- Title: Regional Account Executive, Great Lakes
- Reports to: VP of Sales
- Location: Remote — Northwest Indiana-based
- Territory: IN, IL, WI, MI, OH, MN
- Travel: Up to 25%
- Compensation: $75,000–$90,000 base · approximately $175,000 on-target earnings (OTE), uncapped
- Employment type: Full-time; Exempt
- Level: Individual contributor — full-cycle AE
About Alpha Drive AI
Alpha Drive AI gives automotive dealerships an AI-powered communication layer that answers every call, books every appointment, and captures revenue that would otherwise slip away. Dealerships run on the phone — and most miss a staggering share of the calls that drive service and sales revenue. We fix that. We're a fast-growing team backed by deep automotive retail experience, and we're building our field sales organization region by region, hire by hire.
The Role
This is a full-cycle Account Executive role. You'll run the entire sales process — from the first conversation to a signed agreement — across Indiana, Illinois, Wisconsin, Michigan, Ohio, and Minnesota. It's a builder's seat with a head start: you'll inherit relationships with established dealer groups in the region and have real autonomy to expand from that base into one of the densest dealership markets in the country. You'll also provide interim coverage for select accounts in adjacent markets as we expand the team.
This is an Account Executive position from day one — not an SDR-to-AE track. You'll be closing business, and you'll be generating your own pipeline to do it. If growing a book — both expanding established accounts and opening new ones — energizes you, you'll feel at home here.
What You'll Do
- Own your territory end to end — every stage of the deal, every account, your call.
- Generate your own pipeline through thoughtful, research-driven outreach to dealership leaders. Yes, that includes picking up the phone — proactive prospecting is the heart of this role.
- Lead discovery conversations that help dealers see what better customer communication could do for their business.
- Deliver demos tailored to each dealership's operation and economics — not a one-size-fits-all pitch.
- Negotiate and close, then stay close to new customers through their first wins.
- Represent Alpha Drive AI in the field across the region (up to 25% travel).
What You'll Bring
We care more about how you sell than the boxes you check.
- Around 3–5 years of full-cycle B2B SaaS or automotive-technology sales.
- Experience self-sourcing pipeline and owning a quota.
- A consultative, insight-led style — you teach buyers something new rather than just list features.
- Strong discovery and demo skills, and real curiosity about how your customers' businesses run.
- Self-direction and resilience in a remote, field-based role.
- Based in Northwest Indiana (Merrillville, Crown Point, Valparaiso, or surrounding Lake/Porter County area preferred; South Bend area considered) and able to travel up to 25%.
Nice to have (truly optional): automotive or dealership experience, selling into multi-location or franchise buyers, or familiarity with the Challenger methodology.
Research shows some people only apply when they meet every single requirement. If you're excited about this role but your experience doesn't line up perfectly, apply anyway — you may be exactly who we're looking for.
What Success Looks Like
- First 30 days: Ramped on the product, our ideal-customer profile, and our messaging approach; a written territory plan in place.
- By 60 days: Self-sourced pipeline actively building; first tailored demos delivered to qualified dealership prospects; introductory meetings completed with inherited account groups in the territory.
- By 90 days: Consistent, self-generated qualified pipeline; first closed business in the territory — new logo or expansion within an existing dealer group.
- Year one: On-target quota attainment with healthy self-sourced pipeline coverage and a repeatable outbound motion.
Compensation
We believe in being upfront about pay. This role offers a base salary of $75,000–$90,000 depending on experience, with on-target earnings of approximately $175,000 and no cap on commissions. We support remote work within the territory and give you flexibility in how you manage your day.
Benefits
- Health, dental, vision and life insurance
- 401(k) matching
- Paid time off
- Remote work — approved home office environment
- Paid travel for client visits and team events
How to Apply
Submit your resume and complete any pre-screening questions. Candidates with automotive, call center, B2B sales or SaaS sales experience are reviewed first.
Work Environment
This position operates in a professional home office or approved remote work environment and routinely uses standard office equipment including computers, phones, and video conferencing tools. It requires extended periods of computer and phone use. Regular travel to client sites, team meetings, and industry events is required.
Systems and Tools
Our client operations run on HubSpot (CRM, pipelines, and reporting), and Jira (project and issue tracking). Our AI products are built on a cascading LLM architecture across Anthropic Claude, OpenAI ChatGPT, and Google Gemini, with conversational voice handled through platforms like Bland AI; you should understand these conceptually.
Physical Demands
The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. While performing the duties of this job, the employee is regularly required to talk or hear. The employee frequently is required to sit, stand, walk, use hands to handle and feel, and reach with hands and arms. The employee must occasionally lift and/or move up to 25 pounds, such as marketing materials, product samples, or trade show materials. Ability to communicate effectively in person, via phone, and via video conferencing for extended periods is required. The employee must be comfortable with frequent travel, including air travel, driving, and extended time away from the primary work location.
Position Type and Expected Hours of Work
This is a full-time position. Hours of work may vary and flexibility is required. Evening and weekend availability may occasionally be needed based on client schedules, event commitments, and varying time zones.
Travel
Travel is required up to 25% of the time. This includes regular travel to visit current and prospective clients, attend industry trade shows and conferences, and represent the company at sales events. Travel may be local, regional, or national depending on territory and business needs. Employees must maintain a valid driver's license and the ability to travel by air when required.
Other Duties
Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required of the employee. Duties, responsibilities, and activities may change at any time with or without notice.
FLSA Status
Exempt
AAP/EEO STATEMENT
Dealer’s Greatest Assets d/b/a Alpha Drive AI LLC provides equal opportunity in employment for all qualified persons and prohibits discrimination in employment on the basis of race, color, religion, creed, sex, sexual orientation, gender identity, national origin, ancestry, age, veteran status, disability unrelated to job requirements, genetic information, military service, or other protected status. All qualified applicants will receive consideration for employment without regard to any protected characteristic.
Work Authorization
Applicants must be legally authorized to work in the United States. This is a fully remote position within the United States; visa sponsorship is not available at this time.
Pay: $75,000.00 - $175,000.00 per year
Benefits:
- 401(k) matching
- Dental insurance
- Flexible schedule
- Health insurance
- Life insurance
- Paid time off
- Vision insurance
Application Question(s):
- Is there anything else we should know prior to a phone screen?
Education:
Experience:
- B2B sales: 2 years (Required)
- SaaS Sales: 1 year (Required)
Willingness to travel:
Work Location: Remote
