[Hiring] Enterprise Account Executive @CharterUP

Role Description

As an Enterprise Account Executive at CharterUP, you’ll play a key role in building and scaling our enterprise business. You’ll own the full sales cycle—from identifying and pursuing high-value opportunities to building relationships with senior decision-makers and closing deals across high-growth verticals like construction, traditional shuttle, and events.

This is a high-impact role for a strategic, driven seller who thrives in a fast-moving startup environment. You’ll have the autonomy to open new doors, shape our enterprise sales strategy, and close deals that directly contribute to CharterUP’s growth—all while helping some of the world’s leading companies rethink how they move their people.

With a focus on targeting large organizations that book recurring trips for 30 days or more, your success will directly impact CharterUP’s ambitious growth targets, driving revenue within the enterprise shuttle vertical. If you’re looking to work in a fast-paced, entrepreneurial environment with a focus on team collaboration and customer-centric solutions, this is the role for you.

What You’ll Do

• Prospecting & New Business Development:
  • Source and build relationships with key decision makers in target verticals, positioning CharterUP as the trusted provider for Enterprise group transportation services.
• Sales Strategy & Execution:
  • Design and implement strategic outbound sales motions tailored to enterprise-level clients across key sectors.
  • Ensure seamless navigation through procurement processes to secure approved vendor status while working closely with the VP of Enterprise Sales to align on growth initiatives and maximize new business opportunities.
• Manage the Sales Cycle:
  • Own the full sales cycle from lead generation to closing, navigating complex procurement processes, including RFP submissions, and securing long-term contracts with key clients.
• Account Management:
  • Manage complex sales cycles by proactively pursuing and securing MSAs with large entities that have significant annual spend.
  • Navigate RFP submissions and MSA negotiations to ensure high success rates and alignment with organizational goals.
• Collaboration & Support:
  • Work closely with the account management and operations teams to ensure smooth handoffs and deliver exceptional service to new clients post-sale.
• Account Expansion:
  • Proactively grow revenue within your portfolio by cross-selling additional services and identifying opportunities for increasing wallet share.
• Relationship Building:
  • Establish and nurture strong relationships with key decision-makers across multiple organizational levels, driving consistent adoption of our platform.
• Technology Expertise:
  • Master our cutting-edge platform to demonstrate its capabilities to prospects, positioning CharterUP as an innovative, scalable solution for their transportation needs.
• Market Research:
  • Stay informed about the latest trends and market shifts within target industries, providing valuable insights to help shape CharterUP’s offerings.

Qualifications

• 5+ years of proven experience in enterprise sales, preferably within transportation, construction, engineering, procurement or related industries.
• Proven ability to manage long sales cycles and close deals with a value of $1M+ in annual revenue.
• Demonstrated success in exceeding sales targets and achieving recognition as a top performer.
• Experience in navigating enterprise sales processes, including RFP’s, multi-year agreements, and negotiating MSAs with Fortune 500 organizations.
• Strong skills in building rapport with senior managers and executives within target organizations, ensuring long-term relationships and successful account management.
• Ability to think strategically about prospecting, sales motions, and account management to ensure alignment with company goals.
• Highly motivated with the ability to work independently, manage your time effectively, and take ownership of your sales targets.

Benefits

• Flexible Work Model: Remote-first company with select roles requiring in-office presence based on team and business needs.
• Comprehensive Health & Wellness: Medical, dental, and vision insurance, mental health support, virtual care, gym discounts, and family-building benefits.
• Time Off to Recharge: Paid time off including 15 PTO days (increasing to 20 after 2 years) + 8 paid holidays.
• Financial Peace of Mind: Company-paid life, short-term, and long-term disability insurance where available.
• Performance-Driven Culture: Join a fast-moving, ambitious, and collaborative team that wins together.
• Referral Rewards: Earn bonuses for bringing top talent to the team.
• Planning for the Future: Long-term financial planning support including a 401(k) plan.
• Top-Tier Tech: Choose a Mac or PC, plus monitor, keyboard, and mouse to hit the ground running.