Inside Sales Representative - Level 2

About the role

This is a hybrid inbound and outbound sales role for people who are hungry to drive revenue, build repeat business, and own their results. It rewards individuals who thrive under pressure, act decisively, and operate with high urgency and precision. You will manage hundreds of customer interactions per week, build your own book of business, and ensure every booking experience reinforces CharterUP’s reputation for speed, reliability, and excellence.

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.

Experience and expertise

• 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.

What defines you

• Core Character:
• 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.
• Cognitive & Decision Traits:
• 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.

Recruiting Process

1. 30-minute call with Talent Acquisition
2. 1-hour Video Call with a Hiring Manager
3. 1-hour Video Call / Role Play Interview
4. 30-minute Interview with CEO
5. Offer and Background Check

Global Benefits & Perks at CharterUP

• 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.
• 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.
• 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. 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.

CharterUP is an Equal Opportunity Employer

We are committed to creating an inclusive, accessible, and respectful workplace. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, age, national origin, ancestry, disability, medical condition, marital status, veteran status, or any other protected characteristic in accordance with applicable federal, state, and local laws in the United States and Canada. If you require accommodation during the recruitment process, please let us know. CharterUP is committed to providing reasonable accommodations during the hiring process. If you need assistance or an accommodation, please contact your recruiter.

Hiring Locations

CharterUP U.S.-based candidates and employees must reside in one 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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