Vice President of Sales

About AirGarage 🏙

AirGarage is repurposing the 30% of real estate in the average American city currently dedicated to parking.

We are building a future where real estate is digitized and can be transitioned from one use to another seamlessly on-demand, moving every piece of urban real estate toward its highest and best use.

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.

As a full-stack parking operator, we automate the operation of parking lots and parking garages. We handle everything from advertising to collecting payments from drivers and enforcing against illegal parking. We already operate 250+ parking lots and parking garages across 35 US states and we are growing quickly.

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

Want to learn more about AirGarage and the problem we're tackling?

Check out these podcasts:

https://www.youtube.com/watch?v=AU0NkDK51E4

https://youtu.be/_8aM6NQHYiE?si=p5WIujBWUA1sG-b7

THE ROLE 👩🏾‍💻

We are seeking a Vice President of Sales to lead AirGarage's growth from 300 parking lots and garages to thousands of locations across the United States and Canada.

Currently, our co-founder & CEO leads the Sales team. We have progressed from the "wild west" days of unstructured sales to a “pre-industrial era” with some processes, systems, and repeatable motions in place.

Your role will be to further develop the sales team into a predictable, repeatable "industrial era" that will drive aggressive yet efficient growth.

We have strong product-market fit and a sales team that is performing well despite our current imperfections, as evidenced by this year's results:

• SDR efficiency (SQL output per month) has grown 4.12x

• AE efficiency (ARR signed per quarter) has grown 4.93x

• We signed more revenue in the first half of 2024 than in all of 2023

• We achieved this while improving efficiency, with a Magic Number of $2.33 YTD in 2024

• We have low gross churn (3% - 5% per year) and strong net revenue retention (127% after 12 months, 234% after 24 months)

Your mission will be to elevate the team by refining our sales motion, developing the talent, and gaining a deep understanding of our customers to drive wins.

As an early member of the AirGarage leadership team, you will have the opportunity to make a significant impact as you help build our go-to-market engine and drive both immediate and long-term growth.

The Team 👨‍👩‍👧‍👦

Our sales team currently has 6 Sales Development Representatives setting meetings primarily via outbound (~70%) and 4 Account Executives with varying levels of experience, but the majority of them are in their first full time sales role.

We expect the team to grow as we work to achieve ambitious goals. You will be the architect of that growth - owning recruiting, coaching, and performance management of existing and new team members.

However, we expect to continue improving throughput and efficiency of the existing team and continually raising the bar of expectations. That will involve system improvements, performance management, sales process improvements, and consistent coaching across the board to help the sales team rise to the challenge of this next era of AirGarage.

You will not be embarking on this mission alone: we have a strong SDR manager and Head of Sales Operations in place to support you. You will, however, be the direct manager of the Account Executives at the start and until the team is performing at a level where it makes sense to add additional managers.

You will also be supported by the entire leadership team at AirGarage: our CEO has been deeply involved in sales since the very first customer we signed on, our VP of Operations ran the sales team at one point and is still very in touch with sales, and our Director of Engineering, Chief Technology Officer, and Chief Data Officer are all putting their full energy behind building the best product for sales to distribute.

One of your first priorities in this role will be identifying areas where we can level up the current team and how they are selling. You should be prepared to bring along at least two excellent new AEs that you know run a strong process and have excellent sales fundamentals when you join that can help raise the bar and who will help you understand the unique challenges of our sale without the variable of having never worked together before.

The Market 🏙

Our target customers are real estate owners that own parking lots and parking garages.

These customers come in a variety of shapes and sizes ranging from individual, mom and pop property owners with one small parking lot to mid-size commercial real estate firms with several parking facilities, and national real estate firms that control hundreds or thousands of properties.

Our sales process has to adapt to those different personas as well as the unique property type (surface lot, garage, mixed use, hotel, retail, etc.) that they own and which we are discussing. Each persona can take a different sales approach (SMB, mid-market, enterprise) so having past experience across a range of customer sizes and sales processes will benefit you in this role.

