Sales Representative - Level 2

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, owning 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 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

Requirements

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

Benefits

Flexible Work Model (remote-first company); Comprehensive Health & Wellness: medical, dental, and vision insurance, mental health support, virtual care, gym discounts, and family-building benefits, with 100% of premiums covered for U.S. employees; Time Off to Recharge: 15 PTO days (increasing to 20 after 2 years) plus 8 paid holidays in the U.S.; Financial Peace of Mind: company-paid life, short-term, and long-term disability insurance where available; Performance-Driven Culture; Referral Rewards: bonuses for bringing top talent to the team; Planning for the Future: long-term financial planning support and 401(k) plan in the U.S.; Top-Tier Tech: choice of Mac or PC, plus monitor, keyboard, and mouse