Head of Sales

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

Work arrangement
Yes