We have a strong value proposition for each of these types of customers but we will expect you to develop an expert level perspective on the go-to-market strategy for each of them while staying aware of shifts in the market, new competitors, and becoming an expert on our product.

ACVs range from $18k to $350k with a median of ~$50k (so far — we have increased the ACV ceiling every year in company history!). Sales cycles range from 7 days to 250 days with a median of ~40 days.

WHAT YOU WILL DO 👷‍♀️

• Build a world-class team — coach our existing AEs and SDRs while actively recruiting and developing new talent to help us execute on a plan to scale revenue aggressively but efficiently.

• Work with leadership to develop growth targets, then design and build the infrastructure needed to analyze and track performance, identify bottlenecks, and do whatever it takes to hit our ambitious goals.

• Directly own the development of the Account Executive team through frequent and proactive coaching, 1:1s, and participating directly in customer conversations as often as is physically possible. Work closely with the SDR manager to do the same for the SDR team.

• Build a sales engine that continuously improves by leveraging new strategies and data-driven testing to help us develop disciplined and repeatable sales processes.

• Work with leadership to develop marketing in order to build inbound lead flow and develop a consistent pipeline of high value, qualified inbound leads. SQLs are currently ~70% driven by outbound and we believe it’s possible to increase inbound such that inbound can account for 50% of top of funnel in the future.

• Work with other teams — Product / Engineering, Marketing, Operations / Customer Success — to ensure customers have a clean handoff from Sales to Customer Success and have a consistently positive experience with AirGarage throughout our relationship with them.

• Own sales forecasting and be directly responsible for the sales team’s performance.

• Establish operational excellence by reporting on sales activity and providing accurate sales forecast to the AirGarage leadership team in tandem with the Head of Sales Operations.

WHAT YOU NEED 👩🏼‍🎓

• 4+ years in a quota carrying role in B2B sales and 4+ years of experience in leadership roles with at least 25 team members.

• A 'talent magnet' - a strong track record of recruiting and developing sales teams. You should have at least two strong, proven Account Executives that you have worked with in the past that you plan to bring along with you as you join AirGarage to test our sales process with a known variable to understand where the challenges are.

• Strong track record of hitting your personal quotas, coaching team members to hit their individual goals under your tutelage, and strong mentorship skills in developing talent throughout their careers.

• Have experience managing teams working a mix of inbound & outbound leads. You should have experience leading teams where 70%+ of top-of-funnel is outbound and working to develop inbound lead flow in tandem with marketing to diversity top-of-funnel.

• Strong aptitude in data and analysis; strong organizational skills with software systems, processes, and forecasting.

• Experience developing sales methodology, training, CRM, and iterating on the sales process.

• Passion for and experience coaching and developing sales talent.

• Self-starter and comfortable with ambiguity — experience at high-growth startups scaling from the early tens of millions of revenue to many tens of millions.

• Experience selling to a variety of customer types ranging from SMB to Mid-Market and Enterprise.

• Experience selling into traditional industries that have been slow to adopt technology and where most customers have incumbent solutions i.e. a rip-and-replace sale.

• Bonus: experience selling in the Real Estate industry.

🚨 WHY THIS ROLE MAY NOT BE FOR YOU 🚨

Please review this section before applying. We are sharing this information up front because we don’t expect this job to be appealing to everybody and we do not want to waste your time if you are not on board with all of the following.

Being the Vice President of Sales at a high growth startup means many different things, but there is one thing above all that it certainly means: sales success or failure is ultimately your responsibility.

This will be a hard job. We work long hours at AirGarage, including nights and weekends, because we love what we do. You will be expected to do the same. We are growing fast but our sales team is lean, so every day you will have new challenges and too much on your plate, but you’ll be expected to find a way to deliver anyways.

