Head of Sales

This role is an opportunity to help shape and lead the sales function at a growing company while working side by side with the executive team. You will contribute to sales strategy and direction, refine the foundation already in place, and develop a disciplined, repeatable sales process that can scale with the business.

This is a hands-on leadership role. You will identify and qualify strong opportunities through outbound phone calls, LinkedIn, and personalized emails while helping define how HAH Parking researches prospects, prioritizes accounts, manages its pipeline, and converts opportunities into customers.

Your conversations will focus on understanding how parking owners and operators currently manage their assets and demonstrating how HAH Parking can improve their performance. You will be responsible for generating qualified meetings, advancing opportunities, and working closely with the executive team to win new business.

This is a high-volume dialing position that also requires careful research, customized messaging, and a targeted approach to high-value accounts. We are looking for someone who is resourceful, accountable, motivated to improve, and excited to build something meaningful.

About HAH Parking

HAH Parking is a cloud-based parking management platform that brings payments, dynamic pricing, and enforcement together in one system. We help lot owners and operators earn more from the spaces they already have by replacing outdated hardware, flat-rate pricing, and fragmented tools with one platform that is simple to run.

Drivers pay in seconds by text or QR code. There is no app to download. Owners get real-time visibility and control over revenue, occupancy, pricing, and reporting. Our partners typically see meaningful revenue increases, often in the 30-40% range, with no long-term contracts and no upfront costs.

HAH Parking currently operates in multiple states and works with a wide range of clients, including independent lot owners, parking management companies, real estate investors, event venues, municipalities, and property managers.

Primary Responsibilities

• Help develop, document, and continually improve HAH Parking's sales process, including prospecting, qualification, pipeline management, follow-up, and reporting.
• Turn the company's existing sales foundation into a disciplined, repeatable process that supports consistent execution and future growth.
• Work with the executive team to refine target customer profiles, territory strategy, messaging, sales stages, performance metrics, and revenue goals.
• Personally execute the sales motion by researching prospects, conducting outbound outreach, leading sales conversations, and advancing qualified opportunities.
• Research parking asset owners in your territory using prospecting tools like Reonomy, UnrealCRM, LandGlide, and others. Confirm ownership and decision-makers, prioritize the right accounts, and maintain accurate CRM records.
• Run coordinated, multichannel outreach that includes personalized emails, phone calls, texts, LinkedIn activity, and social selling.
• Schedule and conduct qualified meetings, providing clear research, account context, and documented next steps.
• Monitor activity, conversion rates, pipeline quality, and other key indicators to identify opportunities for improvement.
• Test and refine messaging, outreach sequences, qualification criteria, and sales tactics based on results and feedback from the market.
• Share practical field insights with the executive, marketing, and product teams to improve positioning, processes, and training.
• Help establish the playbooks, operating rhythms, and standards that will support the sales organization as it grows.

What We're Looking For

• Background. Experience in B2B or enterprise sales development, business development, or full-cycle sales is preferred. More important is a history of working independently, consistently meeting or exceeding goals, and combining strong research with meaningful customer conversations.
• Process-building experience. You have built a sales process, helped improve one, or played a meaningful role within a strong sales organization. You understand what makes a sales process effective and are excited by the opportunity to take greater ownership of building and refining one.
• Leadership mindset. You think beyond your individual activity and consider how messaging, systems, metrics, and operating habits work together. You are comfortable making recommendations, testing ideas, learning from results, and turning successful practices into repeatable playbooks.
• Approach. You are self-motivated, accountable, persistent, and comfortable operating in a fast-moving environment. You collaborate well, respond positively to feedback, and find creative ways to solve problems.
• Skills. You bring strong research and prioritization abilities, confidence with outbound calling, clear written and verbal communication, and the judgment to focus on the opportunities most likely to produce results.
• Technology. You are comfortable with modern sales engagement platforms and CRM systems. You also understand how current AI tools can support prospect research, preparation, personalization, and outreach. You use these tools as a force multiplier while maintaining the judgment, authenticity, and personal attention that effective selling requires.

Compensation and Benefits

Qualified candidates can expect a base salary ranging from $85,000 to $115,000, plus commission.

Additional benefits include:

• Unlimited PTO.
• 401(k).
• Health insurance.
• Life insurance.
• Fully remote work.
• A positive and enjoyable work environment.

A Note for Applicants

We know that few people match every line of a job description. What matters most to us is genuine enthusiasm, resilience, and a willingness to take on the challenges of a growing company.

You may have worked within a successful sales organization and seen opportunities to improve its process without being given the chance to lead those improvements yourself. This role is an opportunity to put that experience and perspective into practice.

HAH Parking offers meaningful room to advance, and we encourage you to apply even if your background does not align perfectly with every requirement listed.

Our Culture

HAH Parking is a small team that values ownership, agility, and real results. We measure success by the impact we create for lot owners, not by internal process or vanity metrics.

Team members are given meaningful responsibility early, expected to move quickly, and supported with coaching and autonomy. The environment is collaborative, practical, and energetic, with a strong bias toward solving problems and compounding improvements over time.

We work remotely, trust people to manage their time, and look for individuals who are coachable, resourceful, and motivated by tangible outcomes.