Director, Direct Agent Sales (D2C, Inside Sales)

About the role

We serve as the architect and strategic leader of our high-volume, inside D2C agent sales and operations organization. This is a high-impact, "player-coach" leadership position designed for revenue operators who can balance front-line execution with corporate scale.

Responsibilities

• Build, scale, and inspire a team of licensed sales and operations professionals.
• Establish clear performance metrics, KPIs, and cultural accountability.
• Design, implement, and continuously refine scalable playbooks, advanced scripting, and rigorous coaching rhythms (including call shadowing, systematic reviews, and certifications) to maximize conversion rates.
• Command the end-to-end operational workflow—including state licensing compliance, complex suitability parameters, premium structures, and agent commission architecture.
• Partner directly with Product, Engineering, and Marketing executives to turn customer insights into technical product requirements for our quoting engines, electronic applications (e-apps), and post-issue servicing.
• Tighten the loop between inbound marketing lead quality and agent sales execution to accelerate consumer conversion funnels.
• Actively operate as a premier player-coach; maintain an active life insurance producer license to take live calls, manage pipelines, and lead by example on the floor from day one.

Requirements

• Proven Scale Leadership: 7+ years of total experience in sales, account management, or customer-facing environments within the life insurance ecosystem.
• 3+ years of experience leading inside sales and operations teams in a D2C environment, with a reputation for hiring top talent, building effective playbooks, and rapidly improving performance.
• Licensing Compliance: Active Life Insurance Producer license in your home state, with the mandatory requirement and willingness to rapidly obtain reciprocal licensing across all 50 states and Washington, D.C. Must be up to date with all NAIC guidelines.
• Analytical Command: Mastery of modern CRM data architecture, telephony infrastructure, revenue forecasting, and rigorous pipeline management.
• Startup Agility: Exceptional communication skills coupled with a tech-forward, high-bias-for-action mindset built to thrive within a highly disruptive, agile startup culture.
• Geographic Flexibility: Availability to support standard operational business hours across any of the four mainland U.S. time zones.

Qualifications

• Experience in life insurance sales and operations.
• Ability to build and lead high-performing teams.
• Strong analytical and data-driven decision-making skills.
• Effective communication and interpersonal skills.
• Ability to work in a fast-paced, dynamic environment.

Skills

• Leadership and strategic planning.
• Team management and development.
• Customer relationship management.
• Product and marketing strategy alignment.
• Technical product requirements development.

Benefits

• Excellent medical, dental, and vision coverage.
• Flexible paid time off.
• Stock options.
• Rewarding 401k match program.
• Ladder Fit Program.
• Paid parental leave.
• Work-from-home flexibility and support.
• Fun company-wide events.

Pay

• Tier 1 (SF Bay Area, New York City, Seattle): $165,000 - $200,000
• Tier 2 (LA, Austin, Boston, Chicago, DC, Denver, Philadelphia, San Diego): $147,000 - $175,000
• Tier 3 (All other locations that Ladder hires): $138,000 - $165,000

Schedule

• Standard operational business hours across any of the four mainland U.S. time zones.