About CharterUP. CharterUP is transforming the $30 billion group transportation industry with cutting-edge technology and innovative SaaS software, delivering an industry-leading experience for both customers and operators. Trusted by most Fortune 500 companies, our platform connects users to thousands of charter bus and minibus operators nationwide. In just 60 seconds, customers can access real-time availability, transparent pricing, and detailed vehicle options—whether organizing a corporate event, a company shuttle, or a wedding. By streamlining what was once a fragmented and stressful process, CharterUP brings transparency, accountability, and efficiency to an industry overdue for innovation
With CharterUP, group transportation is no longer a hassle but an elevated, reliable experience. Join us as we lead the future of group travel.
Why Join Us
- Innovative Impact: Be part of the team that's revolutionizing group travel, setting new standards in an industry overdue for change.
- Growth Opportunities: As a hyper growth company and one of the fastest-growing companies recognized by Inc., there’s no better time to join our dynamic, growth-stage organization.
- Driven Team: Collaborate with some of the most driven minds in tech, all while working in a remote-first environment with a tech hub in Austin, TX.
- Funding and Stability: Our $60 million Series A funding was just the start—we’re poised for even greater expansion, and you can be part of this exciting journey. CharterUp has achieved this growth profitability and efficiently, ensuring long-term stability.
Compensation
- Competitive base salary + commission target: $150,000 - $190,000 OTE
- Comprehensive benefits package, including fully subsidized medical coverage for the employee
- 401(k) plan
About the Role
As an Enterprise Account Executive, Shuttles at CharterUP, you will play a critical role in supporting Enterprise Sales by driving new business and expanding our footprint within key verticals such as construction, traditional shuttle industries, and events. You will be responsible for developing and executing outbound sales strategies to acquire and grow enterprise-level accounts. This role involves navigating long sales cycles, working with key decision-makers, and collaborating closely with the senior leadership team to ensure your efforts align with CharterUP’s overarching growth goals.
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 group transportation services
- Sales Strategy & Execution:Design and implement strategic outbound sales motions tailored to enterprise-level clients across key sectors (e.g., construction, events, and large corporations). 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—such as school districts, universities, travel agencies, and DMCs—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.
What You’ll Bring
- Proven Sales Experience: 5+ years of proven experience in enterprise sales, preferably within transportation, construction, engineering, procurement or related industries.
- Track Record of Success: Proven ability to manage long sales cycles and close deals with a value of $500k+ in annual revenue.
- Complex Sales Cycles: Experience in navigating complex sales processes, including RFP submissions, and negotiating MSAs with large organizations.
- Relationship Building: Strong skills in building rapport with stakeholders at multiple levels within target organizations, ensuring long-term relationships and successful account management.
- Strategic Thinking: Ability to think strategically about prospecting, sales motions, and account management to ensure alignment with company goals.
- Communication & Presentation: Excellent verbal and written communication skills, including the ability to present effectively to executive teams and large groups.
- Self-Starter & Entrepreneurial: Highly motivated with the ability to work independently, manage your time effectively, and take ownership of your sales targets.
Preferred Qualifications
- Experience selling into government, large corporate enterprises, or the events industry.
- Previous experience with SaaS or tech-enabled solutions in the transportation or logistics space.
- Demonstrated success in exceeding sales targets and achieving recognition as a top performer.
- Experience managing $1M+ accounts with demonstrated revenue growth and retention success.
Recruiting Process
- Step 1 - Video call: Talent Acquisition interview
- Step 2 - Video call: Hiring Manager interview
- Step 3 - Video call: Sales Presentation
- Step 4 - Offer & reference check
- Welcome aboard!
Benefits & Perks
We take care of our team so you can focus on doing your best work. At CharterUP, you'll get:
- Remote Flexibility – Work from any of our 19 live/work states, with role-dependent exceptions
- Full Health & Wellness Coverage – 100% of premiums paid for medical, dental, and vision plans for employees - including mental health resources, Teledoc, gym discounts, and family planning benefits
- Time to Recharge – 15 days PTO (increases to 20 after 2yrs) + 8 paid holidays so you can actually unplug
- Financial Security – Company-provided life insurance, as well as short-term and long-term disability for employees who qualify
- Winning Culture – Join a high-performing, fast-paced, and supportive team that wins together
- Referral Bonuses – Get rewarded for bringing top talent to the team
- Future Planning – 401(k) retirement plan to help you invest in what’s next
- Tech Setup – Your choice of Mac or PC laptop, plus monitor, keyboard, and mouse.
CharterUP is an Equal Opportunity/Affirmative Action Employer. We make all employment decisions including hiring, evaluation, termination, promotional and training opportunities, without regard to race, religion, color, sex, age, national origin, ancestry, veteran status, sexual orientation, physical handicap, mental disability, medical condition, disability, gender or identity or expression, pregnancy or pregnancy-related condition, marital status, height and/or weight.
CharterUP candidates and employees must reside in any of the following states; Arizona, California, Colorado, Florida, Georgia, Hawaii, Mississippi, Missouri, North Carolina, New Hampshire, Nevada, New York, Oklahoma, South Dakota, Tennessee, Texas, Utah, Washington, and Wyoming.
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