Director, Direct Agent Sales

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).

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.

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. 
• Stock options | We offer competitive stock option packages to participate in the success of building Ladder.
• A rewarding 401k match program | We'll match up to 4% of your contributions as you save for your retirement goals.
• Ladder Fit Program | Your health matters. That’s why Ladder provides a monthly stipend for wellness-related expenses.
• Paid parental leave | We think it's crucial that new parents have time to adjust to their new lives without worrying about work, so we provide all parents inclusive of birthing, adoption, or fostering ten weeks of paid baby bonding.
• Work-from-home flexibility and support | We recognize that everyone's homelife is different and support remote work. Upon joining, we provide a one-time remote office stipend for all team members and then a monthly stipend to cover WFH costs such as the internet.
• Fun company-wide events | We genuinely enjoy spending time together. That’s why we plan fun virtual events to let loose and laugh.

Base pay is determined by the location where the work will be performed and is aligned to one of 3 compensation tiers, as indicated below. Base pay may vary depending on job-related knowledge, skills, experience, and business needs. In addition to the base pay range listed below, this role is also eligible for bonus, equity and benefits as shared above.

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

Ladder is building a diverse team of talented and enthusiastic people. We are an equal opportunity workplace. At Ladder, differences are celebrated and supported to benefit our people, product, and community. Let us know why you're interested in this position and what unique contributions you can make to the Ladder team. We look forward to hearing from you. 

Research shows that candidates from underrepresented backgrounds often don't apply for roles if they don't meet all the criteria – unlike majority candidates meeting significantly fewer requirements. We strongly encourage you to apply if you’re interested: we'd love to know how you can elevate our team with your unique experience!