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.
About the Role
Class Start Date: July, 2025
Shift needs: [Weekday] or [2 weekend and 3 Weekday shifts]
CharterUP is seeking Inside Sales Representatives (ISRs) who are motivated, results-driven, and eager to provide exceptional customer experiences. In this fast-paced role, you’ll help businesses, groups and individuals secure transportation solutions through our cutting-edge marketplace. This position is ideal for individuals passionate about sales, customer engagement, and career growth in a dynamic, high-velocity environment. As the first point of contact for many clients, you’ll play a key role in helping businesses and groups find seamless transportation solutions. This high-energy role is perfect for someone who thrives in a fast-paced environment and has aspirations to grow into more complex, strategic sales within our Enterprise Sales Team.
Responsibilities
- Manage a high-volume of inbound and outbound follow-up sales calls to assist clients in finding and booking transportation solutions efficiently.
- Leverage our proprietary marketplace technology to create tailored trip quotes, minimizing friction in the booking process.
- Meet or exceed performance metrics, including revenue targets, conversion rates, call handle time, and follow-up activity.
- Build urgency and rapport by effectively navigating call scripts while staying concise and customer-focused.
- Apply assumptive sales techniques to overcome objections, create urgency, and close deals quickly.
- Ensure accurate and efficient quoting to reduce customer frustrations and streamline the sales process.
- Continuously improve call control, actively listen to customers, and adapt sales tactics to meet individual client needs.
- Collaborate with team members and participate in post-mortem analyses to refine sales techniques and strategies.
Experience and Expertise
- 2+ years of sales experience in a fast-paced, high-volume environment, consistently meeting or exceeding sales goals.
- Comfortable handling 50-75 calls per day through a combination of direct inbound and outbound follow up calls.
- Demonstrates strong ability to confidently handle objections, create urgency, and guide customers through the sales funnel to close deals effectively.
- Exceptional communication skills with a focus on active listening, concise messaging, and rapport-building.
- Cultivate and nurture ongoing customer relationships beyond the initial transaction, ensuring satisfaction and promoting future business opportunities.
- A proactive, self-driven mindset with the discipline to thrive in a remote-first work environment.
- Exhibits advanced computer/tech skills, with the ability to navigate multiple systems (g-suite, slack, our quote management system, phone line tools) and platforms simultaneously.
- Excels at multitasking during calls by managing interactions, generating quotes, and tracking follow-ups in real-time, ensuring efficiency and accuracy within a fast-paced call center environment.
- High School Diploma or equivalent; sales certifications or additional training are a plus.
- Experience working with CRM tools, Sales Platforms, G-Suite, and other technologies is a plus.
Recruiting Process
- Step 1: Application Questionnaire
- Step 2: 30m Video call with Recruiter
- Step 3: 1h Video call with one of the Hiring Managers
- Step 4: 1h Video call/ Role Play interview with VP of Inside Sales
- Step 5: Offer, background check
- Welcome aboard!
OTE is $75,000: Base Salary $56,250 + $18,750 Variable with uncapped commission!
Compensation:
$56,250—$75,000 USD
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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