Founding Sales & Growth Partner | B2B SaaS

CharterNow.Ai; San Francisco (CA); On-site; USD 100,000 - 200,000; Full time

Job summary

CharterNow.Ai is building the operating platform for luxury and exotic car rental businesses. We are seeking a highly motivated Founding Sales & Growth Partner to lead CharterNow's early customer acquisition and build our GTM engine.

This is not a traditional sales role; you will work directly with the founder to identify target operators, demo the product, close new subscriptions, and establish repeatable processes for growth. Compensation includes commission and equity.

Qualifications

• Experience in B2B/SaaS sales or business development.
• Proven ability to prospect, demo, handle objections, and close.
• Comfortable selling to SMB owners.
• Strong communication, relationship-building, and negotiation skills.
• Experience with outbound prospecting and CRM tools such as HubSpot.
• Self-directed, organized, persistent, and comfortable working in an early-stage environment.

Responsibilities

• Identify and prospect luxury, exotic, and premium car rental operators across the U.S.
• Reach business owners through cold calls, personalized emails, LinkedIn, Instagram, and direct outreach.
• Build relationships with decision-makers and understand their operational challenges.
• Convert qualified prospects into paying CharterNow subscribers.
• Conduct compelling product demonstrations and close SaaS subscriptions.
• Test and refine outbound messaging, sales scripts, and customer acquisition strategies.
• Provide customer feedback to help shape the product roadmap.
• Develop repeatable processes that can support a larger sales team.
• Work directly with the founder on growth strategy and partnerships.

Skills

B2B sales

SaaS sales

Business development

Prospecting

Demos

Negotiation

HubSpot CRM

Tools

HubSpot

Job description

CharterNow.Ai is building the operating platform for luxury and exotic car rental businesses.

Independent rental operators often rely on fragmented tools to manage reservations, customer verification, rental agreements, payments, and fleet operations. CharterNow brings these workflows together in one platform, helping operators spend less time on administration and more time growing their businesses.

Our platform includes:

• Rental & Booking Management: Manage rental applications, reservations, customer communications, and fleet availability.
• Integrated Payments: Stripe-powered payment workflows, including supported buy-now-pay-later options through Affir...
• Driver Verification: Integrated driver's license identity verification, insurance verification, and motor vehicle record (MVR) checks.
• Digital Agreements: Manage rental contracts, documents, and customer signatures.
• Business Analytics: Track bookings, revenue, vehicle performance, and business activity.
• Web & Mobile Access: Manage rental operations through a modern vendor dashboard and dedicated mobile applications.

The product is built and operational. Our next priority is customer acquisition and growth.

We're looking for someone who can help turn a strong product into a growing customer base.

The Opportunity

About CharterNow

CharterNow.Ai is building the operating platform for luxury and exotic car rental businesses.

Independent rental operators often rely on fragmented tools to manage reservations, customer verification, rental agreements, payments, and fleet operations. CharterNow brings these workflows together in one platform, helping operators spend less time on administration and more time growing their businesses.

Our platform includes:

• Rental & Booking Management: Manage rental applications, reservations, customer communications, and fleet availability.
• Integrated Payments: Stripe-powered payment workflows, including supported buy-now-pay-later options through Affir...
• Driver Verification: Integrated driver's license identity verification, insurance verification, and motor vehicle record (MVR) checks.
• Digital Agreements: Manage rental contracts, documents, and customer signatures.
• Business Analytics: Track bookings, revenue, vehicle performance, and business activity.
• Web & Mobile Access: Manage rental operations through a modern vendor dashboard and dedicated mobile applications.

The product is built and operational. Our next priority is customer acquisition and growth.

We're looking for someone who can help turn a strong product into a growing customer base.

The Opportunity

We're seeking a highly motivated Founding Sales & Growth Partner to lead CharterNow's early customer acquisition.

This is not a traditional sales role where you inherit an established pipeline and wait for inbound leads.

You'll work directly with the founder to develop our go-to-market strategy, reach decision-makers, demonstrate the product, close new customers, and build repeatable sales processes.

