Mid Market Account Executive

About the Company

The $13 trillion mortgage industry at the core of the American economy runs on broken assembly lines with human-powered workflows, stitched-together software, and a series of capital markets intermediates. The costs to originate are at an all time high despite foundational shifts in technology.

Pylon is rewiring mortgages from the ground up. We are building the only API-first, programmatic infrastructure that fully automates credit, compliance, capital, and operations. For the first time, originators can build and scale mortgage businesses entirely through software, not people. Our team comes from Stripe, Better, and Affirm, and we are backed by Conversion Capital, QED, Citi, Fifth Wall, Peter Thiel, and the founders of Ramp, Mercury, Blend, and others. As we continue to grow, we are looking for a highly motivated and driven Founding Account Executive (AE) to join our dynamic GTM team.

About the Role

As our Founding Account Executive in the GTM function, you will play a critical role in shaping and executing the sales strategy for our mortgage-as-a-service platform. You will own the full sales cycle, from lead generation and qualification to closed-won, including converting MQLs to high-conviction opportunities. Additionally, you will help build out our GTM systems, processes, and sales materials, working closely with the VP of Business Development to lay the foundation for future aggressive sales growth. It is critical that your default operating mode is inclined toward a structured, repeatable and consultative sales motion.

This is an exciting opportunity for an experienced AE who thrives in a fast-paced, entrepreneurial environment and is eager to contribute to the development of a fundamentally unique approach to serving the mortgage industry with technology.

Key Responsibilities:

• Sales Pipeline Ownership: Own and manage a full sales pipeline from lead qualification through to closed-won deals. You will be responsible for proactively generating new business opportunities and driving the sales process forward at every stage- with a predisposition for creatively chartering a path forward at every opportunity.

• Discovery & Needs Assessment: Conduct thorough discovery calls and meetings to understand customer needs, pain points, and business objectives. Tailor the product pitch to align with these needs and demonstrate the value of our mortgage-as-a-service platform.

• Product Demonstrations: Conduct compelling product demos and presentations to prospects, highlighting the unique capabilities and value proposition of our programmatic mortgage rails.

• Negotiation & Closing: Lead negotiations and close deals in your pipeline, ensuring customer expectations are thoughtfully set and met throughout the sales process.

• Sales Process Development: Collaborate with the VP of Business Development, and the VP of Marketing, to build and refine sales processes, systems, tooling and materials that streamline the sales cycle, improve lead conversion rates, and scale the GTM function. Bring player-coach mindset to help successfully scale team.

• Collaboration with other GTM Teams: Work closely with the marketing, product, capital markets and account management teams to ensure alignment on sales strategy, messaging, and the post-sale customer journey.

• CRM & Reporting: Maintain accurate and up-to-date records in the CRM (currently Hubspot), track key sales metrics, and report on performance to the VP of Business Development and other company leadership.

• Market and Software Intelligence: Stay up-to-date on industry trends, competitive landscape, and customer needs to continuously refine your sales approach and ensure you’re addressing the right pain points for our ‘Switch To’ audiences.

Required Qualifications:

• 5+ years of experience in mid-market (or Enterprise) B2B SaaS sales with a proven track record of meeting or exceeding sales quotas.

• Experience selling complex, technical solutions to mid-market (or Enterprise) customers, preferably fintech, proptech, or a similar industry.

• Strong understanding of the sales process from lead gen through to deal closing.

• Excellent communication and presentation skills with the ability to engage and influence senior stakeholders, including executive decision makers and buying leads.

• Self-starter with the ability to work independently in a fast-paced, dynamic environment.

• Experience using CRM tools (our current stack is centered around Hubspot) and sales enablement tools to manage leads, pipeline, and performance metrics.

• Ability to adapt quickly, build or develop processes, and navigate ambiguity as the first AE in a growing sales organization.

• Strong problem-solving skills and a genuinely consultative approach to selling- we partner deeply with our customers, from lead to launch, to help them achieve their mortgage business goals.

• This role requires 5 days a week in office (SF Bay Area or New York City locations)

Preferred Qualifications:

• Experience in mortgage technology or financial services SaaS sales is a plus

• Previous experience working closely with marketing teams to align on lead qualification, eligible audience and sales materials.