Head of Sales

Kastle; San Francisco (CA); On-site; USD 250,000 - 420,000; Full time

Benefits offered by this job

Competitive base salary

Uncapped commission potential

Executive equity options

Health, dental, vision insurance

401(k) with company match

Job summary

Kastle is seeking a founding Head of Sales to scale a high-value product with large ACVs and rapid sales cycles. You will recruit, coach, and lead the GTM team, overseeing enterprise deals and shaping the sales strategy as the company grows across North America.

this founder-level opportunity requires working closely with founders, closing 7–8 figure deals, and building a world-class sales engine. Location preference is San Francisco, CA.

Qualifications

• 15+ years of formal sales experience, including building or scaling teams for large mid-market or enterprise.
• Proven track record of meeting or exceeding quota in B2B SaaS as an individual contributor.
• Minimum 5 years of experience selling in a startup or high-growth tech company.
• Experience building teams to sell new products that require market education.
• Ability to develop an independent pipeline and navigate multi-stakeholder buying processes.

Responsibilities

• Own Kastle’s revenue target and the core levers to hit it, including hands-on deal management, coaching, and forecasting.
• Collaborate with the CEO and account executives to craft strategic plans for key mortgage, servicing, and consumer banking accounts.
• Recruit, hire, and coach enterprise AE/SAE talent and build a high-performing enterprise SWAT team.
• Hire and mentor reps capable of navigating multi-stakeholder processes (C-suite, InfoSec, legal, procurement).
• Foster a hunter-first culture with aggressive outbound activity and strategic use of champions to close multi-million deals.

Skills

Enterprise sales

Team building

B2B SaaS

Quota attainment

Startup experience

Tools

Outreach

MEDDIC

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.

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