• Drive new business growth by acquiring new dealerships and dealer groups, expanding revenue, and achieving sales targets. • Develop and execute territory sales plans to identify and convert high-potential prospects. • Leverage the MEDDIC sales methodology to qualify leads, structure deals, and close business efficiently. • Conduct compelling product demonstrations that showcase Dealerware’s impact on dealership operations and profitability. • Build long-term, trusted relationships with key decision-makers at dealerships, dealer groups, and OEMs. • Oversee contract negotiations to align on pricing, terms, and long-term success metrics. • Collaborate with internal teams to refine regional sales strategies and drive product adoption. • Maintain accurate pipeline tracking, sales forecasting, and CRM data management in Salesforce. • Serve as the voice of the customer, providing valuable feedback to influence product development and company strategy.

This description is a summary of our understanding of the job description. Click on 'Apply' button to find out more. Role Description This role involves engaging with potential clients and partners in the vacation and short-term rental space. - Maintain a funnel of 50 - 100 active prospects/leads through various phases of the Wheelhouse sales funnel, from prospecting through onboarding. - Meet with prospective clients via phone/video conference, building relationships, resolving customer objections, answering questions, and demoing various features of the Wheelhouse Platform. - Achieve Monthly, Quarterly, and Annual sales goals (evaluated by portfolio size of deal). - Learn to use the Wheelhouse platform to “show” vs “tell” customers how they can successfully onboard to & utilize the Wheelhouse platform. - Coordinate with Sales Engineers and Sales Development Representatives for support in successful customer onboarding. - Develop personal strategies for outreach and sales relationship development. - Collaborate with team members to improve sales processes and strategies to optimize Wheelhouse sales infrastructure. - Shape our product to make it ever easier to sell to potential clients. - Inform our marketing team of potential opportunities to better communicate the Wheelhouse value prop. - Build a massive, industry-leading company with a passionate team. Qualifications - Industry knowledge and experience in revenue management and trends. - Ability to convey a compelling value proposition enthusiastically. - Strategic and critical thinking skills. Requirements - Experience in sales and customer relationship management. - Comfortable with technology and learning new software platforms. - Ability to work in a collaborative and fast-evolving startup environment. Benefits - Competitive salary and equity. - Full medical, dental, and vision benefits for each US employee. - Fidelity 401k available for each US employee. - Unlimited PTO. - Extended & Competitive Benefits plan. Your First 90 Days - Work directly with Wheelhouse sales teammates & leadership, observing conversations with clients and learning the platform. - Learn the systems/software our team leverages and master the ins/outs of our industry. - Develop and maintain a personal funnel of leads and prospects through all phases, starting with smaller clients and eventually taking on larger client relationships. - Collaborate to strategize, optimize, and improve processes, strategies, and experiments for the benefit of the entire Wheelhouse team. Company Description Wheelhouse is a fintech platform for the $500B+ flex rental space, enabling short & mid-length stay providers to earn 20%+ more from their rental properties. - Voted “Innovation of the Year” at the Data & Revenue Management conference in 2021. - Low churn and rapidly growing ARPU. - Closed a significant funding round in 2022 with participation from top tech, travel & real estate investors. - Remote-first, work-anywhere culture that promotes work/life balance. - Experienced business & product builders with a strong cross-functional team.

• Engage customers using a consultative sales approach to understand their insurance needs and recommend personalized solutions across property, casualty, and personal lines. • Proactively identify opportunities for cross-selling and up-selling, and assist customers in transitioning between Roamly and third-party insurance carriers when appropriate. • Clearly explain coverage options, policy terms, and insurance processes in a way that’s easy for customers to understand. • Drive lead conversion through high-volume outbound outreach and responsive handling of inbound inquiries. • Manage the complete sales process—from quoting insurance products using Roamly’s proprietary tools, to gathering underwriting information, and guiding customers through to policy purchase and binding. • Maintain accurate and timely documentation of customer interactions and follow-ups using Close.AI. • Stay current on all available insurance products, systems, and carrier platforms to deliver informed, high-quality service and support.

Pinewood.AI is expanding rapidly in the US, and we’re looking for our first CARS Account Executives to help drive that growth. This is a high-impact, revenue-focused role centred on selling our CARS (Connect, Assist, Reach and Serve) AI solutions to automotive dealerships outside the Top 100–150 groups. You’ll take a consultative approach to selling modular AI products powered by Seez, helping dealership leaders modernise digital operations, improve customer engagement, and unlock measurable performance gains. This role is about fast, repeatable CARS wins - not broad platform sales, and requires someone who thrives in new business development, understands automotive retail, and is energised by building territory momentum from the ground up. If you’re commercially driven, comfortable with outbound prospecting, and motivated by shaping a new market presence in a growing organisation, this is an opportunity to make a visible impact. Key Responsibilities: - Identify, target, and win new automotive dealership accounts within your assigned US territory (excluding Top 100–150 groups) - Focus exclusively on driving CARS (AI) product sales, securing fast, repeatable wins - Develop and execute territory-specific sales strategies aligned with overall company objectives - Build strong relationships with dealership principals, general managers, and digital leaders - Deliver compelling product demonstrations and consultative sales presentations tailored to dealership needs - Create proposals and ROI analyses that clearly articulate the commercial value of CARS solutions - Accurately manage pipeline activity, forecasting, and reporting within the CRM system - Surface signals and opportunities for broader platform engagement, without directly pursuing platform sales - Collaborate closely with implementation and customer success teams to ensure smooth onboarding and early value realisation - Gather and share competitive intelligence and market feedback to inform product and go-to-market strategy - Represent Pinewood.AI at industry events, trade shows, and networking opportunities - Partner with marketing to execute territory-specific campaigns and outbound initiatives