Note: The job is a remote job and is open to candidates in USA. CharterUP is transforming the group transportation and mobility market with an AI native platform. They are seeking an Inside Sales Representative - Level 2 to manage customer interactions, drive revenue, and build repeat business while ensuring a high-quality booking experience.
Responsibilities
- Hit and exceed every metric. Own performance against conversion rates, revenue targets, outbound and inbound activity, repeat bookings, and overall account growth
- Manage a high volume of inbound leads while driving outbound reactivation and expansion efforts to capture repeat and new business
- Leverage CharterUP’s proprietary marketplace technology to create tailored, accurate trip quotes that minimize friction in the booking process
- Execute disciplined call patterns to maintain conversion velocity and follow-up consistency
- Build urgency, rapport, and trust in every interaction, closing decisively through confident communication and assumptive sales techniques
- Drive repeat business by identifying high-value accounts, expanding relationships over time, and turning one-time bookings into repeat relationships
- Apply call control, objection handling, and active listening to diagnose customer needs and drive efficient bookings
- Escalate only when needed, solve problems directly, and push through roadblocks to deliver outcomes
- Use sound judgment and data to decide where to focus for highest yield
- Detect and stop low-value activity early to protect revenue through commercial acumen
- Maintain complete accuracy in quoting, CRM updates, and call documentation, ensuring operational precision across systems including Salesforce, Outreach, G-Suite, Slack, and proprietary tools
- Collaborate with peers and leadership on post-mortems and performance reviews to refine tactics and improve execution
Skills
- 3+ years of experience in sales, account management, or hybrid revenue roles, consistently exceeding performance goals
- Demonstrated ability to manage and grow a book of business, expanding spend, deepening relationships, and driving retention
- Proven success balancing high-volume inbound response with targeted outbound prospecting and account development
- Skilled in navigating multi-contact organizations and identifying new opportunities within existing accounts
- Expert communicator with mastery in objection handling, urgency creation, and assumptive closing across varied customer types
- Proficient in CRM and sales enablement tools (Salesforce, Outreach, G-Suite, Slack), ensuring disciplined follow-up and accurate documentation
- Analytical and data-driven, using performance metrics and conversion insights to guide activity and optimize revenue outcomes
- Comfortable owning end-to-end client relationships from quote generation to post-trip follow-up, feedback, and repeat engagement
- History of competitive achievement or performance-based success in athletics, startups, or other quota-driven environments
- Extreme Ownership: You don't wait for direction; you execute the mission
- Grit & Hunger: You outwork, outlast, and outthink everyone around you
- Self-Starter Energy: You see gaps, fill them, and move before others even notice
- Loyalty & Integrity: You keep your word, play for the team, and own your reputation
- High Intellect: You process fast, connect dots, and make the right call under pressure
- Analytical Judgment: You use data to make decisions, not noise
- Decisive Execution: You don't overthink; you move with conviction
Benefits
- Flexible Work Model: CharterUP operates as a remote-first company, with select roles requiring regular, in-office presence based on team and business needs. Role-specific expectations will be shared during the hiring process. U.S.-based employees may reside in any of our 19 approved states.
- Comprehensive Health & Wellness: Medical, dental, and vision insurance, mental health support, virtual care, gym discounts, and family-building benefits. In the U.S., we cover 100% of premiums for employees. International benefits align with local standards.
- Time Off to Recharge: Paid time off so you can truly unplug. U.S.: 15 PTO days (increasing to 20 after 2 years) + 8 paid holidays. International policies vary by country.
- Financial Peace of Mind: Company-paid life, short-term, and long-term disability insurance where available.
- Referral Rewards: Earn bonuses for bringing top talent to the team.
- Planning for the Future: Long-term financial planning support. U.S.: 401(k) plan. International: region-specific savings programs where applicable.
- Top-Tier Tech: Choose a Mac or PC, plus monitor, keyboard, and mouse to hit the ground running.
Company Overview