Strategic Sales Director-Midwest

Reunion Marketing; Chicago (IL); Remote; USD 90,000 - 150,000; Full time

Job summary

Reunion Marketing is seeking a Strategic Sales Director to drive growth in the Midwest for their innovative digital advertising solutions. This role requires an entrepreneurial leader adept at building relationships and transforming client experiences. The ideal candidate will have a strong sales background in the automotive or digital advertising sectors, with the ability to engage C-level executives and manage a competitive market strategy.

Qualifications

• 5+ years of high-performance, in-market sales experience in automotive or digital advertising.
• Existing network of Midwest dealer contacts is advantageous.
• Strong command of SaaS platforms.

Responsibilities

• Own the market strategy to grow revenue and build long-term dealer relationships.
• Lead consultative sales and challenge existing dealer approaches.
• Deliver compelling product demos showcasing ROI.

Skills

Sales

CRM Discipline

Digital Marketing Metrics

Consultative Sales

Relationship Building

Tools

HubSpot

Gong

Seamless.ai

Job description

Strategic Sales Director – Midwest Region

Location: Remote | Travel Required: Up to 50%

About Reunion Marketing

Reunion Marketing is transforming the digital advertising landscape for automotive dealers. Our proprietary SEO and Paid Media platforms KeyLift, LocalEyes, and Adaptd deliver exceptional results by leveraging transparent data and cutting-edge strategies. As a high-growth, innovation-forward agency, we empower industry leaders to rethink their digital approach and dominate their markets.

We are driven by Grit, Continuous Improvement, Elevating Others, and Embracing Discomfort. If you thrive on growth, freedom, and challenging the status quo, read on.

The Opportunity

We are searching for a Trailblazing Strategic Sales Director to lead regional growth across the Midwest. This role is ideal for an entrepreneurial leader with a relentless drive to win, a passion for transforming the dealer experience, and the confidence to build and lead a book of business in a competitive, fast-moving market.

You will act as the tip of the spear, owning strategy, execution, and results. Your responsibilities include meeting with dealers across the region, challenging their existing digital thinking, and positioning Reunion's platforms as the smarter, more profitable path forward.

What You'll Do

1. Own the Territory: Build and execute a market strategy to grow revenue across the Midwest by closing new business and scaling long-term relationships with dealer groups.
2. Challenge Convention: Lead with insights, use a consultative sales model, and push dealers to rethink their approach to digital advertising.
3. Sell Boldly: Deliver product demos that showcase ROI and the simplicity of our SaaS platforms, helping clients unlock new performance benchmarks.
4. Run Fast, Operate Smart: Leverage tools like HubSpot, Gong, and Seamless.ai to plan visits, manage your funnel, and drive predictable results.
5. Influence All Levels: Cultivate relationships with dealer owners, GMs, and digital teams, earning trust and alignment at every level.
6. Drive Innovation: Stay plugged into industry trends and competitor activity. Adapt strategies to stay ahead and maintain Reunion's market advantage.
7. Collaborate for Success: Partner with Client Success to ensure seamless post-sale experience, client retention, and expansion.

What You Bring

1. 5+ years of high-performance, in-market sales within automotive or digital advertising industries.
2. Existing network of Midwest dealer contacts is a strong advantage.
3. Strong command of SaaS platforms and digital marketing metrics.
4. Self-directed, goal-obsessed, and motivated by challenge.
5. Adept at leading C-suite conversations and influencing decision-makers.
6. Able to travel 50% across the Midwest for face-to-face meetings.
7. Strong CRM discipline and a strategic, data-informed sales approach.

Join Us

This isn't a role for someone looking to maintain the status quo. It's for someone ready to set the pace, redefine what's possible, and lead the charge in a region rich with opportunity. If you're ready to build, challenge, and grow, Reunion Marketing is ready for you.