Location: US-Remote 

Approved States: AL,AZ,CA,CO,CT,DC,FL,GA,ID,IL,IN,MA,MD,MI,MO,NC,NH,NJ,NV,NY,OH,OR,PA,RI,SC,TN,TX,UT,VA,WA,WI 

Type: Full-Time, Salary, Exempt 

Reports to: VP, Agent Revenue

About DMS:

Digital Media Solutions (DMS) is a performance-driven digital marketing company that connects consumers and brands through data, technology, and proprietary media platforms. Our systems power high-volume consumer acquisition across multiple verticals, processing large-scale traffic and real-time decisioning in dynamic market environments.

About the Role:

We're looking for a Sales Director to own day-to-day Sales and Customer Success execution within the ZipQuote and Allstate Lead Marketplace agent divisions. This is a hands-on leadership role: you'll run cadence, coach reps directly, and be accountable for quota attainment and retention within your divisions, not a strategic, hands-off portfolio role.

You'll build and maintain the playbooks, ramp new hires, and drive team culture within the ZipQuote and Allstate Lead Marketplace Core teams, while partnering with the VP of Agent Revenue on how your division fits into the broader agent portfolio.

Why Join DMS?

At Digital Media Solutions, you'll lead the Sales and Customer Success teams driving two of our core agent divisions, with direct line of sight into rep performance, coaching, and results. If you enjoy being close to the business, running cadence, developing talent, and personally owning the numbers for your division, this is a chance to build a high-performing team and see the direct impact of your leadership.

What You'll Do:

• Run day-to-day Sales and Customer Success cadence for the ZipQuote (ZQ) and Allstate Lead Marketplace (ALM) Core teams.
• Coach individual reps on pipeline management, conversion, and customer retention.
• Own quota attainment and revenue/retention performance for ZQ and ALM.
• Partner with L&D to build, maintain, and personally author playbooks, ramp plans, and onboarding for new hires.
• Set and drive team culture and performance management within your division.
• Own Revenue per Agent (RPA) growth, upsell targeting and execution, and establish effective promotional offerings and  guardrails for ZQ and ALM.
• Manage the forecasting relationship with Finance/RevOps for your division.
• Partner with Agent Marketing on campaign-to-sales execution and inbound conversion for your division.
• Execute a proactive retention strategy and at-risk intervention model within ZQ and ALM.
• Own a CS ? Account Management transition process for your team and their respective accounts
• Escalate major retention risks and strategic accounts to the VP as needed.
• Represent ZQ and ALM performance in cross-functional planning with Product, RevOps, Finance, and Agent Marketing.
• Manage day-to-day third-party tool usage for the Sales/CS tech stack within your divisions.
• Partner with HR on leveling, performance management, and flight-risk conversations for your team.

What We're Looking For:

• Proven experience directly managing Sales and/or Customer Success reps in a quota-carrying environment.
• Track record of hitting revenue and retention targets through hands-on cadence and coaching.
• Experience building or maintaining sales/CS playbooks and onboarding programs.
• Strong people-management and performance-management skills.
• Comfort working with forecasting, customer growth, and upsell targeting frameworks.
• Ability to operate independently while aligning with a broader portfolio strategy set above this role.
• Strong cross-functional collaboration skills (Finance, RevOps, Marketing, Product).

Nice to Have:

• Experience specifically within insurance, financial services, or another regulated agent/producer channel.
• Familiarity with lead distribution or agent marketplace models.
• Experience managing a CS ? Account Management structure change process.
• Prior experience being promoted from an individual-contributor or team-lead sales role.

Technical Environment:

• Sales/CS Tooling: CRM and cadence platforms, sales enablement tools
• Analytics & Reporting: Excel, Google Sheets, Tableau, Looker, or similar BI tools
• Forecasting: Finance/RevOps forecasting tools and processes

Compensation:

The anticipated annual base salary for this position is $90,000–130,000 with a performance-based variable of $70,000–100,000. Actual compensation may vary based on work experience, education, and skill level.