Director, Direct Agent Sales

About Ladder

We saw a problem within the life insurance industry: getting covered took too long, involved too much paperwork, and required too many in-person meetings with sales agents. Having lost his father at a young age, our CEO, Jamie, was determined to make it easier for people to get the coverage they needed to provide for their families. So, we got to work. We developed a method of real-time underwriting leveraging AI and, in doing so, reduced the months-long process of applying for life insurance to minutes. Our digital experience is quick (instant decisions!), loved by users (check out our Trustpilot or Google reviews) and prolific ($74 billion+ in coverage provided).

About the Role

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.

Experience Required

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.

What we Offer

Ladder is highly collaborative and fun. To support you in your role, we offer fantastic perks and benefits that reflect our mission of care and support, including:

Excellent medical, dental, and vision coverage | We offer competitive healthcare, dental and vision plans for you and your family.
Flexible paid time off | Take the time that you need to rest and recharge, including our week-long winter holiday closure.
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Director, Direct Agent Sales at Ladder