comfort using data to identify systemic sales problems. Proven experience recruiting, managing, coaching, and developing high-performing sellers. High accountability. When performance misses expectations, your instinct is to diagnose and solve rather than explain and defend. Strongly Preferred Experience selling into or working within one or more of the following: Vertical SaaS MarTech Loyalty or CRM Commerce Retail technology Experience with heavily franchised organizations is particularly valuable. However, exceptional enterprise SaaS sales leadership is more important than restaurant-industry experience. Why unPLUG This is an opportunity to build the commercial engine of a company at an important inflection point. You will have the opportunity to: Own a meaningful portion of the company’s growth trajectory. Personally sell to executives at nationally recognized restaurant and hospitality brands. Build the enterprise sales organization from the ground up. Help define how a new category of digital growth technology is sold. Influence product strategy through direct market exposure. Build and lead the team beneath you. Work directly with the CEO, founders, investors, partners, and senior customer executives. Participate meaningfully in the financial upside created through your work. What We Offer Competitive cash compensation: Approximately 50% base / 50% variable compensation, $300K OTE. Meaningful Equity. Performance-based upside and accelerators. Unlimited Paid Time Off. 401(k). HSA. Medical, dental, and vision insurance. Additional optional benefits through Insperity. unPLUG is committed to attracting, retaining, developing, and promoting the most qualified individuals in a nondiscriminatory manner. We treat all applicants and employees fairly without regard to race, color, religion or belief, sex, national or ethnic origin, ancestry, age, marital status, sexual orientation, gender identity, veteran status or service, physical or mental disability, or any other classification protected by applicable law. Accommodation unPLUG is committed to providing reasonable accommodations to individuals with disabilities. If you need a reasonable accommodation for any part of the application process, please email View email address on click.appcast.io and let us know the nature of your request. #J-18808-Ljbffr