Enterprise Account Executive

Compensation: Up to $280k OTE

About Us

At Leap, we're on a mission to transform the home improvement industry - and we want you to be part of that journey. We're proud to be recognized on the Inc. 5000 and Inc. Regionals lists for 5+ consecutive years, reflecting sustained growth driven by innovation, strong execution, and an incredible team. We build technology that helps contractors work smarter, scale faster, and deliver better experiences to their customers.

When you join Leap, you'll work alongside curious minds, bold innovators, and thoughtful risk-takers who care deeply about doing great work - and doing it together. Our culture is transparent, supportive, and grounded in approachable leadership. We actively listen to our employees through semi-annual engagement surveys, maintain a strong eNPS score, and consistently act on feedback to improve what's working and where we can do better. We believe great work happens when people are supported outside of work, which is why we offer comprehensive benefits and wellness resources for you and your family.

Take the Leap today and help shape what's next.

Position Overview

The Enterprise Account Executive (AE) is responsible for driving new business sales of Leap's enterprise software solutions into top strategic accounts within the retail and home improvement contractor space. This role focuses on building multi-threaded relationships with C-suite and VP-level decision makers, developing tailored value propositions, customer proposals, and managing complex sales cycles to a successful close.


The Enterprise AE will own the full sales process - from strategic research and outreach through discovery, solution design, and contract negotiation - while partnering closely with the VPs of Sales, Channel Partnerships, and Revenue Operations to ensure alignment on go-to-market strategy. This position is highly visible and plays a critical role in Leap's next phase of growth in the enterprise market.


Responsibilities

• Develop and execute a targeted enterprise sales strategy focused on driving new business across Leap's top priority accounts.
• Identify, qualify, and pursue growth opportunities through a consultative, value-based approach tailored to each customer's business challenges.
• Lead and manage complex, multi-stakeholder sales cycles, engaging directly with executive sponsors, operational leaders, and technical stakeholders.
• Build and maintain strong relationships with C-suite and VP-level executives to position Leap as a trusted strategic partner.
• Collaborate cross-functionally with Partnerships, Customer Success, Professional Services, and Marketing to deliver cohesive, industry-specific solutions.
• Prepare and deliver compelling business cases, ROI analyses, and proposals aligned with enterprise needs and value outcomes.
• Utilize Leap's sales tech stack (Salesforce, Gong, Service Cloud, etc.) to manage pipeline, forecast accurately, and document all sales activities.
• Maintain a deep understanding of CRM, ERP, and sales enablement systems, as well as key market and competitive trends.
• Represent Leap at industry trade shows, conferences, and virtual events to engage prospective enterprise clients.
• Maintain an active pipeline equivalent to 3× annual quota through a combination of inbound, outbound, and partner-driven opportunities
• Provide regular updates, forecasts, and account insights to Sales leadership.
• Support cross-team initiatives that refine Leap's enterprise sales process, messaging, and playbook.
• Perform other related duties as assigned.

Qualifications

• 6+ years of B2B SaaS sales experience, ideally with at least 3 years in enterprise or strategic account sales with individual quota ownership.
• Proven track record exceeding $500K+ annual quotas with average deal sizes of $40K+ ARR.
• Demonstrated experience selling into retail home services verticals - or to customers who serve these industries.
• Experience selling into or partnering with contractor-focused or field service businesses; familiarity with industry software such as CRM, ERP, or sales systems.
• Skilled in consultative and solution-oriented selling, with the ability to uncover business challenges and align Leap's value to client goals.
• Exceptional communication and executive presence with the ability to engage and influence VP and C-level stakeholders.
• Experience aligning stakeholders across Sales, Operations, and IT to ensure enterprise-level buy-in and adoption to deliver complex customer solutions.
• Tailor ROI-driven presentations and live demos of SalesPro's capabilities (estimating, financing, digital contracts, pricing control, and reporting).
• Strong technical curiosity and ability to align integrations (CRM, ERP, or financing platforms).
• Excellent forecasting, pipeline management, and CRM hygiene.
• Ability to travel as needed within the U.S.

Benefits

We believe in supporting our employees holistically - your health, financial well-being, time to recharge, and overall happiness matter to us. Here's what you can look forward to:

• Affordable Health & Wellness Coverage - comprehensive and competitive benefits package, starting the first of the month following your hire date.
• Invest in Your Future - 401(k) company match to help you build financial security.
• Time to Recharge - We believe time to rest and recharge matters. Leap offers a Flexible Time Off (FTO) policy, 10 paid sick days, and 8 paid company holidays.
• Comprehensive Employee Assistance Program (EAP) - resources to support your mental health, financial well-being, and everyday challenges.
• Exclusive Discounts with LifeMart (via ADP) - save on groceries, restaurants, entertainment, pet insurance, cell phones, child care, and more!
• MoveSpring Wellness App - stay active and engaged with company step challenges, workout content, meditation tools, and wellness blogs for a healthier you!
• Culture & Team-Building Activities - we love to connect, celebrate, and grow together through team events, fun challenges, and company traditions like our Annual Summit!

Join us and experience a company that truly invests in YOU !

Leap is an Equal Employment Opportunity and Affirmative Action Employer. We are committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants and teammates without regard to race, religion, color, sex, gender identity, sexual orientation, age, non-disqualifying physical or mental disability, national origin, veteran status or any other basis covered by appropriate law. All employment decisions are made based on qualifications, merit, and business needs.