Head of Sales

rentid; Miami (FL); Remote; USD 150,000 - 250,000; Full time

Job summary

Rentid is seeking a bold Head of Sales to build and lead its sales organization for a rapidly growing AI-native mobility platform. You will own both enterprise and SMB revenue, hire and coach the team, and partner with leadership to shape go-to-market strategy.

As a founding sales leader, you will establish repeatable processes, forecast accurately, and develop strategic relationships across rental, mobility, and insurtech ecosystems while operating remotely in a high-growth, early-stage

Qualifications

• Proven experience building and closing B2B sales opportunities.
• Strong leadership including hiring, coaching, and performance management.
• Experience managing both enterprise and SMB sales motions.
• Ability to close meaningful revenue and operate in an early-stage environment.

Responsibilities

• Build and execute Rentid’s sales strategy across SMB and enterprise.
• Personally own and close strategic and high-value opportunities.
• Develop a repeatable and scalable SMB sales motion.
• Build, hire, coach, and manage a high-performance sales team.
• Establish pipeline, forecasting, CRM discipline, KPIs, and revenue accountability.
• Develop outbound, inbound, channel, and partnership-driven sales motions.
• Work with marketing on positioning, campaigns, lead generation, and conversion.
• Work with product and operations to translate market feedback into priorities.
• Develop strategic relationships across rental, mobility, insurance, automotive, fleet, and tech ecosystems.
• Help refine pricing, packaging, sales methodology, and go-to-market strategy.
• Build the sales foundation that future Rentid teams will scale.

Skills

B2B sales

Sales leadership

Enterprise sales

Forecasting

Job description

Rentid is building the AI-native commerce and operating infrastructure for modern mobility operators.

Our platform brings together the critical systems required to run a modern rental business, including commerce and booking, payments, agreements, renter verification, insurance, fleet operations, telematics, roadside, tolls, customer communication, and back-office automation.

Instead of forcing operators to manage disconnected software and manual workflows, Rentid brings the rental lifecycle into one connected ecosystem designed to help businesses operate more efficiently, manage risk, improve the customer experience, and scale.

We serve operators across vehicle rental, car sharing, gig economy, fleet, and other emerging mobility models.

Rentid is being built by operators, technologists, insurance experts, and industry veterans who understand this market firsthand and believe the next generation of mobility businesses needs better infrastructure.

Role Description

Head of Sales

Rentid is building the AI-native commerce and operating infrastructure for modern mobility operators.

Our platform brings together the critical systems required to run a modern rental business, including commerce and booking, payments, agreements, renter verification, insurance, fleet operations, telematics, roadside, tolls, customer communication, and back-office automation.

Instead of forcing operators to manage disconnected software and manual workflows, Rentid brings the rental lifecycle into one connected ecosystem designed to help businesses operate more efficiently, manage risk, improve the customer experience, and scale.

We serve operators across vehicle rental, car sharing, gig economy, fleet, and other emerging mobility models.

Rentid is being built by operators, technologists, insurance experts, and industry veterans who understand this market firsthand and believe the next generation of mobility businesses needs better infrastructure.

Role Description

We are hiring a Head of Sales to build and lead Rentid’s sales organization while remaining directly responsible for revenue.

This is a founding sales leadership role for someone who can operate at both the strategic and execution level.

You will own sales across both enterprise and SMB, personally manage strategic opportunities, build repeatable sales processes, recruit and develop the sales team, and work directly with the founder and leadership team on go-to-market strategy.

This is not a role for someone looking to inherit a mature sales organization.

We are looking for a builder.

You should be equally comfortable closing a strategic enterprise relationship, working directly with a growing fleet operator, developing a new sales process, coaching an Account Executive, and identifying where the company should go next.

What You’ll Own

• Build and execute Rentid’s sales strategy across SMB and enterprise
• Personally own and close strategic and high-value opportunities
• Develop a repeatable and scalable SMB sales motion
• Build, hire, coach, and manage a high-performance sales team
• Establish pipeline, forecasting, CRM discipline, KPIs, and revenue accountability
• Develop outbound, inbound, channel, and partnership-driven sales motions
• Work with marketing on positioning, campaigns, lead generation, and conversion
• Work with product and operations to translate market feedback into company priorities
• Develop strategic relationships across rental, mobility, insurance, automotive, fleet, and technology ecosystems
• Help refine pricing, packaging, sales methodology, and go-to-market strategy
• Build the sales foundation that future Rentid teams will scale

Qualifications

• Proven experience building and closing B2B sales opportunities
• Strong sales leadership experience, including hiring, coaching, and performance management
• Demonstrated ability to manage both enterprise and SMB sales motions
• Track record of personally carrying and closing meaningful revenue
• Strong understanding of pipeline management, forecasting, CRM discipline, and sales operations
• Ability to build process without creating unnecessary bureaucracy
• Entrepreneurial mindset and comfort operating in an early-stage, high-growth environment
• Strong communication, negotiation, relationship-building, and executive presence
• Ability to operate autonomously in a remote environment while working closely with leadership

Experience in vehicle rental, car sharing, mobility, insurtech, commercial insurance, automotive, fleet technology, SaaS, fintech, payments, or adjacent industries is strongly preferred.

Direct experience working with rental or mobility operators is a major advantage.

What We’re Looking For

We want someone who understands that market share and sales activity alone do not create credibility.

In this industry, credibility is earned by understanding the operator, solving real problems, and helping businesses grow.

You should know how operators make money, where operational friction exists, and how technology can materially improve their business.

We disrupted this market once.

Now we’re approaching it again from a different angle, and we’re looking for the sales leader who wants to help build the team that does it.

• Full-time | Remote