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About the Role
Kastle is seeking a founding Head of Sales to build and scale the go-to-market team and systems for a product with high Annual Contract Values (ACVs), fast sales cycles, and early product-market fit. This role involves direct collaboration with founders on large deals, recruiting, coaching sales talent, and acting as a player-coach during scaling.
Responsibilities
- 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.
Requirements
- 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.
Skills
- Sales
- Team Building
- Coaching
- Revenue Forecasting
- Strategic Sales Planning
- Recruiting
- Enterprise Sales
- Consultative Selling
- Outreach
- MEDDIC
Location
- San Francisco, CA
Work Type
- Full-time
Experience Level
- 15+ years of sales experience
- 7+ years of team building/scaling experience
- 5+ years in a startup or high-growth technology company
Salary/Compensations
- Competitive base salary with uncapped commission potential
Benefits
- Executive equity options
- Comprehensive health, dental, and vision insurance
- 401(k) with company match
About the Company
- Kastle is building the AI employee for consumer lending, working with large banks and mortgage lenders to scale contact center and compliance operations using AI Agents.
- The company has processed over $1 billion in transactions and is backed by Y Combinator and Commerce Ventures.
- Kastle offers a career-defining opportunity to build a GTM org and shape the future of consumer lending in a fast-growing AI company in financial services.
- The product is a market-leading AI platform already live in production with 8 of the top 25 servicers in the country.
- Employees can work side-by-side with a world-class founding team from companies like Verkada, NVIDIA, Apple, Redfin, and Intuit.
- Opportunity to work with cutting-edge AI technologies.