Director of Direct Agent Sales, Ladder
$138-200k
Salary varies depending on location. Plus stock options
More information about location
Flexible life insurance provider
Be an early applicant
Flexible life insurance provider
101-200 employees
Be an early applicant
$138-200k
Salary varies depending on location. Plus stock options
More information about location
101-200 employees
Company mission
To help others set their families up for success.
Role
Who you are
- 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
- 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!
What the job involves
- 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
- 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
Our take
Ladder is a life insurance company whose primary aim is to simplify the process of acquiring life insurance. In the past, getting coverage for life insurance has been a lengthy and time-consuming affair, but with Ladder, applicants can answer a few questions and sign up on their phones.
Jamie, the CEO and co-founder, felt the life-changing impact of life insurance on his own family when he lost his father at a young age before struggling to get life insurance policies for himself as an adult.
Ladder will face stiff competition when traditional insurers undergo the digital transformation needed to join Ladder in offering five-minute life insurance policies via smartphone. However, Ladder's strong brand, technology-first approach, and early-mover advantage position it well to capture a meaningful share of this growing market.
Steph
Company Specialist at Welcome to the Jungle
Insights
-5% employee growth in 12 months
Company
Funding (last 2 of 7 rounds)
Oct 2021
$100m
SERIES D
Feb 2020
$37.5m
SERIES C
Total funding: $196.1m
Company benefits
- One-time stipend to support remote and hybrid work
- Recurring stipend to cover WFH costs
- 401k Match: Ladder matches your 401(k) contribution, dollar-for-dollar, up to 4% of your salary.
- Commuter Benefits: We offer a pre-tax transit account, as well as free employee parking.
- Catered Lunch: In-office employees get catered lunch every day from a variety of local restaurants.
- Ladder Fit: Ladder reimburses up to $50 per month for eligible wellness-related expenses.
- Baby Bonding: We offer 10 weeks paid leave when you welcome a new addition.
- Vacation: We encourage our employees to take time off so they can return relaxed and refreshed.
- Awesome Benefits: We offer medical, dental, vision, life, FSA, and short & long term disability.
Company HQ
Downtown North, Palo Alto, CA
Leadership
Jamie Hale
(Co-Founder & CEO)Previously a Founding Partner at Aldenwood Capital and Partner at Oak Hill Investment Management.
Laura Hale
(Co-Founder & CPO)Previously an Associate at Robert M. Bass and The Carlyle Group.
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