Head of Sales B2B Startup

Woburn, MassachusettsOnsiteDirect Hire$150k - $200kA well-funded robotics startup is revolutionizing the automotive service industry by bringing automation and intelligent robotics to a process that has remained largely unchanged for decades. Having successfully secured Series B funding and moved from prototype to commercial deployment, the company is entering an exciting phase of rapid growth and customer expansion.We're looking for a Founding Account Executive / Sales Manager to become the company's first commercial hire. This is a unique opportunity for a proven enterprise sales professional to build a go-to-market organization from the ground up while personally driving revenue growth. This is first and foremost a quota-carrying role where success is measured by your ability to close deals, establish reference customers, and create a repeatable sales motion that will eventually scale into a larger commercial organization.If you've successfully sold enterprise technology into automotive dealerships, fleet operators, tire retailers, or industrial customers—and you're excited by the opportunity to help define an entirely new category of robotics technology—this role offers tremendous upside and career growth. What You'll Be Doing Own the company's enterprise sales pipeline and personally drive new customer acquisition Manage the complete sales cycle from prospecting through contract negotiation and close Develop relationships with dealership groups, national tire retailers, fleet operators, and enterprise automotive organizations Conduct executive-level discovery meetings, product demonstrations, and ROI presentations Build business cases that clearly communicate operational improvements and financial value Create pricing proposals, negotiate contracts, and close complex enterprise sales Establish the company's first lighthouse customers and long-term strategic accounts Develop repeatable sales processes, messaging, playbooks, and qualification criteria Serve as the voice of the customer by providing continuous feedback to Product, Engineering, and Executive Leadership Partner with implementation teams to ensure successful customer deployments and long-term account growth Track pipeline activity, forecasting, and customer engagement using CRM best practices Help recruit, mentor, and onboard future Account Executives and Business Development Representatives as the commercial organization grows Required Skills & Experience 7+ years of successful B2B enterprise sales experience with a proven history of exceeding quota Strong experience personally sourcing, managing, and closing complex enterprise opportunities Background selling Automotive SaaS, Dealer Technology, Fleet Management software, Industrial Technology, Robotics, or related enterprise solutions Experience selling into dealership groups, automotive service organizations, fleet operators, tire retailers, or similar enterprise customers Demonstrated ability to navigate complex buying cycles involving executive leadership and multiple stakeholders Experience selling hardware combined with recurring software or subscription-based solutions Strong financial acumen with experience building ROI models and business cases Proven negotiation, presentation, and executive communication skills Experience using Salesforce, HubSpot, or similar CRM platforms with strong forecasting discipline Ability to travel extensively throughout North America (approximately 40-60%) Desired Skills & Experience Existing relationships within major dealership groups, national tire retailers, or commercial fleet organizations Previous experience as one of the first sales hires within a venture-backed startup Experience helping build sales organizations, processes, and go-to-market strategy Knowledge of dealership operations, fixed operations, service departments, or commercial fleet maintenance Experience selling robotics, automation, industrial equipment, IoT, AI, or connected technology platforms Strong understanding of enterprise software sales methodologies Comfortable working in fast-paced startup environments with evolving priorities Industry Experience We're Looking For Candidates with experience selling into any of the following industries are highly preferred:Automotive SaaS Dealer Management Systems (DMS) Dealer Technology Fleet Management Commercial Fleet Operations Tire & Service Retail Industrial Automation Robotics Connected Equipment Automotive Service Equipment Enterprise SaaS supporting automotive operations Leadership Qualities We're Looking For Highly competitive and motivated by winning new business Entrepreneurial mindset with the ability to thrive in an early-stage startup Self-starter capable of building pipeline without significant internal resources Executive presence with the ability to influence decision makers at every level Process-oriented while remaining adaptable in a rapidly growing company Collaborative team player who enjoys helping shape company strategy Passionate about building something from the ground up and leaving a lasting impact The Offer Competitive base salary plus uncapped commission and equity participation Opportunity to become the company's first commercial hire and help build the sales organization Direct access to executive leadership and company founders Work with a well-funded, rapidly growing robotics company entering commercial scale Significant career advancement opportunities as the organization grows Comprehensive medical, dental, vision, PTO, and retirement benefitsApplicants must be currently authorized to work in