Sales Leader

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

📋 Description

• Directly oversee and mentor our enterprise and strategic Account Executive (AE) team.

• Conduct weekly one-on-one meetings, pipeline assessments, and deal coaching, including live call and email evaluations, rather than solely relying on dashboard reviews.

• Take responsibility for team quota achievement, accuracy of forecasts, and the overall health of the pipeline in HubSpot.

• Guide representatives on discovery processes, objection management, and showcasing Augie's specific automations (quoting, dispatch, tracking, billing, collections) instead of generic AI messaging.

• Collaborate with Sales leadership on territory and account distribution as well as compensation structures for the team.

• Proactively identify and raise deal risks; intervene in strategic or stalled deals as necessary.

• Work alongside Sales Enablement and Revenue Operations to develop new-hire onboarding plans, create live coaching materials, address playbook deficiencies, and fulfill compensation and quota requirements.

• Provide insights from the field—win/loss trends, competitive intelligence, and signals indicating ideal customer profile (ICP) fit—back to leadership and Product teams.

• Offer daily coaching to representatives on our go-to-market technology stack: HubSpot, LinkedIn Sales Navigator, Seamless.ai, and 6sense.

⛳️ Requirements

• 8–10+ years of comprehensive B2B SaaS sales experience, including at least 5 years in a frontline sales management position.

• Proven history of building and mentoring a team to achieve consistent quota success.

• Comfortable engaging hands-on in deals—reviewing calls, participating in crucial meetings, and providing real-time coaching.

• Strong discipline in forecasting and maintaining CRM hygiene that you can instill in a team.

• Thrives in an early-stage setting—focused on developing processes rather than merely operating existing ones.

• Experience in selling and managing enterprise and strategic deals within the freight, supply chain, or logistics technology sectors.

🏝️ Benefits

• Competitive Salary + Stock Options

• Comprehensive Health, Vision, and Dental Benefits

• Flexible Paid Time Off (PTO)

• On-site Gym

• Monthly stipend