Mid-Market Account Executive

Accountabilities: Own the full sales cycle, from prospecting and lead generation through discovery, product demonstrations, negotiation, and closing. Develop and manage a nationwide territory, identifying and pursuing new business opportunities across mid-market and enterprise accounts. Generate at least 50% of your own pipeline through cold outreach, referrals, creative prospecting, and other outbound sales activities. Build relationships with key decision-makers, particularly finance leaders such as CFOs, Controllers, and Accounts Receivable Managers. Engage prospective customers in conversations about their existing processes, identifying inefficiencies and demonstrating the value of transitioning from spreadsheets, manual workflows, and legacy systems. Create urgency and guide prospects through a structured sales process, maintaining momentum from initial contact to signed agreement. Manage complex sales opportunities involving organizations with annual revenues of $200 million or more. Consistently achieve sales targets while managing opportunities with average contract values of $70,000 or more and sales cycles of approximately 45–90 days. Work closely with the Head of Sales to execute and improve the established sales playbook. Collaborate with Marketing and Product teams to strengthen sales strategies, share market feedback, and support continued business growth. Represent the business at on-site customer demonstrations, industry trade shows, and other relevant events, with approximately 10% travel expected. Requirements: At least 6 years of experience in a closing Account Executive role within the technology industry, with a consistent record of meeting or exceeding sales targets. Demonstrated experience selling deals with annual contract values of $70,000 or more to companies generating at least $200 million in annual revenue. Experience managing relatively fast sales cycles, ideally within the 45–90-day range. Proven ability to sell to finance stakeholders, including CFOs, Controllers, and Accounts Receivable Managers, and/or customers in traditionally technology-resistant industries. Experience in construction technology is a strong advantage. Relevant industry exposure may also include architecture, engineering, and construction (AEC), manufacturing, agriculture, real estate, and healthcare. Strong full-cycle sales capabilities, including prospecting, discovery, product demonstrations, negotiation, and closing. Hunter mentality, with a genuine enthusiasm for outbound selling, cold calling, and independently generating and converting pipeline. Proven ability to self-source at least 50% of pipeline through outbound outreach, referrals, and creative prospecting strategies. Ability to challenge the status quo, communicate business value, create urgency, and persuade customers to move away from manual processes and legacy systems. Strong communication, relationship-building, negotiation, and presentation skills. Comfortable working in a fast-paced startup environment that requires ownership, adaptability, initiative, and cross-functional collaboration. Willingness to travel approximately 10% for customer demonstrations and industry events. Experience selling software that integrates with ERP systems is an additional advantage. Benefits: Base salary: $110,000–$120,000, depending on experience. On-target earnings (OTE): $220,000–$240,000, including performance-based compensation. Equity: Stock options, providing an opportunity to share in the company's growth and success. Health coverage: Comprehensive medical, dental, and vision insurance. Wellness: Access to wellness programs and resources. Professional development: Annual $1,000 learning stipend for courses, certifications, conferences, and other career development activities. Paid time off: Unlimited PTO, with an encouraged minimum of three weeks annually. Team culture: Collaborative environment that values creativity, innovation, transparency, and open communication. Team events: Regular social activities and team gatherings, including an annual company-wide offsite.