Head of Sales

Who We Are

Perchwell is the modern real estate listings platform built for agents to search smarter, collaborate better, and close deals faster. We are building the future of residential real estateʼs critical listings infrastructure: a platform where market  research and client collaboration converge. Our modern architecture enables continuous innovation at a pace legacy systems cannot match, with AI-powered features and mobile-first capabilities designed for how agents actually work. As consumer expectations and technology evolve, Perchwell remains focused on our core vision:  empowering real estate professionals with the most intelligent, data-driven, and connected platform in the industry.

Backed by leading venture capital firms including Lux Capital and Founders Fund, along with strategic partnerships with some of the country's top Multiple Listing Services (MLSs), Perchwell represents the first major new platform to enter the listings technology market in decades. This unique combination of institutional investment and deep industry alignment provides both the resources and market validation needed to transform the multi-trillion dollar residential real estate industry.

What We're Looking For

We're looking to bring on a dynamic Head of Sales to scale and lead our next phase of growth. We're starting to scale our proven founder-led motion into a strong sales foundation. We are looking for a hands-on leader from jumping in to close deals while building a sales organization.  This is a rare opportunity to join a rapidly scaling company where we've established strong market validation with customer wins and a burgeoning founder-led motion with a ~75%+  win rate in our core segment , and looking for a leader to start the scale the sales function.

Our ideal candidate is someone who thrives in high-growth environments and is energized by the challenge of building something meaningful. You have a proven track record of not just closing enterprise deals, but also developing the frameworks, processes, and teams that enable predictable revenue growth. You understand that success in this role requires both strategic vision and a willingness to be directly involved in the day-to-day execution. 

This position will report into our CEO, Brendan Fairbanks, and work out of our SoHo NYC Office 4 days/week

What You'll Do

As our Head of Sales, you'll:

• Lead and inspire a high-performing sales team while actively contributing to growing new bookings and ARR 

• Architect and execute the sales strategy and go-to-market approach for both our enterprise sales  and higher velocity sales motions

• Drive the foundational sales playbook that will drive our next phase of growth

• Establish sales process, frameworks, and methodologies to introduce sales pipeline visibility 

• Creatively tackle GTM problems, including building an enterprise business with inherent virality, network effects and a captive user base ready to be sold towards 

• Build relationships with key brokerage and MLS industry leaders and shape the future of real estate technology

• Collaborate closely with cross-functional teams, including product and customer success to ensure seamless internal processes and ongoing sales enablement

Who You Are

Required Experience

• Demonstrable career progression from successful individual contributor to sales leadership roles

• Track record of closing enterprise deals valued at $600K+, with experience in $1M+ deals preferred

• Proven track record of overachievement in previous revenue-generating roles

• Background in selling application SaaS products to non-technical , C-Suite decision makers 

• Proven experience  in leading a team of AEs in consistently acquiring new customers through outbound prospecting

• Experience building and scaling enterprise sales teams in high-growth environments

• Strong background in modern sales technologies and methodologies (ie  Hubspot, Gong)

Key Attributes

• Builder's Mindset: You thrive on creating something from scratch and are energized by the challenge of building systems, processes, and teams

• Strategic Thinker: You develop frameworks and approaches that can scale beyond individual deals

• Continuous Learner: You're intellectually curious and constantly seeking to understand more about our industry, products, and customers

• Results-Driven: You have a track record of not just hitting targets but creating sustainable, long-term growth

Leadership Style

• Hands-on leader who leads by example and isn't afraid to be directly involved in deals

• Strong ability to attract, develop, and retain top sales talent

• Excellence in sales coaching and mentorship

• Strategic approach to building and scaling teams

To provide greater transparency to candidates, we share base salary ranges for all US-based job postings regardless of state. Our ranges are based on function and level benchmarked against similar stage growth companies. Final offer amounts are determined by multiple factors including skills, job-related knowledge and depth of work experience. 

The On Target Earnings (OTE) range for this position is expected to  between $325K- $375K/year (including bonus or commission based on sales performance) + ability to overperform with accelerators + equity + benefits.

Note: At this time, we are only considering candidates who are authorized to work in the U.S.

Compensation Range: $325K - $375K