Remote AI Sales Representative

TAG Software Group is looking for an AI Sales Representative to support growth across key U.S. automotive markets.

ABOUT TAG SOFTWARE GROUP:

TAG Software Group is a team of experienced investors and operators dedicated to acquiring, enhancing, and growing mission-critical software companies serving SMB, enterprise, and public sector customers. Founded as part of Valsoft Corporation, TAG provides a permanent home for software companies we don’t buy to sell. Our focus is on long-term partnerships that protect your legacy, employees, and customers.

Our in-house team delivers an efficient, transparent, and seller-friendly process, ensuring speed and certainty of close. Once part of TAG, your company gains access to proven best practices, dedicated value-creation resources, and the extended ecosystem of our sister companies, including proprietary in-house technology such as ValPay and Sadie AI helping your business reach the next level.

INVESTMENT APPROACH:

Unlike private equity and venture capital firms, we are Entrepreneurs who Buy, Enhance and Grow Software Businesses. That’s right; we don’t sell businesses. We form a strategic alliance with existing management teams. We recognize the dedication and perseverance required to create a firm and place a premium on customers’ and workers’ well-being over short-term goals.

CULTURE:

TAG Software Group is more than just a place to work; we’re a team. We mean it when we say people are our greatest assets, so investing in them is our number one priority. We create an environment where our employees feel first-day-on-the-job excitement day after day, building a culture of high performers and collaboration. We celebrate our milestones, and we’re proud of them. We Dream Big, Stay Humble, and Stay Hungry.

POSITION DESCRIPTION:

We are seeking experienced AI Sales Representatives to drive growth across some of the most advanced automotive markets in the United States. This role focuses on new business acquisition, full-cycle sales, and regional market expansion within one of

three territories: West Coast (CA, WA, OR), Northeast (MA, NY, NJ, PA), or Florida (Miami, Orlando, Tampa). You will prospect dealerships, deliver product demos, manage the full sales cycle, and build market presence through in-person visits and industry events. This is a hunter role suited for individuals with strong dealership experience, a tech-forward mindset, and a proven ability to sell software solutions into the automotive ecosystem.

KEY RESPONSIBILITIES:

· Identify and target dealerships throughout the assigned region (West Coast, Northeast, or Florida).

· Run outbound sequences across phone, email, LinkedIn, and in-person visits.

· Use an existing automotive tech network to accelerate regional penetration.

· Build and manage a strong outbound-driven pipeline.

· Qualify inbound leads from dealerships within the assigned territory.

· Conduct discovery calls to understand dealership workflows and operational bottlenecks.

· Book and run demos, converting interest into qualified opportunities.

· Deliver compelling demonstrations of AI-powered communication solutions.

· Manage the full sales cycle including prospecting, discovery, demo, proposal, negotiation, and close.

· Support customers throughout early activation and hand off accounts to onboarding teams.

· Represent the company at automotive conferences, trade shows, and dealer-group events.

· Build regional brand presence and maintain visibility within key markets.

· Conduct in-person dealership visits for advanced demos or late-stage deal discussions.

· Collaborate with leadership, sales, and product teams.

· Provide regional insights into dealership needs, processes, and common DMS systems (e.g., CDK, Reynolds, Dealertrack, Tekion, XTime).

· Maintain accurate pipeline documentation and activity tracking in HubSpot.

· Provide consistent updates on territory progress and performance.

· 3+ years of experience in automotive software or digital retailing sales.

· Experience selling technology solutions to dealerships within at least one target region.

· Background with companies such as Tekion, CDK Global, Reynolds & Reynolds, XTime, Dealertrack, Keyloop, AutoTrader/Cox, MotorK, or similar automotive SaaS vendors.

· Strong existing network in West Coast, Northeast, or Florida dealership groups.

· Proven success in a hunter-style role with consistent outbound activity.

· Strong demo, presentation, and communication skills.

· CRM experience, ideally HubSpot.

· Ability to self-manage in a fast-paced, remote startup environment.

· Comfort explaining AI-driven or technical solutions to non-technical dealership teams.

· Based in one of the eligible U.S. regions with ability to visit dealerships as needed.

ADDITIONAL or PREFERRED QUALIFICATIONS:

· Experience launching new markets or selling into greenfield territories.

· Background in fixed-ops, service, or dealership communications software.

· Field sales or hybrid inside/outside sales experience.

· Spanish or additional languages (especially valuable in CA and FL).

· Competitive base salary.

· Uncapped commission with strong earning potential.

· Fully remote role within the assigned U.S. region.

· Opportunity to be among the first regional U.S. sales hires.

· Training in AI, automotive workflows, and advanced sales methodologies.

· Fast-paced, ambitious environment with significant growth opportunity.

· Direct impact on expanding presence in the most innovative dealership markets.

Ready to join a collaborative and innovative team where you can make an immediate impact?