The posting
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.
ABOUT LEAP
Built for Contractors Who Move Fast
Leap is the complete platform for residential home improvement contractors—roofers, remodelers, and the specialty trades that keep homes running. Our SMB sales team brings Leap to contractors who run lean and move fast. That team needs a leader who does the same.
THE OPPORTUNITY
Lead the Team That Wins on Speed
You'll lead about 10 Account Executives in a high-velocity motion: deals around $400, short sales cycles, and a number that's won through volume, speed, and discipline. You'll set the standard, run pipeline every day, and coach in tight loops so reps get better every week. Working directly with the VP of Sales, you'll hire, ramp, and scale the team against aggressive growth targets.
RESPONSIBILITIES
Your Team, Your Number, Your Standard
- Team performance. Drive consistent individual and team quota attainment across a team of about 10 AEs.
- The activity standard. Set daily and weekly targets for dials, conversations, demos, and closes, then hold the line.
- Daily pipeline. Run stand-ups and pipeline reviews that catch slippage the same day, not at month-end.
- Fast coaching cycles. Call and demo reviews, live shadowing, and weekly 1:1s with clear, measurable next steps.
- The forecast. Own stage conversion, deal velocity, and an accurate forecast for the VP of Sales.
- Hiring and ramp. Recruit, onboard, and ramp AEs with a repeatable path to full productivity.
- Accountability and growth. Address underperformance early and directly. Build development paths to Senior AE for your top performers.
- Cross-team partnership. Work with the Manager, BDR on clean pipeline handoff, and with Marketing and RevOps on lead flow, routing, and reporting.
- Everything else. Performs other duties as assigned.
This role leads the SMB Account Executive team. Our Enterprise AE team has its own dedicated leadership.
REQUIREMENTS
You've Built This Before
- 4-6+ years of B2B sales experience, including 3-5+ years in a sales management or team lead role.
- Experience leading a high-volume, transactional sales team selling to small businesses: low deal size, short cycles, and a high count of closed deals.
- Track record of hitting and exceeding quota as an individual contributor before moving into management.
- Demonstrated success coaching and developing Account Executives, with measurable improvement in team performance.
- Proven ability to hire, ramp, and scale a sales team through rapid growth.
- Strong understanding of sales process, pipeline management, and forecasting.
- Excellent communication and coaching skills, with the ability to give direct, actionable feedback.
- Hands-on experience with CRM and sales tools (Salesforce, Leap CRM, or similar).
- Strong organizational skills, with the ability to manage a team's pipeline and priorities across multiple deals at once.
- Data-driven mindset, with the ability to use pipeline and performance metrics to guide coaching and decisions.
- Ability to thrive in a fast-paced, growth-stage environment.
- Bachelor's degree preferred, or equivalent practical experience.
- Ability to travel occasionally for team coaching, company events, and industry events.
PREFERRED SKILLS
Bonus Points
- Sales leadership in a high-velocity SMB business such as payments and POS, payroll and HR, SMB SaaS, or staffing.
- Knowledge of the home improvement or field services industry.
WORK LOCATION
Remote-First, With a Home Base
This role is fully remote. Want time on the floor with the team? Our Columbia, MD office is open to you anytime.
Compensation will be determined based on experience, skills, and qualifications.
Pay Range
$180,000—$225,000 USD
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.
Leap, LLC collects personal information from job applicants as part of our recruiting and hiring process. This information is collected directly from you and from third parties such as background check providers and professional references. It is shared only with Greenhouse Software Inc. (our recruiting platform) and others as required by law. We do not sell your personal information.
The categories of information we collect, and the purposes for which we use them, include:
- Identifiers (name, email, phone, address) — to contact you and manage your application
- Professional information (resume, work history, skills, references) — to evaluate your qualifications
- Education information (degrees, certifications) — to verify credentials required for the role
- Background check data (criminal history, employment verification) — to complete pre-employment screening as permitted by law
- Voluntary demographic information (EEO data) — for legally required reporting only; not used in hiring decisions
