Enterprise Account Executive – SaaS Sales

Guideline Guru is simplifying the mortgage process with cutting-edge AI. Our flagship product is an AI Assistant that provides answers to mortgage guideline questions, streamlining complex underwriting processes. Since starting in January 2023, we’ve grown rapidly and are now trusted by mortgage professionals at dozens of lenders, including multiple top-ranked Scotsman Guide™ lenders. With over 150,000 guideline questions answered and a growing customer base, we’re proud to offer a scalable, innovative solution that simplifies the mortgage process and reduces costs for all involved. We have an exciting product roadmap ahead, with opportunities to extend our offering to make it even more valuable for mortgage sales and operations teams.

We’re a proudly bootstrapped company with solid financials and a small, growing team of technology and mortgage industry professionals. We enjoy building impactful software that simplifies the mortgage process and that makes life easier for our lender partners. Learn more about our company and innovative product on our website at guidelineguru.ai.

As our founding Account Executive hire, you’ll play a critical role in driving the growth of Guideline Guru by closing large and mid-market accounts in the mortgage space. This senior-level individual contributor role is focused on enterprise and strategic accounts, including top-25 Scotsman Guide™ ranked lenders. Additionally, you’ll collaborate directly with our CEO and team to shape the future of our sales strategy and product roadmap.

• Full Cycle Sales: Manage the sales process end-to-end, from initial outreach to contract signing and onboarding.
• Lead Generation: Build relationships with inbound leads while proactively generating your own pipeline through outreach methods like conferences, emails, LinkedIn messages, and calls.
• Sales Targets: Achieve and exceed quarterly and annual sales targets, with support from our CEO and engineering leads.
• Account Management: Strategically approach large accounts, engaging multiple stakeholders (COOs, Heads of Underwriting, etc.) to drive deals forward.
• Product Advocacy: Quickly learn and communicate the features and benefits of our product, tailoring your pitch to meet the needs of large lenders.
• Customer Insights: Identify and relay customer needs and product gaps to our team to help evolve and improve our product.
• Process Evolution: Help streamline and evolve our sales process, and contribute to marketing initiatives and customer support as needed.

• Experience:
  • Minimum 8 years of sales experience, with 5+ years in SaaS sales and 2+ years in the mortgage industry (e.g., selling into lenders or working at a lender). While these are our ideal qualifications, we’re open to other exceptional candidates who bring relevant experience and a strong track record of success.
  • Proven success in hitting and exceeding sales targets.
  • Demonstrated experience managing large accounts and closing strategic deals.
• Skills:
  • Strong communication skills and executive presence, capable of pitching to top decision-makers.
  • Project management skills, particularly in navigating complex deals with multiple stakeholders.
  • Strategic thinking, with the ability to map our product’s capabilities to a lender’s business goals. This includes identifying target customers who would benefit most from our solution. 
  • Ability to ask insightful questions, listen actively, and understand a prospect’s pain points.
• Attributes:
  • Thinks like a long-term owner of, and partner in, the business, with a focus on doing what’s best for our customers, culture, and reputation.
  • Self-starter who thrives in and enjoys an entrepreneurial environment.
  • Collaborative and team-oriented, with a mindset that makes them easy and enjoyable to work with.

• Compensation: Competitive base salary with a lucrative commission structure. The on-target earnings (OTE) range for this role is $175,000 - $275,000, with no cap on commissions. Your package will include significant equity (see details below). The OTE includes a fixed base salary and performance-based commissions, both of which have strong potential for growth in future years.
• Equity: A very generous ownership stake in a fast-growing company. We offer significantly more equity than comparable companies because we maintain a small team, and because we value teammates who think like owners and are dedicated to building a long-term, successful business.
• Growth Opportunities: Develop your entrepreneurial skills and grow your expertise in one of the most exciting new areas of technology.
• Work-Life Balance: We target a 40-hour work week and prioritize doing calm, focused work, and  making thoughtful prioritization decisions, to help you perform at your best and have a vibrant life outside of work.
• Empowerment: Have autonomy to shape your role and define how you work, with support to help you succeed.
• Team: Collaborate with a talented, supportive group of professionals who share a commitment to simplifying the mortgage process and making work easier and more efficient for our lender customers.
• Work Setup: Work fully remote or onsite—whatever suits you best. We have a physical office in downtown NYC that you can use if you prefer an office setting.

1. Initial Call: Speak with our CEO to learn more about the role and share your background.
2. Team Interviews: Meet with other team members to discuss your skills and experiences.
3. Sales Skills Interview: Showcase your expertise in a focused session, which may include presenting a past sales pitch (no custom work required). This session will typically last 30-45 minutes and focus on how you’ve managed full-cycle sales for large accounts.
4. Reference Checks: We’ll connect with your references to learn more about your work.
5. Offer: We'll present your full offer package and answer any final questions.

 If you’re excited about this opportunity and meet the qualifications, we’d love to hear from you. Apply now by sending your resume to careers@guidelineguru.ai, and help us build a great product and company!