Head of Sales (Remote)

About AirGarage AirGarage is on a mission to bring real estate online, starting with parking.

We replace broken parking machines, fragmented software, and manual, labor-intensive operations with a unified, data-rich operating system for parking real estate. We handle everything it takes to run and optimize a parking asset: payments, dynamic pricing, enforcement, license plate recognition, analytics, and more.

By building all of our technology in-house, we are able to deliver a magical experience for drivers while providing real-time visibility and revenue increases of 20-50% or more for real estate owners. That’s why national real‑estate leaders like Hines and Greystar, as well as technology companies like Meta, partner with AirGarage to optimize their parking facilities.

AirGarage uses datapoints like real-time occupancy, local events, weather, driver behavior, competitor pricing, and more to bring true intelligence to real estate owners’ assets for the first time.

We’re investing aggressively to make the physical world legible to a digital system: cameras, sensors, and software that generate a firehose of real-time data about the world around us. That data fuels models and algorithms that allow us to optimize performance at each property while giving owners the clarity and control they’ve never had before.

Before you can optimize an asset, you need to observe it. Before you can observe it, you need to bring it online.

We are starting with the $131 billion US parking real estate market because it is one of the most offline and mismanaged commercial real estate asset types. 26% of the land area in the median American urban core is dedicated to parking.

We are backed by top tier investors including Headline Growth, Andreessen Horowitz, Floodgate, Founders Fund, Abstract Ventures, and angel investors who have founded or worked at companies like Uber, Opendoor, Flexport, and more.

AirGarage's growth depends on how well our sales team executes - and this role is on the front lines of making that happen.

We are looking for a hands-on Sales Enablement Manager to build and run the day-to-day enablement programs that help our AEs and SDRs ramp faster, sell more effectively, and operate as a cohesive team. You will work directly with our VP of Sales to deliver onboarding, training, content, certification and tooling programs that compound rep productivity over time.

This is not a content librarian or training coordinator role. While you will own the systems and assets, the broader expectation is to own measurable improvements in ramp time, rep productivity, and sales execution.

You will partner closely with Sales Leadership, Revenue Operations, Head of Sales Development, Marketing, and Product to translate sales strategy into the programs, tools, and content that make every rep better.

If you want to build enablement programs from the ground up at a scaling sales org - and grow into a senior enablement leader as we scale - this role offers the chance to do exactly that.

Operationalize sales methodology (MEDDPICC) into the day-to-day workflows of the sales team

Create and maintain sales content: battlecards, talk tracks, objection handling, discovery libraries, ROI tools, and call libraries

Run ongoing training programs tied to specific funnel gaps and business priorities

Partner with Revenue Operations on Gong, sales tools, and AI capabilities that improve seller productivity

Support frontline managers with coaching enablement, training, and program delivery

Over time, this role will be the foundation of AirGarage's sales execution engine - with real opportunity to grow into a senior enablement leader as the function scales.

1) New Hire Onboarding & Ramp

Deliver new hire training across product, pitch, prospecting, discovery, demo, and methodology

2) Sales Content & Playbooks

Build and maintain the content stack that compounds rep productivity.

Work with Product Marketing to create and own battlecards, talk tracks, objection handling, discovery question libraries, messaging, ROI tools, and call libraries

Maintain a single source of truth for sales content that reps actually use

3) Ongoing Training & Skill Development

Run a calendar of training programs tied to actual business needs.

Identify funnel gaps with RevOps and design targeted training to close them

Run quarterly training calendars covering methodology reinforcement, skill development, and product, pricing, and packaging launches

Deliver training in formats that stick - workshops, role plays, certifications, async modules

Tighten the SDR → AE handoff in partnership with Sales Development leadership

Reinforce training in the field by coaching managers on what to look for in 1:1s and pipeline reviews

Success measured by improvements in the specific funnel metrics each training is designed to move.

4) Sales Tools, Gong & AI

Make the sales tech stack a force multiplier, not a tax.

Partner with RevOps on Gong, CRM workflows, LMS, and sequencing tools

Identify and pilot AI tools - call analysis, deal-risk scoring, automated coaching, generative content - that make every rep meaningfully better

Help administer and roll out new tools with training, certification, and adoption tracking

5) Cross-Functional Partnership

VP of Sales on priorities, methodology rollout, and program design

Head of Sales Development on SDR ramp, outbound playbooks, and handoff quality

Revenue Operations on tooling, data, and instrumentation

Marketing on messaging, references, and competitive intelligence

Operations on customer handoffs, post-sale best practices, and using insights from launching and supporting customers to sharpen the sales motion

This role helps ensure GTM work turns into revenue.

3-5+ years in sales enablement, sales operations, or sales productivity roles

• Hands-on experience building or running an onboarding program at a scaling sales org
• Comfortable creating content from scratch - battlecards, playbooks, training decks, certifications
• Familiarity with MEDDPICC or a comparable sales methodology
• Working knowledge of Gong, Salesforce, LMS, sequencing tools, and emerging AI capabilities
• You expect a fully built playbook, content library, and ramp program to operate from
• You are not comfortable with content creation, training delivery, or tool administration
• You prefer pure project management over building durable systems
• You want to inherit a mature function rather than build the foundation IMPORTANT NOTE AirGarage is a remote-first company, but we also value in-person collaboration to strengthen trust and teamwork. Team members should expect ~6 weeks of travel per year for:
• 2–3 full company offsites, “Remote Weeks”
• Lending a hand to support one new location launch
• In-person onboarding as well as supporting other onboarding sessions for new team members

The rest of the year, team members can work remotely from wherever (US time zones) they’re most comfortable as long as they are performing well in their role. Attendance at in-person events throughout the year is expected—if you’re not open to traveling ~6 weeks per year for work, our team won't be a good fit for you.

Equity: Have a stake in the business that you’re helping to build and grow.

• Work remotely: We currently hire teammates that are located anywhere within North America.
• Health insurance: We offer health insurance and currently cover 85% of the cost of medical, dental, and vision plans for the primary employee and 50% of the cost of plans for dependents.
• Parental Leave: We offer 12 weeks of fully paid parental leave to all parents to bond with a newly born, adopted, or fostered child. The 12 weeks can be taken as a continuous leave or intermittently over the first 18 months of the child's life.
• Home office setup: Get a laptop + additional equipment needed to set you up for success.
• ⛺ We have an unlimited PTO policy with a minimum requirement of 10 days per year.
• Make financial planning right for you with a 401k retirement savings program.
• ✈️ Team Off-sites: ~At AirGarage, we've always been committed to building a thriving team that represents the communities we serve. Our team is currently 40% female and 30%+ from underrepresented communities.

We celebrate diversity and are committed to creating an inclusive environment for all employees. Candidates and employees are always evaluated based on merit, qualifications, and performance. We will never discriminate on the basis of race, color, gender, national origin, ethnicity, veteran status, disability status, age, sexual orientation, gender identity, marital status, mental or physical disability, or any other legally protected status.