Inside Sales Representative II

CharterUP

11h•$63,000 - $120,000•Remote

About The Position

CharterUP is hiring for an inbound and outbound sales role focused on generating revenue, building repeat business, and owning performance outcomes. The role manages a high volume of customer interactions and inbound demand while pursuing new opportunities, reactivating past customers, and growing recurring business. The employee develops a book of business and serves as a trusted contact for high-value accounts, ensuring fast, accurate, and reliable booking experiences. The position works remotely and reports to the Sales Manager. The role requires meeting conversion, revenue, activity, repeat-booking, and account-growth targets. The representative uses CharterUP’s marketplace technology to prepare tailored trip quotes, maintains disciplined call and follow-up practices, and manages client relationships from quote generation through post-trip follow-up and repeat engagement. Success requires urgency, sound judgment, resilience, strong communication, commercial awareness, data-driven prioritization, and accurate use of sales and operational systems.

Requirements

At least 3 years of experience in sales, account management, or hybrid revenue roles, with a record of exceeding performance goals.
Demonstrated ability to manage and grow a book of business, expand customer spend, deepen relationships, and drive retention.
Proven ability to balance high-volume inbound response with targeted outbound prospecting and account development.
Ability to navigate organizations with multiple contacts and identify opportunities within existing accounts.
Strong communication skills, including objection handling, urgency creation, and assumptive closing with varied customer types.
Proficiency with CRM and sales enablement tools, including Salesforce, Outreach, G-Suite, and Slack, with disciplined follow-up and accurate documentation.
Analytical, data-driven approach to using performance metrics and conversion insights to optimize revenue outcomes.
Comfort with end-to-end client relationship ownership, from quote generation through post-trip follow-up and repeat engagement.
History of competitive achievement or performance-based success in athletics, startups, or other quota-driven environments.
Ability to work with urgency, resilience, accountability, and sound judgment in a high-volume, performance-driven environment.

Responsibilities

Meet and exceed conversion, revenue, inbound and outbound activity, repeat-booking, and account-growth metrics.
Manage a high volume of inbound leads while pursuing outbound reactivation and expansion opportunities.
Use CharterUP’s marketplace technology to create tailored, accurate trip quotes and simplify booking.
Execute disciplined call patterns and consistent follow-up to maintain conversion velocity.
Build urgency, rapport, and trust; close decisively using confident communication and assumptive sales techniques.
Identify high-value accounts, expand relationships, and convert one-time bookings into repeat business.
Use call control, objection handling, and active listening to diagnose customer needs and secure efficient bookings.
Resolve problems directly, escalating only when necessary, and overcome obstacles to deliver outcomes.
Use data and judgment to prioritize the highest-yield opportunities and discontinue low-value activity early.
Maintain accurate quotes, CRM updates, and call documentation across Salesforce, Outreach, G-Suite, Slack, and proprietary tools.
Collaborate with peers and leadership in post-mortems and performance reviews to refine tactics and improve execution.
Own client relationships from quote generation through post-trip follow-up, feedback, and repeat engagement.

Benefits

Medical, dental, and vision insurance; U.S. employee premiums are covered at 100%.
Mental health support and virtual care.
Gym discounts and family-building benefits.
Paid time off: 15 days in the U.S., increasing to 20 days after 2 years.
Eight paid holidays in the U.S.
Company-paid life, short-term disability, and long-term disability insurance where available.
Referral bonuses for bringing top talent to the team.
U.S. 401(k) plan; region-specific savings programs internationally where applicable.
Choice of Mac or PC, plus a monitor, keyboard, and mouse.
Remote-first work model.