Head of Sales
Kastle AI
Head of Sales
Kastle AI
AI agents handling lending operations
Kastle is building the AI employee for consumer lending. We work with some of America's largest banks and mortgage lenders, helping them scale their contact center and compliance operations using autonomous AI Agents that process payments, originate loans, and help customers get a world class experience during the biggest financial decisions of their lives. We've processed over $2 billion in transactions and are backed by Insight Partners and Y Combinator. If you are interested in selling the best product in the market and help large enterprise lenders and banks transform their operations, apply below.
We just raised a $24M Series A and are growing fast!
We’re looking for our founding Head of Sales hire who can take a product with large ACVs, fast sales cycles and early PMF, and build out the team and systems to hyperscale as we move past founder-led sales.
This role requires an ability to: work directly with founders selling large deals, recruit, hire, evaluate and coach EAE and SAE talent, and act as a player coach when needed alongside reps as the business scales.
As you succeed in the role, you'll be responsible for building out a world-class GTM team to help Kastle dominate consumer lending across North America.
Location preference: San Francisco, CA.
Own Kastle’s revenue number and the key sales components of reaching it, including hands-on deal management and coaching, buildout of the sales and sales management team, and revenue forecasting.
Work with the CEO and AEs to develop and execute strategic sales plans to penetrate key accounts in mortgage lending, servicing, and consumer banking.
Act as a recruiter, quality bar and coach across AEs, with a focus on building an enterprise SWAT team of EAEs and SAEs closing $1m+ ACV deals with banks and enterprise lenders.
Hire and coach reps that can navigate challenging, multi-stakeholder sales processes (C-suite, InfoSec, legal, and procurement) within large enterprise organizations
Build and maintain a strategic, hunter-first culture where reps are aggressive outbound, creative in storytelling, and strategic in how they use their champions to close 7 and 8 figure deals.
Career-defining opportunity to build a GTM org and shape the future of consumer lending in one of the fastest-growing AI companies in financial services, backed by YC, Insight Partners, Emergence Capital, and Commerce Ventures
Sell a market leading AI platform that’s already live in production with 8 of the top 25 servicers in the country
Competitive base salary with uncapped commission potential
Executive equity options to share in the company's success
Influence not just revenue, but product direction, partnerships, and brand positioning
Ability to work side-by-side with a world-class founding team from Verkada, NVIDIA, Apple, Redfin, and Intuit.
Chance to work with cutting-edge AI technologies
Comprehensive health, dental, and vision insurance
401(k) with company match
15+ years of formal sales experience, with a minimum of 7 years building or scaling teams focused on selling to large mid-market or enterprise organizations
Proven track record of consistently meeting or exceeding quota in a B2B SaaS environment as an individual contributor
Minimum 5 years of experience selling in a startup or high-growth technology company
Demonstrated success building teams in selling "net new" products or services that require market education
Willingness and ability to build an independent pipeline
Experience with modern sales tools and methodologies (e.g. Outreach, MEDDIC)
History of building strong relationships and referenceable network with C-level executives
Strong consultative selling skills with the ability to communicate challenging technical concepts to both technical and non-technical audiences
Proficiency in navigating complex, multi-stakeholder sales processes
Experience as an early executive or sales hire or first non-founder executive hire at a startup
Experience selling to large banks and lenders
Extensive professional network within large banks and lenders
Application: Email [email protected] with: (2 sentences max for each please!)
How long does it take for you to know if a rep will be successful, and how do you know
The most counter-intuitive thing you’ve learned about building an enterprise-focused sales team
Quota + attainment for your teams for your 2 most recent roles
An explanation of any short stints (less than 3 years)
Kastle AI builds an AI workforce for financial services, starting with consumer lending and mortgage servicing. Its product comprises specialized voice and SMS agents that perform high-volume tasks across lenders’ existing core systems—such as collections, payment inquiries, borrower qualification, and servicing—without requiring a multi-year core replacement. The agents are trained to handle FDCPA, TILA, RESPA, and TCPA compliance, and have processed roughly $1.8–2 billion in transactions for large banks and enterprises. The company differentiates itself by integrating directly with lenders’ existing infrastructure rather than rebuilding cores, focusing on compliance-ready automation for financial workflows, and scaling through a software-enabled human-in-the-loop style AI workforce. Kastle’s goal is to expand engineering, product, and go-to-market efforts to broaden the adoption of AI-powered operations in financial services.
Explore more opportunities at Kastle AI