Sales Representative - Level 2

CharterUP, LLC.; Hawaii; Remote; USD 70,000 - 120,000; Full time

Benefits offered by this job

Health insurance

PTO 15 days + 5 holidays (20 after 2y)

8 paid holidays

Life insurance

Disability insurance

Bonuses for top talent

Job summary

CharterUP is a remote-first company transforming the global group transportation market. We are seeking a Sales Manager to close new customers, expand recurring business, and manage a focused portfolio of high-value accounts. You will drive revenue through proactive outreach, smart qualification, and strong relationship building.

You’ll own quotas, leverage CRM tools, and collaborate with leadership to optimize strategies. Flexible in-office presence may be required to support hubs as we scale.

Qualifications

• 3+ years of experience in sales or related roles.
• Experience with both inbound and outbound prospecting.
• Proven ability to close deals and grow recurring revenue.
• Strong written and verbal communication skills.

Responsibilities

• Close new customers and expand recurring ones while managing a mini-portfolio of high-value accounts.
• Own performance metrics, including conversion rates, revenue targets, and activity.
• Maintain accurate CRM data and documentation across Salesforce, Outreach, G‑Suite, Slack.
• Identify opportunities for repeat business and deepen client relationships over time.
• Collaborate with leadership on post-mortems to improve tactics and outcomes.

Skills

Sales experience

Account management

CRM tools

Data analysis

Objection handling

Multi-contact navigation

Communication

Tools

Salesforce

Outreach

G‑Suite

Slack

Job description

CharterUP is transforming the $365 billion global group transportation and mobility market with an AI native platform that powers modern charter, shuttle, and emerging autonomous vehicle operations. Trusted by many Fortune 500 companies, CharterUP connects enterprises, institutions, and event organizers with thousands of vehicles nationwide, while increasingly serving as the operating system for large scale shuttle and transit programs across airports, campuses, industrial sites, and major events. Through real time availability, transparent pricing, intelligent routing, and AI driven dispatch and optimization, CharterUP replaces a fragmented and opaque industry with automation, accountability, and scale.

Innovative Impact: Be part of the team that's revolutionizing group travel, setting new standards in an industry overdue for change.

Growth Opportunities: As a hyper growth company and one of the fastest-growing companies recognized by Inc., Driven Team: Collaborate with some of the most driven minds in tech, all while working in a remote-first environment with a tech hub in Austin, TX.

Sales Manager

Location: Remote

This is a hybrid inbound and outbound sales role for people who are hungry to drive revenue, build repeat business, and own their results. 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.

You’ll be responsible for both closing new customers and expanding recurring ones, managing a mini-portfolio of high-value accounts that rely on you as their trusted CharterUP contact. We’re looking for sharp, decisive, high-judgment sales athletes who can think fast, act faster, and refuse to settle for "good enough." Own performance against conversion rates, revenue targets, outbound and inbound activity, repeat bookings, and overall account growth.

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.

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.

3+ years of experience in sales, account management, or hybrid revenue roles, consistently exceeding performance goals.

• ~ 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.
• ~ History of competitive achievement or performance-based success in athletics, startups, or other quota-driven environments.

You handle rejection, ambiguity, and shifting priorities without losing momentum.

You prefer testing and iterating over waiting for perfect information.

Analytical Judgment: You use data to make decisions, not noise.

Step 2: 1-hour Video Call with a Hiring Manager

Step 3: 1-hour Video Call / Role Play Interview

While offerings may vary slightly by location, we prioritize hiring near our hubs in Austin, Atlanta, Miami, and Denver as we grow our global team.

Flexible Work Model: CharterUP operates as a remote-first company, with select roles requiring regular, in-office presence based on team and business needs.

Comprehensive Health & Wellness: Medical, dental, and vision insurance, mental health support, virtual care, gym discounts, and family-building benefits. International benefits align with local standards.

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: Earn bonuses for bringing top talent to the team.

Planning for the Future: Long-term financial planning support. International: region-specific savings programs where applicable.

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.