Vice President of Sales at Land Gorilla in San Luis Obispo, CA

Apply Description Reports to: Chief Executive Officer (CEO) Employment Type: Full-Time About Land Gorilla Land Gorilla is the leading technology provider of construction loan management software. Our vision is to make construction lending safer, faster, and more profitable. By replacing risky manual processes and spreadsheets with an automated, end-to-end digital ecosystem, we protect construction lenders and their customers from the inherent risks associated with construction finance. Top banks, credit unions, private lenders, and mortgage companies rely on Land Gorilla’s award-winning technology (including our OneSite portal, intelligent document processing, and comprehensive inspection suite) to safely manage up to five times more loans with the same staff. We are a high-growth, innovative company dedicated to transforming the construction lending experience. The Role We are seeking a dynamic, strategic, and hands-on Vice President of Sales to lead our sales organization and drive our next phase of explosive growth. In this executive role, you will be responsible for defining and executing our national sales strategy, scaling our revenue engine, and leading a high-performing team of Account Executives and Customer Success Managers (Account Managers). The ideal candidate has a proven track record of scaling B2B SaaS companies, a deep understanding of selling into financial institutions (FinTech/PropTech experience is highly desired), and a passion for building winning, customer-centric sales cultures. Key Responsibilities Strategic Leadership & Front-Line Execution Develop and execute a comprehensive Go-to-Market (GTM) sales strategy to accelerate New ARR, drive logo acquisition, and expand our footprint within existing accounts. Actively lead by example, maintaining direct involvement in full-cycle sales on key strategic accounts and navigating complex enterprise deals alongside your team. Establish and own ambitious revenue targets, forecasting accurately to the leadership team and Board of Directors. Identify new market opportunities and refine our ideal customer profile (ICP) to maximize penetration in the banking, credit union, independent mortgage bankers, and private capital sectors. Team Building & Hands-On Management Recruit, hire, train, and mentor a top-tier sales organization, including AEs, SDRs, and Sales Operations. Foster a culture of high performance, accountability, continuous learning, and collaboration. Develop robust sales enablement programs and coaching frameworks by personally modeling best practices, reviewing call recordings, and providing direct, actionable, real-time feedback. Customer Success & Account Growth Partner directly with Customer Success Managers to actively secure renewals, drive expansion revenue, and uncover upsell/cross-sell opportunities. Personally participate in and lead Quarterly Business Reviews (QBRs) with top-tier clients to maintain strong executive alignment. Serve as the ultimate point of escalation, jumping in to directly guide resolutions for high-stakes customer issues to ensure retention and long-term satisfaction. Sales Operations & Process Optimize the sales process from lead generation to close, ensuring a frictionless buying journey for our prospects. Leverage CRM (HubSpot) and other sales intelligence tools to build scalable, data-driven processes, maintaining impeccable hygiene and visibility yourself. Work closely with Marketing and Product to align on demand generation, relay market feedback, and shape the product roadmap based on your front-line interactions. Requirements Experience: 8–10+ years of progressive sales experience in B2B SaaS, with at least 4–5 years in a senior sales leadership role (VP or Senior Director level). Industry Knowledge: Proven experience selling software into the financial services sector (Banks, Credit Unions, Mortgage Lenders). FinTech, PropTech, or lending technology experience is a major advantage. Track Record: Demonstrated history of consistently meeting or exceeding revenue targets, successfully scaling a sales organization, and driving significant growth in ARR. Deal Expertise: Deep understanding of complex, enterprise-level sales cycles (6-12+ months) and experience navigating multi-stakeholder purchasing decisions. Player-Coach Mentality: A true practitioner who wants to get their hands dirty. You are expected to be on the front lines— interacting directly with customers—not just managing managers. Analytical Skills: Strong financial acumen and a highly data-driven approach to pipeline management and forecasting. Communication: Exceptional communication, presentation, and negotiation skills. Benefits Competitive executive compensation package (Base + Uncapped Commission + Equity/Stock Options). Comprehensive health, dental, and vision insurance. 401(k) plan with company match. Flexible Paid Time Off (PTO) and paid company holidays. Remote work flexibility with opportunities to visit our beautiful headquarters in San Luis Obispo, CA. A collaborative, forward-thinking culture where your impact will be recognized and rewarded. Compensation: $140,000 - $180,000/year + variable pay The actual pay offered to the successful candidate will be based on multiple factors, including but not limited to job-related knowledge/skills, experience, and geographical location. It is not typical for an individual to be hired at the high end of the range for their role, and compensation decisions are dependent upon the facts and circumstances of each position and candidate. Land Gorilla is an equal-opportunity employer and values diversity at our company. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other protected characteristic.