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.

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.

What We Mean By Grit

• Relentless follow-through: You pursue a clear yes or no; you don’t let deals stall.
• High output as a habit: You work the plan daily and maintain volume during busy seasons.
• Resilient under pressure: You handle rejection, ambiguity, and shifting priorities without losing momentum.
• Competitive drive: You want to be at the top of the board and treat targets as non-negotiable.
• Bias to action: You prefer testing and iterating over waiting for perfect information.

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

Pay

$63,000 USD - $120,000 USD

Global Benefits & Perks at CharterUP

• Flexible Work Model: Remote-first company with select roles requiring in-office presence. U.S.-based employees may reside in 19 approved states.
• Comprehensive Health & Wellness: Medical, dental, vision, mental health support, virtual care, gym discounts, and family-building benefits. U.S.: 100% premium coverage for employees.
• Time Off to Recharge: Paid time off. U.S.: 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. U.S.: 401(k) plan.
• Performance-Driven Culture: Fast-moving, ambitious, and collaborative team.
• Referral Rewards: Bonuses for bringing top talent.
• Top-Tier Tech: Choose a Mac or PC, plus monitor, keyboard, and mouse.

Location: Remote. U.S.-based candidates must reside in approved states: Arizona, Colorado, Florida, Georgia, Hawaii, Mississippi, Missouri, North Carolina, New Hampshire, Nevada, New York, Oklahoma, South Dakota, Tennessee, Texas, Utah, Washington, Wyoming.