Head of Sales

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.

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)