[Hiring] Director, Direct Agent Life Insurance Sales @Ladder

Role Description

As the Director, Direct Agent Sales, you will 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. You will oversee the complete sales pipeline, build the foundational operational framework for a rapidly expanding team, and directly influence our cross-functional product and marketing roadmaps to optimize unit economics and conversion velocity.

Please note, this is a remote role based in one of the 23 States Ladder is currently hiring in - AZ, CA, CO, CT, FL, GA, IA, KS, MA, MD, MN, NC, NH, NJ, NV, NY, OH, OR, PA, TX, VA, WA, WI.

Please note, Ladder is not currently sponsoring or transferring OPT or H1-B visa's.

What You’ll Do

• Leadership & Scaling: Build, scale, and inspire a team of licensed sales and operations professionals. Establish clear performance metrics, KPIs, and cultural accountability.
• Sales Architecture & Playbooks: Design, implement, and continuously refine scalable playbooks, advanced scripting, and rigorous coaching rhythms (including call shadowing, systematic reviews, and certifications) to maximize conversion rates.
• Operational Backbone Ownership: Command the end-to-end operational workflow—including state licensing compliance, complex suitability parameters, premium structures, and agent commission architecture.
• Cross-Functional Strategy: 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.
• Growth and Go-To-Market Alignment: Tighten the loop between inbound marketing lead quality and agent sales execution to accelerate consumer conversion funnels.
• Hands-on Execution: 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.

Qualifications

• 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.
• 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.
• Mastery of modern CRM data architecture, telephony infrastructure, revenue forecasting, and rigorous pipeline management.
• Exceptional communication skills coupled with a tech-forward, high-bias-for-action mindset built to thrive within a highly disruptive, agile startup culture.
• Availability to support standard operational business hours across any of the four mainland U.S. time zones.

Benefits

• Excellent medical, dental, and vision coverage for you and your family.
• Flexible paid time off, including a week-long winter holiday closure.
• Competitive stock option packages to participate in the success of building Ladder.
• 401k match program, matching up to 4% of your contributions.
• Monthly stipend for wellness-related expenses through the Ladder Fit Program.
• Ten weeks of paid parental leave for all parents, inclusive of birthing, adoption, or fostering.
• Work-from-home flexibility and support, including a one-time remote office stipend and monthly stipends for WFH costs.
• Fun company-wide events to foster team bonding.