Your first mission: Help CharterNow acquire its first 10 paying rental operators, validate a repeatable outbound sales process, and establish the foundation for scaling to 100+ customers.

You'll have the opportunity to make a measurable impact on the company's growth and potentially develop into a long-term sales leadership or co-founder role.

We're looking for a builder, a closer, and someone excited about creating something from the ground up.

What You'll Do

Own Customer Acquisition

• Identify and prospect independent luxury, exotic, and premium car rental operators across the U.S.
• Reach business owners through cold calls, personalized emails, LinkedIn, Instagram, and direct outreach.
• Build relationships with decision-makers and understand their operational challenges.
• Convert qualified prospects into paying CharterNow subscribers.

Run Demos & Close Deals

• Conduct compelling 10-20 minute product demonstrations.
• Communicate CharterNow's value clearly to business owners.
• Handle objections, negotiate, and close SaaS subscriptions.
• Manage follow-ups, pipeline activity, and opportunities through HubSpot CRM.

Build Our Go-to-Market Engine

• Test and refine outbound messaging, sales scripts, and customer acquisition strategies.
• Identify the most promising customer segments and geographic markets.
• Provide customer feedback to help shape the product roadmap.
• Develop repeatable processes that can eventually support a larger sales team.

Help Shape the Business

• Work directly with the founder on growth strategy and positioning.
• Identify partnership and referral opportunities within the automotive rental industry.
• Take ownership of measurable customer acquisition and revenue goals.

Who We're Looking For

Ideal Experience

• Experience in B2B sales, SaaS sales, business development, or a comparable revenue-generating role. Proven sales ability matters more than years of experience.
• Demonstrated ability to prospect, conduct demos, overcome objections, and close deals.
• Comfortable selling directly to small and medium-sized business owners.
• Strong communication, relationship-building, and negotiation skills.
• Experience with outbound prospecting and CRM tools such as HubSpot.
• Self-directed, organized, persistent, and comfortable working in an early-stage environment.

Bonus Points

• Experience selling software to automotive, rental, travel, hospitality, or local service businesses.
• Existing relationships with independent car rental operators, fleet owners, or automotive entrepreneurs.
• Experience building an outbound sales process from scratch.
• Previous startup, founding sales, or entrepreneurial experience.

What Matters Most

We care more about your ability to generate conversations, earn trust, and close customers than impressive job titles.

If you've successfully sold a product to business owners, built your own pipeline, or helped grow an early-stage company, we'd like to hear from you.

What You'll Have to Work With

You won't be starting with just an idea.

CharterNow already has:

• A functioning SaaS platform with real product workflows.
• A live website and vendor demonstration environment.
• A defined target customer segment and subscription business model.
• An initial list of targeted rental operators and an established HubSpot CRM workspace.
• Competitive positioning research and product demonstration resources.
• A technical founder responsible for product development, integrations, infrastructure, and engineering.

Your focus will be customer acquisition, sales execution, and revenue growth — not building the software.

Compensation & Ownership

CharterNow is a bootstrapped, early-stage company. We're seeking an entrepreneurial sales partner interested in performance-based compensation and potential long-term ownership.

• Sales Commission: 25% of net subscription revenue collected during the first 12 months from customers you directly acquire, subject to the commission agreement.
• Equity Opportunity: Meaningful equity participation may be available for the right candidate, based on experience, contribution, long-term commitment, and mutually agreed performance milestones.
• Base Compensation: No guaranteed base salary is currently budgeted for the initial phase. Any engagement and compensation arrangement will be finalized in accordance with applicable employment laws.
• Long-Term Growth: Opportunity to take on greater ownership of sales strategy, customer acquisition, partnerships, and future sales team development.

Specific equity terms, performance milestones, and long-term responsibilities will be discussed individually with qualified candidates.

How to Apply

Apply through LinkedIn and include a brief note answering these three questions:

• What B2B product or service have you successfully sold, and to whom?
• How would you acquire your first 10 paying customers for CharterNow?
• What interests you about joining an early-stage company in a founding sales capacity?

We're looking for someone who wants to help build CharterNow into a leading software platform for the luxury and exotic vehicle rental industry.

Build the pipeline. Close the customers. Help shape the company.