Head of SMB Sales - Remote, High-Velocity Growth

Leap; Oregon; Hybrid; USD 180,000 - 225,000; Full time

Benefits offered by this job

Health & Wellness Coverage

401(k) company match

Flexible Time Off (FTO)

EAP - mental health & financial well­-

Employee discounts

Job summary

Leap, LLC is seeking a remote-first Sales Leader to guide the SMB Account Executive team. You will oversee ~10 AEs, set targets, manage daily activity, and drive pipeline health while collaborating with Marketing and RevOps.

You will hire, ramp, and scale the team toward aggressive growth targets, reporting to the VP of Sales. Strong CRM experience and a track record in fast-paced environments are essential.

Qualifications

• 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.

Responsibilities

• Team performance: Drive consistent quota attainment across a team of about 10 AEs.
• Set daily/weekly targets for dials, conversations, demos, and closes, then maintain discipline.
• Run stand-ups and pipeline reviews to catch slippage the same day.
• Fast coaching cycles: call and demo reviews, live shadowing, 1:1s with measurable next steps.
• Own stage conversion, deal velocity, and an accurate forecast for the VP of Sales.
• Recruit, onboard, and ramp AEs with a repeatable path to full productivity.
• Address underperformance early and build development paths to Senior AE.
• Work with BDR manager on clean pipeline handoff and with Marketing/RevOps on lead flow and reporting.
• Performs other duties as assigned.

Skills

Sales leadership

Coaching

Forecasting

Communication

CRM experience

Team leadership

Education

Bachelor's degree preferred

Tools

Salesforce

Leap CRM

Job description

Leap, LLC is seeking a remote-first Sales Leader to guide the SMB Account Executive team. You will oversee ~10 AEs, set targets, manage daily activity, and drive pipeline health while collaborating with Marketing and RevOps.

You will hire, ramp, and scale the team toward aggressive growth targets, reporting to the VP of Sales. Strong CRM experience and a track record in fast-paced environments are essential.