About the RoleWe'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
- 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)
