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Kastle is building AI agents for consumer lending, working with America's largest banks and mortgage lenders to scale contact center and compliance operations. The company has processed over $1 billion in transactions and is backed by Y Combinator and Commerce Ventures.
You will be Kastle's founding Head of Sales, responsible for scaling the sales organization from founder-led sales to a high-performing enterprise team. The role combines hands-on deal management with team building and strategic leadership. You'll own the revenue number and all key sales components, including deal management, coaching, team buildout, and revenue forecasting.
Key responsibilities include:
- Working directly with the CEO and Account Executives to develop and execute strategic sales plans targeting mortgage lending, servicing, and consumer banking segments
- Recruiting, hiring, evaluating, and coaching Enterprise Account Executives (EAEs) and Sales Account Executives (SAEs) focused on closing $1M+ ACV deals with banks and enterprise lenders
- Building a hunter-first sales culture emphasizing aggressive outbound prospecting, creative storytelling, and strategic use of champions to close 7 and 8-figure deals
- Hiring and coaching reps who can navigate complex, multi-stakeholder sales processes involving C-suite, InfoSec, legal, and procurement teams
- Acting as a player-coach alongside reps as the business scales
- Influencing not just revenue but also product direction, partnerships, and brand positioning
The company offers a competitive base salary with uncapped commission, executive equity options, comprehensive health/dental/vision insurance, and 401(k) with company match. You'll work alongside a founding team with backgrounds from Verkada, NVIDIA, Apple, Redfin, and Intuit, selling a market-leading AI platform already live in production with 8 of the top 25 servicers in the country.
REQUIREMENTS:
- 15+ years of formal sales experience, with minimum 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 selling "net new" products or services requiring 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 ability to communicate challenging technical concepts to 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
