The Role

We’re looking for a sales leader to build and scale our new business engine. You’ll lead a small team of inbound setters and closers, stand up an outbound function, and partner closely with Marketing to drive revenue. This is a VP role with both near-term team building and long-term scale responsibilities. You’ll start by leading a lean team and be expected to build toward a larger, repeatable structure as we grow.

Location: Fully remote (U.S.).

Travel: ~4-day trips 7×/year for leadership meetings, industry events, and client visits.

Reports to: COO. Works closely with the VP of Marketing.

The Company

Dealer Image Pro provides hardware, software, and training to auto dealers so they can capture high-quality inventory content and quickly get it online. We’re a small, bootstrapped company that’s grown rapidly since 2020 when we pivoted from a lot services provider to selling merchandising software directly to auto dealers.

The Problem You’re Solving

As we grow, we need a repeatable, scalable net-new motion tuned for auto dealerships; that means rebuilding sales scripts and enablement, standing up consistent outbound, sharpening how we qualify and manage deals, and keeping forecasts and pipelines clear and reliable.

Key Responsibilities

Own net-new revenue: set the strategy, targets, and day-to-day rhythm for building pipeline and closing new dealers.
Hire, onboard, and develop setters and closers; stand up an outbound motion from near-zero; set clear roles, territories, and activity standards.
Design and test repeatable outbound plays (messaging, sequencing, list strategy) and coach the team on call and email execution.
Improve qualified-to-won conversion.
Run weekly pipeline and forecast reviews, enforce CRM standards.
Work with Marketing for inbound and outbound efforts, share market insights with Product and leadership.
Build and maintain talk tracks, objection handling, competitive positioning, and quick-reference playbooks.
Create a high-trust, high-accountability culture with clear goals, transparent feedback, and ongoing coaching.

Required Skills and Qualifications

Experience selling into auto dealerships (required) with a track record of net-new success.
7+ years in B2B sales with 3+ years leading multi-IC teams.
Demonstrated ability to build inbound and outbound from near-zero and scale a small team into a consistent, predictable motion.
Proven ability to write clear sales playbooks, scripts, and messaging that drive consistency and results.
Strong operator skilled in pipeline management and forecasting for a short sales cycle.
Strategic thinker with the ability to set up simple reporting and forecasting processes that provide visibility today and scale as we grow.
Clear communication, practical problem-solving, and steady leadership under growth pressure.
Salesforce strongly preferred; broad familiarity with modern sales tools (e.g., sequencing, intent, call recording, data enrichment) , we value your perspective on what the stack should be.
An understanding of how to use AI in modern sales processes is strongly preferred. We’re looking for someone who embraces new tools and technologies to make their team sharper, faster, and more effective.

Compensation

$250 - 275k/yr OTE — base/commission/bonuses: 60/30/10
Health, dental, and vision — 50% employee, 0% dependents
401(k) plan
Starts at 3 weeks PTO plus company holidays

Job Type: Full-time

Pay: $250,000.00 - $275,000.00 OTE per year

Dealer Image Pro

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