Below are some of the reasons you might not want this job:

• You are not willing to regularly get on a plane to meet customers face to face. Our CEO has been on 50+ flights in 2024 while running the sales team in the spirit of doing whatever it takes to win over customers and close deals. Real estate owners often like to shake your hand and look you in the eye to know they can trust you with their property.

• You think the solution to poor sales results is hiring more people rather than taking a hard look at what is not working in the current sales process to improve it before growing the team.

• You are not willing to carry a bag and personally run the full sales cycle many times when you first join to deeply understand our customers, the sales process, and the challenges that we face.

• You are not comfortable running a deal process that includes financial modeling, real world operations, and which is not pure B2B SaaS being sold to other tech companies.

• You don’t want to work for a CEO that has personally run the sales team and been involved in closing deals since day 1. He will be your closest ally and your number one supporter if you embrace that, but if having a CEO who deeply understands sales, our process, our customers, and what it takes to win — and therefore will expect you to do the same — scares you, then you should not apply.

• You aren’t comfortable doing basic spreadsheet work and analyzing P&Ls for properties that we are selling to in order to support Account Executives in crafting deals that are win-win while being profitable for the company.

• You don’t want to work deeply with product to influence our roadmap and ensure we are building technology that will be the most impactful for our customers and therefore help us Win More Deals.

• You want to spend all day looking at reports in Salesforce instead of talking to customers and closing deals.

• You aren’t willing to be the direct, front line manager for the Account Executive team for the foreseeable future.

• You aren’t comfortable working in an early stage startup where you will not have a 100 person support team around you. We are building an enduring company that controls it own destiny and we therefore tend to be frugal in all areas from management to sales operations to data to financial modeling and you must be comfortable rolling up your sleeves to push the flywheel yourself as we grow.

• You think it’s product’s fault for why your last company didn’t grow faster.

However, if you are willing to sign up for all of that, there is a lot to be excited about with this role:

• You will learn a ton.

• You will be supported by a leadership team that is eager to see you succeed and will go to the ends of the Earth to support you.

• You will be selling a product with strong PMF in its core ICP and room for expansion into new verticals. Our product is already meaningfully differentiated from the incumbent players that we sell against and getting better every day.

• You have a passionate, hard working team already in place on day one that has achieved revenue scale far beyond what most startups do with a team this small. You will have the opportunity to grow and develop that team according to your vision as we scale.

• The business has strong fundamentals and excellent investors backing us. We are cash flow positive / profitable, have fresh funding, strong customer and revenue retention, healthy ACVs and relatively fast sales cycles. All of these ingredients have helped us get to where we are today without executing perfectly on sales throughout the whole journey. Those tailwinds will benefit us even more as we execute at higher and higher levels on sales.

THE UPSIDE 📈

• By joining as one of our early team members, there is enormous opportunity ahead for you to have an outsized impact and shape the future of AirGarage in this role.

• Competitive salary and benefits including unlimited PTO, health / dental / vision insurance, 401k, and more.

• A lot of room to grow -- the sales team will be orders of magnitude larger within a few years, and you’ll be the driving force behind that team.

• Work closely with our CEO, co-founders, and leadership team to drive strategy and execute key initiatives.

• The opportunity to change the way that the world thinks about real estate use in our cities.

• A diverse team -- we are currently 35%+ female and 30%+ non-white and we hope to continue hiring thoughtfully to build a team that represents the fact that our customers come from all walks of life.

• You’ll be joining a sharp, motivated team and have the option to work in an office in San Francisco or work remotely. Our company is remote-first but we know some people thrive in the in-person energy of working in an office.

We understand that there's no such thing as a 'perfect' candidate. We're looking for someone passionate, with grit and determination, who is excited to face the challenges of a rapidly growing startup. AirGarage is the type of company where you can grow exponentially, and we encourage you to apply to us even if you don't 100% match the candidate description.

AirGarage is an Equal Opportunity Employer. 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, martial status, mental or physical disability, or any other legally protected status.