Inside Sales Representative – Level 2

CharterUP

Inside Sales Representative responsible for managing sales through inbound and outbound efforts. Driving growth and servicing accounts while working in a remote-first environment.

Posted 7/8/2026full-timeRemote • Arizona, California, Colorado, Florida, Hawaii, Mississippi, Montana, Nevada, New Hampshire, New York, North Carolina, Oklahoma, South Dakota, Tennessee, Texas, Utah, Washington, Wyoming • 🇺🇸 United StatesMid-LevelSenior💰 $63,000 - $120,000 per yearWebsite

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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

Comp & perks

Flexible Work Model: CharterUP operates as a remote-first company, with select roles requiring regular, in-office presence.
Comprehensive Health & Wellness: Medical, dental, and vision insurance, mental health support, virtual care, gym discounts, and family-building benefits.
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.
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.
Top-Tier Tech: Choose a Mac or PC, plus monitor, keyboard, and mouse to hit the ground running.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Sales StrategyAccount ManagementLead GenerationPerformance Metrics AnalysisQuote Generation

Soft Skills

Effective CommunicationRelationship BuildingProblem SolvingActive ListeningUrgency Creation