Head of Sales

This is a fully remote position, open to applicants in United States.

📋 Description

• Take charge of the sales strategy and execution for the mid-market sector, as well as the enterprise portfolio at the time of hire.

• Oversee the mid-market sales team, which includes 3–4 Account Executives (AEs) in the short term, along with Business Development Representative (BDR) support.

• Recruit, mentor, and manage team performance effectively.

• Establish territory design, qualification methods, pipeline stages, and forecasting cadence.

• Conduct a weekly, deal-specific forecasting process to evaluate the gap to target and strategies for closing it.

• Collaborate with AEs on significant mid-market and enterprise deals.

• Provide executive-level escalation during strategic customer calls.

• Participate in regular site visits alongside the account team.

• Act as the representative of the customer-facing organization to the CEO and executive team by delivering accurate pipeline and risk assessments.

• Collaborate with Marketing on priorities for messaging and content.

• Work with Engineering to create a product differentiation narrative based on current capabilities.

• Assist the CFO with the design of compensation and incentives in collaboration with HR.

• Perform pipeline and CRM audits to evaluate forecast accuracy.

• Set up regular team coaching, pipeline reviews, forecasting, territory management, and qualification cadences.

• Implement a structured territory design and qualification methodology, such as MEDDICC.

• Enhance pipeline coverage, win rates, quota attainment distribution, representative productivity, and retention.

⛳️ Requirements

• A minimum of 8 years in B2B sales, including at least 4 years managing AE teams at a Senior Manager level or higher.

• Background in industrial automation, robotics, logistics, or related fields.

• Proven track record in leading a mid-market sector within a sales organization.

• Demonstrated discipline in forecasting and pipeline management within a CRM.

• History of coaching representatives to achieve consistent quota attainment.

• Experience selling technical products to multi-stakeholder buying groups.

• Proficiency in a structured sales methodology (e.g., MEDDICC, Challenger, or similar) and outbound prospecting techniques.

• Background in the distribution or logistics industry.

• Experience with hardware sales.

• Familiarity with CapEx sales cycles within the past approximately 10 years.

• Experience in developing individual contributors into first-line managers.

• Collaborative experience with HR on commission plan design.

• Experience in a fast-paced, small team, or startup environment.

🏝️ Benefits

• Comprehensive health benefits (Medical, Dental, Vision) through Aetna, Kaiser Permanente, and Guardian, with various plan tiers available.

• Additional benefits including accident, critical illness, and hospital indemnity plans (Voya).

• Company-paid basic life insurance, plus optional (supplemental) life coverage for you and your dependents.

• Fully covered short-term and long-term disability insurance provided by Cyngn.

• Health Savings Account (HSA) and Flexible Spending Account (FSA) for Health & Dependent Daycare.

• Employee Assistance Program available.

• Personalized 1:1 Health Concierge service.

• Company-sponsored 401(k) plan.

• Commuter Benefits offered.

• Flexible Paid Time Off (PTO) policy in place.

• Paid Parental Leave available.

• Daily lunches provided for in-office employees.

• Fully stocked kitchen with snacks and beverages available.