---
title: 'Head of Sales at Kastle'
canonical: 'https://feeny.ai/job/head-of-sales-kastle-san-francisco-d0xkyqh7a74w'
type: 'job'
last_seen: '2026-09-05'
---

# Head of Sales at Kastle

- **Company:** Kastle
- **Location:** San Francisco, CA
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-08-24
- **Last confirmed live:** 2026-09-05
- **Apply:** https://jobs.ashbyhq.com/kastle/735bed91-3179-4511-88a8-d87b7e0804db

## Job description

## ABOUT KASTLE

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 $1 billion in transactions and are backed by Y Combinator and Commerce Ventures. If you are interested in selling the best product in the market and help large enterprise lenders and banks transform their operations, apply below.

## ABOUT THE ROLE

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.

## WHAT YOU’LL DO

- 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.

## WHY JOIN KASTLE

- 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

## WHAT WE ARE LOOKING FOR

- 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

## PREFERRED QUALIFICATIONS

- 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 rishi@kastle.ai 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)

## About Kastle

## Core Business
- **Primary industry**: Consumer lending / Mortgage servicing technology (Fintech)
- **Target customers**: FDIC-insured banks, independent mortgage banks (IMBs), and large consumer lenders (B2B, Enterprise)
- **Mission or purpose statement**: To help traditional financial services companies better interface with their customers by automating high-volume phone calls with compliant AI agents.

## Products & Services
- **Avery (Servicing Agent)**: AI voice agent that handles borrower inquiries, payment collection, escrow questions, and loss mitigation. Integrates with ICE’s MSP system.
- **Collections Agent**: Automates payment reminders, engages delinquent borrowers early, and recovers past-due accounts.
- **Compliance Agent**: Monitors and scores every interaction against regulations (FDCPA, TILA, UDAAP, RESPA, TCPA) for 100% QA coverage.
- **Loan Officer Assistant**: Qualifies new loan inquiries and automates pre-qualification calls.
- **Sentinel (QA & Compliance Agent)**: Real-time monitoring and automated scorecards for borrower calls and servicing documentation.
- **Agent Builder**: Allows lenders to turn SOPs into AI agents using natural language, with no-code configuration.
- **Platform features**: Omnichannel support (voice, SMS, email, chat), simulation testing, transparent observability, and integration with existing contact center, payment processor, and LMS systems.

## Market Standing
- **Valuation**: Not disclosed (private startup)
- **Key Metric**: Total funding of $510,000 (Pre-seed round led by Y Combinator, June 2024)
- **Notable Investors/Partners**: Y Combinator (lead), ICE Mortgage Technology (integration partner)
- **Growth Signals**:
  - Headcount: 10 employees (+66.7% YoY)
  - Won LendingTree’s 2024 Innovation Challenge (Nov 2024)
  - Featured in a16z’s February 2025 fintech newsletter on voice AI
  - Integration with ICE’s MSP servicing system (April 2026)
  - Most deployed AI voice agents in the mortgage industry (per website)
  - Active job postings: 8 positions, with 300% yearly increase in listings

## Competitive Advantages
- **Purpose-built for compliance**: Pre-trained on key lending regulations (FDCPA, TILA, UDAAP, RESPA, TCPA) with a proprietary Compliance Engine.
- **Enterprise-grade integrations**: Direct connectivity with ICE’s MSP (the dominant mortgage servicing system) and other core systems.
- **Fast time to value**: Go-live in days with out-of-the-box agents that map to existing workflows.
- **Transparent AI**: All responses are fully explainable with built-in reasoning, enabling audit-ready operations.
- **Battle-tested track record**: Claims to have the most deployed AI voice agents in the mortgage industry, with proven metrics (70% lower cost per call, 40% lower handle time, 90%+ CSAT).

## Strategic Focus
- Deepening integrations with core mortgage systems (e.g., MSP) to reduce friction for large lenders.
- Scaling the AI agent workforce across the full lending lifecycle (origination, servicing, collections, compliance).
- Expanding from voice to true omnichannel (SMS, email, chat) and adding more pre-built agent types.
- Growing the enterprise customer base among FDIC-insured banks and IMBs.

## Why Work Here
- **Culture**: Early-stage YC startup with a small, high-agency team (10 people). Founders have strong product/engineering backgrounds (Redfin, Verkada). Emphasis on building mission-critical AI for a regulated industry.
- **Work policy**: Based in San Francisco (185 Channel Street). Likely in-office given the early stage and need for close collaboration.
- **Notable perks/engineering culture**: Opportunity to work on proprietary inference technology, compliance engine, and real-time AI systems. Roles span applied AI, forward deployment, and product management. High ownership and impact from day one.
- **Growth trajectory**: Rapid headcount growth (66% YoY), multiple open roles, and strong market traction suggest significant career growth potential.

## Sources
1. [kastle.ai](https://www.kastle.ai/)
2. [ycombinator.com](https://www.ycombinator.com/companies/kastle)
3. [linkedin.com](https://www.linkedin.com/company/kastleai)
4. [cbinsights.com](https://www.cbinsights.com/company/kastle)
5. [ycombinator.com/jobs](https://www.ycombinator.com/companies/kastle/jobs)

## Other roles at Kastle

- [Software Engineer - Intern](https://feeny.ai/job/software-engineer-intern-kastle-san-francisco-25ekajcm3kk7) — San Francisco, CA
- [Senior Product Manager](https://feeny.ai/job/senior-product-manager-kastle-san-francisco-w8f083jn8y91) — San Francisco, CA
- [AI Deployments Lead](https://feeny.ai/job/ai-deployments-lead-kastle-san-francisco-dk0d9gy0kw3b) — San Francisco, CA
- [Mortgage Originations Process Specialist](https://feeny.ai/job/mortgage-originations-process-specialist-kastle-san-francisco-cpcar50m80p4) — San Francisco, CA
- [Founder's Office](https://feeny.ai/job/founder-s-office-kastle-san-francisco-cfysxyhxtfnp) — San Francisco, CA
- [AI Trainer (Part-time)](https://feeny.ai/job/ai-trainer-part-time-kastle-remote-gawt2gvp2g56)
- [Agent Product Manager](https://feeny.ai/job/agent-product-manager-kastle-san-francisco-2mq46j3a94ka) — San Francisco, CA
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- [Enterprise Account Executive](https://feeny.ai/job/enterprise-account-executive-kastle-san-francisco-h9mz7tqdf5ww) — San Francisco, CA
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