the United States on a full-time basis. A well-funded robotics startup is revolutionizing the automotive service industry by bringing automation and intelligent robotics to a process that has remained largely unchanged for decades. Having successfully secured Series B funding and moved from prototype to commercial deployment, the company is entering an exciting phase of rapid growth and customer expansion.We're looking for a Founding Account Executive / Sales Manager to become the company's first commercial hire. This is a unique opportunity for a proven enterprise sales professional to build a go-to-market organization from the ground up while personally driving revenue growth. This is first and foremost a quota-carrying role where success is measured by your ability to close deals, establish reference customers, and create a repeatable sales motion that will eventually scale into a larger commercial organization.If you've successfully sold enterprise technology into automotive dealerships, fleet operators, tire retailers, or industrial customers—and you're excited by the opportunity to help define an entirely new category of robotics technology—this role offers tremendous upside and career growth. What You'll Be Doing Own the company's enterprise sales pipeline and personally drive new customer acquisition Manage the complete sales cycle from prospecting through contract negotiation and close Develop relationships with dealership groups, national tire retailers, fleet operators, and enterprise automotive organizations Conduct executive-level discovery meetings, product demonstrations, and ROI presentations Build business cases that clearly communicate operational improvements and financial value Create pricing proposals, negotiate contracts, and close complex enterprise sales Establish the company's first lighthouse customers and long-term strategic accounts Develop repeatable sales processes, messaging, playbooks, and qualification criteria Serve as the voice of the customer by providing continuous feedback to Product, Engineering, and Executive Leadership Partner with implementation teams to ensure successful customer deployments and long-term account growth Track pipeline activity, forecasting, and customer engagement using CRM best practices Help recruit, mentor, and onboard future Account Executives and Business Development Representatives as the commercial organization grows Required Skills & Experience 7+ years of successful B2B enterprise sales experience with a proven history of exceeding quota Strong experience personally sourcing, managing, and closing complex enterprise opportunities Background selling Automotive SaaS, Dealer Technology, Fleet Management software, Industrial Technology, Robotics, or related enterprise solutions Experience selling into dealership groups, automotive service organizations, fleet operators, tire retailers, or similar enterprise customers Demonstrated ability to navigate complex buying cycles involving executive leadership and multiple stakeholders Experience selling hardware combined with recurring software or subscription-based solutions Strong financial acumen with experience building ROI models and business cases Proven negotiation, presentation, and executive communication skills Experience using Salesforce, HubSpot, or similar CRM platforms with strong forecasting discipline Ability to travel extensively throughout North America (approximately 40-60%) Desired Skills & Experience Existing relationships within major dealership groups, national tire retailers, or commercial fleet organizations Previous experience as one of the first sales hires within a venture-backed startup Experience helping build sales organizations, processes, and go-to-market strategy Knowledge of dealership operations, fixed operations, service departments, or commercial fleet maintenance Experience selling robotics, automation, industrial equipment, IoT, AI, or connected technology platforms Strong understanding of enterprise software sales methodologies Comfortable working in fast-paced startup environments with evolving priorities Industry Experience We're Looking For Candidates with experience selling into any of the following industries are highly preferred:Automotive SaaS Dealer Management Systems (DMS) Dealer Technology Fleet Management Commercial Fleet Operations Tire & Service Retail Industrial Automation Robotics Connected Equipment Automotive Service Equipment Enterprise SaaS supporting automotive operations Leadership Qualities We're Looking For Highly competitive and motivated by winning new business Entrepreneurial mindset with the ability to thrive in an early-stage startup Self-starter capable of building pipeline without significant internal resources Executive presence with the ability to influence decision makers at every level Process-oriented while remaining adaptable in a rapidly growing company Collaborative team player who enjoys helping shape company strategy Passionate about building something from the ground up and leaving a lasting impact The Offer Competitive base salary plus uncapped commission and equity participation Opportunity to become the company's first commercial hire and help build the sales organization Direct access to executive leadership and company founders Work with a well-funded, rapidly growing robotics company entering commercial scale Significant career advancement opportunities as the organization grows Comprehensive medical, dental, vision, PTO, and retirement benefitsApplicants must be currently authorized to work in the United States on a full-time basis.